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630: How to Work with a Boss You Don’t Like with Katherine Crowley

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Katherine Crowley says: "If you're feeling hysterical, it's usually historical."

Katherine Crowley discusses what to do when your boss is holding you back.

You’ll Learn:

  1. What to do when your boss gets under your skin 
  2. The 20 bad boss behaviors that drive employees nuts 
  3. The most important thing you can do when managing up 

About Katherine

Katherine Crowley is a Harvard-trained psychotherapist and career consultant. She helps individuals identify and tackle psychological and interpersonal obstacles to success. She assists with career assessment, developing a personal vision, improving interpersonal skills, and creating work/life balance. 

Katherine is also the co-founder of K Squared Enterprises, a Management Consulting firm dedicated to helping individuals and companies accomplish their business objectives while navigating the psychological challenges of working with others. She is the co-host of the podcast, My Crazy Office, which is a weekly workplace podcast dedicated to helping listeners navigate their careers. 

Resources mentioned in the show:

Katherine Crowley Interview Transcript

Pete Mockaitis
Katherine, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Katherine Crowley
Hi, it’s so fun to be with you.

Pete Mockaitis
Well, I’m excited to dig into your wisdom. And you also got your own podcast called My Crazy Office. Could you tell us perhaps one of the craziest office stories you ever heard.

Katherine Crowley
Oh, my gosh. Well, actually interesting, one of my most strange experiences was when I was working for a business owner, and she was running two businesses at the same time. And so, my entire workday consisted of finding notes passed under the door of the office that I work in, in her home, and fulfilling whatever the task was that was required, having no idea what the output was, you know, what the outcome of my work was actually creating, and rarely seeing her except once or twice every couple of weeks. So, that was a strange, that’s what we call an absentee boss situation but it was just so strange because I was living in this world where I don’t fully understand what went on.

Pete Mockaitis
Okay. Well, so you have logged a whole host of such boss behaviors, and you’ve got a great title in your book Working for You Isn’t Working for Me: How to Get Ahead When Your Boss Holds You Back. So, tell us, what’s the big idea behind the book?

Katherine Crowley
Well, actually, what’s interesting is that book, Working for You Isn’t Working for Me, came out of the first book we wrote Working for You is Killing Me, which was actually more about peer-to-peer managing up, managing down. And when that book came out, it was a national/international bestseller because it spoke to the pain of so many people. But the one thing that everyone told us, because Kathi Elster and I traveled all over the country giving talks and workshops about how to handle difficult people at work, and every lecture someone would come up and say, “You don’t understand. It’s my boss. That’s different. This person can fire me or demote me.”

And so, we realized that we needed to write a book specifically about dealing with the boss because what we learned was that people don’t quit jobs, they actually quit bosses. So, Working for You Isn’t Working for Me was about coming to terms with, “If you have a difficult boss, how do you manage them rather than waiting for them to manage you?”

Pete Mockaitis
Oh, well, there’s much to dig into here. So, let’s start with your four-step program for dealing with difficult bosses. Can you lay out those four steps and give us some examples of them in action?

Katherine Crowley
Absolutely. And the interesting thing is from the Working for You is Killing Me there’s a four-step of unhooking, and we apply the similar thing to the Working for You Isn’t Working for Me. So, I want to talk about the unhooking process because I think it’s very effective if you can do it. So, the four steps are that you unhook physically, you unhook mentally, you unhook verbally, and you unhook with a business tool. And that means nothing except that the first thing you have to realize is that you’re hooked. So, you know that a boss is getting under your skin if you find that you’re having physical, emotional, mental reactions every time you interact with this person.

And so, if you notice that you get a headache, that your stomach feels tight, that your shoulders hurt, that you have a hard time breathing, that you feel exacerbated after every meeting, you then can establish that you are hooked. Once you established that, then you can start to unhook. And the unhooking physically part, so let’s imagine the favorite tough boss, which is the micromanager, the super controlling, oversees everything you do, and doesn’t let you make any decisions on your own. If you had that kind of a boss, what you could do to unhook physically would be that you might, at the day’s end, work out, or go for a run, or go for a walk. You could splash water on your face, you could go for a drive, you could do something physically that helps you release the toxic energy that you may generate by having to deal with this person day in and day out. So, that’s unhooking physically.

Then, unhooking mentally has to do with kind of talking yourself off the ledge. So, let’s say your – this is very common – micromanaging boss insists that you report on every single thing that you do and everything your team does, and you find that to be just offensive. Unhooking mentally, after you’ve cooled your system down by physically unhooking, would be to ask yourself some important questions, like, “What’s happening here? What are the facts of the situation? What’s their part? What’s my part? And what are my options?”

So, going back to the micromanager, what’s happening? “This person is insisting that I give reports on a daily basis about what everyone is doing and it’s ridiculous.” What are the facts? “My boss is requiring this of me and it’s part of my job.” What’s their part? “So, maybe they’re super controlling. They don’t trust anything we do. It drives me crazy.” That’s the fun question to answer. But then what’s my part? And in this case, it could be that, “My part is that I’m taking their behavior personally, that I’m assuming that this person only doesn’t trust me, and that it’s all about not respecting my work ethic.”

So, then your options are, with a micromanaging boss, you could continue to resent them. That’s always…you’re allowed to do that. You could quit. You could badmouth this person and tell everyone how horrible they are and hope that they quit. Or you could say, “Okay, I’m working with someone who needs control. And so, what would happen if I just followed their requests and see if I can establish trust with this person?” So, that’s where you could get to by mentally unhooking.

Next, unhooking verbally is saying something to move the situation forward. So, with this boss, there’s a high-road and low-road verbal communication. Low-road would be, “I can’t believe we have to write these stupid reports. Don’t you think we can do our jobs?” High-road could be, “I understand that you’re concerned that we’re all on the same page, so let’s try this out and meet in a month and see if it really works as a system.”

And then, unhooking with a business tool is to pick from some kind of thing, whether it’s a procedure, a policy, a document, to complete the transaction. And so, in this case, you could say, you could send a follow-up email and say, “I understand that we’re going to be doing this reporting system for a period of time. I look forward to tracking it and seeing if it really works for you and open to feedback along the way.”

And so, now you’re taking yourself from the hooked part where you’re furious, you can’t stand the person, and you are in a powerful struggle with them, which is usually what happens with bosses that we don’t like, we get in power struggles, to calming your system down, finding viable solutions, and moving the situation forward.

Pete Mockaitis
And so, the business tool piece there, that was just sort of an email or are there different business tools? Tell us what you mean by that.

Katherine Crowley
It in this case it’s an email. So, business tools, what we’d say about those is those are…they’re actually, they’re always with you. They take the emotion out of a situation, because, so often, what happens with bosses and coworkers who drive us crazy is we take them personally, right? So, business tools, anything that clarifies the parameters of your work situation. It could be a job description. It could be company policies. It could be documentation. If someone does something over and over that drives you nuts, usually we just store the instance in our mind and feed a big ball of resentment. What you could do instead is document. That’s a business tool, to write down what happened, to describe the effects that it’s having on your job, to be clear about the costs that may come, that it may cause the company.

So, it’s taking whatever the situation is and looking, “What’s the business tool I can apply here?” whether it’s, let’s say, if someone’s a chronically late person, well, there may be time policies at your workplace that you could apply to the situation rather than feeling insulted by their tardiness.

Pete Mockaitis
Okay. Thank you. Well, so those are the four steps of unhooking there. And you’ve zeroed in on 20 of these behaviors that drive you bonkers. And so, I’d love to get a quick rundown of those if you can give us the cool 30-second version list of all 20. But I’d also, first, actually, I want to hear, you say that often these can even escape detection in the first place. So, can you tell us a little bit about the detect side of things?

Katherine Crowley
Yeah. So, detecting, that’s a very good question. What usually happens is we start to feel irritated. We start to get angry if someone starts to really bother us, and then we get into a whole tailspin, emotional tailspin, about what’s happening. Detecting requires that I look up from my situation, try to figure out “What is going on here?”

So, for example, if there’s a kind of boss that we would call a calculating confidant. And this is a kind of boss that would pull you in and ask you a lot of personal questions and look like they want to get to know all about you, and then use that information against you later on down the road. Of course, when that happens, it feels horrible and like betrayal, and, “How could this person do that?”

But if you actually detect or figure out that, “I’m working with someone for whom this is their style, this is how they operate,” then it gives you just a little distance so that you aren’t just feeling manipulated and poorly treated by this individual. So, does that make sense?

Pete Mockaitis
Understood. So, detected, in so doing you would sort of give a label and some distance, and you say, “Okay, this is not personal. They’re not sticking it to me in particular. This is just sort of how they operate and I hate it.”

Katherine Crowley
Right. Exactly. And if it’s something, like there are bosses who are chronically late. So, if they’re chronically late, to detect and understand that this is, again, this is what they do. It’s probably what they’ve done with every employee that they’ve ever worked with. Then it just gives you a little modicum, I think, of control that, “This is what I’m dealing with, not I’m doing something wrong and it’s driving me crazy.”

Pete Mockaitis
Okay. Well, can you give us the listing of these 20 bad boss behaviors because I’m sure we could talk for hours about them? But I wanna hear just the quick rundown like, “Okay, we got this and this and this,” so folks can recognize it in your telling.

Katherine Crowley
All right. So, I’ll just give you the list and then you can see what you think. First of all, we have categories. So, the first category is called the game players, head game players. And the top of that list is what we call the chronic critic. Then we have the rule changer, the yeller, and the underminer. Next category are the bigshots and the mother superiors. Under that we have “I’m always right,” “You threaten me,” grandiose, and control freak.

Next category is called the line crossers. These are the people who have bad boundaries. So, the first of those is lovestruck, next is the calculating confidant that I mentioned before, the tell-all, the first person who tells you more than you ever wanted to know about their life, and then the liar-liar. Next category is ambivalent leaders, and this is always interesting, I think. The first is the sacred cow, which I’d be happy to describe at greater lengths; the checked-out boss also known as the absentee; the spineless; and the artful bosses, the person you can never find in your hour of need.

Then, finally, we have what we call delicate circumstances. And that is the junior boss, someone who is younger than you, significantly younger than you; the former colleague, a colleague who gets promoted above you; the unconscious discriminator which is, these days, a very hot topic; and the persecutor. That’s the cast of characters.

Pete Mockaitis
Okay. Well, thank you. I think it’s handy just to have a sort of typology in terms of, “Okay. I recognize that.” So, we could talk about these 20 in depth. But, maybe, you could zero in on maybe one, two, or three of these that are both particularly demoralizing for people as well as super prevalent? So, there’s both a high frequency and a high intensity of damage, so let’s talk about those three in terms of how we deal with them.

Katherine Crowley
Yeah, I would be happy to. I actually want to start with the sacred cow, Pete, because this is one…what’s interesting is this is a boss who will feel so frustrating but they’re often like nice people. You know what I mean? So, a sacred cow is someone who’s been in their position for a long time, they’ve climbed up the ladder of the office, whatever it is, the company, whatever it is. They usually are…the people at the top are loyal to this person because they were loyal to them, and they’re now in a position where they probably don’t have the competence really to do anything significant. So, what they want to do is just toe the line, not make any ruffles, and just do a basic job but not cause any problems.

Pete Mockaitis
And so, in this instance, the boss is the sacred cow that a lot of people say, “Ooh, maybe I don’t want to cross them because they’ve historically been really good to me and…”

Katherine Crowley
That’s right. The sacred cow has friends, usually, at the top. They’re protected in some way. And so, what could happen is, let’s say you’re a very inventive or creative person and you get hired by this person, and as you’re getting higher, they’re saying to you, “We really need innovation in this department,” which may be true. But then once you get into the position, you experience that you are blocked at every step of the way. Any new ideas, they’ll say, “We’ve done that already. It won’t work.” They’ll ignore your best thoughts about how to solve a problem. They will tell you that upper management doesn’t want that kind of thing. So, they’ll do whatever they need to do to sort of put a road stop onto anything you’re trying to accomplish.

And for people who are real performers and who like to achieve and contribute, this kind of boss is deadly. Yeah, and so the thing with the sacred cow is that, going back to detect, the four Ds: detect, detach, de-personalize, deal. With the sacred cow, the first is to detect, like, okay, if you find out that someone has been there for many years, and they’re not going anywhere, and you keep pushing up against this person, which is usually what happens when you’re working for a sacred cow, you get in power struggles of constantly trying to push your ideas forward. Then you detect, you’ve got, “I’m working for a sacred cow. They’re not going to become comfortable with change. They’re not going to want to do anything innovative.”

Then the detaching would be, “Okay, this is not about me. This is about them.” And de-personalizing would be to say, “All right. So, this person is afraid of change, but maybe they need to look good.” Sacred cows still want to look good in whatever position they’re in. And so then, the deal, what can you do, would be to find out, and this is very hard if you’ve already pushed hard and been rejected and feel resentment, but the deal part would be to find out if there are any projects that the sacred cow is interested in, like things that they would love to accomplish if they had the ability, and get behind those ideas or try to make your ideas their ideas. So, if you’re willing to make the sacred cow look good, you may actually be able to make progress.

Pete Mockaitis
Okay. Thank you. All right. So, that’s a handy one then. Can we hear another boss here and how we’d approach it?

Katherine Crowley
Yeah. So, a commonly occurring and destructive, I would go to the very top of the list, which is the chronic critic. And it’s funny because we have another version of the chronic critic in Working With You is Killing Me called the pedestal smasher. And these are the bosses who have very high standards for everything, and often when they first bring you onboard, they tell you that you’re wonderful and that you’re finally going to solve their problems and that they really admire your work capacity.

Once you start working for this kind of boss, the chronic critic, they then begin to find fault with everything that you do. And so, they slowly start to erode your confidence because they can always find the wrong thing. One client we had who worked for a chronic critic used red highlighter, under-liner, even online with documents to show where the mistakes were. And, literally, it got to the point where the client was like, you know, they’d go to meetings with their neck in a brace because it was so hard to deal with this person.

So, they slowly can erode your confidence and, therefore, detecting as soon as possible becomes a really important thing when you find out, and you can always ask around to see, “Is this person, have they always been so critical of everyone or is it just me?” You detect but nothing. They don’t ever find things good enough because part of what they’re doing is trying to keep you below them so that you don’t threaten them, right? So, you detect that.

Then, again, detaching, realizing this is not about you. And chances are you’re never going to have the experience where they say, “You did an amazing job.” De-personalizing is, “Okay, so if that’s how this person operates, then my job is to continue along and try to create, try to do a good job but not take their statements personally.”

And then dealing would be to do your job, to go to other places to get recognition. So, you may want to join a taskforce, or go work with another department on a special project, or go outside and join a professional association. Nowadays, those are all happening in online and meetups and things. But you do something like that to pump up your confidence again so that you can figure out what your next best move will be.

Pete Mockaitis
Okay. Well, now, could you tell us an inspiring story of someone who did just that, they figured out, “Okay, we got a troubling thing in this behavior,” what they did, and then the cool outcomes that unfolded from that?

Katherine Crowley
Yes. So, actually, I can tell you about someone who worked for a sacred cow and it was actually for a very prestigious institution, he was very excited about the job, got there, and then had pushback for every single thing that he did. He was able to befriend that sacred cow after much frustration, a lot of hitting walls. He was able to befriend that sacred cow and found out that that individual, the boss, had a very specific project that she’d always wanted done but had never had the resources to do. He made it happen and, as a result, their department won an award, and he went on to be offered another job at another institution.

Pete Mockaitis
All right.

Katherine Crowley
So, there’s a good story.

Pete Mockaitis
Beautiful. And I’d also love to zoom in and hear sort of navigating these tricky situations, are there any particularly powerful scripts, phrases, questions, that you recommend and see are helpful over and over again?

Katherine Crowley
Yeah. Well, I think that’s such a good question. When we wrote, in both of our books, when we talk about talking to whoever the individual involved is, we always talk about how important it is to prepare yourself. Like, one thing that’s valuable, I think, actually in knowing, like, let’s say you know that you work for a boss who always has to be right, for example. And there are those bosses, so you don’t want to go into the conversation looking to convince them that you’re right. You would prepare for that kind of a conversation by thinking, “Okay, how can I join with this person and their approach?”

So, you could say to this individual, “I know your opinion is very important to me, and I know that you usually understand things in a way that I don’t, but here are my thoughts about doing X, Y, and Z.” So, you confirm the individual’s capabilities, you try to talk to them in a way that makes sense based on how they hear and reason with things, and then you make a concrete suggestion about how you can move forward.

Pete Mockaitis
Okay, cool. Well, now, can you tell us a favorite quote, something you find inspiring?

Katherine Crowley
My favorite quote may seem odd but it is by Hoagy Carmichael, a jazz musician, and it is, “Slow motion gets you there faster.” And I like it especially because in the digital age we’re all constantly running – I certainly am, I’m sure you are as well – and constantly on the go, and wanting things to happen quickly. And so, I find that quote “Slow motion gets you there faster” really helpful because it helps me slow down, focus on what needs to happen in the moment, and have patience with the process. I think that’s one of the biggest challenges in any situation, and certainly in a difficult work situation is to be patient with the process.

Pete Mockaitis
And now could you share a favorite study or experiment or bit of research?

Katherine Crowley
Yes. So, one of the studies that we did actually was for our third book, which was Mean Girls at Work. And there, we put out a request for any stories that women had about other women who they found difficult to work with. And what we were able to glean was that, I would say, 40% of the studies, or 40% of the stories rather, what was interesting was they were not about blatantly mean cruel individuals. They were what we call passively-mean situations where people were excluded, where they were taken out of an email link, where they were not asked to join an event, a work event, or even a social event, where they were contradicted at a meeting but in a nice way, it’s that sort of passive-aggressive looks like.

And so, we found that really interesting that 40% of the women who had difficult relationships with other women, it was more of a passive-aggressive experience, and it really informed a lot of what we wrote about in the book because women do a thing called tending and befriending. We believe we need to be nice to each other and yet what happens in the workplace, because we’re not that comfortable with direct confrontation, is that people end up tending, acting friendly, and then doing subversive things.

Pete Mockaitis
Well, thank you. And how about a favorite book?

Katherine Crowley
So, my favorite book is Eckhart Tolle, Towards a New Earth.

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

Katherine Crowley
So, I practice what we preach, so I will say that I do, on a daily basis, every morning I exercise and I write a list of what are my top three priorities. And at the end of every day, I also exercise again, and I practice gratitude. And I know that those things don’t sound like business tools per se, but those set the tone for the rest of my day.

Pete Mockaitis
And is there a particular nugget that you share that really seems to connect or resonate with folks, readers, listeners, they quote it back over and over again?

Katherine Crowley
Yes, there are two. And one is…

Pete Mockaitis
Nice job.

Katherine Crowley
So, I’m a psychotherapist by training, so one of the things that I will tell people is that, “If you’re feeling hysterical, it’s usually historical.” Now, I did not make that up but it is such a truism that whenever I say it, people are like, “Oh, my God, that’s so true,” because it’s not the person showing up late for a meeting. It’s probably the 35 times they showed up late, and the time they were late on a deadline, and the time, you know, whatever. And that’s a valuable statement just in the sense that, again, going back to the things we were talking about, unhooking, detaching, you have to calm yourself down so that you respond in a right-sized way to whatever the situation may be.

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

Katherine Crowley
I would point them to our website KSquaredEnterprises.com and also to our podcast which is My Crazy Office.

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

Katherine Crowley
Yes. My final challenge, actually my call to action is to whatever your situation, if there’s someone who is really bothering you, there are two things that you can do. One is that you need to stop and see whether you are in a power struggle with this person, because power struggles you will not win. The second thing is you need to consider whether you’re expecting this person to behave exactly the same way you do. So, it’s always important to examine your expectations. We often get furious of people who do things that you say, “I would never do that,” and yet the most important thing for figuring out how to work with people is to understand that each person is operating from a different set of expectations and behaviors.

Pete Mockaitis
Well, Katherine, this has been a real treat. I wish you luck and success, and hope that working with people is working for you.

Katherine Crowley
Thank you, and talking with you has been lovely for me.

629: How to Find and Use Your Strengths with Lea Waters

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Lea Waters says: "When you feel good, you function well."

Psychologist Lea Waters talks about tools you need to tap into your strengths.

You’ll Learn:

  1. The best way to tap into your strengths
  2. Why our strengths are often hiding–and how to find them
  3. The hack that halts anxiety 

About Lea

Lea Waters AM, PhD is a psychologist, researcher, professor, published author, internationally-celebrated keynote speaker and one of the world’s leading experts on Positive Education, Positive Organizations and Strength-Based Parenting and Teaching. 

Professor Waters is the Founding Director and Inaugural Gerry Higgins Chair in Positive Psychology at the Centre for Positive Psychology, University of Melbourne where she has held an academic position for more than 23 years. 

Resources mentioned in the show:

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Lea Waters Interview Transcript

Pete Mockaitis
Lea, thanks for joining us here on the How to be Awesome at Your Job podcast.

Lea Waters
Hey, Pete, thanks for having me.

Pete Mockaitis
Oh, I’m so glad to dig into your goodness here. But, first, I need to hear about the time you won a rap dancing competition.

Lea Waters
Okay, that was a long time ago. Well, firstly, you can probably tell from my accent, I am Australian, and I grew up in a very small little country town in Australia. The town had 800 people, now has 8,000, which is still a very small town, but 40 years ago we’re talking now. So, when I was 14, I went along to the local townhall on a Friday night, it was a sort of disco back then in the early to mid ‘80s, and they had a tap dancing competition, which I won, because I did the worm and I did the robot rap dancing thing, and I had just learnt the Michael Jackson moonwalk, and it was only just Michael Jackson that just sort of perfected his moonwalking.

So, I was able to do the moonwalk and the worm and some little computer robot dancing, and, somehow, I won this little local rap dancing competition for teenagers. I think I won a can of Coke, I know, and I won a…because back then we’re talking records, we weren’t even at CDs, let alone what we’re at now, so I won a little like 6-inch record of a local band in Australia who had done a remake of “Oh, won’t you take me to funky town.” So, yes, that was my prized possession.

Pete Mockaitis
Well, congratulations.

Lea Waters
Thank you.

Pete Mockaitis
I remember I won a karaoke contest when I was a teenager at a Relay for Life, a cancer fundraising event, and that were just good memories of just being ridiculous and cutting loose. So, hopefully, we’ll bring some of that fun and energy into this exchange.

Lea Waters
I hope so. Yes.

Pete Mockaitis
Even though we can’t see the dance moves.

Lea Waters
No, no, no. Well, you just got a little sort of you through the Zoom but, yeah, your listeners are probably better off not having seen me attempting to do that now as a 49-year old when I did it as a 14-year old.

Pete Mockaitis
Okay. Well, it seems like you’ve taken some of that positive goodness into your current career. You are an expert in positive psychology. Can you orient listeners who are not familiar with that term? What’s that all about?

Lea Waters
Hmm, sure. A great place to start too, Pete. Thanks. So, I’m a psychologist, been a psychologist for 27 years, and I’m also a university researcher in the field of positive psychology. And so, positive psychology is a subfield of psychology, and it distinguishes itself because it’s the science and practice of studying the positive end of the human experience.

So, we’re looking at, “How do we scientifically study and understand and, therefore, amplify joy, wonder, curiosity, or love, compassion, empathy, altruism?” It’s a strength-based science so it’s really focusing on, “Who are we at our best? What are the inherent strengths that we bring to work, bring to our life outside of work, bring into our teams? And then how do we use those strengths to sort of be at our best to be pro social and help other people, and to help ourselves and our team reach our full potential?”

Pete Mockaitis
Okay. Well, amplifying some of those things sounds certainly pleasant. I would enjoy that and really the course of experience in life. Can you also share with us a bit of the case associated for how that helps folks be all the more awesome at their jobs?

Lea Waters
Okay. So, what the science tells us, and, look, honestly, even as I’m saying this, people just know this intuitively. When you feel good, you function well. When you are able to bring the best of yourself to work, when you’re in a position where you can utilize your unique strengths, the things that give you energy, the things that sort of come easily to you, the things that you are sort of self-motivated to do, that’s going to flip into higher levels of performance, productivity. And it’s really sort of challenging this assumption about, “How do we create improvement in ourselves or in our work team or in an organization?” because most of us, Pete, were sort of raised on this assumption that improvement is a process of fixing what is wrong with us.

So, let me give you a scenario. Let’s just say that you and I did work in the same workplace, and I happen to be your boss, and we’re passing each other in the hallway, and I stopped for a minute, and I say, “Hey, Pete, can you make an appointment with my assistant? I want to catch up on Friday afternoon because I’ve got some areas of improvement that I’d really love to talk to you about.” What do you think would be the first sort of response inside your head when your boss says, “Come and have a meeting with me to talk about some areas of improvement”?

Pete Mockaitis
“Oh, I’m screwing some things up, and so I’m kind of on high alert now.”

Lea Waters
Exactly, yeah. So, we’ve all been conditioned to think that improvement is this process of fixing what is wrong with us. And so, we have that scenario and you immediately think, “Oh, goodness. What have I done wrong? What do I need to fix? What’s not going so well?” And yet improvement can also be a process of building up and amplifying what is right about us.

So, unbeknownst to you, I actually want to meet with you on Friday because your sales figures are through the roof, and I’m like, “All right, if he’s already at this level, and this is clearly a skillset of his, if we can figure out what and why he’s doing so well, and we can improve that, he’s going to sell even more. If we can then figure out his sort of secret sauce and get him to help his fellow teammates, then we’re doing better.”

And so, our natural inclination is to sort of engaging improvement by fixing what is wrong with us. And I’m not saying we shouldn’t do that. We still need to look at areas of weakness and faults and flaws, and try and sort of shore those up. But what does science shows us is that you can spend a lot of time working on a weakness, and you can improve it, but it’s never going to turn into a strength. A weakness is never going to turn into a strength. You can improve it up to a point of a level of proficiency, but beyond that you’re better off just spending your time actually working on what are the strengths, what are the things that come naturally to you, what are the things that you enjoy doing, you get energy from, you perform well.

Pete Mockaitis
Okay. Well, so understood. Well, then I’m curious, when it comes to these strengths, well, first, let’s zero in on how does one identify them?

Lea Waters
Yeah. There’s a number of different ways you can identify your strengths, and the most obvious way is surveys. There’s quite a lot of surveys out there that allow you to identify what your unique strengths are in a workplace but also outside of work. So, many of the listeners here are probably familiar and they may have done these kinds of surveys at work that help you to identify where are those areas of self-energy and self-motivation. And I do have a free survey on my website, if people want to go to that, and sort of get a start on using a survey to identify.

More deeply than a survey, it really is about tuning into yourself and looking at where are those moments where you get into flow, you have high levels of energy. There’s a quick learning curve, so it’s a skill or a process that you’re able to learn with relative ease and more quickly than someone else. Where are the areas where you seem to learn quickly, do it a little bit better than anyone else? And also, as I mentioned just, you’ll know a strength because this is energizing.

When we use our strengths, using your strengths gives you more energy. When you’re using a weakness, it’s exhausting, it’s depleting. Often, when I run my workshops, for example, I ask people or invite people, “Pick up your pen with your non-dominant hand, and for the next few minutes, when we do this exercise, use your non-dominant hand.” It’s always quite amusing, Pete, because you see people with their tongue out and their brows are really kind of furrowed, really concentrating on, “How do I write with my non-dominant hand?” And it’s a slower process, it’s frustrating, it’s messy, you don’t perform as well.

And then I say, “Okay, now swap back to your dominant hand.” And it’s a good example of the energy and effort that’s required to build up a weakness in contrast to leaning towards using our strengths more often. So, we can identify our strengths through surveys, we can identify our strengths just by tuning in and saying, “Where are the areas where I feel energy, where I have passion, where I perform well with relative ease, where I’ve got a fast learning curve?”

But another key way of identifying our strengths is through social mirror. And what I mean by that is other people are a mirror to us for our strengths. So, tuning into or deliberately asking, intentionally asking other people, “Where do you see my strengths?” having those conversations at work where you’re engaging in this technique called strengths spotting.

So, strengths spotting, as the name would suggest, is just a technique of looking at where you see the strengths in other people and acknowledging those, “You know, I really love your curiosity, Pete, and the way that you’ve come to this, and you thought about the questions beforehand, and you’ve done a little bit of research. So, that says to me that you’ve got these strengths of sort of curiosity, and love of learning, and being organized, and wanting to share things with other people.”

So, using, allowing other people to be that social mirror, because the research shows us that, for many of us, we have this phenomenon called strength blindness. And strength blindness, as the name would suggest, is that we can become a little bit blind to our own strengths, sort of an interesting and cruel irony because our strengths are partly nature and partly nurture. And what the developmental psychologists have shown us is that we’re all born with our own unique kind of inherent strengths potential.

Some of you were born with the gift of the gab. You’re really, really good communicators. Others of you were just born with the natural ability, for example, around math. Some people are really, really good at problem-solving. Some people just have those really natural kind of social intelligence skills. And so, because we’re born with our strengths, and then the environment helps us to cultivate them, we can end up having this experience of strength blindness.

Because if you were born as a person who could do math fairly easily, or have very good organization skills, or great people skills, when you’re utilizing those skills and utilizing those strengths, they’ve come so easily to you and they’ve been with you your whole life, so you don’t think of them as an asset. You don’t realize that, “This is actually a strength. This is something that I’ve got that other people don’t necessarily have.” So, we become blind to our own strengths. And that’s why using your work colleagues, your friends outside of work, as that social mirror is a sort of third key way of finding out what our strengths are.

Pete Mockaitis
Okay. And now when you talked about the surveys, I know about StrengthsFinder, which I think is great, and so you’ve got yours. You talked about the left hand, right hand assignment, I thought about Myers-Briggs. I’ve done the exercise in many workshops. I’ve facilitated as well. But what are some of your other just total favorite tools in the survey realm that really elucidate this for people?

Lea Waters
There’s a fantastic survey called the VIA survey, V-I-A, and it stands for values in action. And what I like about that survey is it’s based on our strength of character. So, strengths are kind of coming to broad back. So, we’ve got our strengths of talent and then we’ve got our strengths of character. So, strengths of talent are performance-based, they’re observable. You can see if someone is a fast runner, you can hear if they’re a gifted debater, you can see if they’re a gifted artist, you can taste if they’re a gifted chef.

The VIA strength survey identifies that second bucket which is our strength of character. So, where our strengths of talent are observable and performance-based, our strengths of character are personality-based rather than performance-based. And, in a way, they’re less observable because they sit inside us. So, strengths of character include things like courage, perspective, wisdom, kindness, humility. So, these are not necessarily observable. They’re positive strengths, positive aspects of our personality that sit inside of us, and come out through our choices, through our decisions, through the way we relate to other people.

And so, that VIA Character Strengths, that survey that I’m talking about focuses on those inner assets, the character strengths. And I also like because it’s free, and it’s been around for about two decades, and it’s been validated, and it’s got population norms, it’s been validated and translated into 20 plus different languages, so it’s a really, really useful survey for our listeners to go in and have a look at. And you can do it as a team within your workplace and sort of identify, “Well, what are the unique constellation of this team? Who’s got humor?” which we really kind of need right now during COVID times, “Who’s got perspective? Who’s got grit? Who’s got those fantastic sort of curiosity, love of learning, problem-solving type skills?”

And I also love it because, for any of the parents who are listening, there’s a youth version. So, if you have younger kids, they can also do the equivalent survey so you can have that conversation at home, of like, “Well, these are my strengths, as mom or dad, and these are my children’s strengths.” So, that’s a lovely family bonding thing to do.

And there’s another survey that I’ll mention, too, which comes from the UK called Cappify, C-A-P-P-I-F-Y. What I really like about that particular survey is that it also identifies your weaknesses. So, a lot of the strength surveys are really nice because we have this strength blindness where we’re not so good at identifying our own strengths, we’re all pretty articulate when it comes to identifying our weaknesses. When it comes to identifying our strengths, we don’t have that same level of knowledge. So, strengths surveys are really useful for that. But what I like about Cappify is that it gives you your strengths and your weaknesses so you sort of got that balanced profile. And it also identifies this third category called learned behaviors.

And, for me, that was something…that was a real sort of epiphany moment because our strengths, in order for something to be a true strength, so normally if you ask someone, “How would you define a strength?” And most people would say, “Strengths are the things I’m good at,” and, yes, that’s absolutely true, but it’s only part of the answer. So, psychology research tells us that a strength is something you are good at, but it’s also something that gives you energy and you’re self-motivated to do.

And why it’s important to have those sort of three elements of a true strength is because there’s lots of things that we grew up to be good at. We grew up to be good at them because it’s expected of us, because it’s part of our role at work, because we were praised by parents, teachers, our boss, so we have that performance element, and we mistake it as a strength. And in the Cappify research, what they would say is it’s not actually a strength. It’s a learned behavior. You’ve learned to be good at it. You’ve got the performance element of it but it’s not giving you energy, and it’s not something that you would choose to do. You’re not self-motivated to do it.

And, for me, that was a real eye-opener because, in my role at the university, I was being asked to chair a lot of projects and a lot of sort of committee meetings, and so, over time, I’ve learnt to become good at that. A quick meeting is always a good meeting as far as I’m concerned. We set an agenda, I’m a trained psychologist so I’m reasonably good at sort of group dynamics, and people would leave those meetings and say, “Oh, that’s such a strength of yours, Lea.” But I would leave those meetings feeling quite depleted, quite de-energized, and thinking, “Oh, God, all right. Well, I got through that. Now let’s get back to the things that actually give me energy at work.”

And so, I learnt through the Cappify that, yes, I was good at chairing meetings, I had the performance element of it, but I do not have the energy or the self-motivation piece behind it, so it wasn’t a true strength. It was perceived as a strength by others. But when I started, “That’s not actually a strength of mine,” it was helpful for me to say, “Okay, I need to know that when, if I can, when I’m structuring my week, if I’m chairing a meeting that the hour after that is time-tabled for something that is going to re-energize me, something that using my natural strengths. And, for me, that’ll be research and writing, or working with my students, or going out and doing some corporate work because that’s what gives me my energy back.

Pete Mockaitis
That’s great. All right. So, we’ve got some good views for strengths, what they are, how to find them, why we’re better off trying to improve those than work on a weakness forever. So, let’s shift gears a little bit over to some of the other tools in the positive psychology toolkit. If folks are feeling an extra dose of stress and anxiety and blah in the midst of pandemic, or even, hey, months, years after the pandemic, what are some positive psychology tools that are ideal for this challenge?

Lea Waters
I love that question, Pete. We’re all, I think, so many of us have got just this classic case of mental fatigue because we’re way too many months into a global pandemic, and we’re tired, and we’re working from home and we’re stressed, and it’s playing out in our body. So, I guess, one of the questions is, “To what degree do we engage in stress management? And then to what degree do we say, ‘Okay, I can only do so much to manage my levels of stress. I’m going to turn my attention more towards boosting my positive emotions.’”

And so, there’s lots of things that we can do in positive psychology. Savoring, ecotherapy, the use of laughter, capitalizing on these sorts of micro moments of positivity. These are all about amplifying the positive moments that are still in our day despite everything that’s going on. And I can go into the detail of some of those for us in a moment. But then, also, one of the things that positive psychology does is recognizes that we can gain from adversity, that positivity can come out of negativity. And, in fact, you can’t really appreciate the feeling of warmth until you understand the sting of the cold. The two things kind of go hand in hand.

So, we can definitely talk about amplifying those positive moments but I think one of the other things that positive psychology science really lends to us right now in the moment of this sort of global crisis is techniques on how to better handle those negative emotions. So, mindfulness, how to grow from adversity, this notion of post-traumatic growth, or adversarial growth, and how to practice self-compassion. So, take your pick, Pete, because we really got a whole list of things in the field of positive psychology that we can do.

Pete Mockaitis
Well, so we’ve talked about savoring a couple of times in the show. So, ecotherapy, what is this?

Lea Waters
Yeah, lovely. Okay. So, ecotherapy is basically having an intentional relationship with nature. So, that can be things like using urban spaces, going for a walk around your neighborhood, going to the local park. It can be getting out into nature reserves if you have some that are close to you. It can be as simple as going out and looking at the skyline at the end of the evening. Plant therapy, so saying if I have a garden outside, I’m going to do a little bit more gardening at the moment, or I’m going to setup a little plant wall or an indoor area for plants. Even using wood, wooden materials.

And so, this kind of broad idea of, “Let’s connect back with nature,” is really, really helpful to us all right now during COVID. In fact, some of the research is now coming out to say that we must have this in-built wisdom because there’s a lot more people now who are going out, exploring their local neighborhood, connecting back with nature in various ways. And what’s important about that is that when we do connect with nature, whether it’s real nature, as in sort of a wildlife park or whether it’s using our urban spaces or plant therapy or just looking up at the sky and looking at the clouds, when we do that, it changes our physiology.

And what the research shows is that even within five minutes of intentionally connecting back with an outside space, intentionally taking your shoes off if you go to your local park, take your shoes off and feel what it’s like to have grass and earth on your feet, that when we do that, it triggers our relaxation response in our nervous system. Your heartrate decreases, your parasympathetic nervous system starts to kind of get activated. And so, the parasympathetic nervous system is the nervous system that helps to calm us down, have good digestion, clear our mind of cortisol. So, ecotherapy is such an important thing for us all to be doing during this time.

Pete Mockaitis
And I’d love to get your take on, let’s say I’m in Chicago, winter, cold, a lot of parks, etc., shut down, what are some…I like the notion of using wooden things because it’s sort of like, “Okay, I can do that anywhere no matter what their restrictions are.” Any other goodies like that?

Lea Waters
Yeah, okay. So, using wood plant therapy, I can see a plant right behind you, Pete. So, bringing some plants into…getting some indoor plants, and saying, “Okay, over these really chilly winter months, my focus is going to be on taking care of this plant.” Skylines, like I said, anything to do with skylines. So, even though it’s very ridiculously cold where you are, sort of getting out onto your balcony, ragging yourself up so you pretty much just got your eyes that are showing, but spending that five minutes at the end of the day watching the sunset, feeling the…

Anything to do with water as well, even though it’s water inside. Water is a part of nature so connecting ourselves with water intentionally, doing that through showers, footbaths, hand baths. We have to wash our hands a lot at the moment because of biosafety and hygiene measures with COVID. So, instead of just washing your hands, do it intentionally, really experience the flow of water, use it as a kind of mindfulness hack in that moment. So, tuning into, “How am I feeling? What does it feel like to have water sprinkling on my hands? What does it feel like as I’m sort of patting my hands dry with a towel?” So, giving myself a little kind of emotional vacation for that minute as we’re washing our hands.

And then even short of that is nature apps. So, there are quite a lot of apps out there now where you can listen to the sound of water, you can listen to the sound of clouds, you can listen to the sound of rain, birds, etc. So, obviously, it’s not quite the same as being out in a nature reserve but it still has that physiological healing benefit for us.

Pete Mockaitis
That’s great. Okay, thank you.

Lea Waters
A pleasure.

Pete Mockaitis
So, now let’s talk about dealing with stuff that isn’t so pleasant. What’s the post-traumatic growth concept and how can we do more of that?

Lea Waters
Post-traumatic growth is, I mean, we all know about PTSD and the fact that if we go through adversity or a trauma, it can compromise our ability to cope, and it can lead to sort of more permanent stress. So, post-traumatic growth is sort of the positive opposite of that, and it was borne initially out of psychology research that was looking at PTSD and how it is that we can help people who have experienced a trauma or adversity or grief or loss, how it is that we can help them to go from a weakened state and adapt back to their sort of level of happiness and functioning that was there prior to the trauma or the adversity.

And as psychology research was studying, “How do we help people diminish and manage PTSD?” what they identified was that there was a certain percentage of people who had been through that same experience, that same loss, that same trauma, and were not only…this is going to please…I’m going to apologize in advance for some bad grammar here, but they were not only not experiencing stress, they were actually saying, “Look, I wouldn’t wish this experience on my worst enemy, but I’ve actually grown. I’ve grown as a result of this experience. I have a different perspective on life. I’ve got different priorities now. I’ve learnt that I can handle more than I thought I could. I found out really who my true friendships were and what it is that I want to move forward, spending my time on.”

So, this was a curiosity for these psychologists because they hadn’t really considered their role about, “How do we help people deal with the negatives of trauma or adversity or stress?” And, it turns out, that there are some people who not only didn’t have the negatives but have this positive. And so, that was kind of the origins of post-traumatic growth. It’s been studied a lot since then, and it’s really relevant for us all right now because so many of us are going through trauma and stress and adversity.

And just to know that this doesn’t have to permanently affect us in a negative way, that if we approach this adversity by asking ourselves, “What can I learn from this? How can I grow from this? What strengths do I have to bring to this situation? How can I learn that, in the midst of a lot of darkness, there are still these small little pockets of light? How can I help myself develop those skills to look at those things?” then we come out of that with a different skill set.

And we also come out of this experience knowing, “Okay, that was not a great experience. There was a lot of adversity, there was a lot of distress but I learnt about myself, I learnt that I’m stronger than I thought I was. I learnt to let go of some of those small issues that I used to put a lot of energy into and stress about. It’s not important to me anymore. I’ve changed my priorities.” And we’re seeing that already, Pete.

There’s a psychology research that’s coming out now through the pandemic is showing that people are saying, “This is a distressing experience but I’m enjoying more downtime, I’m enjoying time with my family. I’ve made more of an effort to stay connected with my friends even though it’s a virtual connection. I’ve learnt something new about my colleagues that I didn’t know.” So, we’re coming out with some positives through this. And, individually, a big factor that influences whether you come out of adversity, having grown, is the questions you ask yourself, is the way you frame that adversity in the moment.
It’s not about denying the adversity by any means but it is about saying, “Okay, this is really hard. I’m tired today. I can’t understand why I’ve got brain fog. I can’t think clearly. I’m feeling overwhelmed. What am I going to do about this?” It’s not about ignoring it. It’s about acknowledging, and saying, “Oh, okay, what meaning can I make from this? How can I grow from this? And what can I learn about myself? Maybe what I can learn is my limits, and I need to know. So, pushing myself as hard as I used to,” for example.

Pete Mockaitis
Well, so then it sounds like these are all productive questions, “What can I learn from this? How can I grow from this? What meaning can I make from this?” Maybe the hard part is just sort of shutting down the alternative voice that can crowd out those questions before they start, like, “Oh, I was stupid. What was I thinking? Aargh, this sucks. I hate this. I want it to end right now.” So, any pro tips for, right in the heat of battle, how do we kind of head that off with a pass and shift gears into the more helpful questions?

Lea Waters
I think there’s two ways to go with that one, Pete, and one is mindfulness and the other is self-compassion. So, let’s start with mindfulness, and I think mindfulness helps you to slow your brain down, have that moment of perspective and pause where you can hear what the inner voice is saying, and so you’re able to catch that inner voice more quickly, and then make a decision, “Do I head off that inner voice or do I just show compassion because it does suck?”

What we’re going through does suck, Pete, and we do have our own overlay on top of that of, “I’m not good enough. I’m not getting enough work done. I’m not managing my time well enough. I’m not being a good colleague. I’m not being a good parent. I’m tired all the time.” And so, sometimes it’s about heading off those thoughts and then going on to those more constructive questions, and other times it’s actually more about that moment of self-compassion, which is a big area of study in positive psychology. And it’s about sort of reversing the Golden Rule and turning it back onto yourself, “Do to yourself,” and be kind to yourself and have that moment of mindfulness where you’re recognizing, “I’m struggling right now. I’m not feeling so good right now.”

And giving yourself that same compassion you would give to your colleagues or your friends when you see that they are struggling. So, just witnessing that struggle, embracing the suffering, “I’m tired. I’m distressed. I’m fearful. I’m fat, ugly,” whatever comes to you in that moment, and just being with it, and saying, “I’m sorry that you feel that way. Like, I recognize that you feel that way right now.” So, being in that moment, having that mindfulness, showing that sort of self-kindness, that self-compassion. And a big part of compassion is embracing the suffering but not feeling lonely in the suffering.

And so, recognizing that we’re all…everyone struggles, everyone suffers in their own way. Right now, that’s easier to see because it’s a global pandemic, and so we’re having this kind of shared struggle. But recognizing that, “I’m not alone and there are other people who are going through this,” and engaging in self-soothing techniques. Those self-soothing techniques can be just as simple as, like I said, that inner voice that says, “Oh, you know what? Yeah, you’re really tired. Maybe we can go to bed early tonight.” Or, self-soothing through ecotherapy that we talked about before. Self-soothing by reaching out to a friend.

One of the really basic parts of self-soothing is actually holding yourself. You can emotionally hold yourself but physically holding yourself, it seems like a funny or silly or embarrassing thing to do, but, literally, like wrapping your arms around your shoulders and giving yourself a hug in that moment, or patting yourself on the back. Or, a big one, and people tend to do this quite naturally, and you’ll often watch, our little kids will do this too, they do it quite naturally. So, getting your hand and just gently rubbing from your ear down to your shoulder blades, so rubbing that kind of right side of your neck, because what’s sitting underneath that right side of your neck, if you rub from your ear sort of down the right side of your neck and across your shoulder, is the vagus nerve, and that’s a major nerve that helps communicates between our brain and our digestive system, but also helps to calm us down.

Pete Mockaitis
So, this would be the right side and not the left?

Lea Waters
Right side, yeah.

Pete Mockaitis
Our right. It’s like I’m looking forward, I got my right eyeball, and it’s…and I’m on it, all right.

Lea Waters
Yeah. So, just gentle self-touch that’s why going back to that hand massage, when you’re washing your hands and having that moment of mindfulness. And another key self-soothing technique is helping yourself to laugh. And laughter doesn’t mean that you’re ignoring that we’re in the middle of a global pandemic, or whatever it happens to be. I had the very sad loss of, I lost my sister a couple of years ago, and she has a son, and we had that sort of moment a couple of weeks after she had died, and we’re deep in grief and just missing her so, so, so desperately.

And my nephew, who was 20 at that time, said a joke, and, honestly, it was dark humor but it was this funny little moment of like “How mom would’ve felt about this particular thing,” and we both cracked up laughing. But then he looked at me, and I could see he had this like feeling of this flash of like guilt, like, “Oh, was I allowed to do that? Was I allowed to have this moment of laughter?” in his really intense deep grief, and I was able to sort of look at him, and say, “It’s okay, mate. You’re allowed to. We’re still allowed to laugh even in the dark times.”

And so, for me, at the moment, I’m very intentionally looking at funny YouTube clips, funny memes. I’m asking my friends, “Anything you see funny? Like, pass it my way,” because in that moment of laughter, that changes our brain chemistry. Laughter triggers endorphins and it triggers dopamine. Laughter also resets our nervous system and, particularly, if you’re having that big belly laugh. When we laugh, our ribcage expands so our diaphragm expands as we’re sort of engaging in that laughter. And the reason that it does that is because, when we laugh, we exhale more forcefully, so we, “Ha, ha, ha.”

Because we’re exhaling more forcefully, we’re actually releasing more air, and so our lungs take back in, they have to kind of counterbalance by taking back in more. And because we inhale more deeply, it expands our thoracic region and it expands our ribcage. And why that’s important is because when we’re expanding our ribcage through laughter, the body’s intuitive system means that the expansion of the ribcage and its thoracic system, we’ve got a whole lot of nerves that run through that area. And so, it’s like the ribcage talks to the nerves, and says, “Hey, we’re expanding and we’re laughing and we’re happy.” And what that does is it triggers a relaxation response in our nervous system.

So, laughter changes our brain chemistry and it gives us endorphins and dopamine. It helps our brain but it helps our body because it talks to our nervous system. That’s why when you have that laugh, you have that really big belly laugh, and then you kind of sigh and kind of sit back in your chair, and like your shoulders kind of drop. And so, I’ve listed a whole bunch of self-soothing techniques there, Pete. I don’t know if there’s anything you want to sort of go into in more depth or…?

Pete Mockaitis
Oh, no, that’s lovely. Thank you. And I’m just sort of imagining in my own mind’s eye how to enhance that all the more, like, “And do it in a bathtub or do it with a great blanket and space heater,” kind of whatever, just make the most of it.

Lea Waters
Yeah, absolutely. And the bathtub gets us back to the ecotherapy, and the blankets get us back to self-soothing and touch, particularly for those listeners who are experiencing heightened anxiety at the moment, and that’s really common for a lot of us. In fact, the sort of global research is coming back to show that, on average, people across the globe are experiencing sort of double the amount of anxiety than they were pre-pandemic. And I’m a person who struggles a lot with anxiety and always have all throughout my childhood and adult life, so my anxiety has really, really spiked at the moment. And touch is a really, really important part of helping to reduce our anxiety.

So, it can be that self-touch that we talked about before, washing our hands, massaging your vagal nerve, giving yourself a hug. But if you have a pet, hugging your pet as much as possible because that also releases oxytocin. And oxytocin is a neuropeptide. It’s a hormone that’s known as the love hormone or the bonding hormone. But when we have oxytocin, through touching ourselves, through touching another person, so hugging family, friend, obviously at the moment we’ve got physical distancing so you can only kind of hug those people that you live with or you know are safe, like pets. But you mentioned blankets.

So, blankets and pillows also create touch, and they calm our nervous system, and particularly weighted blankets. There’s some really interesting research now on weighted blankets. And weighted blankets, being helpful, if you are struggling with anxiety. Sleeping under a weighted blanket helps you feel safe, and it puts an extra level of just sort of weight onto you, which, again, sort of talks to your nervous system and helps to calm you down.

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

Lea Waters
No, I think we’ve covered a lot. I would probably just circle back to there’s lots of techniques to use. What has to underpin that, I think, are these sorts of three more enduring approaches. The first approach is the strength-based approach. So, identifying what our strengths are and how we can bring them into…how we can use our strengths to amplify our life when things are going well, and how we can bring them into times of challenge, in times of adversity. I think it was Winston Churchill who said, “Never let a good crisis go to waste.” So, how can we come out of this, utilizing and knowing our strengths? So, that’s kind of the first approach.

Then the second one is just this idea that, “I can grow from this actually. That recent past that make me feel bad, I’ll have moments of distress, I’ll have days where I’m tired and I’m struggling, but I can come out of this with new priorities. I can come out of this with closer relationships. I can come out of this recognizing that I’m stronger than I thought I was.”

So, coming out with going in, and being in this experience, knowing that I can grow from it using our strengths, and then that third kind of underlying approach, which I think, at the moment, is just being compassionate to ourselves and others.

Pete Mockaitis
Well, thank you. Now, can you share with us a favorite quote, something you find inspiring?

Lea Waters
A quote?

Pete Mockaitis
Mm-hmm.

Lea Waters
Yeah. I’ve really been living on quotes this last seven months during the pandemic. So, I started with Dr. Norman Vincent Peale. The quote was, “Tough times don’t last, but tough people do.” I was like, “Yeah.”

Pete Mockaitis
All right. And how about a favorite book?

Lea Waters
Whoa, I’ve so many favorite books, I don’t know which one to say. What would be a favorite book of mine at the moment? I am re-reading Charles Dickens.

Lea Waters
I do have A Tale of Two Cities.

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

Lea Waters
I have a website which is LeaWaters.com. And remembering that my name is spelt L-E-A so LeaWaters.com. And please follow me on socials, Insta, LinkedIn, Facebook, Twitter. I’m putting a lot out at the moment on just these basic little small micro-techniques that we can use to help ourselves cope with stress and amplify the best of us, our strengths and positive emotions, during this difficult time.

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

Lea Waters
I think our final challenge right now is know your strengths, use your strengths, and go to work tomorrow and be that strength mirror for someone else. If you see someone using a strength, call it out, acknowledge it.

Pete Mockaitis
All right. Lea, this has been fun. I wish you lots of luck and positivity in your adventures.

Lea Waters
Thanks, Pete. It’s been a pleasure to be on the show.

628: How to Stay Challenged and Grow Your Career with Daniel Scrivner

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Daniel Scriver shares insights on how to develop your career from his experience as a college dropout turned designer turned CEO.

You’ll Learn:

  1. How to develop new skills through self-teaching 
  2. Why Daniel left a dream job at Apple
  3. Why you should always seek discomfort 

About Daniel

Daniel Scrivner is the CEO of Flow. Previously he was the Head of Design at Digit and Square. He’s worked for some of the most respected brands in the world including Apple, Nike, Disney, and Target. 

Daniel advises world-class teams at companies like LendingHome, Empower, TrustToken, Designer Fund, and Notation Capital. He’s an early-stage investor in businesses like Superhuman, MixMax, Notion, Good Eggs, Burrow, Madison Reed, Stance, Almanac Brewing, and many more. And he’s been invited to speak at some of the world’s most prestigious organizations including Andreessen Horowitz (A16Z), General Assembly, Techstars, Designer Fund, and 500 Startups. 

Resources mentioned in the show:

Thank you, sponsors!

Daniel Scrivner Interview Transcript

Pete Mockaitis
Daniel, thanks for joining us here on the How to be Awesome at Your Job podcast.

Daniel Scrivner
Thank you so much for having me on, Pete.

Pete Mockaitis
Well, I’m excited to dig into this conversation not the least reason of which because you have the fanciest microphone a guest has ever brought onto the show. Can you tell us the backstory of why you have such a piece of equipment?

Daniel Scrivner
Yeah, sure. So, I actually started recording my own podcast a few months ago and was debating in my mind kind of, as everybody does that cares about audio, what sort of a setup to get. The microphone that I use is the Neumann U 87. And I don’t have a great reason for that. I mean, just the only thing that I would say is, in my life, if there’s something that I enjoy, I never feel bad about buying, going for quality if I know that I’m going to use it for a really long period of time, and this seems fit to that vein.

Pete Mockaitis
I hear you. Okay. Well, I love it. So, I also love your story, so it’s pretty wild in terms of so you went from a dropout experience all the way to becoming a CEO with some exciting adventures in the middle. Can you please tell us the story of your climb and maybe the most compelling lessons along the way? And we’ll have a little back and forth as we do so.

Daniel Scrivner
Oh, sure. And I’ll try to keep it brief and feel free to jump in any time. But, yeah, as you alluded to, I definitely have an unconventional background. But what’s funny is it makes a ton of sense to me, obviously looking in hindsight, but when you said the words “the climb” I don’t know why but I don’t feel like it was really that. I guess that for just a little bit of context, a few things that maybe will help kind of makes sense of my journey is, one, I’ve always been a huge believer that if there’s anything in life you’re excited about, if you care enough about it, if you’re curious enough, you can teach yourself how to get good at almost anything.

So, what that’s I’ve done, and I sorted out my career, I focused on design. Specifically kind of web, digital design. This was back in the early 2000s, I’m a child of the 80s and 90s so I grew up with the internet being a really exciting, cool, new part of my life. And the quick backstory is, growing up, I was never attracted to anything design related. In fact, I hated art classes growing up. I never considered myself a very artistic person. So, how I kind of stumbled into design, as I think about it, is I was getting ready to graduate early from high school, this is going way, way back, I ended up taking a course one summer to get some extra credits, I just thought it would be a nice easy fun course about how to create HTML websites. And back in that point in time, creating websites now is a lot more complicated, back then all you needed to know was HTML.

So, I learned that class and I just got hooked on that I suddenly had the skill where I could take an idea in my mind, be able to use HTML to build it, and then I could tell my friends, “Hey, go and visit this URL,” or, “Hi, go and check this out,” and they could pull it up. And that just seemed like this magical thing to me.

And so, the way I stumbled into design was I started making these websites and thought I was going to be excited to share them with friends, but then nothing ended up looking like something I was proud of. So, it’s that moment where I was like, “I can make something but I want it to be cooler. Like, I care about this thing, I want it to be nice.” And so, that led me to this question of, “Well, what is that?” And, for me, it still is how I think about design as I think a lot shaped by that early experience. But my career now, I’ve been doing design at some level for 15 plus years, I’ve worked at companies like Apple and Square and with a bunch of other interesting cool brands.

But, for me, design is just the intersection of solving really hard technical or business problems and trying to pull it off in a way that you can create something that’s singular. So, ideally, it’s remarkable and that it’s unique and interesting and you’re contributing a new note to the melody but, at the same time, is beautiful and you’re kind of pulling off an artful twist.

Pete Mockaitis
Okay. Well, yeah, why don’t we get the broader view first and then we’ll dig into the details with one exception. Okay, so design, I’m not great at design and it always sort of kind of struck me as something – it’s funny, this show is about how to be awesome at your job and skills learning and growth and development, so I almost feel contradictory saying this. But it almost strikes me as something you’re born with, like you’ve got the designer’s eye, like you’ve got the touch, and I was like, “I don’t think I have it.” So, I always outsource my design and I think I know enough to say, “I don’t like that,” and “I love that.”

Daniel Scrivner
You’re a great client.

Pete Mockaitis
Well, it’s so funny, I love designers, I love working with them because I’ll tell them exactly, sometimes I feel crazy about my feedback, like, “As I behold that image, that part of it makes me feel like a little kid and you’re patronizing me,” and they say, “Oh, thank you. That’s great feedback.” I was like, “Really? Because I feel silly saying that out loud and like you’re going to bite my head off,” but the designer is like, “Oh, perfect. I know just where to go based on what you’ve said.” It’s like, “Great.”

Daniel Scrivner
No, I think that’s really all designers, I think, are looking for a lot of the times is just specific actionable feedback. As an example, one, probably the vaguest piece of feedback that I’ve ever received, and it was while I was at Square, and it was from the CEO Jack Dorsey who was looking at a design I did, and said something along the lines of, like, “It’s not whimsical enough.” And that definitely sent me down a like, “Oh, my God, what does that even mean? Like, what is that? Is it the color? Is it the structure? Is it the…?” I don’t even know. I didn’t even know where to go with that.

Pete Mockaitis
It’s not whimsical. Well, because, oh, man, I think for like corporate design, it’s really easy to be too whimsical real fast, and it’s like, “I don’t trust this, what I’m looking, at all. This spinning helicopter hat.”

Daniel Scrivner
He wanted that dial cranked up and I was scratching my head for a long time.

Pete Mockaitis
So, let’s start there. So, learning design, that seems like a skill that’s hard for people to pick up if they don’t have some kind of aptitude for it but it sounds like you disagree. Lay it on me.

Daniel Scrivner
Yeah, I definitely disagree. So, I think, well, just to take a step back. I have definitely worked with a lot of engineers that have led me to believe that there are certainly some people that probably don’t get design, like don’t understand colors, just kind of don’t understand just aesthetics in general. So, I think you have to have some inclination or curiosity or a desire to do a lot of research to just develop a point of view about like what looks good and what doesn’t and what is that. And that’s something that’s very difficult to build up.

If someone were to ask me, “How do I figure that out?” I would say, “I don’t know. You need to watch a lot of movies, read a lot of books, look at magazines about architecture and car magazines,” because I think that’s one thing that’s always fascinated me about it is great design can work in any industry whether it’s an interior designer using color and shapes and symmetry and patterns and textures to create a beautiful inside of a house, whether it’s an architect using some of those same tools to create a beautiful structure.

What’s interesting about design is kind of, if you boil it down, it is extremely primitive in that it’s largely shapes, colors, tones, moods, so, I definitely believe that anybody can learn it. And I think that, for a little bit of the backstory there, so I’ve mentioned I’ve been doing design at some level for 15 plus years, and every single year I continue to get probably a handful of emails from somebody that saw my work or listened to an interview that I did, who writes in and says something along the lines of like, “I’m inspired by your story. This is something that I want to do. How do I figure this out? How do I start working as a designer?”

And the reply I always write back is probably not the reply they were expecting. In fact, rarely do I ever receive a reply back. But it’s just along the lines of, “Like, the way I was able to do that,” so if someone kind of understands my story and knows that I dropped out of college so I don’t have a college degree, I did that because I found in this thing that I loved and I didn’t want to put that off anymore.

But the way that I learned it was extremely basic and probably it’s just like hustle applied to trying to learn. But, for me, it was very much like, “I want to do this thing,” so my approach was just, “Okay. Well, I’m going to do free work to start,” so I literally got paid nothing when I first started, and I was going to, honestly, anybody I knew or anybody that knew somebody that I knew that wanted something designed, and typically that would be a business card or a logo or a website, and I would just do it for free because I knew that I wanted to be doing it, I needed to have a portfolio so I can get better work, land better clients, eventually start paying. And so, I really just worked my way up that way from literally the lowest level on the totem pole of doing free design work for people that I just knew, all the way to working for some of the largest companies and most respected brands in the world. But it very much was a, “I’m just going to take it one step at a time.”

And, for me, one thing that ties back to, which we can certainly explore, is something that’s played a big role in my life is what I refer to, what I call the growth curve. And, for me, it’s just the sense that I think the way I’ve been able to get to where I am today is by constantly trying to challenge myself. And I’ve done that multiple times in my career where I’ve left really comfortable jobs, not because I wasn’t excited about that work anymore, I was still very excited about the work I was doing at those companies, but because I felt like I needed a new challenge.

And I don’t really know, I sort of know where that comes from, but there’s something in me that once I’ve kind of figured something out, I get a little bit uncomfortable and restless. And so, I’m always trying to challenge myself and kind of climb this growth curve.

Pete Mockaitis
All right. Well, so there’s a lot in there right there in terms of going out and doing it and getting a lot of reps. It sounds like whether that’s doing your own work or observing other work. And I found, I think, it is interesting with design in that I think it’s taken me a while to get here and not that I’m a pro by any means but it really is, for me, it’s kind of uncomfortable for a while, it’s like, “I just need to kind of…” I feel it first and then I had to articulate it in terms of, “Being in this room feels awesome. I love it here.” It’s like, “Why?”

Pete Mockaitis
But then you start to get a few things. In, like, realtors, like they’re taking photographs of places, it’s like, “The top thing is it’s free of cluttered garbage.”

Daniel Scrivner
“It’s bright. It’s airy. It’s typically lots of light, lots of very clean white and stainless steel.”

Pete Mockaitis
“And there’s just not a lot of clutter.” And I think that’s huge right there in terms of…and that can apply to a space or to a layout or a website or whatever. Like, I think Oli Gardner, I heard on an Unbounce event, had a slide wherein someone was like begging like Oliver Twist, “Please, sir, one more link shoved into this website.” It is like, “No, you got to keep it focused.”

Okay, so by doing a large volume of work, and by pushing and challenging yourself, and by observing and reflecting, you got really good at this skill. So, the here we are in your story.

Daniel Scrivner
Over a long period of time.

Pete Mockaitis
So, now you’re great at design and you have made some stuff that looks good, and where does this story go next?

Daniel Scrivner
Yeah, so maybe that was the kind of first formative part of my career, and I think for me there was a moment in time that I still remember very vividly but at the time didn’t feel…honestly felt scary and I don’t know if I was optimistic but I was excited about it but, basically, to share a little bit of the story. So, I’m in high school, I take this class, I start doing work for free, literally, when I’m in high school, end up graduating six months early. A big reason why I did that was I just wanted to do more time doing design work and I felt like, “Why spend all my day in school if I can kind do more of this work that I really enjoy?”

So, I graduated six months early. Fast forward a couple of years, and I’m suddenly at the point in my early 20s at this point in time, probably 21, something like that, say, and I suddenly have this kind of fork-in-the-road experience where I’m in college at the time, I’m about to finish my undergraduate degree, getting ready to kind of pick and transfer to the university that I want to go to which, in my mind, is kind of my parents’ voices. They were always very much, “You have to kind of go through this order,” and one of those things that was non-negotiable was going to college, so I was like, “Okay.” And I know that’s what I should do or that’s what felt like what I should do.

But the other thing I had in the other hand was, at this point, I had done enough design work that I actually was getting paid to do it, and was really enjoying it, and had enough work that I actually had to turn down projects. And so, the fork-in-the-road moment was, “Do I continue with college, kind of go to a university, really focus on that experience for the next two years or do I decide to take a bet on myself?” And at that point in time, the way I was framing it, which was probably a little bit nice, is kind of pause school for six months. I ended up quitting the job that I had at the time so I kind of severed all of those things so I could go all in. And my only goal was, “Let me see if I can survive basically doing everything by myself.”

So, I would pitch clients, I would quote clients, I would give them estimates, I would do the design work obviously, hand off the designs, do all the kind of the clerical stuff and accounting stuff. I just did everything. In those six months, I ended up doing that. Initially, my goal was just to make it six months. I ended up making it six months and it wasn’t pretty. A lot of that was extremely challenging, it was extremely difficult, it wasn’t all stuff I was super excited about. Balancing books or collecting invoices or following up on payments is not the most exciting thing in the world compared to design, but I ended up doing that.

And what that ultimately led to was, fast forward another year past that, I ended up getting offered a job to go and work for an advertising agency in L.A. called DDB. That led, about a year and a half after that, to getting offered a job at Apple to join their marketing communications team which was when I moved to San Francisco, and I ended up being at Apple for three and a half years. And I credit that a lot with being my…if there was any real-world bootcamp-like education experience in my career, it was absolutely being a designer at Apple.

Pete Mockaitis
Okay. Well, so let’s zero in on these particular bridges, leaps, transitions to DDB and to Apple. How did they find you and interview you, etc.? Was it just like, “Your stuff looks good, come on down”?

Daniel Scrivner
It’s effectively that’s the gist but the DDB, to be super honest, I have no clue. I cannot remember if they found me, if I found them, I’d never really heard of the firm before so it’s made me think.

Pete Mockaitis
Oh, they’re huge.

Daniel Scrivner
They’re a big advertising agency but they’re not Ogilvy. They don’t have that kind of brand name recognition necessarily so that one I’m not sure.

The Apple one is, I think, a little bit more interesting. So, the Apple one was, at this point, I was, I don’t know, mid-20s, probably 25, something like that, 26, and I, for sure, obviously, Apple was an incredibly exciting company, and I think for a lot of designers, it’s the place you hope you can get to at some point in your career. And so, the way that kind of transpired for me is I have this job at DDB at the time in L.A. so I’m commuting to L.A. and I’m doing all that and I’m enjoying my work. It’s not the most exciting. I’m not doing the most challenging interesting modern stuff but I’m doing it. I’m an actual designer getting paid to do design work which is crazy.

And I end up getting an email from a recruiter at Apple. And for those that don’t know, Apple is definitely one of the companies that they have a large recruiting team, and their recruiting team, they really are looking for the best of the best or people that they feel like can succeed as designers in some department at Apple. And for people that don’t know as well, Apple is massive. Even in the marketing communications team, I joined as a marketing designer, I worked on a lot of Apple.com projects, I ended up getting to do a lot more interesting stuff kind of in my time there.

But Apple also has motion graphics designers which just do things like animations and transitions and videos. They have graphic designers which do the packaging and the identities for some of their products. If you look at like AirPods Pro, like that name on the box, that’s something that a graphic designer put together letter by letter, playing with the kerning, playing with the weight, trying to get that just right, so it’s a huge department.

So, to kind of get back to the story, my first thought, honestly, was this is spam. Like, “Let me see where this email is from. Let’s me see if it’s actually from Apple.com.” So, I end up looking at it a little bit, kind of looked up the name of the person who sent it, and it all checks out. And the way that worked initially was I was offered an opportunity to come to Apple and cover for a woman who was going on maternity leave for six months, so it wasn’t like, “Here you go, here’s a full-time offer.” It was, “We really like your work. We would like to have you on the team to start,” and this is also very common at Apple about, I would say, probably 50% of the creative team is all contractors so it’s not full-time employees, so that’s not uncommon.

But I came in on contract and kind of my approach was, “I’m going to soak up everything I can, learn everything I can in these six months, and I’m also going to try to prove that I have a place on this team, that I can contribute and I can be a good designer and a good kind of member on the team,” that’s a little bit of that story.

Pete Mockaitis
Okay. And so, recruiter. I’m curious, in both of these instances, did they just not care, like it doesn’t matter in the design world, or for you in particular, “Oh, you don’t have a degree? No problem”?

Daniel Scrivner
So, it’s really interesting. I would say, for both designers and engineers, number one, I think there are a lot of technology companies, it’s definitely not a deal-breaker. Like, I think Google, they’ve relaxed this policy, but Google is definitely out of the norm in their requirement, which I’m not sure if they have anymore, but they have had for a very long time, is a requirement that you can’t get hired unless you have some sort of a college degree. But, typically, at technology companies and at startups, it doesn’t matter.

And the way that I’ve always thought about it is the majority of designers I’ve worked with do not have a design degree, and I think that’s part of the problem is if you were to try to go get a design degree, you can get one but it’s what is typically called a Masters in Fine Arts. You’re going to be doing it for six years, you’re going to learn all these kinds of fundamental skills, which I would argue you could learn just as well on your own by teaching yourself because it’s just literally going in kind of design history, looking up work of famous designers, doing these mock projects.

And part of that was, the way that I thought about it was, because if we go back to the part of my story where I was deciding whether to go to college or whether to take this kind of six-month bet on myself, definitely in the back of my mind was, like, “I can go and study design,” but the sense that I had was I was going to be learning fake design. So, part of what you do if you go to a Masters of Fine Arts program is kind of like going to business school, and you do a bunch of case studies, which are perfectly fine. They definitely help exercise some of your mental muscles of like, “Here’s a problem. How do you figure it out?” But does it map to the real-world job of being a designer? Absolutely not.

The most difficult things involved in kind of being a designer at any level is stuff like, “How do you gracefully take feedback that you agree with or don’t agree with? How do you ask really great questions of another person’s work where you don’t want to offend them, you want to know and respect that they put a lot of work and energy and love into what they’re creating?” But you want to try to ask great questions to kind of spur and make sure that it’s as good as it can be. And so, there are all these skills in design that are largely very powerful but very soft skills. And the only way you can really learn them is by doing it.

And so, that was kind of my perspective at the time. And what’s been interesting is I’ve had the opportunity to work with quite a few people that have a Masters in Fine Arts degree, and I don’t say this out of disrespect for any of those people, it takes, obviously, a huge amount of hard work to go and get a Masters in Fine Arts degree. But did I think they were necessarily better day in, day out designers? No. And I think, typically, they would have kind of a chip on their shoulder a little bit of, “Well, this project is too good for me.” And I think part of what helped me was there was no project that was too good or not good enough for me. Like, I was excited to work on it and take it on if it was a design challenge. And I also just loved it and I think that there’s this kind of sense of enthusiasm and love that, I don’t know, maybe I didn’t get it beat out of me in college but I was lucky that way.

Pete Mockaitis
And that’s a great perspective when you’re at Apple, it’s like, “I’m going to learn as much as possible in this place,” and in so doing your skills are sharpened. And so, what happens next?

Daniel Scrivner
So, I ended up at the end of those six months, I got offered a full-time position and I joined the Apple marketing they called it. I don’t know what’s called anymore but they called it MarCom internally which was short for marketing communications. But, basically, at the end of the day it’s like everything that’s not an ad on TV, that team did it.

So, I ended up getting offered a full-time position. Fast forward a little bit, about three years later, I found myself in a position I found myself in a few times now where when I first got offered the opportunity to join Apple, I thought, “Oh, my God, this is it. This is the place I’ve wanted to be. I can’t wait to be on this team.” And three and a half years later, again, really, like for me, I think a word that sums up a lot of how I approach the things that I love, which is both good and bad, but I think largely good is obsessive. And so, for me, with design, I just obsess over it. I would think about it all the time, I would constantly be working on little projects to try to improve my skills.

So, one of the things that I would always do when I was at Apple, and I think this is great advice for anybody that has a job, where it’s like you’re going to get better the more you do it. And if you challenge yourself with things that are slightly out of your comfort zone, you’re going to show up to work just a better all-around employee. But I would do things like, when I first joined…I knew how to put together a layout. In a layout, you can sometimes describe that as like if you go to, I don’t know, Apple.com, a layout is “What generally does this page look like? How do you chunk it out? What’s the typography there? Where are kind of the images?” It’s very similar to doing product design if you’re doing a layout for a screen.

So, I could do that but I suck at doing icons, and icons are this thing that they are like if you go and you open up your iPhone, if you have one, or Android phone, if you don’t, you look at kind of the app icons or the little graphics or symbols that you click on to get around an app, that’s icon design, and it’s both a very ancient form of communication. It’s based on hieroglyphs and cave paintings, and there’s a lot of those things that map almost literally one-to-one for kind of icons that we have today. So, it’s a very old form of kind of communications but I was really bad at it.

And so, one of the things I would do is just challenge myself, like, “I’m going to make an icon set of 30 icons I’m excited about.” And the way these projects always go is they’re absolutely brutal in that for 80% of the time I’m just like, “Oh, God, I’m not getting any better. What’s going on here?” And I just keep chugging through and trying to put one foot in front of the other again and again and again. And, inevitably, what happens is if I can just persist long enough, I’ll finally get to a place where it all snaps into place. So, I would do stuff like that.

But about three and a half years in, I just had this moment where I felt like I knew how to be successful at Apple. And what I mean by that, and hopefully it doesn’t sound egotistical, but in my mind, if you kind of take a step back and think of a place like Apple, they have a very recognizable aesthetic. Well, what does that mean? That means that there are rules that inform it and that there’s kind of like a construct and a framework for how they think about it. And so, if you can understand those things and get good at those, you can take on almost any project and figure out end time how to execute it in an Apple way.

And so, I’ve kind of gotten to that point and I had this moment where, again, I did this kind of flash forward, saw myself at Apple 10 years in the future, and thought that that would’ve been perfectly fine. And there are still times when I think back and wished that maybe I’d stayed a little bit longer just because there were such incredible people there and I learned so much and just enjoyed working with them, but I felt like that probably wasn’t the best thing for me. And part of what inspired me in that was, what I alluded to earlier, Apple has a lot of contract designers, and typically those contract designers, they don’t work at one company for longer than six months.

And one thing I observed that I thought was really interesting and different about the best of these contract designers were that when they were teed up a problem, they could look at it from ten different angles. And so, they could say, “Okay, I know,” as an example, say, something like take an example that came out today. So, Apple announced these AirPod Max, like headsets that you put on your head that literally are like headphones. And so, you would get teed up a project, like, “Hey, here’s this thing we’re going to launch soon. Figure out how to tell this story on a marketing website.” And you need to think that through.

But what I found fascinating about the people who had kind of a broad body of experience was they could look at it from a bunch of different angles. They could do a dark version of that layout, a light version of that layout. They could do something that felt super pop culture-y. They could do something that felt really minimal and restrained, and I thought that there was something really special there. And so, the kind of story I put together in my mind was, “Okay. Well, I think part of that is they just get to flex different muscles. They’re constantly taking on different challenges.”

And so, what that led me to think about was rather than stay at Apple, which would’ve been perfectly fine and would’ve been a great outcome, but rather than doing that, I think it’s time for me to challenge myself. And so, what I ended up doing, which was not at all common at the time, was leaving Apple, which when I was there no one left Apple. You didn’t leave Apple to go work somewhere else especially as a designer, and you definitely didn’t go to a startup, but I decided that I wanted to go and join Square. And Square, at that time, was about 50 people in size, it was in San Francisco, it was right in the city, I didn’t have commute, so that’s why I made that leap.

Pete Mockaitis
Very cool. Well, I want to push fast forward a little bit. So, you went to Square, you did some great things, and now you’re the CEO of Flow. How did that come to be? And what is Flow?

Daniel Scrivner
Great question. So, yeah, I guess I’m trying to figure out how to back it into this question. So, if we go back a little bit in my story when I was really young, one of the things I talk about was just this belief that if you are interested in something that you could figure out how to do that. And I give a tremendous amount of credit to my parents. So, growing up, we would do things like it was very common, probably happened once a month where we would all get in the car, drive down to the biggest library nearby, spend hours and hours in a library.

And so, one of the things that I got, I have two younger brothers, we would all, literally all five of us, we’re a five-person family, we would split out, all go to different levels, find the books that we were interested in, and we would spend hours there. And at that point in time, we were kind of young, say, 10, 11, 12 kind of age. And so, one thing I got fascinated, just hooked on, that I can’t really still put my finger on it, and say, “Why?” was business and investing.

And so, in high school, I was reading books like The Millionaire Next Door, or, Rich Dad, Poor Dad, or, I can’t think of other ones, but like largely business and investing books that typically people aren’t interested in let alone in high school. I’ve just always been fascinated by that, and that’s something that still, today, I’m always…it’s another obsession I have, is I just love learning from investors. Why? Because I think they’re experts at kind of thinking through industries and companies and which company has the best odds to success and why. And I’m also really fascinated with entrepreneurs, and this is the idea of creating something of value that you end up charging more for than it takes to create, which still, to me, feels like kind of pulling off a magic trick that someone is willing to pay for that even though it costs less to make it. It generates profit and you can invest that in other things, so I have these interests.

So, fast forward, I end up leaving Square after five and a half years. At that point, the company had IPO’s, we were 1,500, probably 2,000 plus people at that time, had an incredible experience. But for anyone that doesn’t know, being at a company that goes from 50 people to 1,500 or 2,000, and from having a little bit of venture capital money all the way to IPO in five years, it is a brutal experience. It’s wonderful in so many ways but it is also an incredibly trying and difficult experience.

So, I got to the end of that, was super proud of what I had done when I was at Square, and the team that I was able to work with and helped build, but I knew, again, that I wanted to flex some different muscles. And so, what I did leaving Square was I started kind of exploring things that was entrepreneurial-like and investor-like, so I did. I started doing some venture capital investing, some seed investing in companies. I now have a portfolio of over a hundred that I’ve built up and I’ve learned a lot from that. I also started advising companies. One thing in San Francisco that, this is maybe changing today, you know, San Francisco is changing quite a bit at the moment with the coronavirus and just all the effects that that city is feeling.

But at the time I was there, it’s just packed with people that are really good at what they do, they have really interesting ideas. And so, what that means is there are a lot of startups that don’t get design but need design to be successful. And so, I started working with some of those to help them think about how to think about design on their side.

Fast forward a few more years, and I ended up…so Flow is owned by a company in Canada called Tiny. And Tiny is like a mini conglomerate. You can kind of think of it like a mini-Berkshire Hathaway. And I knew one of those founders, Andrew Wilkinson, for about 10 years, and this was going back, it’s like very serendipitous, but going back to being a designer early on. It’s a really small community. So, we kept in touch and kind of he was a designer, I was a designer, we would both kind of check out each other’s work and loosely stay in touch. Long story short, fast forward a bunch of years in the future, and he now has this company that has many sub-companies, Flow is one of them.

And so, for a little context about what Flow is. Flow, at this point in time, it’s a 10-year-old company. We focus on task and project management, software, largely for teams. And the way we excel, the way we kind of compete is by offering people a beautifully made product that is powerful but it doesn’t feel bloated and it feels like something you’re excited to work in. And the metaphor I use there a lot of the times is like WeWork office versus a cubicle. And if you think about productivity software, a lot of productivity software is the cubicle land, and we try to create this beautifully crafted piece of software that teams need.

So, we went to grab coffee. Flow, at that point in time, was not doing super well and they felt like they wanted somebody to come in and take over and someone ideally with design background that could kind of invest a ton in the product, create a vision for the product of where it was going to go from there. And so, I joined Flow two years ago, and over the last two years, I’ve been working on turning around the company.

Pete Mockaitis
All right. Well, what a beautiful tale from making websites to you are heading up a company and are investing in businesses that are really cool. By the way, I use Superhuman for my email and I love it.

Daniel Scrivner
I love that.

Pete Mockaitis
So, wow, so what a journey. I’m drawing my own little lessons about really digging deep and then challenging yourself and learning from the people around you and keeping those relationships alive. But since we’re actually towards our final minutes here, why don’t you boil it down for us in terms of what do you think are the top do’s and don’ts for professionals looking to grow a career and advance in, hey, more fun wins, meaning in money, as we say here? If you want more of that over the long arc of your career from age 20 to age 60, 70, top do’s and don’ts, lay it on us.

Daniel Scrivner
I could probably talk about this for an hour so I’ll try to be as concise as possible just because I think there’s so many…like, one thing I think you’ll learn over time by working in a lot of different companies, by being at different stages of your life at different companies, it’s a very nuanced thing. So, I will share, I think, what’s helped me and people can decide whether that’s useful. But I think the big things for me is, ideally, you’re doing something that meets that bar of obsession. Like, in my mind, I’ve got a two-year old now, we’ve got another one coming on the way this right around Christmas, and with my kids, I think, the focus there is very much I just want them to find something that is energy-giving and life-sustaining. And I think if you can do that, then you have this…it’s almost like a nuclear fusion reactor where you have something that is just never going to run out of juice.

The goal, in my mind, initially was I wanted to find a couple of things, and at this point in time, that’s design, business, and investing, that I can think about, obsess about, read about, and try to get better at over the long course of my life. And so, find those things and then pour yourself into them. And what I mean by that is I highly encourage people, and again life is a single-player game, you have to decide if this is applicable for you. But, for me, something that’s always been really helpful is you find that thing that you love, then pour yourself into it. And what that means is not only giving 100% at work but, ideally, also doing stuff outside of work that challenges yourself and develops muscles that are probably related to what you at work but might help you prepare you for your next job, might help you prepare for the job you want five years or ten years, or what you want to be doing.

And I think back to my time at Apple, and I would work a full 10-, 12-hour day, get on the bus, do this fun little icon project. I didn’t do it every day. There were definitely days I was burnout or I just needed to shut off my brain but I’ve always had stuff like that going on the side. And I think people have different opinions about that. In my mind, I do the things that I love, and so what that means is there’s very little distinction between work and play, or work and real life. And so, I think that blurriness is really helpful.

And then I think another thing that I would suggest is to challenge yourself. Like, something that I have distinctly found is that the majority of people I’ve worked with are kind of limit their own trajectory by the belief they’re willing to have in themselves, the confidence they’re willing to have that they can overcome any hurdle, and just this deep sense that if they’re interested enough in something, if they want something bad enough, they can figure it out and they can do it.

And this isn’t a anything-in-the-world-you-can-have-go-for-it type kind of pep rally or speech. It’s just I think the way to kind of think about it is this very soft, just in the background confidence of if there’s a challenge that you see in front of you, believe in yourself, bet on yourself, and know that if you just keep putting one foot in front of the other, and you can find a way to push through discomfort, that there are really good things on the other side of that.

And then the other thing I would say is really throw yourself into that growth curve. I almost try to visualize it in my mind of I always want to be in a place where I’m pretty uncomfortable. Ideally, if I’m in a job or doing something and I’m committed to it, I’m really excited about it, I want it to be slightly out of my comfort zone. And I think this role that I’ve taken on with Flow is certainly that. The role I took on early on at Square was certainly that. When I was at Apple, it was certainly that. And I think if you string together kind of subsequent experiences that step, by step, by step, challenge you a little bit more, get you a little bit out of your comfort zone, make you do things that you don’t feel like you’re qualified for or you don’t think you can really do yet, I think the trick there is like a lot of people have this idea that, “I’ll do that once I can do it.”

And if that’s the way you think about it, you’re never going to do it. You just have to start doing, be willing to be bad at it, be willing to be uncomfortable, be willing to kind of cringe even at the quality of your work initially because that’s the price you have to pay in order to get better.

Pete Mockaitis
Well-said. Thank you. Well, now, could you share with us a favorite book, something that you really dig?

Daniel Scrivner
Yeah. The book I was thinking about kind of before this interview that I think might be really applicable, maybe people haven’t heard of, that I really enjoy is a book called Principles by Ray Dalio.

And for a little bit of background there, Ray is the founder of a hedge fund called Bridgewater, it’s the largest in the world, they have a very different culture where they really try to go all in on this idea of meritocracy which is that there’s not really any hierarchy; it’s just kind of a group of peers, and anybody is as good as anybody else and it’s all about kind of the arguments you can make and the work that you’re able to do.

And so, that book is the output of the last 30 plus years of trying to build this company, and it really is what’s in the title. It’s a handful of principles that apply to working in groups and working as an individual. And I’ll stop there, I won’t spoil it, but it’s a thick book. I highly recommend you get the hardcover just so you can open it up and flip through it. You do not need to read it from cover to cover but it is an incredible work.

Pete Mockaitis
And a favorite habit?

Daniel Scrivner
So, something I’ve been thinking a lot about, and this falls into the vein of like, “I’m not good at this yet, but I see the value in it and I want to double down on it,” is taking time to reflect each week. And this is something that I think, if I were to go back in time, this idea of reflection and what does that even mean, where you’re kind of pausing, you’re not doing any work, you’re going to stop sprinting, you’re going to stop focusing on your to-do list, you’re going to stop caring about your email, you’re just going to stop. Ideally, go somewhere where you can kind of think by yourself and sit down, and just really reflect on how things are going at the moment.

And, for me, I try to do that once a week for at least an hour. I have somewhat of a structure, I’ve a few questions I ask myself every single time. Some of those are really simply things but these are, at the end of the day, really profound questions, like, “Are there opportunities that are around me, or I have access to, or I see that maybe I just haven’t recognized?” And, especially in my role now, that’s true all the time.

Another one is, “Are there risks I haven’t recognized? How are things going? What’s going well and what’s not?” But I think taking time to reflect, the kind of metaphor I would have with that is, I think, reflection is something that almost none of us do often enough. The reason it’s important is because anytime in your life that you have a goal, you need to be able to know how you’re tracking and course-correct. And what I found in my own life is I would reflect once a year, maybe by doing New Year’s resolutions, or once a month, or once every six months, and that’s okay. But I think if you can get that down to where you’re spending a little bit of time, it can even be 20 minutes or 15 minutes once a week, what it allows you to do is it just tighten up and kind of keep you on track with where you’re headed. So, I would say reflection is big.

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

Daniel Scrivner
They can visit my website to see the podcast episodes I record, to see the stuff that I write at DanielScrivner.com. You can also follow me on Twitter @DanielScrivner and they can learn a little bit more about my podcast if they’re interested at Outliers.fm, and about Flow at Getflow.com.

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

Daniel Scrivner
I call it kind of the alpha challenge but one thing that I have written on a Post-It that’s a little bit trite but I find it really helpful is just, “If you weren’t afraid of the consequences, what’s something that you would try that you likely wouldn’t try otherwise?” And so, I think asking yourself that question, really thinking about that and being open with what that answer is, bring that whatever answer you write down, you have to give yourself permission, you have to believe in yourself that you can go and figure that out, and you can go and do it.

And so, I would challenge people to ask themselves that question, “What’s something that you would want to do that if you didn’t care about the consequences and weren’t looking at feeling or any of that stuff?” and take that answer and bet on yourself and figure out where to take that.

Pete Mockaitis
Daniel, this has been such a treat. I wish you lots of luck with Flow and your challenges and all you’re up to.

Daniel Scrivner
Thank you so much, Pete. It’s been awesome.