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940: How to Find the Best Job for You that Actually Exists with Lauren McGoodwin

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Lauren McGoodwin challenges the notion of the “dream job” and makes the case for pursuing the “good-enough” job.

You’ll Learn:

  1. Why the dream job actually doesn’t exist 
  2. The true drivers of happiness at work 
  3. Why to become invaluable–not indispensable 

About Lauren

Lauren founded Career Contessa in 2013 after experiencing a gap in career development resources for women who might be job searching, soul searching, leading and managing, or trying to find new ways to advance within their careers. With women accounting for more than 50% of the workforce and the workforce being less defined than ever before, it seemed crazy (and outdated) that a resource for us didn’t exist.

Fast-forward to today, Career Contessa is now the largest online career site built inclusively for women. Lauren is also author of Power Moves: How Women Can Pivot, Reboot, and Build a Career of Purpose (2020), co-host of The Career Contessa podcast, and an educator/speaker on a variety of career topics. 

Formerly, Lauren was a University Recruiter for Hulu focused on hiring, employer branding, and program management. Lauren has a Bachelors in Education from the University of Oregon and a Masters in Communication Management from the University of Southern California where she wrote her thesis on millennials and career resources. 

When not Contessa-ing, you can find Lauren spending time with her family in Redondo Beach, CA where she lives with her husband and daughter. 

Resources Mentioned

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Lauren McGoodwin Interview Transcript

Pete Mockaitis

Lauren, welcome to How to be Awesome at Your Job.

Lauren McGoodwin

Hi, Pete. Thanks for having me.

Pete Mockaitis

Well, I am super excited to dig into your wisdom. And could you start us off by sharing, so you’ve been in this Career Contessa game for a while, great brand.

Lauren McGoodwin
Thank you.

Pete Mockaitis

And it even existed before How to be Awesome at Your Job, so kudos on a long run here. Can you share with us a particularly surprising or counterintuitive piece of career advice that you’ve come to learn and adopt and share during your reign as the Career Contessa?

Lauren McGoodwin

Yeah, absolutely. We’ve been around for 10 years, I’ve talked to a lot of successful, very fulfilled people. I think the biggest thing, the biggest misconception I’m sort of very much on brand for that millennial woman who was striving for perfect, was that the dream job does not exist, it’s a myth. It’s a myth that kind of keeps you perpetually stuck. So, that’s probably the biggest one from talking, and basically having the job that I do, which is finding out “What does make a successful career? People who are fulfilled, how do they do it?”

And that’s a big one, I think, because it starts to sort of managing your expectations and actually not expecting to have this dream job that checks every box in your life. It’s similar to trying to find a perfect partner, right? But with jobs, for some reason, we believe not only do dream jobs exist but that, “I should have one. And if I don’t have one, something about me is missing and wrong, and I’ve messed up,” and turn yourself into this personal DIY project to fix that part of your life.

Pete Mockaitis

Oh, that’s good. That’s good. So, the implications of that then is if we’re not in a dream job, that’s okay, nobody is because they don’t exist. That’s your view on the world?

Lauren McGoodwin

Yeah, it is my view on the working world, that there is no such thing as a dream job. And you’ll see it makes a really good saying as a meme on Instagram and TikTok and whatnot of the dream job exists and hustle harder to get that dream job, and a job should check all these multiple boxes but what I find is that, really, what the dream job is made up of is this elusive kind of lifestyle piece of a job, where it doesn’t include hellish commutes or return-to-office mandates that you don’t agree with, it doesn’t include manipulative coworkers or bad bosses who actually don’t know how to manage.

And so, you’re sort of looking for this thing that doesn’t exist, and so your expectations are consistently misaligned with reality. That is equivalent, for me, of someone who has a very fixed mindset versus having a growth mindset, someone who can say, “Hey, my ability to learn and adapt is more important than, okay, my ability to be perfect at this presentation.”

So, I think what happens is dream job isn’t just like your job title and your company. It’s really inclusive more of like a lifestyle, and a mindset, and these realities that, one, don’t exist, as COVID, I think, is such a good reminder of, like, things can change quickly, and being able to be adaptable, and be able to lean into uncertainty, is really kind of the stuff that makes you more invaluable at work versus the person who’s like, “I found the perfect job title, and it looks really good on LinkedIn, and I’m able to share these…” I call it, like, glitter and glue moments, “All these glitter moments in my career but the glue is what holds the career together.”

And so, that’s why I’m actually a big advocate for people who always say, “Well, if I’m not looking for a dream job, what am I looking for?” And I will advocate for a good-enough job. A good-enough is really practical, it’s not perfect, and that’s the problem. But dream jobs is you’re stuck there.

One of the things that people will ask me “If I’m not looking for a dream job, what should I be striving for?” which this is unique for each person, but this is why I’m a huge advocate for the good-enough job. The good-enough job is practical. It’s not perfect. It’s not having you strive for that perfectionist tendency that can keep you stuck. And so, the good-enough job, again, it’s practical. It allows you to still have a life outside of work. It doesn’t ask that work check every box of your life and fulfill every part of you.

And I think COVID was a good reminder of that for people, and I worry that now, in 2024, we’re starting to forget about that and try to go back to those tendencies. So, I would just say, to answer kind of the very first question, the piece of advice I have learned the most that kind of counteracts, actually, building a fulfilling career is trying to go after that dream job.

Pete Mockaitis

Well, so that’s a cool distinction there, a dream job versus a good-enough job, and I like what you had to say with regard to partners in terms of, like, no human being is perfect, and no job is perfect. And so, I would say, I think that my dear bride is a good wife, and she’s not perfect, and I’m not perfect. So, help us orient to things a little bit in terms of good-enough.

Lauren, lay it on us, four levels of job, if I may.

One, unacceptable, you should probably get out of there as soon as you can. Two, good enough, yeah, you should probably hold on to this. All right. Three, about as good as actually exists in real life, so hold on with all your might. And, four, just unrealistic, like, that probably doesn’t exist for anybody, so disabuse yourself from that notion readily. So, I put you on the spot there, Lauren. Give us four levels of job, starting with a rung that’s, “Yeah, I should probably get out of here.”

Lauren McGoodwin
Yeah. So, an example of this is like the person who has their “dream job,” they’re a lawyer, they worked their whole life for this, this is the thing they wanted to do, they’ve got that corner office, but they’re miserable. They’re working nonstop. Maybe they’re paid well but it doesn’t matter because they have no life, they have no friends, they’re not able to have any hobby.

And so, it’s that mix of, like, “But this is what I thought I wanted so I need to continue it.” They’re burnt out, they’re all the negative things. That’s sort of what I would think is the rung of like, “But this was supposed to be my dream job. I worked so hard to get this.” It just never, never goes away.

So, then the good-enough job, again, it’s practical but it’s not perfect. Maybe it’s something that you’re really good, you’re not particularly, like, dying over passion for whatever industry, you work in manufacturing, but you’re really good at your job, and it gives you work-life balance that works for you. Maybe for you that means, “I want a really high salary, and I’m willing to sacrifice having to go into an office and commute every day.” That works for the chapter you’re in right now.

Like, stages of your life are similar to stages of your career. I talked to someone the other day, who she got a new job, and she’s been working at a startup, but she has kids now, and the startup has a lot of it can feel a little unpredictable about what’s going to happen, so she’s like, “I really like that but I kind of made a little bit of a career pivot, and I wanted to go to a bigger company because I was looking for something that was more stable, offered me remote role, was an increase in pay because a lot of times startups will give equity.”

And so, again, that is a good-enough job for her. She’s like, “I like this thing well enough, I don’t have to be a die-hard for it, but also it’s not asking more from me than what I think is reasonable given the exchange of money,” the exchange of the paycheck part for her. That can be a good-enough job. Then you have the person who maybe go even like a step further, where they have this deep passion of being able to reclaim their life from work.

And so, they have a job that allows them to have more PTO, or maybe they do, like I talked to someone the other day, she’s a teacher and she’s doing like a job-share with somebody else. So, for her, that’s a good-enough situation. She doesn’t want to totally leave the workplace but she wants to reimagine how it works for her.

So, there’s all these variations of what the good-enough job can be for you. The teacher is deeply passionate about what she’s working on. She’s just struggling with how to make that work with her life, so a job-share works. Then you have the other person who’s like, “I’m not deeply passionate about it but I’m good at it and I’m paid well for it, and so that works.”

And then the top, or the first rung I said is the person who’s like, “I thought I was passionate about this. This is a dream job, it looks good on paper, I’m working for the right company, I’ve reached all these achievements, and it’s not working for me. And now I have this piece of me where I feel like I failed or, somehow, I have this expectation hangover of this isn’t what I expected to be, on top of the fact that I’m burnt out and all these other things.”

So, I think there’s obviously a lot of variations, careers are super personal, but I think what it comes down to is managing those expectations, understanding that the dream job, this concept of a dream job is more about the lifestyle that goes with it. And so, restudying those expectations and then going out, and kind of I always tell people, like when I was a recruiter, “You don’t get everything.” It’s like, the realtor will ask, “What are the top three most important things to you? Neighborhood? Number of bedrooms?”

I think that’s also important to do in your career, and I think it starts with aligning with your values. So, thinking about, “What do you really value personally? And then, how can you translate your top values into the career that you have?” Those are just all good starting places. There’s obviously a lot of intricacies to this but when you are trying to make the shift from dream job to good-enough job, I think that’s a really good starting place.

Pete Mockaitis

All right. So, I dig it. So, we’ve got a picture of the lowest level of job, bad, and then a picture of good enough. Could you also paint a picture for us for the highest levels, like about as good as it gets in the real world, as well as this is just impossible and unrealistic in the world of reality?

Lauren McGoodwin

Like, this job doesn’t actually exist, but if we could make it exist, this is what it would look like?

Pete Mockaitis

Kind of like a fantasy dream job people have that is harmful because they are comparing it to an unrealistic thing?

Lauren McGoodwin
I think that’s a little bit like lazy girl job, which is this TikTok phenomenon that went off, where it’s like you basically don’t have to do anything, and you don’t have to be involved or engaged in any way, but you’re paid really well. I think of that as almost like this true fantasy. Like, one, it is an exchange for you creating impact and value for the company, the exchanges they’re going to pay you. So, you’re not going to be able to actually gives you or never asks you to take a call that’s inconvenient. The realities of life are sort of that is going to happen.

So, to paint that picture, I almost think the comparison is this lazy-girl job thing that people were talking about. I’m not saying that it doesn’t exist but, for me, I look at a “lazy-girl job” which I hate because you wouldn’t hear a lazy-boy job, but, anyway, that’s a whole other topic. But, for me, it’s like I actually have had a job before. My very first job, I was an admin assistant. My only job was to basically wait for the phone to ring.

Now, I wasn’t well-paid, and I had to show up to an office so I wasn’t able to just do what I want all day long, but, for me, I was, as a human being, part of our wellbeing is we want to be engaged, we want to create something, we want to use our brains. And, for me, that was really mind-numbing work, but if we wanted to paint this picture of this “lazy-girl job” or this ultimate job that really doesn’t ask you to do anything, I think people think that would be fulfilling, but I don’t think it would.

I think us, as human beings, we want to move forward, we want to make an impact, and you wouldn’t get that in that situation, but I could see that being this, like, ultimate dream job for somebody.

Pete Mockaitis

Lauren, I love that so much, that notion of a dream scenario would be that you don’t have to do much but you get tons of money. And what’s interesting is, I think, we can see that in real life in terms of if you’ve been on vacation for a while, it’s like you’re actually kind of bored, “And I want to get to it and start being able, contributing somewhere,” there’s that.

And if you look at folks who, I don’t think you can even call them jobs but they have some sort of a subsidized living situation, like a trust fund or some kinds of funds are just flowing into their life without effort, and often these folks are as susceptible or more so, I think the data show, to depression and other kinds of challenges because there’s something that’s not quite being met there.

So, I think that’s a great thing to call out, that you might imagine this thing exists but it kind of doesn’t from a job perspective. And even if you were subsidized magically, that often has its own perils with regard to mental health and fulfillment. So, give us that level that’s maybe just below that in terms of, “This is about as good as it really gets in terms of, I wouldn’t call it a dream job because it doesn’t exist, but this is as close to optimal as one might hope for in this life.”

Well, now can you paint a picture for, if we’ve got four levels, like terrible job, good-enough job, then as good as is realistically optimally possible in real-life job, and then the fake dream job. I think we covered levels one, two, and four. But paint a picture for number three, the best realistically optimal job we might have in life.

Lauren McGoodwin

I think going back to the example of my friend, she was working in one type of marketing, and she’s transitioning to a different type of marketing. She was working for more of a startup-type company that had a little unpredictability with it, she’s going to go to a manufacturing company. So, on the surface, working for a big brand name, way cooler. The type of marketing she was doing? Flashy, cool, really, again, kind of that glitter and glue metaphor, it’s using that, fits into the glitter side.

But she is moving over to manufacturing, definitely not as flashy and cool, doesn’t look as good as a big brand name on LinkedIn, and she’s going to be doing kind of a more traditional marketing route. Now, for someone who’s looking at this, they’re like, “Wait, she’s going from this really cool job to this really boring job.”

But that, for her, she maybe sees this shift from being like, “I had my dream job and it hasn’t necessarily been a ‘dream.’ I’m really ready to go to a good-enough job, a job that I can close my laptop at 5:00 p.m. because I do have young kids, and I want to be able to spend time with them. I get flexibility. I have remote work status with this one. Instead of getting equity, I’m getting a higher paycheck.”

So, again, thinking about “What are my top priorities? And I’m going to get them at this place. Even though it might not be the ‘dream’ on paper to somebody, for me it’s a good-enough job. It doesn’t ask me to give up my life in exchange for the job.” And that is something that I think is really important. A good-enough job is going to take you out of that tunnel vision you have or that fixed mindset that you have.

It’s maybe going to take the pressure off you that you’re feeling right now. Maybe it’s going to give you clarity because you’re not going to see your workplace as your dream, so maybe you’ll be able to recognize when there’s toxicity happening in a workplace more often, things like that. And so, for me, when I hear someone who saying, “You know, I’m kind of leaving the cool, flashy thing. I’m going to go over here but I’m being paid more. It seems like I’m going to have really good work-life balance. So far, from the people I’ve interviewed with, I really like them.”

It’s like they have this surprise factor, where they’re like, “But I should like this big, cool company, checking the box for me.” And I think that is the dream job versus good-enough job kind of conundrum, is sort of this mindset of, like, “I should want this thing. This thing should kind fulfill me, and why doesn’t it?” And so, I’m really proud of people who can make the shift over to “those good-enough jobs” for them.

And it’s not easy to make those decisions and determine, “What are my values? What are my top priorities? Now I have to find a company that fits.” I’m making this sound like it just landed onto their lap but I think it does take some internal work of getting over these preconceived misconceptions of what you should want.

Pete Mockaitis

That’s really cool. And this conversation about dream jobs is making me think about, I guess, there’s been a recent trend of big personalities on YouTube quitting YouTube, which is funny because I understand that the data reveal that young people now, more than they want to be teachers or firefighters, they want to be YouTubers. So, that’s the job, I guess, everyone wants. They think it’s the coolest. Not an astronaut but a YouTuber.

And so, folks who are YouTubers, who are collecting over half a million dollars of income for creatively making videos, are like, “I can’t take this anymore,” which is fascinating in terms of a picture of the dream job doesn’t exist. And if you dig deeper, you sort of learn that, “Oh, well, behind the surface of just making cool videos, they got to manage a team, and brand deals, and books, and accounting, and everyone wants a piece of them.”

Lauren McGoodwin

And the comments, yeah.

Pete Mockaitis

It’s like, the reality is, “Huh, it’s not just a creative wonderland of nonstop adulation for me being me, but there’s a ton of responsibilities that are sufficient to overwhelm a portion of these people who have what appears to be an ultimate dream job.”

Lauren McGoodwin

Yeah, absolutely. And that’s tough, I’m sure. It’s very hard for them to walk away from that because it’s that feeling of, like, “You’re not just going to get this back if you change your mind,” meaning, like, the person who worked all the way to become the partner of a law firm, and I’m only using that as an example because I feel we hear a lot about lawyers who are, like, “It wasn’t what I thought it’s going to be.”

But anybody who kind of gets in that golden handcuff rut sort of thing in their career, it’s very hard to walk away from that. And that’s why I think it’s important to kind of share the message early on about good-enough job versus dream jobs. Careers are long and windy, and you take U-turns and left turns and right turns, and up and down. It’s not this linear career path.

And the more we can kind of, I think, spread this education about what a career is, or what a career path looks like, I mean, I came from the generation very much of, like, this ladder and the lean in, just lean in to saying yes to things. That just hasn’t been the reality I’ve experienced, and I think many of the women I’ve talked to and interviewed, or experts that I’ve interviewed, that hasn’t been their experience.

And same with our audience at Career Contessa, it’s like your best skillset to building a fulfilling career is a person who is being proactive in the driver’s seat of their career versus the reactive to whatever is coming your way. And then, again, also studying this mindset of, like, “I’m part of that world, too,” just thinking about your values, determining kind of your purpose, thinking about, again, I have this phrase about how to be invaluable at work.

And people are always asking because they’re like, “Oh, I thought you want to be indispensable.” And I always say, “Look, but if you’re indispensable to a role, how can you grow because they can’t afford to lose you?” So, that’s a different mentality when you’re indispensable, the company is saying you’re primed for overwork because they can’t afford to lose you versus the mentality of, “We don’t want to lose you,” so you’re primed for more valuable work, for example.

So, again, these are just like this is the lessons that I think is kind of one can learn early on. It’s actually very helpful throughout your career. A lot of us, to your point about the YouTuber that many of us learn at mid-life or later on, and so that’s why I’m here to spread this information

Pete Mockaitis

That’s lovely. Well, I do want to hear more about your unique vantage point. So, with the Career Contessa podcast and YouTube channel and speaking, you have a fun vantage point. And I know when I dork out and look into all my analytics and things, and emails from listeners and see, “Okay, what’s really the hot stuff in terms of what people really want to know, and what kind of content advice, wisdom, is resonantly transformational for them?”

So, Lauren, if I could put you on the spot to share with us maybe three super nuggets that you’ve collected from your time podcasting and engaging with so many folks, what have been some of your favorite discoveries?

Lauren McGoodwin

I interviewed a woman once on what actually drives happiness at work, and I still love this conversation, and they were relationships, purpose, and autonomy. And I really loved that because I feel like happiness at work sometimes feel like this very elusive thing, and I guess in a way it is, but I thought that was a really fun conversation. Sometimes you have conversations where you learn something, and you’re like, “Wow, that’s certainly a puzzle piece to the career puzzle.”

I think another big piece for me is the difference between, like I said, being invaluable at work versus being indispensable. I really fit this millennial woman stereotype of the, like, work hard until they recognize your work. I very much learned through my own experiences, but also through our audience and talking to people, it’s really important to advocate for yourself.

There are good ways to advocate, bragging, however you want to call it. Some people don’t like it. They’re like, instead of advocating, think of it as self-expression. However you need to see this, it is very important that you are able to talk about your wins, and your accomplishments, and your achievements. So, those have been some big wins for me.

The other thing, I think, that’s been kind of eye-opening in terms of stuff I’d learned is, like, it’s interesting that you can outperform someone and not necessarily be better than them, and I think that’s a hard reality. And part of that comes down to they might be better at telling their story, they’re better at managing that, I guess, “playing the game.” And I think that sometimes, again, like a hard reality to come to terms with, but I also think it’s very true.

And so, again, self-advocating, learning how to tell your story, making sure that you’re aligned with the right stakeholders and getting in front of them, that’s really important. And, also, that confidence is not something you’re born with. It’s built by taking action. So, nothing is going to just come to you. You have to have the confidence and the willingness to try something in order to start getting traction.

So, if I could drop it into three nuggets of wisdom, those are like some three big takeaways I’ve had in the last year of talking. I have the best job because, through the podcast, YouTube channel, what we do at the side, our whole job is basically trying to find out, “How can you build a healthy fulfilling and successful career?” It is not a perfect black and white formula that fits in a box for everybody. But there are certain trends that I hear over and over again, and those are a few of them.

Pete Mockaitis

Cool. Well, could you tell us a cool story of someone that you’ve worked with who saw a real cool transformation in terms of they had one perspective, and then they learned some things, changed some things, and saw a fantastic result on the other side of things?

Lauren McGoodwin

Well, I have a couple. I have a friend who recently was working for a thing company, and their whole career was, like, the Googles, the LinkedIns, the Amazons, the Facebook, very much like you look at her career path, you’d be like, “You’ve got one very linear career path at a certain type of company,” was part of the layoffs that happened, has been searching for a job, and was kind of only searching one way for a job, which was, essentially, using her network, referrals, applying, things like that, introductions to hire, relying on her network.

For a whole year, she’s been looking for a job. She’s incredibly talented. And one of the things that I thought was really interesting is she recently hit the Easy Apply button on LinkedIn to a job that had been reposted a couple of times, had less than 50 people apply for it, it was a very different industry than she had been in before but a similar job, like job function, and ended up going for two interviews, got a job offer, meaning the process was like weeks’ long versus multi-months long.

And I was talking to her, and she was like, “I’m almost afraid to take this because it’s the complete opposite of anything I’ve ever done, and it flips all the logic I’ve thought of on its head.” And so, it was almost like she was uncomfortable with this unknown for herself, of like, “Shouldn’t I just keep sticking with what I’m doing even if it’s not working? Eventually it will work.” And she ultimately decided she’s going to take this new job, couldn’t be happier. It very much fits the description of this “good-enough job.”

She goes into the office once a month. They really value her experience in a certain industry. She was feeling very discouraged from the job search before. And I feel this breathes new life into her, and watching her just have this new motivation. And I thought that was really interesting because so many of us sometimes do have this fear of the unknown, or the fear or doing something different. And there were a couple of takeaways from it.

One, there’s no right way to job search. So, if you’re job searching right now, try a lot of different strategies. Yes, tap your network. Yes, try to get referrals. Also hit Easy Apply to the jobs that you think are really interesting to you, or the companies where you’re like, “I like the company well enough. I need to learn more about them.”

So, I love that story. I love the fact that it reminds you that find a target company, network, absolutely. This job market, absolutely has taught me that there are no rules so you have to try a little bit of everything and test out, and see what strategy works best for you. But ultimately, I think, also, going in with if you can manage your expectations to not be too fixed mindset on it has to go a certain way, if you take some those, I think it’s a really freeing thing as well.

Pete Mockaitis

Cool. Thank you. Well, now I’m curious, anything else you really make sure to mention before we shift gears and hear about some of your favorite things?

Lauren McGoodwin

Well, my book is called Power Moves so if you’re interested in exploring more of these topics related to the dream job and going after the good-enough job, Power Moves is really a framework on how to build a career that is based in a proactive approach versus a reactive approach. And then, of course, my podcast is called Career Contessa. I’ve really made it easy, and that’s where I get to talk to people who share what drives happiness at work. And I love being able to have those interesting conversations. So, if you’re interested in podcast advice, or career advice, check out Career Contessa as well.

Pete Mockaitis

All right. Well, now could you share with us a favorite quote, something you find inspiring?

Lauren McGoodwin

My favorite quote that I learned from someone the other day is, “This or something better.” And I think that is an incredible quote especially for 2024 with this economic climate, this tough job market, it’s “This or something better.” So, remind yourself of that when you feel like, “I’m not making any progress. I’ve got a rejection.” And I always try to remind people, if they don’t look at your resume, they’re not rejecting you. My point being they look at your resume for seven seconds, or not at all, having a fresh mindset of, “That’s not necessarily a rejection that way,” but it’s, “This or something better.”

Pete Mockaitis

And a favorite study or experiment or bit of research?

Lauren McGoodwin

I’m loving people who are doing research on remote work or distributed work. So, there’s a lot of CEOs out there who want to call everyone back to the office because of productivity, collaboration. And what these people who do this research are finding is, like, absolutely not necessary to be in office to collaborate, to be productive. And they’re actually doing a lot of research on what does drive those things.

Pete Mockaitis

Awesome. And a favorite book?

Lauren McGoodwin

A favorite book, Atomic Habits. I love that book. I quote it a lot. That and Essentialism I think they were like books I’ve read at the right time of my life to help me kind of get organized and focus, and gave me that fresh perspective that was really important.

Pete Mockaitis

All right. And a favorite tool, something you use to help you be awesome at your job?

Lauren McGoodwin

Loom video recordings where, basically, you’re able to audio record yourself, or you can be on video, and then a screenshare. So, I’ll use it for trainings. It’s great for asynchronous work where you want to be able to send feedback to someone on something. So, on our team, we’re a fully remote company, so I will use Loom to send feedback on, “Hey, I read this article. Here’s something I would change. I’m going to edit here, edit there.” Sometimes we’ll use it for resume reviews for clients, too. So, I love Loom absolutely.

Pete Mockaitis

All right. And a favorite habit?

Lauren McGoodwin

Favorite habit, probably a to-do list. Definitely a to-do list. And I’m not fancy. I use pen and paper but that’s probably one of my favorite habits. I also am really big on 10,000 steps a day, so I just got a walking pad, and I have a standing desk, so that’s a big part of my personality is I’m a very 10,000 steps a day.

Pete Mockaitis

Okay. And is there a key nugget you share that really seems to connect and resonate with folks; they quote it back to you often?

Lauren McGoodwin

Certainly, just the dream job myth, I think, is something that people are starting to know me by, is that they’ll say, “I know you don’t believe in dream jobs, but I’m looking for a dream job,” or something like that. Or, “I know you don’t believe in dream jobs, but then what do I find instead?” So, I would say the dream job myth is definitely something I’m quoted back and used on myself a lot.

Pete Mockaitis

And if folks want to learn more or get in touch, where would you point them?

Lauren McGoodwin

Everything is on the Career Contessa website, so CareerContessa.com. Podcast is called Career Contessa, and the book is Power Moves. And then you can connect with me on LinkedIn, I’m Lauren McGoodwin on LinkedIn, and I post tips daily on there, and I would love to connect with you.

Pete Mockaitis

And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Lauren McGoodwin

My final action, I think, going back to one of the nuggets of things I’ve learned is “How can you advocate for yourself this week? Or, how can you make your accomplishments or achievements known this week?” Does that mean you can send a quick email to your boss, of, “Here’s a quick recap of what I’ve been working on”? Can you mention yourself in that Slack channel, like, “Here’s my win for the week”? What can you do to make sure that you are advocating and letting your wins be known?

Pete Mockaitis

All right. Lauren, thank you and good luck.

Lauren McGoodwin

Thank you.

922: How to Reinvent Yourself and Your Career with Herminia Ibarra

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Herminia Ibarra shares counter-intuitive perspectives on how to make successful career transitions.

You’ll Learn:

  1. How to craft and execute your “identity experiments”
  2. How to figure out your next best option in two questions
  3. How to reach out and build your network

About Herminia

Herminia Ibarra is the Charles Handy Professor of Organisational Behaviour at London Business School. Prior to joining LBS, she served on the INSEAD and Harvard Business School faculties.

An authority on leadership and career development, Thinkers 50 ranks Herminia among the top management thinkers in the world. She is a member of the World Economic Forum’s Expert Network, a judge for the Financial Times Business Book of the Year Award, a Fellow of the British Academy, and the 2018 recipient of the Academy of Management’s Scholar-Practitioner Award for her research’s contribution to management practice.

Herminia is the author of two bestselling books, Act Like a Leader, Think Like a Leader and Working Identity. 

A native of Cuba, Herminia received her MA and PhD from Yale University, where she was a National Science Fellow.

Resources Mentioned

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Herminia Ibarra Interview Transcript

Pete Mockaitis
Herminia, welcome to How to be Awesome at Your Job.

Herminia Ibarra
Hi, how are you?

Pete Mockaitis
Oh, I’m doing well. I’m doing well. I’m excited to talk career transitions and your latest edition of the book Working Identity. But to kick us off, I’d love it if you could tell us a couple stories of any particularly memorable career transitions that you’ve had the pleasure of studying or working with. And maybe for funsies, let’s have one be amazingly delightful and one totally disastrous.

Herminia Ibarra
All right. Let me try. Delightful and disastrous, all of them have an aspect of delightful and all of them have their challenges. The one that’s coming to mind is a really fun one was a very straight-laced mid-career person who felt that he had always done what he was supposed to do, got really thinking about what he himself wanted.

And so, at some point, he decided to explore. He took a sabbatical and started to explore. And in his head, one of his big ideas was he loves scuba diving, and, “Could I do this for a living?” And so, one of the things that he did was to take the sabbatical and to get certified, and to explore the financials for buying a scuba diving operation.

And, very fortunately for him, as the sabbatical played out over a couple of months, he realized towards the end of it that it might not be so much fun to spend his whole life doing that, and that the salary he would take relative to the business work that he was doing was probably not worth it. But he was able to say, “I explored this to the hilt, and now I know it’s not what I want but at least I gave it a go.” And so, he was very happy to be able to cross that off his list.

Pete Mockaitis
That’s good. And do you have another side?

Herminia Ibarra
Yeah. Well, a disastrous one, I’ll tell you a disastrous one that eventually worked out. The disastrous one was a woman who was leading the change leadership practice of a consulting firm, and she wanted more balance, she wanted to run something, there were a lot of things that were wrong with it.

Pete Mockaitis
She needed to lead a change in her own career, it seems.

Herminia Ibarra

Yeah, and she did not have time to explore other possibilities. This is a challenge a lot of people face, “I work too much. I don’t have the time or the energy.” So, she saved up, she really planned, and got ready to start exploring but, in no time at all, was feeling, like, “Oh, my gosh, what do I do? And what’s going to happen? And what next?” And she would notice that in her networking, that since she was out of job, people didn’t want to network with her. She wasn’t especially useful.

And so, as she got nervous, she ended up taking a role that a headhunter brought her, which was to do something similar in a company to be heading up strategy. And she thought, “Okay, here’s a change,” and she thought she had negotiated more that work-life balance she was seeking, but as soon as she started the job, it became obvious that it was worse from a trial and work-life balance point of view. And not only that, as a newcomer, she hadn’t built up any capital to be able to kind of work around it.

And so, she felt really, really stuck, and came to the conclusion that she had to quit before it really took off because it was just, really, she wouldn’t be able to extricate herself for a couple of years. So, she quit and then really found herself with nothing at all.

Pete Mockaitis
Well, yeah, that sounds disastrous. Shucks! Well, I hope she’s okay. Do we know what happened after that?

Herminia Ibarra
Well, yeah, yeah, yeah, it ended happily ever after, in the sense that she said, “All right. I obviously am not trusting my instincts here. Let me try to do a bunch of different things.” She set up kind of a freelance advisory that allowed her to pay the bills, which she was able to do because she was very good and she had a great network.

But this time, she set aside a little bit of time to kind of play around with things that she was interested in. She did some nonprofit volunteering. She did a bunch of stuff. And over time, she made her way towards developing a whole new career in the space around consulting for nonprofits, which she was very happy about but it took a while for that to materialize. It really started out as a kind of, “Here’s a hobby. Here’s a thing I enjoy doing. And let me do that. Just stay sane.” And it became her next career.

Pete Mockaitis
Well, good news. Thank you for sharing how that unfolded there. Well, these stories are awesome because they’re already pointing to some key points associated with doing this career transition thing effectively, is having the opportunity to try some things out, to get a taste of things in advance, and sometimes you learn, “Oh, wow, cross that off the list. Scuba diving is not the thing,” and that’s valuable.

And that reminds me. I had a conversation, this was funny. There was a period of time in my career in which I did thousands of case interview coaching sessions for aspiring consultants wanting to prepare for those interviews. And one of my favorite sessions, this happened only once, was I worked through the case, and I said, “Okay. Well, hey, here’s some feedback. So, kind of what I was looking for is for you to put forward a hypothesis and then a structure, and then you game plan for what sorts of things you were going to investigate in order to assess whether or not that’s what’s going on, and to drill down into the more relevant issues.”

And he said, “Oh, wow, my brain doesn’t go that way at all. I guess I don’t want to be a consultant.” And it was awesome.

Herminia Ibarra
That’s fantastic.

Pete Mockaitis
He paid for the session, and I was a little worried, like, “Uh-oh, did he get what he paid for?” And he was thrilled, he’s like, “Wow, in one hour, I have determined that I am going to not pursue consulting at all, and look at these other opportunities instead. Thank you so much, Pete.” I was like, “Well, thank you. I’m so glad we had a positive exchange here.”

Herminia Ibarra

See, that’s fantastic because one of the things that I have found is that people have all kinds of ideas in their heads of what they like and they don’t like, and they often don’t check out in reality. Just last week, I was talking to a reporter, a journalist from the Wall Street Journal, and she told me that she had dreamed forever of being able to write for a living, to just write books.

And she gave it a try and she couldn’t stand it. She got her book but jumped right back into a journalism job because she just did not want to do that exclusively. She realized it wasn’t for her. And so, the big lesson is really to try as actively as you can, especially before making any kind of big leap, because we don’t really know whether we would really enjoy these things or not. All we know really well is what we don’t like anymore or what we don’t like about our current job, but we don’t know what we’d like to do instead. And so, exploring and experimenting is really vital.

Pete Mockaitis
Certainly. And that seems to be a real theme associated with the book Working Identity is that we’ve got to try and do things, we have to experiment, get a taste and see how it fits, how it feels. Can you share with us what are some of the alternative viewpoints in terms of doing a career transition? Like, what would you say, Herminia, is what not to do when you’re making a career transition?

Herminia Ibarra
Well, the conventional approach is to figure out what you want and then create a plan to execute it. You know the answer, “Where do you want to be five years from now? And then what are the steps? And then what class do I have to take? Or, who do I need to meet?” And then just kind put it all in place. It works quite well when you do know what you want. And it also works quite well earlier in your career where you’re more likely to go into kind of, like, a structured setup.

It works less well, or not at all, when you don’t know what you want, as is the case for most of the people that I talk to who, for mid-career on, they know what they don’t want, but they do not know what they want instead. And it works less well also when you’re more experienced because there’s just more pathways from A to Z, or from A to D. There’s more different approaches that you could take to get to where you want to go.

Pete Mockaitis
So, figure out what you want is perhaps easier said than done, or folks have a misunderstanding of what they thought they wanted. Or, can you unpack this for us?

Herminia Ibarra
Yeah, see, there’s all kinds of things. We pigeonhole ourselves, you say, “Oh, I’m not a creative person,” or, “I’m not an entrepreneurial person,” or whatever. We pigeonhole ourselves. There’s all kinds of things we’ve never been exposed to before. Sometimes you meet somebody by serendipity, discover what they’re doing, think, “Gosh, this would be fascinating.”

So, there’s lots of reasons, you haven’t seen it before, you don’t know it exists. It wasn’t necessarily what you were thinking about. Whereas, we get fixated on this one thing, and the problem is that stresses people up because they don’t know what that one thing might be, and then they think, “Oh, maybe I shouldn’t do anything at all because I’m not very self-aware, or I don’t know myself. I need to introspect and discover who I really am.”

But that doesn’t really help either because the only thing that really gets us going is to get exposed to possibilities that are real, and to get into contact with people who do those things, who can help us investigate them further and learn more about them.

Pete Mockaitis
Okay.

Herminia Ibarra
And serendipity happens, too. I’ll tell you another quick story. This is someone who was in the financial world, and had always dreamed of doing something in interior design, something more artsy, and it just wasn’t going to happen because the financials didn’t work out. And so, she got to stay doing what she was doing.

Kind of out the blue, one of her clients, who had really appreciated her financial savvy, said, “As you know, I have this film company, and I’d really like you to be my chief financial officer and COO. I’d like you to run this.” She’d never thought, “I’d like to be in film.” She’d never thought, “I’d like to run a company.” But this was a relationship that worked very well for her, it was a way of doing something more creative, she knew the person. She took the leap, did it, and has really found it to be a fantastic move for her.

Pete Mockaitis
Okay. Beautiful.

Herminia Ibarra
How could you extract that out of your head? Never.

Pete Mockaitis
Certainly. So, lay it on us then, you’ve got some concepts associated with the possible selves and doing some identity experiments to explore the possible selves. Can you define or unpack these terms for us?

Herminia Ibarra
Yes, of course. So, the conventional approach, which I call an implement is you start out with the right answer and then you follow the steps. The less conventional approach, which is what I have found tends to happen when people make career change, I call experiment and learn. And the way that unfolds is you start to envision what I call possible selves.

Possible selves are ideas about who you might become in the future. They could be anything. They could be a very clear idea you have. They could be what other people think you want to do. They could be your feared possible self who you don’t want to become. They could be very nascent, very vague and fuzzy possibilities, “I think I’d like to do something more creative,” for example. So, you start with that, with some hunches. And what I always recommend to people is to not be afraid to make the list long and divergent, kind of the opposite of the conventional wisdom.

The conventional wisdom is “Focus. Know what you want.” This is not. Brainstorm with yourself. What are they? And then start somewhere. Now, for some people, this is pretty organic, and that is they’re working their day job and they’ve started on a project, maybe they were helping a friend who had a startup, maybe they had a side hustle on Etsy, maybe they took a course. Somebody I know took a course in – what’s it called – gemology, having to do with stones and jewelry, and that kind of led her on a path.

So, for a lot of people, you have this side activity that you’re interested in and it leads you on a path towards where you realize this could be your next job and career. And once it’s developed enough, you leave and you take it on. And so, it’s a possible self that is nascent that’s been developing, “Oh, maybe this might be my next career,” “Oh, maybe this could be a good thing to do.”

For other people, they don’t have that. They don’t have that. They’re kind of stuck, “I know I don’t like what I’m doing,” or, “I’ve lost my job,” that happens more and more today, “What should I do instead?” Brainstorm a list of possibilities. Don’t be afraid to have things that are a little bit more conventional or a little bit less conventional.

My friend, the scuba diver who I told you about, he had a three-pronged list. One list was conventional jobs that he talked to headhunters about, kind of his line. Another one was kind more of artsy, folkloric kind of things, the scuba dive, the wine business, a BNB business. And a third was identifying entrepreneurs that he found interesting, and tried to see if he could get a role working with them to learn from them. So, three-pronged kind of approach.

But the idea is to generate a bunch of possibilities and then start exploring one. Maybe you take a course in that area. Maybe some people want to have at least as a side hustle, being on boards of directors so they’ll a course on being a non-executive director. Or, some people, a very popular thing, is to become a coach, an executive coach, a business coach. People will take a course, and they’ll take the course. If they’re still in their job, they take it on the side. If they’re not working, they take it and they practice it.

And that’s a possibility that they’re exploring. It may not be the thing that you move into, but it has the advantage of getting you going. If it’s not it, it makes you understand why not. If it’s promising and it allows you to explore more, it gets you in touch with other people who are also in the process of making changes, and that’s always helpful because you don’t want to be alone in your head, thinking, “I’m the only one who’s taking forever, who’s unsure about what to do.”

It creates a sense of kinship with other people who are going through a journey as well, and it creates a context in which you have to explain yourself all the time, which is also helpful because the more you have to explain yourself, the clearer you become about what you’re trying to do and why. So, any action, basically, is helpful. If you know, follow your nose. If you don’t, take any action and get started on a path.

Pete Mockaitis
That’s cool. Well, I’d love it if we could generate just a big list of experiments and approaches for getting a taste of things. And so, volunteering, taking a course, maybe going to events and meeting the people at the events. I guess there’s even more passive stuff in the earliest of steps, like, “Well, let’s listen to a podcast about artificial intelligence…” if that’s the thing you think you’re into, “…and let’s start having some conversations with people who are there.” Like, “Hey, I read your thing. I listened to your episode,” and sort of step-by-step we get a taste for what’s going on.

What are some of your other favorite experiments or approaches you found really yield a boatload of insight for effort that you put into it?

Herminia Ibarra
Yeah, you’ve got the basics of the list there – take a course, volunteer, start up a business on the side, do advisory, get on a board, get class, give a class, all those things, all of those things. And one side is what you do, the activity. The other side is the new networks that gets you into. And the two of those things together help you understand, “Do I want to take the next step or do I not?”

Pete Mockaitis
I like that and it’s much less intimidating in terms of all at once, one giant leap, yes or no, launch, don’t launch versus, “Huh, okay. That was cool. How about another step?” I suppose at some points there are big old milestones, like, “No, for real. Like, I got to decide if I’ve got to pursue a doctorate in order to do the science thingy that I think sounds cool, or I’m not.” So, I’m curious, are there any particular questions, either for the internal reflection or for your new network, that you think are supremely useful and insightful as you’re navigating your experiments?

Herminia Ibarra
Well, there’s basically two questions you’re asking yourself, “Is this an attractive option? Yes. No.” “Is this feasible in terms of my need to make a living in the world? Yes. No.” And you are kind of inching your way through those questions, “Is it attractive? Is it feasible?” And feasible is not just only in terms of the money. It’s also in terms of, “Will I be able to develop the skill set necessary to truly plant a foot in that world?”

Pete Mockaitis
Certainly. Well, the consultant in me is creating a two-by-two matrix in my mind’s eye. I can’t help myself. Let’s hear some examples of things that might be in each of those quadrants. And I guess it’ll be super individually specific, like, what’s attractive to one person is totally repulsive to another. But I guess in terms of not feasible, like, I could probably not be an Olympic gymnast now as a 40-year-old man who has not trained in that domain. But I guess I’m such a big dreamer, I think almost anything is possible.

So, maybe you could ground us. You be the dream-killer for a moment, what are some areas where you’ve had to gently encourage folks, like, “You know what, maybe back off or rethink that a little bit. That’s probably highly risky and not quite feasible in its current incarnation”?

Herminia Ibarra
Yeah, that doesn’t really happen. Nobody does to themselves, “At age 45, I want to be an astronaut or I want to be a rocket scientist.”

Pete Mockaitis
Oh, in a way, I’m a little sad.

Herminia Ibarra
Although, you do have people. You do have people. This is not somebody that I studied but I ran across, somebody told me a story recently of somebody, you know how they tell people, “What did you want to do when you were a kid?” and this person had always wanted to be an astronaut, and he ended up, I don’t know, either training astronauts or coaching astronauts, but kind of found his way into the aerospace industry via some things that he had done before and some things he was able to acquire as skills, and found himself delighted to be in that kind of atmosphere.

Pete Mockaitis
Yeah, what I love about that is you may have a desire to be an astronaut, and I guess the right answer is not to dismiss that, “That’s ridiculous. Let’s throw that away,” but rather to dig a little deeper, it’s like, “Well, what is it about being astronaut that seems cool?” It’s like, “I like the idea of being in a rocket going superfast.” Like, okay, maybe you can just start flying small planes as a hobby or something, and you can scratch that itch.”

Or, maybe it’s, “Space is so fascinating.” “Well, there’s many space-adjacent sorts of opportunities that you can go for.” Or, “I always admire the astronauts themselves, their stories and their heroism and their bravery.” It’s like, “Oh, well, then you could train astronauts and get close to them even if you’re not going out into outer space.” So, I think that’s pretty cool that those initial seeds can grow in some handy directions.

Herminia Ibarra
Yup.

Pete Mockaitis
Well, I’m curious on the networking side of things, do you have any pro tips on how you recommend reaching out, asking for help or guidance or input or conversations as you’re navigating these experiments?

Herminia Ibarra
So, the first is start right away. A lot of people don’t start because they say to themselves, “I don’t know what I want. I’m going to sound confused so I’m going to kind of blow a good contact and I’m not going to make a good impression.” However, if you don’t start, you’re not going to figure it out. And so, by this point, everybody is familiar with the informational interview and kind of the exploratory coffee.

Maybe reach out to people who are not the CEO of the company you’d like to work for until you’ve had a little bit of practice. But the most important thing is to start right away and to contact a lot of people. Most people don’t realize how many conversations it takes, how many coffees, how many times reaching out on LinkedIn.

Just recently, I did a webinar online for people who are interested in career change, and we asked them, we did a survey ahead of time, and we asked them, “How confident are you in your ability to make this change, to make a change successfully?” And we also asked them about their networks, we asked them how many conversations they’ve had already about career change, and it varied wildly from hundreds of them, or hundred something, to very few. And there was a very strong correlation.

The more people you talk to, the more confident you felt about the possibility because, as you talk to people, first of all, you find out everybody has got a story about career change. Lots of people do. It’s very reassuring to hear that other people with a similar background as you ended up doing something very different, and successfully so, and happily so. And they’ll encourage you, and you’ll get more ideas about what to do, let alone than actually find leads and referrals for specific positions.

Pete Mockaitis
Okay.

Herminia Ibarra
So, start, reach out, be honest. At first, you might be saying, “I’m exploring the possibility of a change. I’m looking into different options. I’m trying to kind of brainstorm some possibilities.” Afterwards, you might say, “I’m really interested in this sector and I’m trying to figure out which way to position myself in or which way to go in it.” After that, “I’m trying to get a foot in this door.” It’s a progression.

Pete Mockaitis
Okay. Cool. I like those questions. Any particularly magical turns of phrases that you’re fond of?

Herminia Ibarra
No, there’s no magic. Yeah, the magic is, “I’d like your help. I’d like your input. I’d like to hear your story.” It’s very simple things.

Pete Mockaitis
I suppose what I found, and what I really like about your answer, “No, there’s no magic,” is that I have witnessed before, I think there’s one guy in particular, he reached out to me, wants some career advice, and he was a total stranger. I think we were in the same LinkedIn Group, so about the weakest of connections that there can exists, so I had no idea who this person was but, what the heck, I chat with them.

 

And then, I asked him out of curiosity, “Hey, so you just kind of found me out of the blue and in the cold on LinkedIn, like have you been reaching out to other people? And how often do people say yes?” And, to my delight, he had a very detailed notebook of everybody he reached out to, and the results of those reach-outs, and I believe the number was something like 28% of total strangers were willing to have a chat with him. And I thought that was cool.

And his message wasn’t magical. It was short. It was direct. It was clear. He made it easy for me, it’s like, “Hey, I’d love to come get coffee with you wherever it’s convenient, perhaps A, B, C times to hear more about this and that.” And I was like, “Okay, sure.” And I thought that was pretty encouraging.

Herminia Ibarra
That’s it. That’s it.

Pete Mockaitis
Yeah. All right. Well, Herminia, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Herminia Ibarra
Well, on that note about the weakest of ties, we know that those are the ones that are the most helpful, in fact, because friends and family and close colleagues, they have the same information you do. And when it comes to career change, they’re more apt to worry that you’re going to do something foolish. Whereas, perfect strangers might think that your kookiest plans are actually wonderful.

And LinkedIn studied this directly because there’s this famous theory about the strength of weak ties, how we tend to get our next job through people we don’t know so well or don’t see that often. And there was an experiment with LinkedIn in which they manipulated what people you were fed as people you might know, and in some cases, they gave you closer connections, and in another case, more distant. And the more distance were indeed the ones that were the most productive for figuring out a next job.

Pete Mockaitis
Okay. That’s good. Well, now could you share with us a favorite study or experiment or bit of research?

Herminia Ibarra
Well, a favorite study is the original strength of weak ties research in which researchers studied how people found jobs and what were the contacts that led them to leads that became their next jobs. And it was all personal contacts by and large. This was before LinkedIn, which is not quite can be personal but also a bit institutionalized. But it was mostly personal contacts that led people to their next job, but the surprising thing was that it was not close colleagues. It was distant acquaintances.

And the reason was not people always think, “It’s because your close colleagues know your fatal flaws.” That’s not it. The reason was that they have the same information you do because they circulate in the same circles and the same waters. Whereas, more distant acquaintances are more likely to be working somewhere else and to be seeing different things, and, therefore, are more likely to suggest something novel to you.

But it’s a wonderful study because it’s counterintuitive, and I see this over and over again. People get started, trying to make a career change, and they turn to friends and family because it’s more reassuring, because they don’t want everybody to know, but it is really these weak ties, these more distant acquaintances that really make a difference. People we used to work with, for example, are huge in terms of generating leads for next possible things to do.

Pete Mockaitis
All right. And could you share a favorite book?

Herminia Ibarra
A favorite book. I’m just looking at my bookshelf. I’ve always loved the old classic, William Bridges’ Transitions, about beginnings. No, he goes, endings, middles, and beginnings about the phases of transition and why it’s so difficult. That’s a favorite.

Pete Mockaitis
Okay. And a favorite tool, something you use that helps you be awesome at your job?

Herminia Ibarra
Well, now I use ChatGPT for everything, not to write anything for me but for some basic research and ideas.

Pete Mockaitis

Okay. Well, now I’ve been playing with it myself. Tell me, what are some of your favorite use cases where you think this thing really shines?

Herminia Ibarra

Well, I had, for example, a bunch of open-ended answers to a survey. It was kind of a long number. And I asked it to code them for me into categories, and then do counts of different categories. So, that’s kind of like a research assistant. It’s very good at outlining things. I’d never taken care of my Wikipedia entry. If somebody had written it, it was not accurate. And so, I asked it to write it for me, and it outlined it very well. It did hallucinate articles I had never written but that’s okay. I knew which ones to put in but it was perfect.

Pete Mockaitis
That’s flattering. The robot assumed that you must’ve written that because of your notoriety and wit and insight. So, with the coding of results, that’s intriguing. Did you just straight up drag and drop a spreadsheet file into it? Or, how did that work in terms of tactical execution?

Herminia Ibarra
When I first did it, yeah, I just entered all the…I don’t remember now if it was in the spreadsheet. Then my research assistant took over, and she did use it with Excel, but I think I just dropped everything in. And it got a little bit overwhelmed, and so we had to work it in some batches but, yeah, it did a pretty good job. And then we kind of negotiated on the categories a bit. You have to work with it but it did a great job.

Pete Mockaitis
That’s cool. And could you share a favorite habit, something you do that supports you in being awesome at your job?

Herminia Ibarra
No, this is actually a real thing. My habit is to work from home as long as possible in the morning, which is when my brain is at its best. And so, I try to do any kind of writing or course development that I need to get done at that time, and then go into the office later, or go into the other things later.

Pete Mockaitis
And is there a particular you share that really seems to connect and resonate with people and they quote it back to you often?

Herminia Ibarra

It’s this idea that we tend to know what we don’t want but we don’t know what we want instead, but the only way that we figure it out is by going out and exploring as opposed to waiting until we figure it out in our head. That resonates with people. The other thing that resonates a lot is that when people read Working Identity, one of the things they always come back to me on is, “Oh, my gosh, I’m not the only one. It gave me relief I’m not the only one that was so confused or nonlinear.”

And the nugget is that no matter how clear you are in your head about what you want next, career transitions always take longer and are messier than anyone ever imagined, and that’s just part of the process.

Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you point them?

Herminia Ibarra
HerminiaIbarra.com, Herminia Ibarra at LinkedIn, and Herminia Ibarra at X.

Pete Mockaitis
Okay. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Herminia Ibarra
Well, the funny thing is that my subject is not so much about being awesome at your job but being awesome at extricating yourself from that job. But I guess what I would say is if it’s not been awesome for some time, it is really a good moment to start dabbling on the side with other ideas and possibilities.

Pete Mockaitis
Okay. Herminia, thank you. This has been a lot of fun.

Herminia Ibarra
Thanks so much, Pete. I really enjoyed it.

902: How to Ensure Great Career Fit with André Martin

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André Martin discusses how to avoid wrong career fit and ensure your career aligns with your needs.

You’ll Learn:

  1. What right fit and wrong fit look like in practice
  2. Four powerful questions to know if a job is the right fit
  3. Why it’s OK to have a boring job

About André

Dr. André Martin is an organizational psychologist and author of the book Wrong Fit, Right Fit – Why How We Work Matters More Than Ever. He has spent 20+ years as the Chief Talent Officer of iconic brands such as Mars, Nike, Google, and Target. Now, acting as an operating advisor, coach, and consultant, André continues to counsel leaders and founders to peak performance. When André isn’t working, he can be found with his wife and two English labs on the rain-soaked trails around Portland, Oregon.

Resources Mentioned

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André Martin Interview Transcript

Pete Mockaitis
André, welcome to How to be Awesome at Your Job.

André Martin
Hey, thanks, Pete. Glad to be here. Thanks for having me.

Pete Mockaitis
Oh, thank you. I’m fired up to get into some wisdom from your book Wrong Fit, Right Fit: Why How We Work Matters More Than Ever. But, first, I think we need to hear a little bit about your mushroom farm. What’s the story here? You do that on top of everything else?

André Martin
I do it on top of everything else, although I’m not in the day-to-day operations of it. So, the farm was a passion project by some buddies of mine that grew up in southern Missouri, and the concept behind the farm is we actually grow mushrooms in empty grain silos to the tune of about 20,000 pounds a week.

Pete Mockaitis
Wow! How many grain silos does it take for that volume of mushrooms?

André Martin
That’s one grain silo.

Pete Mockaitis
One grain silo?

André Martin
Yup.

Pete Mockaitis
Wow! One of my first jobs, actually, was I audited, like, local municipalities and farms. I was a little auditor intern for an accounting company. And I had the privilege of getting to climb up grain silos to drop a measuring tape to assess the inventory value of the grain in the silos on the balance sheets of these farms. So, I’m quite familiar with grain silos. And I’m thinking that sounds somewhat lucrative based on the price point of mushrooms and the cost point of a grain silo. Am I overlooking something, André?

André Martin
I think you’re overlooking the length of time it takes to get it right consistently when it’s the first time it’s been done. So, the team has been at this for about four and a half years, and we’re still trying to make it consistent enough that we can guarantee that we can continue to make that kind of production month over month over month. So, we’re getting close. Hopefully, someday it’s lucrative and, even more importantly, I hope it helps us get rid of food deserts around the world someday. That’s the goal.

Pete Mockaitis
Well, yeah, that’s so clever. And so then, do I have multiple, like, layer cake inside that grain silo? Like, how many stories, I guess, of mushrooms am I looking at?

André Martin
Think of it more like a helix.

Pete Mockaitis
Okay.

André Martin
It’s gravity-based. And so, what we’re really trying to do is remove a lot of barriers to mushroom farming, one of which is the cost to do indoor farming is significant but the cool thing about mushrooms is they thrive in dark and humid environments. So, these grain silos provide a really great sort of architecture to do some cool work off of. And, again, the team has been at it for a while and we’re learning every day.

Pete Mockaitis
Well, now I’m curious to hear, what is, in your opinion, the most delicious species of mushroom and recipe for that mushroom to be in?

André Martin
Oh, that’s a great question. So, I grew up in southern Missouri, and I remember one of my best friend’s mom, Ruth Lorman, made beef stroganoff, and that was your basic button mushroom done up with a lot of cream, a lot of goodness, and a lot of heart. So, that’s my best memory of a mushroom dish. What about yourself, Pete?

Pete Mockaitis
That is good. I’m thinking about my buddy, Father Jim Herbert, and we went to get some morel mushrooms, and they were just very simple. We just grilled them up and had them as like a side dish in the middle of the rest of the meal, and there’s life for you.

André Martin
Oh, that’s great. I love them. They’re super good and great for you, so we hope they’re around and an even bigger food in the future.

Pete Mockaitis
All right. Well, I’m glad we covered that, André. We got it now.

André Martin
Yes, sir.

Pete Mockaitis
We set the record straight on mushrooms and grain silos. Now, let’s hear about Wrong Fit, Right Fit. Any particularly surprising or counterintuitive discoveries you guys made when researching and putting this together?

André Martin
Quite a few. I think I’d start with the first one, is that, hey, when we looked at the issues around employee engagement today, we know that Gallup tells us there’s an estimated $7.9 trillion of lost productivity due to disengagement. A lot of the time, we like to think that it’s good or bad culture. It’s a toxic environment or it’s an engaging environment.

And the truth is it’s a lot more nuanced than that. So, when we talked to the hundred or so interviewees that we interviewed for the book, one of the things that came out really quickly is this idea that every company starts off wanting to create a great experience for their employees. They want to be a great place to work. It’d be counterintuitive to create anything other than that.

And so, if you start with that truth, the thing that we found that’s most surprising is that, for about 60% of people in the company, they’re pretty happy. Maybe not totally engaged but they’re content. And then for the other 40% who have the same skill set, the same background, the same affinities, they struggle, it’s like they’re slogging through mud.

And so, really one surprising idea is that there’s probably not a single best practice because every company has a different way of getting work done day to day.

Pete Mockaitis
All right. So, then when it comes to fit, there’s multiple styles, approaches that can work. How do we think about fit in terms of which one is good for me or not so good for me?

André Martin
Yeah, Pete, it comes down to a couple of things. The obvious things that align us to an organization are things like purpose, values and mission, the team I’m working on, the manager, the job that I have. But one of the things that came up in the book, too, was there’s this whole piece of information below the surface, which is how the company works day to day. How do we solve problems? How do we make decisions? How do we manage conflict? How do we develop people and give feedback? How do we gather and convene? What’s our relationship with time? How does information flow?

And those were the things that when we talked to talent, they were saying when the company works like you like to work in those areas, it’s easy. It’s like writing with your dominant hand every day. When it doesn’t, it can feel hard, it can be stressful, your quality goes down, you lose confidence and competence, and you end up in a place that’s really hard to go to work every day. It’s sort of the origin of the Sunday Scaries in many ways.

Pete Mockaitis
So, could you share with us an inspiring story of someone who went from feeling like their job was the wrong fit to the right fit? And what did they do? And what did they discover?

André Martin
Well, I’ll start with a story that’ll answer that question sort of in the other direction, so someone who was looking from a wrong fit experience back at what actually was right fit for them. And this was a creative marketer, and one of the places that this person started their career had very standard and consistent ways of working, so those things we mentioned: how they collaborate, how they socialize ideas, how they solve problems.

And early in their career, this person felt like that was constraining. And one of the insights from this story that was really interesting is, looking back now, what they said is, “Because I didn’t have to worry about how to present an idea, back then and that right fit experience, it was actually a pure execution or experience of my craft. That is, I was being able to do what I do best every day because all my creative energy was flowing to the thing that I do really well, as opposed to how work gets done.”

And that was sort of the big insight from the story, is this idea that your creative energy is always flowing. But for many people in wrong fit experiences, it’s flowing to how work gets done as opposed to what they’re really gifted at in this world.

Pete Mockaitis
So, can you give us some examples of some of this “how work gets done” stuff?

André Martin
Yes. So, think about it this way. There are some organizations that socialize ideas via beautiful decks. You create PowerPoint slides with wonderful images and pithy poetry. And then there’s other companies that do that via two-page memos. Amazon is one of the most popular examples of that. And then there’s others that expect really deep research papers, which is something we saw a lot at Google when you’re working in technology and machine-learning. And so, if the way that ideas get socialized don’t match the ways that you prefer to do work, it just feels harder than it should.

Pete Mockaitis
Understood. Okay. Well, so then, I’m curious, how do we go about clearly identifying what an organization does on these dimensions? And what is our preference to really determine: do we have a wrong fit or a right fit and making some adjustments where we can?

André Martin
Yeah, Pete, this is one of the most interesting parts of the book. And, again, through the interviews, one thing that became really clear is that work decisions are one of the most high-value decisions we make in our lifetime. Think about it this way. We spend about 13.5 years of our adult lives at work. That’s every second, every minute, every year. It’s a huge chunk of our lives. It’s actually second only to sleeping if you think about the distribution of our time as adults. And yet we tend to make those decisions about where we work on very little information.

The interview processes, if you think about it, they’re more like first dates than they are really getting under the hood to understand what the reality is going to feel like. And if you’ve ever had a first date, I know I had many before I met my wife, although you feel that excitement on the first date, by the second, third, fourth, or fifth date, things change as you get to know the person.

And what we’re finding in companies today is that’s happening more and more regularly to talent. They get recruited with this idea of what the company is going to feel like, what the job is going to be like, and then when we get into the company on the first day, it feels radically different. And it’s in that sort of discrepancy that we’re seeing a lot of engagements start to suffer.

Pete Mockaitis
Certainly. So, what is your recommendation for a prudent, practical research approach by which we can learn the stuff before it’s too late, and we go, “Uh-oh, wrong choice”?

André Martin
I think there’s a few things I’d say, and as a psychologist, I’ll start with some of the cognitive things. First, you have to understand that there’s a few things that are at play as you’re making a big decision. And that could be the cereal you’re going to buy in the grocery store, to the house you’re going to buy, to the job you’re going to take.

First and foremost is we tend to be very influenced by successful brands and successful companies. And there’s a phenomenon in social science called BIRGing. It’s called basking in reflected glory. It’s this idea that we are going to buy into things that have had past success. And so, one of the first things I’d say to talent is just watch that. The biggest coolest brands might not be the best place for you to work.

The second thing that happens is, once you open up a job description, and you get in a recruiting process, you have to realize you’re in a marketing effort. Think about it. Every talent that is showing up for an interview, we show up on our best behavior. We’re first-date ready. We have scripted answers. We’re dressed in our best outfits. We’ve thought about what we’re going to say and how we want to present ourselves. And the same is true for the company.

And so, instead of getting a realistic idea of who each other is going to be like on a random Tuesday morning, we actually are seeing us at our best, which we know isn’t necessarily who we are day-to-day. And the third thing, from just a cognitive standpoint, is this idea of confirmation bias. Because talent is so motivated to find a job, to get the job, to work at a great brand, we tend to pay attention to only a small sliver of the available information given to us, and most of that’s subjective and from the internal source of the company, career sites, recruiters, the interviewees.

And so, the first thing I tell talent is, “Make sure you’re using a broad set of information. Pay attention to what happens in the interview. Pay attention to what’s on the website, but go and find videos. Talk to people who have recently left the company. Look at annual reports. Find all the public information on the company to sort of round out what you’re seeing.” And my rule of thumb is if it doesn’t show up in three sources, really ask yourself if it’s likely going to be true day-to-day.

Pete Mockaitis
Okay. Well, so could you perhaps walk us through a research process by which someone is assessing what’s up with their prospective employer, and they have a few specific questions they want answered, and how they might get after them via these different sources of information?

André Martin
That’s great, Pete. The first thing I would tell any talent at the start of a process is the first thing you should do is not open a job description and apply for a job. The first thing you should do is take some time to really understand who you are, how you work, what you’re solving for right now, the kind of life you’re trying to build, what kind of leader or manager you work really well for.

And in the book, we have this set of excursions that really helps talent to do that. When we were talking in the interviews, one of the things that talent told me when we asked them, “When did you know it wasn’t a right fit?” And they said, “If I’m being totally honest, I knew it in the interview but I chose not to pay attention to those things.” And so, the first step is make sure you know who you are, how you work, and what you’re solving for.

The second step is to really do a lot of external research on the company. So, before the interview happens, don’t just depend on what the company sends you. Look at all those assets we talked about: annual reports, and videos of leaders, and past folks that have worked there, and really get a good sense on, “What does this company look like day-to-day?”

And then when you’re in the interviews, there’s a few key questions that will help you sort of discern a little bit more about what it’s going to be like to work there, and it’s hard because these are first dates. So, a few of the questions I really like, the first one is, “What’s the profile of the person that’s really successful here?” That gives you a sense on… and ask the follow-up question, “How do they show up for work? What does it look like when they’re in a team meeting?” And really get at, “What’s the success profile? Who’s really successful?” And ask yourself if that’s you.

The second thing I like to have people do is have someone walk you through a-day-in-the-life. So, in an interview, have them pull up their calendar and walk you through what’s on their calendar for the day. This gives you a sense on what’s important, what they’ll be working on, how they think about time, what’s their meeting cadence, all those kinds of things.

And then I also love to ask the question, “What’s the reputation of the team? And what’s the reputation of the leader?” because, again, that tells you where the team is going to be and what you can expect of some of the work that you’re going to have to do upon arriving there. And we have, again, about 10 or so questions in the book that help talent get a little bit deeper into how the company works.

Pete Mockaitis
And is the timing for these questions, is it your recommendation that it’s sort of right there in the interview, “Do you have any questions for me, André?” Like, right there?

André Martin
You know what, it’s really funny, Pete, I love the way that you bring that up because we often feel, in an interview process, like we’re being interviewed. And the truth is that you have to be at your best as an investigative journalist inside an interview process. And so, in those last five minutes, which we all get to, “Hey, André, do you have any questions for me?” often we don’t take advantage of those.

We ask a layup question, something that makes us look good or sound good. And this is your moment to really dig in and get to know the company at a deep level. So, I always would say have two or three really strong questions, and use that time. And then if you don’t get them answered, ask for more time because, again, this is one of the highest-value decisions you’re going to make in your life, and you don’t want to just be dependent on the small bit of narrowed information that you get from the company through the process.

Pete Mockaitis
That’s good. And I’m curious, do you recommend, from a timing perspective, we’ve got the “Do you have any questions for me?” right there, first interview or second interview or third interview, and then there’s a whole another zone of time in which, ideally, you have the offer, and you’ve not yet said yes to the offer.

And it’s funny because, as I’m imagining this, I sort of think about, like, “Ooh, that’s the time when I can really just get after it in terms of my investigations and talking to people and all of that.” And so, how do you think about the timing and the sequencing? Does one line of investigation work better at one time versus another? Or, can we just do all the investigating all the time and it’s all good?

André Martin
Well, here’s what I would say, is those early questions you ask in an interview, you absolutely want to be able to convey that you’re both highly interested in the role, and also that you’re a very curious person. And so, I think it’s okay to ask some very pointed, very high-impact and meaningful questions during the interview. It can actually make you look like a better candidate.

The other thing I would say to you, and you mentioned it, Pete, there’s that moment after you get the offer and before you take it, and then there’s also a moment after you take the offer and before you start, where often we just sit and breathe, we just sort of go, “God, I got the job. I’m so happy and my job is over.” I would tell any candidate that that’s the time when you really start increasing your efforts, both so you can be really ready to onboard and get to high productivity quickly.

But the second reason is because this is your time to really find out more and more about the truth of the company. And a couple places I like to look is I almost always reach out to my LinkedIn network, and look for people that I know that have recently worked at that company but might’ve just left because they’re going to be willing to sort of tell you the truth, the whole truth, and nothing but the truth about the experience and being there.

And because they’re in your network, or second in your network, they’ll usually pick up the phone, and most people want to talk about their past experiences. So, that’s a really good place to do some digging if you don’t feel comfortable about doing it in the interview process itself.

Pete Mockaitis
Okay. And these high-impact questions, we talked about a couple, like a-day-in-the-life, let’s see the calendar. Can you just give us bullet after bullet after bullet of some of your favorite high-impact questions you like to ask?

André Martin
Yeah. So, I talk about the person, what’s the profile of success, that’s a big one. A-day-in-the-life I do love. The reputation question is really important. And often, if you’re doing interviews with people outside of your function or your team, they’ll tell you sort of what the reputation is. I like to also get after, “What are going to be the two or three most important pieces of work I’ll do in the first 12 months?”

Because here’s the deal, Pete, as we know that job descriptions, they are a litany of bullet points about all the possible things you could do in a job really for the rest of your life. And that’s very different than what you’re going to be asked to do in the first 90 to 120 days of being there. Often, what we find is if this is the job description, this big long list of all the things you could do, often the job that you get is going to be a very narrow set of those things plus a lot of additional duties that never showed up in the job description.

So, I like to ask that question for two reasons. One, it’s important to really get out, “What is this role in reality day-to-day?” The second reason is that you want to make sure that the near-term deliverables fit areas where you’re best in class because the easiest way to be a success in a company early on is to be given deliverables that are in your wheelhouse or they’re something you’re really good at.

And when I’m looking at a job, if I look at the near-term deliverables, and I say, “Yeah, I can do those things,” but I’m not best in class at it, I might sort of think twice about taking that job because you’re transitioning into a new company, you’re building a brand-new reputation, a brand-new network, and people are going to start looking at you to say, “What kind of talent do we have?”

And if you’re doing work that you’re not great at, it can sort of cause you to create maybe a less impactful reputation than you could’ve otherwise.

Pete Mockaitis
Understood. Okay. Well, let’s fast-forward in time, and so we’re in a job right now. As we think about fit, are there any telltale signs that it’s just like, “Yes, this fit is fantastic” versus “Oh, no, this fit isn’t quite right” that maybe is escaping our immediate conscious awareness at the moment?

André Martin
There’s a few. And so, one of the parts of the book that resonates, at least for me, personally, is the metaphor of what it feels like to be in a wrong fit experience. One of my favorite quotes from the book is someone mentioned they’re in the wrong fit when it felt like everyone else had a secret decoder ring for success except for them.

They were seeing people in the company that looked like them, acted like them, had the same experiences as them, had the same job, and they were excelling, when this person go, “Something just doesn’t feel right.” And so, one of the ways I think about it is if you’ve ever tried to write with your non-dominant hand, that’s what it feels like to be in a wrong fit situation.

It’s harder than it should be. You’re frustrated. You’re stressed. Your quality of work isn’t where it used to be. You start questioning whether or not you’re good enough. And I think your first instincts in that is if work feels hard, you might want to think about whether or not, long term, this is going to be a fit for you.

Some of the telltale signs are things like, “I tend to work harder. I’m putting in more and more hours because I’m trying to be impressive.” That can be a sign many of the interviews talked about, “When I didn’t have a right fit, when it was a wrong fit, I tried harder. I spent more time.” And that’s because you’re trying to make up for fit in effort, and it just doesn’t work out that well.

Pete Mockaitis
Okay. Understood. Well, André, tell me, is there anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

André Martin
The only other thing I would say is one of the aspects of fit that I find really important is this idea that sometimes we mistake the excitement for something new with the comfort that comes from a committed relationship. And so, again, the analogy that’s really great is if you compare a first date to being married or being in a long-term relationship, a first date is all dopamine. It’s excitement. It gets your blood flowing. It’s the unknown. All those things produce dopamine which is this really powerful neurotransmitter that causes us to react in a certain way.

There’s a very different neurotransmitter that’s activated in long-term committed relationships, and that’s oxytocin. And what oxytocin feels like is it feels like more like a deep hug, like this really warm pleasant feeling. And what I worry about is, since we’re in this world where everybody’s infinitely browsing, we’re all looking for greener grass, we can sometimes mistake comfort for boredom, for lack of momentum, and we will jump ship from right fit experiences in search of dopamine or excitement when we really had maybe a place we were thriving at and we just mistook the feeling we had for something other than what it was.

Pete Mockaitis
Ooh, André, that’s powerful stuff. It’s funny, as we speak, just yesterday, I started listening to Anna Lembke’s Dopamine Nation, which I’m digging. I recommend it. And you’re right, that idea, especially if we’ve become so acclimated to stimulation nonstop in every format from social media to games or alcohol, you name it, that you think, “My job is boring. I got to go find something more exciting.” And yet if our job is boring, as opposed to horrific, like, that might be a good thing.

André Martin
Pete, it’s a great thing. If you think about where creativity comes from, where inspiration comes from, having a firm grounding, a sense of comfort to explore, that’s the basis of what Amy Edmondson talks about in terms of psychological safety. That is the feeling of comfort that we often are like, “I’m bored. I got to go do something else.”

And I looked at some of the stats data that are out there, 29% of employees leave their company after their first promotion. That’s stats from ADP. And 70% of Gen Z cited that they were potentially thinking about leaving their current job inside of 2023. And so, you just get this feeling that everybody has sort of mistaken this idea of comfort for boredom, and we’re jumping way too fast.

And transitions take effort, right, Pete? Like, the thing that we know psychologically is every time you move companies, every time you hop jobs, you are having to rebuild your understanding of how a company works, you’re having to rebuild the understanding of the products and services that are offered to customers, you’re having to rebuild your social network, you’re having to rebuild your reputation.

And, therefore, if you think about, in every transition you go through, your creative energy in that first year, it goes to rebuilding those things, not to your craft so you’re probably getting better at transitions but you’re not actually getting better at the thing that you’re trying to do as your craft, day to day in the world.

Pete Mockaitis
Yeah, that’s good. Well, André, this is probably a whole other conversation but how do we get better at being okay with being bored in our careers or, I guess, anything?

André Martin
One of my strategies, Pete, is I do a lot of self-reflection about what I’m solving for. And so, I go back, not to make this about the book, but those excursions in the book are personally made, because the one thing we don’t do enough in this high-information, high-excitement, high-dopamine world is we don’t stop, take a deep breath, take three steps back, and open our eyes really wide, and ask the question, like, “What am I solving for? What am I trying to build in terms of my life? What do I want out of my job? What kind of career am I building?”

There’s three different types of careers, for instance. Like, you can build a career around craft, company, or cause, but you can’t do all three of those things. What kind of person do I want to work for? What do I want my life to be 10 years from now? And what’s really interesting is, if you do that work, you can sort of start to see the signal in the noise, and you will, I guarantee it, look at your current experience very different, and you will look at every experience that comes after very different as well.

But we have to do that work a lot more often than we used to because there’s just an onslaught of greener grass coming at us every day.

Pete Mockaitis
Can you expand upon this notion of craft, company, and cause? You say we can’t have all three.

André Martin
Well, that’s the unicorn. I’m not saying you can’t but it’s really difficult. What I try to tell people is each of those careers has a very different trajectory and a very different choice you make around the types of jobs you take. So, I’ll give you, for instance, let’s say you’re of company. I don’t know what your favorite consumer brand is but let’s say you’re working for this company that you just believe in your heart and soul in what it stands for, and the products it brings to bear.

You want to be at this company for the next 25 years because you love it so much. I would tell you that your career then needs to have as many different jobs and as many different functions as possible because the strength of being part of a company as a career is that you know the system and the people in the system better than anybody else.

Right now, very different than craft. If you think about craft, craft is about this question of saying, “I want a career that ensures that I will be the best in class in a very narrow and specific area.” To be the best in craft in any specific area, let’s say my area. I was a chief talent and learning officer, and started my career in leadership development.

To be one of the best in leadership development, it’s really hard to do that and stay at a single company, because if I stayed at a single company, I see one approach to those things. If I’m at multiple companies over a career, I see five, six, or seven different ways of doing it, and, therefore, I have a lot more tools to use as I develop those assets. So, if you’re doing a career around craft, it’s really important that you think about having as many different systems as you can, within reason, to see how to do this in many different industries, in types of companies, and even sizes of companies.

And then cause, cause is the ultimate. Cause is all about, “I have this really big injustice, opportunity, or thing I’m trying to solve for in the world.” And when you have a career around cause, you really want to be at the middle of whatever is happening in that space. So, again, if you’re wanting to solve for the environment, get to a place where the environment is at risk. You want to save the oceans on the coast of California, you want to save the rainforest, but you need to be in the middle of where the action, where the thought leaders are, where all the discussions are happening. And that’ll take you wherever that movement is sort of in the world.

And so, my younger brother spent a lot of time in the Peace Corps, and he was of cause, and he went to Kazakhstan for a longer part of a year and a half because he wanted to help drive education in developing countries, and so he was definitely of cause. But I would say this, it’s not impossible to have all three, but you create very different experiences and design very different careers based on what you’re really making primary.

Pete Mockaitis
Yeah, that’s a very helpful framework there. And it’s nice how it seems like, “Oh, those are the opposite in some instances,” in terms of, like, craft and company, and I know folks who have gone both ways. I’m thinking about web design or systems architecture, it’s like, yeah, they probably know that better than, I don’t know, 99.99% of humans on the planet because they’d gone deep into it. And then once they’ve exhausted the learning that organization can give to them, it’s like, “If craft is your thing, then it’s time to move on.”

And, likewise, I’ve got buddies at Nike, that was their dream, and they’re still there from college to now because they think it’s just the coolest thing ever, in terms of, like, the shoes and the sports and the athletes. It’s so cool, and, likewise, he has been in a lot of different roles, and that makes you all the more valuable and hard to fire in terms of, “This guy is the glue who knows about the manufacturing, and about marketing, and about the new product design, and then the athlete partnerships.”

It’s, like, you think twice before, your next cost-cutting endeavor, you slash that guy because you’re going to miss a lot of the good connectivity that makes a behemoth of an organization function smoothly.

André Martin
Pete, I couldn’t say it better myself. And what I love about your description and your story there is, often people who are of company, they’re not maximizing their ability to be invaluable because they’re not thinking about their job progression as, “Wow, I need to broaden my network. I need to broaden my experience. I need to know every corner of this company.” And that’s the way you protect yourself and allow yourself to be invaluable over time if you truly are in love with the place, like Nike, which many are.

Pete Mockaitis
Yeah, you’re in Oregon. So, you’ve seen that before, I bet.

André Martin
That’s right, I have.

Pete Mockaitis
All right. Well, now could you share with us a favorite quote, something you find inspiring?

André Martin
One of my favorite quotes is “Joy cometh in the morning.”

Pete Mockaitis
That is hopeful on those days.

André Martin
I’m a hopeful person, Pete, 100%.

Pete Mockaitis
Okay. And a favorite study or experiment or bit of research?

André Martin
It’s a new one. So, there’s a recent study by MIT, it just came out with a company called Culture 500, and they did this really cool study on culture. And what they did is they took the espoused values of all these companies that are high on culture, and they grabbed those from annual reports, and videos, and communication with the company, and then they weighted them.

And then what they did is they took those espoused values, what companies said they were about, and they compared those with the felt experience of employees on the employee review sites. And the net of the study was there’s zero correlation between the two, that what companies are espousing they stand for isn’t necessarily what’s showing up in what the felt experiences for the employees that are part of their company.

Now, that study is fraught with a little bit of a hardship because we know that the employee review sites aren’t necessarily all the employees but it gives you a good indication that, “Hey, often what we’re talking about that’s important isn’t necessarily what’s showing up in the day-to-day lives of our employees as they work for us.”

Pete Mockaitis
Well, I hope there’s at least a few companies that have a good match up, but, across the board, they weren’t seeing it.

André Martin
They weren’t seeing it. And I find that really fascinating.

Pete Mockaitis
Yeah, okay. And a favorite book?

André Martin
Dedicated by Pete Davis. He has written a book on how to get through this crisis of commitment that we’re living in the world. And I really like his perspective that it’s not a loss cause. We can still be committed to things. We just have to stop infinitely browsing as much as we currently are.

Pete Mockaitis
Okay. And a favorite tool, something you use to be awesome at your job?

André Martin
Favorite tool, I have been recently using Arist.co. It’s a text-based learning platform that allows the small micro doses of learning to hit you every morning via your phone, and then you can have the option to go deep or wait until the next day’s lesson. And it just allows learning to be spread over a long time, and it’s with me every day in the flow of work.

Pete Mockaitis
Okay. And a favorite habit, something you do to be awesome at your job?

André Martin
Favorite habit, this is more of something I did to be awesome as a husband and a father. We practice no-text Sundays. So, from the moment all of us got out of bed until 3:00 o’clock, we would turn off our phones and our technology, and make sure that we were eye-to-eye, knee-to-knee, elbow-to-elbow out in the world. And that was a pretty fun way to put technology aside just for a little while, and have some fun as a family.

Pete Mockaitis
Okay. And is there a particular nugget you share that really seems to connect and resonate with folks; they quote it back to you often?

André Martin
Yeah, this nugget that resonates for me is that “Opportunity is infinite, and human energy is not.” So, really try to spend every day at your highest and best use because we just don’t have enough time.

Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you point them?

André Martin
I’d point them to www.WrongFitRightFit.com and also to a newsletter that I run called Monday Matters. It’s meant to be practical tips to make your week better, and that’s at MondayMatters.substack.com.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

André Martin
I do. I think my final challenge is back to what we talked about, because it’s one that is core to why I wrote the book, which is just be careful not to mistake comfort for boredom. The grass is inherently often not greener, and comfort is something that allows us to be at our best, and so cherish it if you have it. If you don’t, I believe it’s out there, and you can find it if you keep looking.

Pete Mockaitis
All right. André, this has been a treat. I wish you much luck and many good fits.

André Martin
Hey, thank you much, Pete. Thanks for having me.

864: How to Design a Career Portfolio that Beats Burnout, Navigates Disruption, and Future-Proofs Your Career with Christina Wallace

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Christina Wallace discusses the benefits of having a diverse work portfolio that will help you weather any storm.

You’ll Learn:

  1. How to diversify your work
  2. How to lessen friction and hit your flow
  3. The three questions that surface your hidden needs 

About Christina 

Christina Wallace is a human Venn diagram with a career at the intersection of business, technology and the arts. A writer, podcaster, serial entrepreneur, and erstwhile theater producer, Christina spent a decade building businesses in New York City. She is currently a Senior Lecturer at Harvard Business School, an active startup mentor, and angel investor. Christina holds undergraduate degrees in mathematics and theater studies from Emory University and an MBA from Harvard. In her free time she likes to sing in choirs, climb mountains, and run marathons (slowly). She lives in Cambridge with her husband and their two energetic children. 

Resources Mentioned

Christina Wallace Interview Transcript

Pete Mockaitis

Christina, welcome to How to be Awesome at Your Job.

Christina Wallace

Thanks for having me. I’m excited to be here.

Pete Mockaitis

I’m excited, too. We’re talking about The Portfolio Life: How to Future-Proof Your Career, Avoid Burnout, and Build a Life Bigger than Your Business Card. That sounds pretty cool.

Christina Wallace

It’s a lot of promise, right?

Pete Mockaitis
Yeah, but no pressure, Christina, but we’re going to hold you to every one of these. Could you kick us off by sharing any really surprising, fascinating, counterintuitive discoveries you’ve made while doing the research and putting together this book?

Christina Wallace

So, one of my favorite little tidbits from this, I am someone who is not great at taking time off. Like many type A overachievers, I sort of aspire to be the sort of person who rests, who relaxes. I’m not great at it. And a little part of me has always been, like, slightly, you know, felt some superiority over that, like I work so hard.

And part of the research, when I got into some operations management and some research into sabbaticals and all of this, it was a little bit humbling, where it points out just how important rest and planned downtime is for not just productivity but for happiness, for the ability to not burn out. It seems fairly obvious, you got to have some time to recharge.

But I found some really fantastic research, particularly borrowing from the world in operations management of manufacturing, where the top-performing manufacturing lines only ever schedule 85% of their capacity. They always leave downtime for planned maintenance, for do-overs, for surges. They don’t start from the point of 100%, and then say, “Well, we’ll just do 110% if we have to.”

And I thought that was a good reminder with some great science behind it of why this notion of, like, “Hey, let’s have everyone give 110% all the time” is not realistic. And that’s why we are all in a constant state of burnout.

Pete Mockaitis

Well, Christina, that’s intriguing right there, and you’re bringing me back to fond memories of one time I had a consulting project at one of the world’s largest cookie factories. All day long you could smell that chocolate in the air.

Christina Wallace

Oh, man.

Pete Mockaitis

And so, 85% is a top-performing manufacturing line. I’m curious, what do we know about top-performing humans? So, some sabbatical is good, some vacation is good, some rest is good. Do we know – there’s probably a range based on different temperaments, etc. – what’s optimal for us?

Christina Wallace

Certainly, there’s an expectation of having some downtime every day, every week. You have to have it as part of your practice but I found some research from The Sabbatical Project, DJ DiDonna, one of my colleagues here at HBS has done, that really emphasizes the value of taking a meaningful sabbatical every, call it, ten years or so. And by meaningful, they mean really in the realm of, like, three to six months off, taking a significant intentional break where you have a moment to step back, reflect, and really consider, “What do I want to do for the next chapter?”

And sometimes people come back feeling refreshed and renewed energy to keep doing what they were doing. And sometimes people come back, and say, “Okay, I actually needed that space to realize I want to go off in a different direction or I want to make a major life choice.” But I thought there was an interesting reflection of sort of six months every ten years. Like, that doesn’t seem unreasonable to have, call it three or four sabbaticals over the course of your career. That’s not that much time off.

And, yet, without the intentionality behind it, ten years pops up, and you’re like, “Oh, I can’t take six months off. That feels impossible.” So, it was a nice reminder that with a little bit of planning and strategy, these breaks are absolutely doable.

Pete Mockaitis

Okay. And so then, that’s on the sabbatical side of things. I’m curious in terms of a workweek side of things. I’ve seen some studies that suggest a certain number of hours. After that, you’re actually negatively productive. What have you found there?

Christina Wallace

Yes. So, what’s interesting about a portfolio approach is that there’s some research that shows being able to toggle between different activities, different types of working, different types of thinking and interacting, like, collectively helps actually recharge, renew the way that you are working, the energy that you bring to the table.

And so, it’s not sort of just additive. It’s not saying, obviously, there’s research that says 10, 12, 14 hours, at a certain point, there’s diminishing returns if you’re doing the same thing hour after hour. But if you are complementing, say, a day job with a moonlighting gig, a side hustle, or a serious hobby, or something you really love that works a completely different part of you and that offers you a different way of thinking, and of creating, and of interacting, that doesn’t feel like you just pulled a 12- or a 14-hour day. It can actually help you feel rejuvenated.

So, I don’t want you to work 20 hours a day between your side hustle and your day job. There is a breaking point but I think this notion of your total load across your portfolio is a lot more flexible than you might think, depending on what’s in your portfolio.

Pete Mockaitis

And when you talk about a different type of work, sometimes it’s like how we define different is really kind of fluid. Because, in some ways, it’s like, well, I’ve got two companies. One is in the world of training and people development, and the other is in the world of outsourcing and media production. And so, in some ways, it’s saying, because we’re dealing with words and thinking about words and making words good.

Christina Wallace

Sure. And you’re still writing emails and trying to make the numbers balanced, and maybe making a slide or two. Like, I can see how that could feel like the very same work but managing a different project. When I think about maybe a different ways of working, I think about some of the folks in my book where one person, by day, is a teacher, and then her moonlighting project is writing novels for middle grade readers.

And so, by day, she was dealing with 4th graders, and their sticky hands, and how to teach them math, and how to teach them emotional maturity, and all of these things. And then, by night, she’s inventing these stories and sort of just going deep into this continuous creativity in these worlds that she’s building. That’s a very different way. Like, one allows her to recharge after she’s been giving and giving and giving all day long to her students.

So, you’re absolutely right, that really can come down to, like, “What is that mix? And do they complement each other? Or, are you just doing the same thing but in a different context?”

Pete Mockaitis

And when it comes to recharging-ness, is there a means by which you recommend people reflect, or assess, or gauge that?

Christina Wallace

So, one of the tactics that I recommend for putting together your portfolio is an assessment of two things. One is what do you need to be your best self? And everyone’s needs are going to be a little different. Your needs are going to be a little different depending on the chapter or season of life you’re in but you will likely have some combination of financial needs, growth needs, community needs. There could be other elements of security that you have needs, that need to be met.

And then, in addition to your needs, you’re going to have a set of wants, or, as I like to call them, your wishes. What are the big things that you care about doing, seeing, experiencing, leaving behind by the end of your life? We’re talking this could be minor, “I want to run a marathon.” These could be major, “I want to, I don’t know, walk on the moon,” so whatever. Putting together this kind of list of wishes for your life.

And as you’re assembling your portfolio, you want to be thoughtful of, like, “Are the different things that I do over the course of my day, or my week, or my month, collectively, are my needs being met?” We got to start there, “Are my needs being met?” If you’re doing two or three or four things that all maybe make you money, but they’re all solo projects, you have no colleagues, you’re not being given this community or this opportunity to just have conversations with other humans, you’re over-indexing on one need and your under-indexing on another.

And so, as you think about recharging and rebalancing, it’s, like, “Am I getting my needs met across my day, my week? And am I having a good balance across these things?” The wishes piece is relevant, too, “Am I doing all of this work and all of it only goes toward one or two or a handful of things that I care about? Or, do I have a nice breadth across what I’m doing that maybe this thing gets me closer to this professional goal, and that work gets me closer to this crazy artistic goal that maybe I even felt weird about writing down because it seems so out of this world but I kind of really do want to do before I die?”

Pete Mockaitis

All right. And I imagine it’s a common experience for people to not even be aware that they have a need of a particular flavor or stripe. Any suggestions on how to surface those?

Christina Wallace

I think part of this is the reflection or the delving into stories, into your past experiences, and having that opportunity to say, like, “When have I been my best self? And when have I haven’t? Like, what are those moments where I found myself crying at work or doing less than I thought I could or should be able to?” I’ll give you an example, one of my needs is an office with a door that closes.

I do not do well in open office plans. And I have so many examples of working in startups and other organizations where I loved the work, I was a good fit for my role, I had great relationships, everything felt like it should be clicking, but I was in an open office plan where I couldn’t focus. I have high sensitivity to sounds. I couldn’t focus. I was always being interrupted. I couldn’t get into a flow, ever. And that friction wore at me every day to the point where I couldn’t do what I was there to do.

So, I made that on my checklist, of like, “When I’m at my best is when I’m able to shut the door and be able to focus.” And so, in some ways, if you’re just starting out, you might not have a good sense of your needs yet, and that’s okay. But if you’ve been at this a while, or if you have that opportunity to look back and reflect, whether it’s in school or in your jobs, where are you at your best? And where did you find sort of constant friction that you’re like, “Ugh, it doesn’t have to be this way”? That’s a great place to start to surface your needs.

Pete Mockaitis

Well, Christina, now I’m thinking about the notion of friction and some philosophies saying, “Well, hey, if it doesn’t kill you, it makes you stronger. And if you can endure that, you’re going to grow and get tougher. And we’ve got it so easy in the 21st century with all of our luxuries and conveniences and comforts, and maybe we need a little friction to toughen us up.” What do you think about this perspective, Christina?

Christina Wallace

So, I hear you, a little bit of friction, not necessarily a bad thing but here’s maybe my counterpoint to that. Many of us, I might argue all of us, are what I would call weirdly shaped puzzle pieces. We all have a different set of skills, and communication styles, and interests, and personality quirks, and all of these things that we bring to the table when we show up over the course of our lives. And there are rooms that have a space that is shaped like your puzzle piece, and then there are rooms that don’t.

And if you try to shove your strangely shaped puzzle piece into what is a nice, square, neat opening, maybe it’s the last piece we’re waiting to put in this puzzle, and you don’t fit, if you try to shove yourself in there, you’re going to have to carve off a meaningful amount of yourself in order to even approximate what they’re looking for.

And I think there are lots of folks who feel this on a daily basis, whether it’s code switching, or whether it’s just the adjustments they make to who they are in order to feel acceptable on a team, at a company. And you realize that, on any given day, it’s not that big of a deal, but every day for years on end, you’re literally using some percentage of your energy, your mental capacity just to show up and be able to do your job, which leaves so much less to do the job itself.

And I think one of the biggest learnings I had through my 20s was that I would rather find the rooms that wanted what I had to offer than try to squeeze myself into a box that didn’t fit me, or into a hole in the puzzle that didn’t fit me. And part of that work was really uncovering what the shape of my puzzle piece was, what do I show with, what do I have to offer, and why is that actually awesome. And so, the people who do want me really do want me.

Pete Mockaitis
That’s good. And I’m thinking right now just about an experience I had recently. So, nowadays, with three young kiddos, I find I’m spending most of my mornings hanging out with them, watching them, taking care of things.

Christina Wallace

How old are they?

Pete Mockaitis

They are five, four, and six months.

Christina Wallace

I’ve got a three and a one-year-old.

Pete Mockaitis

Yeah. And then some things happen in terms of travel where I have the opportunity to just wake up and start doing some work at 7:00 a.m., and it felt absolutely amazing. It’s like, “Wow, I didn’t even know.” I thought, “Oh, I guess I used to do this a lot. I don’t think I even remembered that that was a thing I did that worked really well for me, and I have been not doing that, and I miss it.”

And so, in a way that’s kind of tricky, it’s like, “Well, what’s to be done?” There’s probably some clever things to happen there but I guess, Christina, where you’re nudging me here is one response to that internally is, “Oh, hey, man, that’s just the stage of life we’re in, you know. We got to take care of the kids in the morning. That’s where it’s at.”

But I’m thinking, with your puzzle piece analogy, perhaps you might advocate it’s worth putting some serious thought and effort into thinking, “Is there an arrangement by which this creative morning, productive, energized groove can be deployed in that direction because it’s worthwhile to do so?”

Christina Wallace
Yeah, I think your example is perfect on two dimensions. One is you get to see sort of the difference between what is it like to have that friction versus just to hit your flow. And I think, from like a metaphorically standpoint, that’s exactly the difference between being in a room that wants you and being in a room that doesn’t.

Or, a version of you, if you would, like, soften these things and change that thing, and don’t use too many exclamation points in your emails. But in the same way, I think that’s a perfect example of, you are at a stage of life where your mornings, for the most part, look a certain way. And so, the question is, “Is there an opportunity to either create a version of this that gives you that creative morning, maybe some sort of an arrangement with your partner, or figuring out how you set up your morning differently?”

And if you were working at a company or somewhere else where you had a manager or a boss, there might be a situation where you say, like, “Hey, can I adjust my hours? Can I think about maybe working from home in the mornings so I can get the kids out, and then I can have a couple of hours before I have to sit in traffic, or a couple of days from home?” Like, there’s a way to be thoughtful about, “How can I construct the context of how I do my work to maybe lower some of that friction and give me that opportunity to hit flow better?”

So, I am now a professor. For this stage of my life with young children, this is what fit me better than running a startup. And, as part of what I need, I have the same morning experience, getting my kids out the door, off to daycare, all these things. I can’t teach before 9:30, like it just doesn’t work, and I’m in the position to say that, and to proactively design my day to fit the needs that I have for this stage.

Pete Mockaitis

Okay. Thank you. All right. Well, we just jumped into a lot of specific things because you kept fascinating me, Christina. And now, maybe I’ll zoom out a little bit. So, this book The Portfolio Life seems like we’ve got some taste for what it’s about. But could you articulate the core big idea or thesis here for us?

Christina Wallace

Sure. So, this idea, everyone is likely familiar with a portfolio from a financial standpoint, you build your financial portfolio with a mix allocation across stocks, bonds, real estate, whatever these assets are that fits the stage of life you’re in, that matches the risks and the returns that you need. And then, as your life changes, you rebalance that portfolio to rematch what you need at that stage. And this is taking that exact approach but applying it to not just your career but your life. I think career is a huge part of many of our lives but it is in the context of your life.

And so, what does that look like? It means that you are assembling work, hobbies, relationships, family time, community time, rest, you’re designing an allocation of your time across these different pieces in a way that meets your needs and moves you forward toward your goals. And what that can look like is several sources of income. It can look like a meaningful sort of hobby or growth opportunity, a project, something you want to learn more about, that you’re going to dive into, that then sets you up for your next professional zigzag.

It could mean keeping your hands in a lot of different buckets, a lot of different communities and networks, you say, “Well, I came from this world, I’m now in this world, I care a lot about that world, and I’m going to stay connected to all of them.” And the reason I advocate for this approach, one, it actually matches much better the full sort of three-dimensional version of who you are as a person. Very few people, from the day they’re born to the day they die, say, “You know, I really am, and I only am, a marketing manager in a pharmaceutical company. Like, that’s who I am. That’s it.” Like, we all have these different aspects.

And so, it’s a way to reflect on and mimic this three-dimensional version of you rather than having your identity be formed by your job. But, secondly, it sets you up with diversification and flexibility to better weather this constant state of disruption that we are now in. This world, whether it is bank collapses, or ecological disasters, or technological advancements, like AI that are going to massively change the face of white-collar work in the next five years. Whatever these things are, they’re coming at us, lifechanging disruptions every three, five, seven years. This is a pace of change the previous generations never had to deal with.

And so, thinking about your career and your life through a portfolio that helps you diversify and build some flexibility against that disruption is truly the only way you’re going to navigate this without having the rug pulled out from under you, like many folks have had in the last few months.

Pete Mockaitis

So, can you share with us perhaps a story that brings that to bear? Like, “Ooh, here’s someone who did not have a portfolio, and, uh-oh, look how that went down,” versus someone who did, and, “Oh, what a softer landing and what it provided for them.”

Christina Wallace

Sure. I have a great example of this. Heading into the pandemic, I come from an artistic background. I went to a boarding school for the arts, I trained as a classical musician, and I majored in theater among other things, and so I know a lot of folks in the arts. And I used a lot of case studies in the book of folks that have a creative pursuit as part of their portfolio.

Going into the pandemic, I have a lot of friends who were actors, directors, designers on Broadway who went from being gainfully employed at the top of their industry to having, literally, no income for two years while live performances were shut down. And many of them had sort of a backup job as a waiter or a bartender. That’s how a lot of actors make their work between gigs but a lot of those jobs got shut down, too. So, there were a huge number of artists in New York who just, literally, had no income for up to two years, minus whatever unemployment checks they were able to collect. And it was devastating. Many of them are still digging out from under that.

But I have one friend, Carla Stickler, who, in addition to being an actress, she was the understudy for Elphaba in Wicked for many, many years, a fantastic Broadway actress, in addition to that, she started learning to code. Many years ago, she took a bootcamp through the Flatiron School. She wasn’t really sure what she wanted to do with it but it interested her, and she decided to learn more.

And so, between gigs, backstage, when she wasn’t in a scene, she was working on code, building projects, writing apps. And when the pandemic came, she’s like, “Well, I didn’t think I was ready to leave Broadway, but I think Broadway is ready to leave me, so it’s time to pivot.” And she took her coding resume, and went out and got a job as an engineer at a startup, and was able to seamlessly move into the world of tech startups, and has a thriving career now as an engineer in Chicago, and was able to navigate that unexpected disruption so much better than her peers.

And what I think is fascinating about Carla, I’m sort of giving away the ending here, but it’s not like she walked away from performing altogether. She kept teaching a little bit. She had a private voice studio. She stayed in touch with folks. And when Broadway came back, this is right around the time that, like, the Omicron surged, it became problematic, they reopened, they started performing again, and then there was this big variant that took out, it was devastating.

It took out a lot of performers really quickly, and Broadway started going through their list of understudies, and backup understudies, and swings, and backup, backup swings. And they got to the point where they needed an Elphaba, they had no one else to perform. They, literally, called Carla in Chicago, she got on a plane to New York, had one rehearsal, and went on stage, painted green, flying 40 feet over the stage, singing, literally, the hardest role on Broadway. And then she got off stage and, two days later, went back to her coding job in Chicago.

So, I think that is a great example of how you can have a mix of skills and interests and networks that maybe you’re not monetizing just yet but can position you to have optionality and flexibility when the time comes.

Pete Mockaitis

Okay. Cool. And so, as we think about this design process, you mentioned doing reflection associated with seeing when have you been at your best and when have you been at your worst. Are there any other ways to help surface that which is going to help keep us feeling alive and flourishing as well as surfacing cool opportunities to get after those things?

Christina Wallace

So, one of my favorite tools, I developed this short list of questions after my first startup failed. I had built this company, we had raised the money, we thought it was going to be amazing, spoiler, it was not. And I had this moment of complete and total sort of paralyzation. I was like, “I don’t know who I am. I don’t know what I have to offer. I don’t know why anyone would want to hire me,” and tried to be reflective, tried to journal and figure out what I brought to the table, and I was coming up with a blank piece of paper.

And so, I went out and had coffee, a lot of coffee, with basically everyone in my network. I did, like, 70 coffee chats in 30 days. That was overkill. You don’t have to do that many. But I went out and asked the folks who had known me the longest and some who’ve actually only known me a few months. I asked them three questions.

Number one, “When have you seen me happiest?” Number two, “What do you come to me for? Like, what is that moment where you go, ‘Oh, I should see what Christina thinks about this.’?” And then, number three, “Where do I stand out against my peers?” Because one of the things that I recognize was there might be, like, a superpower that I bring that is easy for me and so I don’t even realize how valuable it is elsewhere.

And having those same three questions kind of across all these conversations helped pull out some themes that really gave me an insight into where I should go next. And then, once I had something more specific of, like, “I’m looking for this type of a role, in this type of an industry, with this type of a job title or an opportunity,” then my network could surface those opportunities because I was being really specific.

I wasn’t saying, like, “Hey, do you know anyone who’s hiring?” I was like, “Do you know anyone who’s hiring a general manager role for a company, not based in New York, that wants to expand to New York, and who’s at a seed or series A stage of financing in the startup world?” Like, super specific. And I landed that job in a couple of days.

So, part of this is, like, you can do some self-reflection, and there are great exercises in the book to do that but you can also go and ask the people who know you what they see when they look at you. And you might be surprised that some parts of you that you don’t even realize are that exciting or valuable really stand out to other people.

Pete Mockaitis

And could you share with us a couple things you heard when you had these 70 conversations that surprised you, like, “Huh, how about that?”

Christina Wallace

So, one of the interesting things when I asked them when they had seen me happiest, the consensus was when I was in charge of my own calendar, meaning I’m not afraid of working hard. I work hard. I work a lot. But I want to do it on my own terms. And for a while, I had been at a consulting firm for one of these big national consulting, international consulting firms. And in client services, you jump when the client says jump, and I didn’t have control over my calendar, and I wasn’t able to slot in the things I cared about or show up for the people that I wanted to show up for. And it really made me miserable.

So, I came out of that realizing, like, “Okay, me and client services, like not a good fit. What do they come to me for?” They come to me to help find the story. So, whether it’s their resume, or it’s a product they want to launch, or it’s just connecting the dots of, like, “I did this thing and that thing and the other thing,” and I’m like, “I don’t see how they connect but I’m sure they do.” I can give them the language. I can help them find the story and frame it in such a way. It’s sort of a communication skill.

And then, “Where do I stand out against my peers?” I thrive in moments of uncertainty. I’m really good at the zero to two stage of company-building, or a project generation, or launching a play, whatever that thing is. Going from an idea to a thing, and getting other people excited by it, onboard with it, and all driving in the same direction, is where I excel.

I’m less great at the 10- to 100-stage, where you’re optimizing something that already exists. And so, I thought that was really helpful to be, like, “You know what, I should stay in early-stage startups or in creative projects, like producing theater, where going from nothing to something is what’s on the table.

Pete Mockaitis

Cool. All right. That’s very clear. And I could see how, in your world, it’s just like, well, yes, it’s kind of, “Isn’t everybody good with that?” how strings can be hidden in that kind of a way. Okay. Well, then can you share, so that’s sort of the insight, personal, wisdom gathering there. And then what are your top tips in terms of surfacing cool opportunities and things to put into your portfolio?

Christina Wallace

A lot of this comes down to your network. There’s some great research I referenced in the book that a lot of the opportunities don’t come from the people you know but the people they know, second-generation networks. And part of helping that one level-removed network surface things that might be interesting requires you to be really specific on what you’re looking for.

And so, that is sort of a two-pronged approach. One part is having the language to talk about who you are, what you’re looking for, and how someone might be able to help you. That was what I needed after I did all these coffee chats, coming up with the specific asks. And then the second thing was keeping in touch with those networks so they know that you’re looking for help, that you want something to surface up.

And this can be a challenge if you sit in multiple worlds, as I do, I have built a career at the intersection of business, technology, and the arts. Those are somewhat overlapping but, in many ways, distinct communities. To stay connected to them takes effort, it takes relationship-building over time not just sort of networking where I show up with a business card and throw it in everyone’s hands. But doing that allows me to stay top of mind, and having a very clear ask allows them to surface things that might be really interesting.

Because a lot of what people love, can get excited about, is really these opportunistic things rather than the, “What’s your five-year plan?” The five-year plan thing hardly worked for our parents. I don’t think it can work for any of us because there are so much that is changing and there are so much that’s unknown. So, having much more of an emergent strategy rather than a deliberate strategy is what’s going to be effective here. And to do that, you have to stay connected.

Pete Mockaitis

Okay. Well, Christina, tell me, anything else you want to make sure to mention before we shift gears and  hear about some of your favorite things?

Christina Wallace

I think that’s it.

Pete Mockaitis

Okay. Could you tell us a favorite quote, something you find inspiring?

Christina Wallace

Madeleine Albright, “There is a special place in hell for women who don’t help other women.”

Pete Mockaitis

All right. And a favorite study or experiment or bit of research?

Christina Wallace

Clay Christensen and his team, when they were writing The Innovator’s DNA, interviewed and studied hundreds of the most creative innovative people, and they identified these five traits that make up the DNA, that make up kind of how these people worked. And at the core of these five traits, the backbone that the other four sort of rotate around, like the double helix of DNA, is the power of associating.

That’s the ability to connect seemingly unconnected ideas, or networks, or industries. That is what made people the most innovative. So, it doesn’t require you to have a net new idea, a cutting-edge technology. It often can come from just being connected and translating something you’ve seen in one world into another.

Pete Mockaitis

All right. And a favorite book?

Christina Wallace

Oh, man, I think it’s probably an upcoming book. I can still call it a favorite because I got to read an advanced copy. It’s called The Anxious Achiever by Morra Aarons-Mele.

Pete Mockaitis

Oh, Morra. She’s on the show.

Christina Wallace

Yeah, it is just I feel like it was written for me and, like, all of my friends.

Pete Mockaitis

All right. And a favorite tool?

Christina Wallace

Trello. I live and die by Trello. I’ve probably been using this Trello board for, like, 12 years.

Pete Mockaitis

Okay. And a favorite habit?

Christina Wallace

Putting my phone away an hour before I go to bed.

Pete Mockaitis

Okay. And a key nugget you share that really seems to connect and resonate with folks; they quote it back to you often?

Christina Wallace

Honestly, it comes from one of the pieces of my book, “There’s no such thing as a left-brained or a right-brained person.” This is fake science that was misinterpreted from a real study back in the 1960s. And so, this notion that we are one or the other, logical or creative, it’s not true. You are both.

Pete Mockaitis

Okay. And if folks want to learn more or get in touch, where would you point them?

Christina Wallace

PortfolioLife.com or you can follow me on LinkedIn or Instagram.

Pete Mockaitis

And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Christina Wallace

Honestly, I would go and talk to your boss, talk to your manager about the thing that you want to try, or learn more about, or explore this year that has nothing to do with your current job description, and see if there’s a way to get a stretch assignment, or a rotation, or a zigzag promotion that allows you to sort of expand that portfolio even in the context of your day job.

Pete Mockaitis

All right. Christina, this has been a treat. I wish you much luck and fun in your portfolio.

Christina Wallace

Thank you so much.

850: How to Reinvent Yourself in Life and Work with Joanne Lipman

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Joanne Lipman says: "Everybody else’s journey looks so nice and neat, and we feel like we’re the only ones who are a mess, but, frankly, we all go through that struggle."

Joanne Lipman reveals her strategies for reinventing how you live, work, and lead.

You’ll Learn:

  1. How struggle makes you better.
  2. Three tricks to make any transition easier.
  3. How to take the most efficient brain breaks.

About Joanne

Joanne Lipman is a pioneering journalist and the author of the No. 1 bestseller THAT’S WHAT SHE SAID: What Men and Women Need to Know About Working Together and NEXT! The Power of Reinvention in Life and Work. She has served as Editor-in-Chief of USA Today, USA Today Network, Conde Nast Portfolio, and The Wall Street Journal’s Weekend Journal, leading those organizations to six Pulitzer Prizes. She is also an on-air CNBC contributor and Yale University journalism lecturer.

Resources Mentioned

Joanne Lipman Interview Transcript

Pete Mockaitis
Joanne, welcome to How to be Awesome at Your Job.

Joanne Lipman
Thank you. It’s great to be here.

Pete Mockaitis
Well, I’m excited to dig into the wisdom of your book Next!: The Power of Reinvention in Life and Work but, first, I just got to know, you have had such an impressive career in the heights of senior journalism.

Pete Mockaitis
So, given your perspectives from having worked in journalism for a long time, what can you tell us about humanity, those of us here who make and choose to consume the news? What have you discovered that most of us don’t know?

Joanne Lipman
One of the things that I’ve discovered is that I really, really, really respond and appreciate the audience, the people who are listening. I think that our best insights come from when we’re talking to lots of people, when we’re out and about, when we also listen to people throughout the country. I think that one of the issues that we’ve had with trust in media is the idea that there are…we have media centers on both coasts.

We don’t have as much national media in the middle of the country, and I think it’s really important to have people represented in the newsroom from every community, from different localities, different genders experiences, socioeconomic backgrounds. And that, to me, is what builds trust in the news. And, to me, that’s the most exciting part of being in the newsroom when you’re surrounded by people who come from all different perspectives, and everybody brings something else to the party, which is, I think, helpful for all of us.

Pete Mockaitis
And then what happens when that’s not done, in terms of what’s the vibe or the impact?

Joanne Lipman
Yeah, I think there’s been some legitimate criticism that we’ve had too much sort of parachuting in. So, you’ve got your…because media is, and this is a whole other conversation, but media is under pressure, financial pressure, and there’s been a lot of cuts to journalism jobs. And, as a result, what sometimes ends up happening is there’s a story somewhere where there’s not a big news organization, and one of the big national news organizations, we call it they parachute in. Like, it’s every presidential election, there’s 50 big-time journalists who descend on Iowa and go to a diner.

Diner journalism is not great journalism. What you really want are the people who live there to be the reporters, to tell you to really understand what’s happening on the ground. And I think this is a reason why the media has – and this is all legitimate criticism – missed a lot of the rise of populism, the rise of Trump, certainly, but also just sort of through the last 20 years, the rise of the Tea Party. There’s a lot of really smart, informed people throughout the country whose voices are not heard.

And I think anything we can do to elevate those voices and have a broader perspective about…and an on-the-ground perspective of what’s happening. This is actually one of the great things when I was working with Gannett, which owns over a hundred local newspapers, and it was fantastic to be able to have when there’s an earthquake, a fire, a natural disaster, a shooting, to have local reporters who are on the ground who understood the community, and it really helps to understand the whole country. We’re a very diverse place with lots of perspectives and we need to understand ourselves better.

Pete Mockaitis
Well, now can you tell us your book Next! what’s the big idea here?

Joanne Lipman
Sure. So, Next! it’s the power of reinvention in life and work, and I’m so excited about this book because it grew out of what we are all going through right now at this moment, which is we’ve had three years, we’re at the three-year mark, which is crazy, from the start of the pandemic, and the entire world was sort of upended.

No matter what you do or who you are, your life was upended, and it really got so many people rethinking, “What are our priorities? Am I in the right job? Is this the career I want? Is this the life I want? Is this where I want to live?” So many questions, and it occurred to me very early in the pandemic that we’re all going to have to figure out what’s next.

And so, the big idea is I wanted to help people to navigate big changes, navigate change in how we live, how we work, how we lead, and really to help people to move toward finding their real purpose.

Pete Mockaitis
All right. Well, so when it comes to doing that, you’ve got a reinvention roadmap. Can you walk us through how that works?

Joanne Lipman
Sure. So, I’ll tell you a little bit about what the reporting was. When I started reporting the book, it was so interesting. I was looking for stories of people, and I did hundreds of interviews, there’s tons of research, scientific research in the book Next! And what I started with was talking with people who had already gone through these major transformations in different ways.

Some had had huge career changes, like one of my favorites. A guy named Chris Donovan who spent years, decades, as a telephone repairman but he secretly would, like, doodle pictures of shoes. And at the age of 50, left the phone company, went back to school, and now is a couture women shoe designer who was named Best of Boston, Boston Magazine, best shoe designer. It’s a beautiful story.

I found all these wonderful stories where people had these amazing transformations, but then what I did was I went back and talked to the academics, the researchers, who study these different kinds of change. And what was so fascinating was I talked to people who had gone through very different kinds of transformations, some were career, some were people who came back from, like, huge failures, some were people who had had trauma in their life, and some were actually people who had these grand aha moments that just changed their life.

So, these all seemed, on the face of it, to be very different kinds of transformation. And then I went and talked to these academics. There’s different academics who study each kind of change that I’ve just gone through, and they all walked me through sort of the steps of transformation, and they all used different words, different language, but they were all describing the same set of steps. And it was such a revelation to understand how this works.

So, they’re basically there’s four steps that pretty much everyone will go through. So, the first step, like, I will tell you the four steps, what we call them are search, struggle, stop, solution, and I will walk you through them. So, the search, almost everyone who I spoke to, no matter what kind of transformation they went through, they actually started before they even knew they started. They started moving in this direction, they started collecting information.

So, if you think about someone who changes careers, that is somebody who maybe has a hobby, or a side hustle, or even just some random interest that just grows and grows. I talked to everybody from James Patterson, the mega-selling novelist, who spent 30 years at an ad agency. He was actually at an ad agency, and he wrote books on the side, some of which got published, many of them kind of did not do well. He was, like, finding his voice, but he was working toward it.

The shoe designer I mentioned was doodling shoes. One of my other favorites was a bank economist. He worked for years, for decades, at JP Morgan, and he had a weekend house. And on the weekend house, it was a farmhouse, and he leased out the land around it to a cattle farmer. And when the cattle farmer died, he just bought the cows, he said, “I just thought all they do is eat grass. It doesn’t really take any work.”

Well, fast forward 20 years later, the guy is a full-time cattle farmer. He used to be a Harvard-educated economist, and now he’s, like, a guy who gets up and shoos the cows from one pasture to another and could not be happier. So, anyway, that’s the search, that people start moving in that direction. The struggle is very often particularly with careers, this is true. You leave one identity behind but you haven’t quite gotten to the other.

There’s a wonderful professor, Herminia Ibarra, who studies career transitions. She calls this the liminal period. It’s where it’s an uncomfortable period where you’re still haven’t quite figured out the future but you’re escaping the past.

The third step, which not everyone goes through but very often they do, which we call the stop. Very, very often, I found that there is a moment, and it’s either you choose it or it chooses you, where you just stop. So, where it’s either you’re banging your head against the wall and you can’t figure out that next step, again, uncomfortable, or, in some cases, for example, the shoe designer who I was mentioning, what prompted him was he got struck by cancer.

He had prostate cancer, and it was one of those moments where he said, “Wait a second. I’ve got to stop and think. Is this the life I want to have? Or, is this the life that I need to follow the path that I think I was put on this earth to do?” and he had that stop. And so many people do. And, by the way, if you talked to creativity researchers, people who study that, this is why we all have those aha moments.

I bet you’ve had this, right, where you wake up in the middle of the night, or you’re in the shower, or you’re going for a run, and suddenly you have that aha moment. It’s because you’re puzzling through something, and you can’t quite figure it out, and then what ends up happening is you have to put it out of your mind, you have to shut off the conscious thinking about it, and that’s what allows all these sorts of random thoughts in the back of your head kind of coalesce in your subconscious and then emerge as this aha moment.

So, there’s your stop. And then that is, again, what takes you finally to the solution. So, these four steps are very common to every kind of transition, and I found that very, very encouraging to understand how that process works.

Pete Mockaitis
All right. Yes, very much. And that struggle, it’s interesting that notion of identity. So, our identities are often quite wrapped up in our work careers. Is that a finding you saw again and again?

Joanne Lipman
A thousand percent, yes. Very often, somebody said to me, “You are, like, your title, and when somebody takes that away from you, you lose that title, people are really lost.” There really is an issue with, there’s an Atlantic writer who calls workism, which is it’s almost like a religion where we are so focused on work, and it is so much of our identity, and when that goes away, it’s very hard to come back.

But that struggle is also sort of the pathway. It’s really uncomfortable. What I found almost universally is when you’re going through that struggle, whoever it is that’s going through that struggle, you think you’re the only person in the world who’s dealing with that. You feel like, “I’m a loser, and everybody around me is getting ahead, and they’ve figured it out and I haven’t.” But it is actually a universal feeling.

And it’s also where the really, really important work gets done. It’s not necessarily fun but it’s helpful to know that, first of all, everyone goes through it, and, secondly, it is actually where the most important part gets done. And I think one of the issues that we have in this, with society at large, is we have this sort of fantasy of instant overnight success, overnight transformation, and it starts from childhood with Cinderella, and then it goes to adolescence with Superman and Spiderman, and then it goes to adulthood with American Idol.

And then we hear these amazing stories, like John Legend was a management consultant, and now he’s a superstar. And Mark Zuckerberg was a college kid, and now he’s a tech billionaire. We hear these stories and it just seems so far from our own experience. It just seems like it’s impossible we shouldn’t even try because we’ll never get there.

And it’s really a damaging myth. It’s a complete myth that the important thing is we all need to go through that middle period. It’s really important, great work is being done in that middle period. We all go through it. And so, again, it’s something that we shouldn’t beat ourselves up about.

Pete Mockaitis
Well, you mentioned John Legend, a management consultant to music, and I remember when I was making my transition, I was in management consulting at Bain. And I remember when I was sort of an odd duck, like people typically didn’t believe that company to go be speaker-author-people. So, I did feel that discomfort, it’s just like, “Oh, so what do you do?” I was like, “Oh, I’m a speaker and an author, and I’m kind of still figuring it out. My market is in topics and audiences, but I was a consultant at Bain.”

So, it’s like, “But I’m not a loser, I promise.” I don’t know, it’s like that insecurity that I had in that moment, it’s like, “I’m still figuring out what the heck that I’m doing here, but before I had a pretty prestigious role, so don’t think less of me.”

Joanne Lipman
Everybody. Everybody has been in your position because so many people, they meet you and they’re like, “Okay, what do you do?” and it leaves you tongue-tied. I’ve experienced that myself. I ran a magazine that closed, and then I was meeting people, and they’re like, “What do you do?” I’m like, “I used to…” What do you say, right? It’s a very awkward situation.

I have a whole chapter, by the way, on what I call necessity entrepreneurs, which is women, people of color, and, increasingly, Baby Boomers, people who are actually being squeezed out of the traditional workforce or the traditional jobs, and very often end up with far more fulfilling careers, actually, as a result. But the women who I talked to, in particular, said, “You feel invisible.”

There’s a fabulous woman I talked to who had a big consulting career, and left to raise her children, and for 12 years, she was out of the workforce, and she said, “These 12 years of feeling invisible, it’s tough. It’s tough.” I do love, by the way, that LinkedIn now allows you to have that career gap as, like, a legitimate part of your resume because I think those are…these career gaps, we’re increasingly in a nonlinear world with careers, which is so much about what Next! is about, is this sort of nonlinear life and how do you navigate the nonlinear life.

And we see it with Boomers, and now we’re seeing it with the younger generation, which they expect to have, 10 or 12 careers in the course of their working life.

Pete Mockaitis
Well, now you got me intrigued. So, LinkedIn, so gaps, you have the option, you have a start date and end date for things that don’t have to overlap within the programming. Is that what you’re saying?

Joanne Lipman
Yeah, exactly. And it’s made for people who have career gaps or people who maybe dropped out of the workforce, paid workforce, I should say, because they’re still working, but paid workforce, you know, they raised their kids or for other reasons, they take care of older relatives, for whatever reason it is. And I think that’s incredibly important.

I also think that there’s an increasing recognition that during those gaps in paid employment, there’s a lot of learning that’s going on, and there are a lot of people who I’ve talked to who had these wonderful career transitions because of what they learned during these gaps in their careers. The woman who I just referenced, who said she felt invisible for 12 years, she poured her energy and her business skills into community issues.

So, the zoning board, and getting a playground by the school, and getting a stop sign, and joining the PTA. All these kinds of things, civic engagement, and she met a lot of women like herself. Ultimately, what this woman did was she did two things, which is so awesome. She started a nonprofit that she is now the CEO of, that is expanding nationally, called The Acceleration Project. Its volunteers like herself and other moms who had big careers, and they mentor local business owners to help them with things like marketing and finance.

She did that, and then she was elected mayor of Scarsdale, New York, her town, and she now gives speeches all over. And she told me when she gives these speeches, she says, “When I talk about my career path, it sounds like it was so intentional, and that you can tie it up with a bow. But, frankly, when you’re in the middle of it, when you’re in that struggle,” she said, “you have no idea where it’s going.”

And this is sort of that myth that we were talking about. Everybody else’s journey looks so nice and neat, and we feel like we’re the only ones who are a mess, but, frankly, we all go through that struggle.

Pete Mockaitis
Okay. Well, we touched on a number of stories as examples here and there. Could you walk us through a story from beginning to end that you find the most clearly illustrative of these stages, “Hey, here’s the search, here’s the struggle, here’s the stop, here’s the solution”?

Joanne Lipman
Yes, okay. So, there’s a fabulous woman who I met, named Marla Ginsburg. So, Marla Ginsburg was a big-time television executive, and she had a great job, and she told me this story about how she got a promotion, she moves to California, gets the big house with the pool, and the nannies for the kids, the whole works, then comes a writers’ strike, and she loses the job.

And so, now she has to think about, “What am I going to do next?” And she says the only thing she can think of is she was always really interested in clothing design, and she’d always hoped to be, in her dream, her dream life was to be a television host. And she said the only problem was she didn’t know how to sew, she didn’t know how to design, and she’d never done television.

So, she, though, was in this struggle phase of, like, “What do I do next?” As she said, she was over 50 in a town that really prizes youth. Her old life, she could see, was fading away but she was in the midst of this struggle, saying, “How do I get to this new life?” And so, she went out, she bought a sewing machine at Sears, she Googled how to use it, and she Googled how to sew.

She Googled everything about design, she starts trying to put together these designs, and then she’s learning, she’s struggling, she’s hoping to get to this next step, and then she gets slammed again, that her son gets ill, he needs treatment. She no longer has insurance, and it’s one of those stop moments. He goes overseas, where her ex-husband is, to get treatment, and she follows.

She’s in a bar department, and this was her stop. She’s struggling, and now this is a dead stop. She is only there to be there for her son. And she said she was all alone, like while he was getting his treatments and such, she’s all by herself and she’s in a new place where she doesn’t know anybody. And she says, “You know, for some reason, during this moment, it was a dead stop, and yet,” she said, “my creativity just flourished.”

And she had all of these ideas about creating new designs and new ways that she could…she thought about the women who could use the designs for, particularly women in her age group, over 50 kinds of women, and she said it was the most creative period of her life. It was an amazing thing. Thankfully, her son recovered. She came back to the United States, she found a manufacturer, and fast forward to today, Marla Ginsburg is one of the biggest stars on Home Shopping Network.

She has a line called MarlaWynne. And PS, she is the face of MarlaWynne, so she, actually, made both of her dreams come true. She’s a clothing designer and she’s, essentially, a talk show host because you can find her on TV talking. And she’s awesome on TV talking about her designs. And it was an amazing thing to see for someone who went through such a struggle and had that stop that was just forced on her that was just horrendous, and yet that was…everything that happened to her was what allowed her to be what she considers the best expression of herself as a clothing designer and being on television.

So, so many stories work out in that manner. It’s been pretty amazing to speak to so many of these people from different walks of life.

Pete Mockaitis
Well, that is a lovely story, and it’s cool to see the pattern and the life cycle there. Could you share with us some mistakes, things not to do when we are thinking about making a switch and reinventing?

Joanne Lipman
Yes. So, one thing is if you read all of the traditional business books, they will tell you, you have to have the goal in mind and work backwards. So, if you read like Think and Grow Rich or any of these books that have been around for many decades, that’s how they lay it out but, in fact, that is a myth also. Almost all of the people that I spoke to, some had a goal in mind, but many of the people that I spoke to kind of had the sort of circuitous paths. They would never imagine that this is where they would end up.

And so, one thing is to really keep an open mind. One of the best examples of that, sports fans will remember Len Elmore, who was on the Knicks and on the Pacers and various other teams, big basketball star in the ‘80s. And Len, after he retired, he actually went on to Harvard Law School, he’s had an illustrious career both as a commentator and also practicing law and management in sports.

And his stop was he turned 65 years old and he just had this just series of terrible things. He was hospitalized, and he had a terrible illness, which he had a heart attack. He was let go from his sports commentating job. So, he’s 65 and, suddenly, he’s done all of these, had this great career, and, suddenly, he’s like, “Wait a second. Who am I? What is my identity? What can I do?”

And he said, “I felt like I had so much more to offer.” And he said, “You know what I did, instead of saying ‘Here’s where I want to go’” he said, “I sat down and I actually wrote down what are all of the skills that I bring to the party. And then I looked to see what are opportunities I never would’ve thought of that my skills matched.”

And guess what? He ended up being, now, and he is currently a Columbia University professor, which is not the career he ever thought he would end up in when he was playing for the Knicks, but all of his skills, the fact that he had this law degree and had practice, and the fact he was interested in social justice with athletes, and his knowledge of sports management, all of it rolled into becoming a professor and a scholar, which is, again, not where he thought his career was taking him.

And we saw that a lot, but there are also things that you can do, which perhaps we want to talk about. Things that you can do to help figure out where it is that you want to go.

Pete Mockaitis
Oh, sure thing. Let’s hear it.

Joanne Lipman
Yeah. Well, there’s a number but I’ll just mention three. So, the first is there is a concept that is called possible selves. This is a concept in psychology, a couple psychologists actually coined this phrase, and it means you’re imagining who you might be, who you might become. And that is something that a lot of people sort of felt was very helpful.

James Patterson told me that while he was an ad executive, he imagined himself as a bestselling novelist. It was the kind of thing, it seemed like a far-off dream. Marla Ginsburg did the same with thinking about being a clothing designer. But just imagining it isn’t sufficient. You actually want to do something. So, you want to either take some action as in a hobby or something.

But the second thing that I would say, because this ties in with this first idea of possible selves, is talk to what we would call, I’m calling an expert companion. Expert companion is somebody who knows you really, really well, who can reflect back to you what are your strengths that you may not even be aware of. Again, I saw this very frequently with people who, they’re so close to their own strengths that they don’t even see that they have them.

And then the third thing I would say is reach out to your network, particularly weak ties and dormant ties. And I think you’ve talked about this on the show before. Your most helpful career advice very often will come from, not from your direct circle – you kind of all know the same things and the same people – but from somebody who either you lost touch with, or somebody who you know tangentially. There’s been a lot of research that’s been done on this over the past 50 years. And for people who switched careers, the majority will tell you, it came through weak ties or dormant ties, people who you lost touch with.

There was a really cool experiment that was done fairly recently where executives were asked to reach out to try and solve a business problem that they had by reaching out to someone who they hadn’t spoken to in at least five years. And the results were quite remarkable. They were like, first of all, they got better advice than they got from their inner circle but, also, they just found that it was really gratifying to reconnect with these people.

And they also said, “It was also quite efficient because they could kind of pick up where they left off,” so you didn’t have that sort of awkward get-to-know-you kind of thing. They could kind of dive right into it. So, it was really a win-win for everybody.

Pete Mockaitis
That’s very cool. Well, Joanne, tell me. Anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Joanne Lipman
Yeah, you know what, there’s two things I want to mention, actually, that I came across that I think can be really helpful to people. I know you’ve done some shows about burnout. There’s a lot of burnout in this particular moment, and I think it is with the pandemic, it really did get people to rethink and reprioritize. And one of the things that I found, and I found this to be true in the research as well as with the people I talked to, is listen to your gut.

If your gut is telling you you’re not in the right place, listen. It turns out there’s a lot of research behind gut instinct, and very often your gut instinct is correct. And I would also say give yourself a break. This is also so important. When I talk about that stop phase, sometimes it was somebody who either shows to take a career break or had one forced on them when they were, let’s say, laid off.

And every piece of research will tell you that when you take that break, it is a way for your brain to reset, but also when you’re not so actively thinking and focusing and losing sleep over trying to solve a problem, that is when your brain is at its best. When the thoughts that are swirling around in your head can coalesce into some fabulous new idea.

And, by the way, and I think a lot of listeners probably know this, but you cannot say it enough that it’s so important, even during the course of your day, take a walk, take a break. One of the great pieces of advice I got was what we call the 90-minute rule. And the 90-minute rule is if you’re working on a project, you focus intensely on it with no distractions for 90 minutes. So, you turn off the cellphone and you don’t look at your email, you just focus on whatever you’re doing, this task at hand, for 90 minutes. But then, after 90 minutes, you must take a break.

And it doesn’t matter what you do during your break. You can go for a run, you can eat something, you can do whatever you feel like doing but you have to take that break, and then you can do another 90-minute segment. And you can do about three of these in one day and get far more work done than if you just, like, sit at your desk and stare at your computer for eight hours.

There’s the famous research that was done that Malcolm Gladwell popularized about you need 10,000 hours, but the professor who actually did that research on the 10,000 hours, that was only one piece of what makes you an expert. The other piece of it was exactly what I just talked about, which is that his research was on violinists that needed 10,000 hours to be an expert. But what these violinists did is they practiced for 90 minutes, they took a break, they practiced for another 90 minutes, and they did it no more than three times a day. So, it’s so important to take that break to allow your brain to reset.

Pete Mockaitis
Well, now, Joanne, could you share a favorite quote, something you find inspiring?

Joanne Lipman
Absolutely. I don’t know who said this but I repeat it almost every day, which is, “If something is bothering you, and it won’t matter five years from today, it doesn’t matter now.”

Pete Mockaitis
That’s good. And we heard about a favorite study, so how about a favorite book?

Joanne Lipman
So, favorite book, my favorite book of all time is Anna Karenina. However, I would say there’s a book that I absolutely love that I highly recommend called The Eureka Factor, and it’s by two academics, John Kounios and Mark Beeman, who are the reigning experts on aha moments, why they happen, and how you can have more of them.

Pete Mockaitis
All right. And a favorite tool, something you use to be awesome at your job?

Joanne Lipman
Yeah, one that I came across while researching the book is a CV of Failure. And I found that people who are highly successful, some of them, there’s an academic who I met along the way, who, she said the best thing she ever did was she sat down and created a resume, not of all her great successes, but of everything she failed at, every research project she didn’t get, or grant she didn’t get, and every rejection she got.

And she said it was really helpful in helping her understand, first of all, all the amazing things she tried, but also it helped her understand where her strengths were, and it actually led her to a different field of research. So, I love the idea of a CV of Failure.

Pete Mockaitis
All right. And a favorite habit?

Joanne Lipman
My favorite habit is definitely the 90-minute rule that I referred to earlier. I use it every day.

Pete Mockaitis
And is there a key nugget you share that really seems to connect and resonate with folks; you hear people quote it back to you often?

Joanne Lipman
Yes. Yes. I was once asked, “What advice would you give to your younger self?” and I said, “Exhale.” I hear that all the time. All the time. The idea that we get so caught up in our careers, and we worry so much about the future, and just if you exhale.

Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you point them?

Joanne Lipman
My website is JoanneLipman.com, and you can find Next!: The Power of Reinvention in Life and Work on Amazon or anywhere where you buy books.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Joanne Lipman
Two things related. First is if you have a hobby or an interest or something that you think possibly you might be interested in, take action, learn about it, talk about it, follow somebody in the field. And second, and so related to this, is be open to the unexpected. You never know where your interests may take you. And for the people who I interviewed for Next! so many of them ended up in places they never dreamed, and they’re so much more fulfilled in their careers because of it.

Pete Mockaitis
All right. Joanne, this has been a treat. I wish you much luck and many quality reinventions.

Joanne Lipman
Thank you, and you as well. This has been a terrific conversation.