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Career Management

264: Navigating the Treacherous Ascent to Leadership with Ron Carucci

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Ron Carucci says: "Your vulnerability and your humanity are your two greatest resources."

Ron Carucci shares his groundbreaking research on the patterns of successful–unsuccessful–rises to greater organizational power.

You’ll Learn:

  1. How resumes and interviews routinely mislead
  2. How to minimize alienation
  3. The four patterns of successful leaders

About Ron

Ron is a seasoned consultant with more than 25 years of experience working with CEOs and senior executives of organizations ranging from Fortune 50s to start-ups in pursuit of transformational change. His consulting has taken him to more than 20 different countries on four continents. He has consulted to some of the world’s most influential CEOs and executives on issues ranging from strategy to organization to leadership. He has worked extensively in the health sciences, biotech, and healthcare provider sectors and in the technology, consumer products, and retail food and beverage industries.

Items Mentioned in this Show:

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

Ron Carucci
Pete, great to be with you. Thanks for having me.

Pete Mockaitis
Well, I think the first thing that we’ve got to cover head on is that you possess a doorknob collection. What’s the story here?

Ron Carucci
Gosh, you know, you never know how to answer the classic question interviews ask you about, “What’s an interesting fact about you that nobody would know?” And, you know, I was looking around my office and I looked at these big jars I have of these beautiful antique knobs, “Oh, I’m going to put that,” knowing that it would bait somebody to ask.

So a long time ago, as an art endeavor to give a gift to somebody whose life is about opening doors, I created this beautiful sculpture, this sort of glass sculpture which is basically a beautiful tall glass jar filled with, you know, all kinds of antique doorknobs from hundreds of years ago, 50 years ago, every era. So you see decades and decades of stories.

And the metaphor for me was imagine all of the hands that touched these knobs over the years, and the entrances people made into rooms, and all the conversations that ensued. And so I made them for people whose life was about opening doors, was about creating access, creating doorways for people. And then people started asking me to make them.

And so probably, for people where I felt like it was more than I made them, and then I made a giant one for myself because, I thought, I want one of these. But I made it so large that the glass jar broke and exploded and I got really impressed over that. So then I made three little ones out of that same set of collection. So those are sitting in my office on the coffee table by the couch.

And so they’re just a wonderful reminder of, you know, the stories of our life came long before us, and they will go on long after us, and many people had to open doors for us and there are many people relying on us to open doors for them. And it’s a great reminder to think about being part of a much bigger story than the one we just see.

Pete Mockaitis
Well, that is cool. And you got me thinking, you know, I spend a lot of time looking at doors recently because we just bought this home and we’re doing some renovation. I want my home office to have some sound blocking, you know, studio-esque and did all this research and looking at different doorknobs and their impact on the blocking of sound which is funny, it’s like the opposite metaphor, “Do not pass through here. I need the quiet for a good recording.” And so I’m intrigued. So do you have a preference when it comes to an appearance, a finish of bras or copper or satin nickel, or polished chrome?

Ron Carucci
There’s glass ones in there, there’s crystal ones, there’s leathers, there’s ones that came right, you can tell, right out of the ‘50s, the houses I grew up in. There are door knockers in there. There are skeleton keys. Yeah, there’s just all kinds of…there’s wooden ones from the 1800s in there. There’s ones from fancy large doors. There’s ones from cabinet doors. So, yeah, it’s quite a variety of collection.

Pete Mockaitis
That’s wild. Well, thank you for sharing. That is intriguing and it kind of sets up a cool metaphor here. So I want to talk mostly about Rising to Power, the book. But could you maybe orient us a little bit, what’s your company Navalent all about? And am I pronouncing it correctly?

Ron Carucci
You are.

Pete Mockaitis
Okay. Good.

Ron Carucci
And I’m glad to tell you about us. So I and my colleagues at Navalent get to spend our days traipsing through the hallways of all kinds of organizations: small ones, startup ones, mid-cap ones, large global powerhouses, alongside the journeys of leaders on some pursuit of change, some pursuit of transformation, some pursuit of something better, improved, or get out of some ditch, and helping them construct very complicated journeys of change whether those are strategic or organizational or cultural or their own personal leadership. We help carefully curate the journey with them so that they could actually be successful and reach the aspirations that they dream of reaching.

Pete Mockaitis
Cool. Alright. Well, it sounds like my kind of place. Well, so now, I want to dig into your book. It’s called Rising to Power which is a juicy title. So, first tell me, what is the main idea and what is it not? Is it about a dictator’s upcoming into their own?

Ron Carucci
No, it’s not about that. We thought we might find them in the research. It’s based on a ten-year longitudinal study of about 2800 people who are all pursuing positions of broader influence in their lives, mostly at the higher ranks of organizations, but it’s a variety. So I know your audience is mostly in their mid-30s and professionals, and so I think that the point in the book certainly apply to all of us in that all of us are pursuing greater influence. We all want to have greater impact. We all want to reach more people and leave positive things behind in our work and make a difference.

And we’ve known for a long time that more than half of those who take on positions of broader influence in organizations fail in their first 18 months. And we’ve known that for 20 years, and it’s just become the new normal. Recruiters love it because it’s an annuity for them but for everybody else it’s a tremendous amount of carnage and wastes in our path and unnecessarily so.

The book began in a personal level when somebody that I had been working with called and I was assuming point of check in, and I was going to hear about great things they had done, and they had been fired. They had started much bigger job 10 months earlier and, yeah, everybody saw them as having great potential and was going to go the distance and could make great impact. And so I couldn’t imagine why it was we could’ve misjudged his potential so greatly, and that I wanted to go back in and find out what happened.

And that investigation led us to the 10-year study to find out that he was really just one more statistic. I thought, “Gosh, we can do better. This is insane that we just accept this as normal.” Why is it that people who look so breathtakingly wonderful in the middle suddenly become disastrous when you move them up? Makes no sense.

And it turns out, after 2700 interviews and a lot of digging, and we sort of stopped about 100 leaders in mid-ascent to see if we could watch in slow motion what was going on to find out what’s causing these people to go tap dancing in these landmines, and how can we up and not do that. So it was a wildly instructive study, difficult in some of the things it revealed in that it’s a wonder any of them are succeeding given all the landmines companies put in their way, and it was inspiring to see that there are many leaders, not only rising and thriving, but sticking a landing and having great impact when they get there, and begin to isolate what it was they were doing that enabled them to be successful.

So it was a pretty robust experience to study all that.

Pete Mockaitis
Well, Ron, this is so juicy and I’m so intrigued. And so I’d say, hey, just take us there on the story in terms of, with particular emphasis maybe on kind of the most leveraged forces both in terms of what we see in the organizational landscape, and in terms of the actions folks are taking, the mistakes that seem to trip folks up again and again.

Ron Carucci
One of the most common ones, Pete, is right in the very beginning when we start beginning to prepare people or invite them to bigger jobs. And this is any one of us who go on job interviews or who conduct job interviews, can fall under this trap. So the two most common devices we use to make decisions about people’s jobs are the two least reliable: the resume and the interview. Right? But we’re still using those mechanisms to make choices, and people walk through their resume and we tell them stories.

But one of the most dangerous parts of that conversation begins to sound something like, “Wow, look at that great team you led to that result. That’s what we need.” Or, “Look at this brand you built. That’s what we need.” Or, “My gosh, look at the sales team you’re able to drive such results through. That’s what we need.”

And whether you’re on the asking or receiving end of that question, a red flag should go off. The minute someone starts implying that there is this past set of successes that you’re meant to come and repeat, because the implication is that you have a formula, you have a recipe, you have some tried and true approach that you should come apply here, and that is almost always a setup for failure because it’s devoid of any context, right?

And so somebody comes in, starts slapping on their formula, it starts not to work, I start slapping harder, then I get frustrated, people start backing away and failure set in motion. And so never assume that any success you had is repeatable. Never assume anybody else’s success that they’ve had is something you should want repeated. There may be wisdom, principles, ideas, things that gave me experience that they might apply to the next chapter, but it is never a formulaic recipe that they should just simply repeat.

And so how you ask the question and how you help them adapt or how you help yourself adapt, successes or experiences, to the environment you’re going to is critical. And that starts with you understanding that you have to adapt yourself to the environment as much as you have to change it. It’s a two-way process, and most people who believe they have this mythical mandate to repeat some past success skip the part of their own need to adapt.

Pete Mockaitis
Ooh, wow. That’s fascinating. And it’s sort of intuitive like as you were speaking, it’s like, “Okay, I’m not seeing the problem, I’m not seeing the problem. Oh, okay,” you know? Because it’s just so sort of natural to do just that. It’s like, “We’re looking for someone who had done this. You have done this. Therefore, you will do this and we’re excited.” And so you’re saying that that is by no means predictive, and you’ve shared some stats earlier. In fact, the majority of the time it’s not going to work out the way you had hoped.

Ron Carucci
Just having done it in and of itself is not predictive. If you isolate what competence, right, and that’s what more scientific parts to interviews are showing that if you show a demonstration of competence, tenacity, problem solving, collaboration, working with difficult people, you know, if you can help people extract what was good about what they did but contextualize that to the situation they’re going to be in, that’s predictive.

Just having checked the box off, even if they’d done it three times in their career, is not at all predictive that they can do it again in your environment or your context or in your particular culture, and send them the implied message that you believe they can and, in fact, that’s what you’re hiring them for, is in fact almost always a setup for failure.

Pete Mockaitis
Okay. Intriguing. Can you speak more about this? That message is a setup for failure in what way and how?

Ron Carucci
In that I’m telling you, “Just come here and repeat what I’ve done.” So I don’t come in looking to learn, I don’t come in looking to understand, “How did the problem you’re in even get here? How did the situation that seems to need what I bring arise? Who caused it? Who are the people here? What have they tried? And how do I need to build credibility with them, build respect with them? How do I need to adapt in this environment in order to be credible here, in order for my ideas to prevail?”

“If I simply come in and start doing, well, my first thing is always that I, you know, start with assigning these taskforces, or I’ve always gone out and just gotten this customer segmentation data, or I’ve always gone out and this is the technology I use. I’ll bring this technology in.” And without any sense for the havoc I’m wreaking, how others are metabolizing this, what ideas they might have, without any sense of the people who I have to live with what I’m building, why would they want to—because now is an indictment, right? All you’re doing is judging and indicting.

Pete Mockaitis
“Yeah, you did it wrong. Let me show you how it’s really done. Watch and learn, guys.”

Ron Carucci
Exactly, Pete, that’s the posture. And how often the one thing you hear that people get most sick of new people is when they begin every sentence for the first four months, “Well, when I was at Johnson & Johnson what we did was…” or, “…the change we did was…” So you got hired because you came from this iconic brand, “Well, at Microsoft what we did was…” and all I hear, and the minute you say that name I stop listening.

But within 10 weeks, you can almost bet casino money on this, people in the break room saying, “If I hear Microsoft one more time, if I hear Johnson & Johnson one more time, I’m going to throw up.” Now, it could be that anything that followed that statement is brilliant. It could be that the idea is perfectly suited. Nobody is going to hear it.

Pete Mockaitis
Right. And so I guess I’m more diplomatically suave astute way to even if you wanted to share that it just maybe have a bit more of a Socratic or curious questioning approach in terms of, “Have you tried to do this?” Or, “What are our thoughts around that?”

Ron Carucci
Exactly. Absolutely. Ask questions, be curious, find out what they’ve learned, and if you have to offer an idea, offer an idea. The origins of the idea are irrelevant.

Pete Mockaitis
Right.

Ron Carucci
Let the idea start its own narrative. If you think that talking about the last big company you came from as the place you saw the idea worked is the basis of its credibility, then why do I care about the idea?

Pete Mockaitis
Perfect.

Ron Carucci
As I say, that’s great. We’re not J&J.

Pete Mockaitis
Yes.

Ron Carucci
That’s great. We’re not Microsoft, right? And so all I’m telling you is I’m judging you because you’re not.

Pete Mockaitis
Awesome. Okay. That’s very instructive. So there’s a whole sort of cluster theme associated with, “Hey, you did that there. We want you to repeat it.” And then you tried to repeat it and then all sorts of havoc can unfold with regard to you’re annoying people because you keep mentioning that you’re not having a posture of curiosity and learning and adaptation, so that’s sort of one cluster of trouble that emerges there. Are there some other findings that are noteworthy in this study?

Ron Carucci
Well, so the other thing is that, you know, when you start getting frustrated with your brilliant ideas not working, you start to judge people. You start to walk around and saying things like, “How did these people made any money here?” Or you go to your hiring manager and you say, “You didn’t tell me it was this bad,” right? And then the halo becomes a noose, you start hanging yourself.

And as people are backing away from you, you don’t realize you’re becoming isolated, right? And that is sure signs of death. And, of course, then the classic statement we all hear when they had to boot your butt out is, “Well, he just wasn’t a fit.”

Pete Mockaitis
Yeah.

Ron Carucci
Right? I mean, it’s almost so cliché at how predictable this is. The other one is when your whole relationship landscape changes. So let’s imagine you rise up to a position where the people who used to be your peers now report to you, the people who used to be your bosses are now your peers, people who used to report to you aren’t anywhere near you anymore.

And the entire relational landscape changes, and people either treat you like you’ve changed or they try and treat you like you haven’t changed, right? And so all those boundaries, if you don’t intentionally renegotiate them, they become really awkward. And so people either start expecting to create favor with you, or they start withholding information from you because they’re not sure they can trust you now, and you feel really alienated, you feel like an alien.

You feel like you’re this guy who just arrived from a different planet and people are looking at you funny, or you walk into a room and they stop talking, or they walk into your office and they start asking really innuendo kinds of questions, trying to get information out of you, or leverage a level of intimacy they had with you before to try and get special treatment.

Or that relational disruption, for some people who aren’t ready for it, can really be paralyzing, can be really uncomfortable, can feel really off-balancing, and people who do it make the mistake of going native and getting all in, or they pull away from people and severe relationships rather than saying, “Okay, how does this relationship need to be redefined in my new world? What parts of how we used to interact can we keep?” And what parts have to change and really having healthy honest forward-looking conversation so that you don’t unnecessarily severe relationships or unnecessarily go native and get exploited.

Pete Mockaitis
Ron, this is so good. You know, it shows that you’ve had a lot of conversations, a lot of people, and have zeroed in on patterns, and there’s a real realness and practicality to it. It’s so good. Is there more?

Ron Carucci
Well, sure. So I think the last one I’d offer, and this maybe for some of your listeners who maybe are aspiring to bigger jobs, or maybe who just got one. But the problem becomes when you’re leading a large organization, so that everybody that you lead is not directly touching you or near you or physically with you, where you may have people you lead in other locations, around the country or maybe even around the world. Or there’s several levels between you and everybody you lead.

The biggest alienation from many leaders there is that now their life plays out on the Jumbotron, right? They’re now this bigger than life version of them. I tell these leaders, “Just assume that there’s a megaphone strapped to your mouth 24/7. Everything you say and do is amplified. Everything you do has meaning attached to it. If you walk down the hallway fast, ‘Oh, she’s angry.’ If you walk out of a meeting scratching your head, ‘Oh, my gosh, she’s upset.’”

The best people would just read cues. They could be wildly irrational and inaccurate but just know that you’re now on the Jumbotron and a way for people to concoct to you, people to create versions of you, people that you now have folk-loving told about you in the hinterlands and places you’ve never been before, people are going to quote things you said you never said, “Well, John said…” “I never said it.”

And for many leaders that just can be so off-putting and disorienting because they don’t understand, “How is this happening?” It’s just the price of leadership. It’s the price of walking in organizations where people have to make up a story if they don’t know the answer, and so they have to interpret reality in ways that makes sense to them even if it’s not rational.

And there are ways to counterbalance some of this with how transparent you are, how you communicate, how you choose to be accessible and how you make people know you in ways that mitigate their need to make you up. But you can’t get away from all of it. And, to me, leaders try and set out on making sure that they neutralize all of that stuff. And, of course, it’s can’t be done. It’s a full-time job.

So just getting used to the higher altitude and the thinnest of the oxygen up there, you need to take more breaths just like climbing a mountain, you have to get used to the fact that there are some elements of how you lead and how you’re perceived that are simply out of your control.

Pete Mockaitis
Right. Well, so maybe we could get sort of one hopeful note within that. You said there are a number of things you can do. Do you have a sort of 80/20 prescription in terms of, “And this is probably one that has a lot of bang for the buck when you find yourself there”?

Ron Carucci
Well, I think the best defense is a good offense, right? If there’s important messaging you need to get out, if there’s important influence you want to have, be vulnerable. Your vulnerability and your humanity are your two greatest assets. Let people know you and let people know that you know you’re flawed.

Talk about the places you know you’re not good. Talk about the things you’re working on. Talk about your own personal values, what you want for the group. Be accessible in a human way to people, that way you’re not having to, you know, so we have people in countries around the world, or locations around the country that you can’t always get to, and obviously use video conference when you can so you can be seen versus just written communications. Do whatever you can to create cohesive intimacy, acknowledging the distance that’s there without having to be physically present and down the hallway and be able to pop in to everybody you lead.

Pete Mockaitis
That’s excellent. And I can recall in some of the early days of my career, I remember I was working at Bain, starting a new case, you’ve got a manager who’s almost a partner and you’re working alongside, and you sort of talk a little bit about professional development goals, and I say, “Oh, yeah, I’m kind of looking to work on this, this, and this.” And then he just said, “Okay, yeah, great. Thank you. I’ll keep that in mind. And here’s some things I’m working on.”

And it’s like it’s so… it was like my mind was blown in the sense of that level of humility and vulnerability, just made me go, “Whoa. This person is real.” And I just felt instantly like, “Oh, I can talk to this guy about stuff,” instead of having to worry about the things that are permissible and impermissible to be shared with them.

Ron Carucci
Yup. Well, that’s one reason why Bain continues to get voted in the top three companies to work for, right? You have leaders who are really people know they care. And impressionable service where you can have all kinds of cutthroat rivalry and all kinds of horrible individualistic cannibalistic behavior. It’s wonderful that they have worked so hard. I’ve always thought, “Gosh, if I didn’t have my own consulting firm, Bain would be one of the places I’d love to work.”

Pete Mockaitis
Yeah, it was a great experience in many ways

Ron Carucci
Yup.

Pete Mockaitis
But I want to touch based on, so, I think a number of listeners will say, “Okay, not yet an executive. Those sound like interesting and problems that I hope to have some years down the line.” What are some of your pro tips for what can just convey this guy or gal is a rising executive and can set folks up for success in seeing that altitude sooner rather than later?

Ron Carucci
Well, the reality is that the four dimensions that we found, in the data, these four patterns, no matter how we cut the data up, almost a hundred regression analysis, these four patterns were the continued hallmark of those whose influence stuck, whose impact was sustained, and their patterns of behavior and influence we can all use, it doesn’t matter where you are.

So the first one we call breadth. This was people who understood that the organization was made up of many parts, right? So when you get to the top you can glue it together. But even from where you’re at, you know, there are some border, there are some other department, there are some colleague, there’s somebody across a moat that you have to work with, that relies on you, you have to collaborate with. Do you understand how to bring cohesion where there’s fragmentation?

Organizations are natural fragmenting parts, they are naturally pulled apart with centrifugal force. Can you cross a border? Do you know how to create connections across boundaries? Can you appreciate the world? If you’re in finance, do you understand what sales has to do? If you’re marketing, do you understand what supply chain has to do?

Who are the counterparts around the organization who you tend to get annoyed with or you tend to be frustrated by and think, “Gosh, if they knew how much havoc they wreak in my life.” Well, the chances are you probably wreak the same havoc in their life. So how do you cross those borders and understood how you work this into a larger story? The more you can see how the whole organization works the more general a contributor you can be.

The second we call context. So this is the person who comes in and read the tea leaves, right? Are you curious? Are you asking questions? Do you know the trends to disrupt your industry? Do you know what the competitive moods are? Regardless of where you are in the organization, do you know why your customers are choosing you? Do you understand the landscape of which you sit? And are you seriously asking questions to learn what’s happening around you and why? Can you read context? Can you read the context of your culture, and why certain norms and behaviors are accepted and those that aren’t?

The third one we call choice. So this is the ability to make really hard calls. Leadership is being able to disappoint people, that’s what it means, right? So, can you say no? Can you narrow the focus of the organization? Can you prioritize people’s work so that you aren’t over-committing them?

You never walk around an organization and hear somebody say, “Wow, we just have too few priorities. Gosh, we’re way too focused.” Right? You hear, “My gosh, how many more things you’re going to put on my plate? How much resource do you think I have?” Over-committed, over-extended, under-focused, priorities du jour, changing priorities by the day. And so great choice makers can make hard calls. They can narrow people’s focus.

Pete Mockaitis
That’s so powerful.

Ron Carucci
They can choose what to work on and choose to what to say no to. And it’s not about saying no to bad ideas. Any dummy can do that. But say no to even great ideas because other great ideas have to prevail.

Pete Mockaitis
Absolutely. You know, we had Greg McKeown who wrote Essentialism back in episode 38, and he said that originally the word priority was never pluralized. There’s only one.

Ron Carucci
Yup. I love that but I actually interviewed Greg a few times for my Forbes column. Great guy and a great book.

And the last one we call connection. You know, not surprisingly these are the relationships that you have with people above you, alongside you, and below you. All around you, direct reports, peers and bosses, you build relationships of deep trust, deep credibility and reliability. And one of the key differentiating factors of these, they call the relationships, were not so much asking, “Who do I need things from?” But these people set themselves apart by actively seeking ways to help others succeed.

They actively ask the question, “Who can I help? Who needs what I have to offer?” And so if you haven’t done it, seek down a map of your stakeholders, the key relationships in your organization regardless of where you sit, and whose success can you contribute to. Who can you say to, “How can I help you be better at what you do today?”

And people who actively seek to put others’ needs on their agenda, those are the folks that are remembered and given opportunities to have greater impact.

Pete Mockaitis
Oh, that is so good. That is so good. Ron, this is excellent overview which I know has a lot of depth underneath it. But tell me, is there anything else you really want to make sure to mention before we shift gears and hear about a few of your favorite things?

Ron Carucci
No, I think we’re good.

Pete Mockaitis
Okay. Cool. Well, then can you share with us a favorite quote, something you find inspiring?

Ron Carucci
My mentor, she’s still my mentor, has been for 30 something years. Early in my career she said to me, “Nothing is irrevocable except death.” And the reminder is every day we get second chances, we get do-overs. Not on everything but on many more things than we give ourselves access to. And if we could free ourselves from the fears, the anxieties, the projections and judgments of others about us, if we could shed those we might make more courageous and optimal choices.

So, remember it’s okay to skin your knees. You get do-overs.

Pete Mockaitis
Thank you. And how about a favorite study or experiment or bit of research?

Ron Carucci
So my favorite Jim Collins book is actually one of his most extreme books but I love How the Mighty Fall. It was this interesting leftover bit of research about patterns on arrogance and failure. It’s a brilliant piece of work and it’s one of my favorite pieces of research.

Pete Mockaitis
Oh, thank you. Well, my next question is about a favorite book. Is it the same or you have another?

Ron Carucci
I think David Whyte’s book Crossing the Unknown Sea should be required reading for the planet. I love the notion of work as a pilgrimage of life.

Pete Mockaitis
Thank you. And how about a favorite tool, something that helps you be awesome at your job?

Ron Carucci
In business, I’m a big fan of Zoom. I know we’re not on it but I just love Zoom. It’s all the cool things it can do to connect people, to communicate people, to capture great conversations. It’s really cool.

Pete Mockaitis
Agreed. And how about a favorite habit?

Ron Carucci
Gosh, my wife would say, “How are you going to answer that one?” You know, one of them is, I know a habit or a ritual, but down the hallway from my office in the conference room where our kitchen is, I have this collection of coffee mugs. People that are listening will say I’m a hoarder, my doorknobs.

But they’re mugs that I’ve gathered from all over the world, from different experiences with different trips and different people. But each of them is attached to a person or an experience I had with a friend or someone in my family or a colleague. And so when I have coffee in the morning, when I pick that mug, it forces me to remember somebody really important to me to grateful, and I start my day remembering that my life is bigger than just the one…the story I made up, whatever challenges I have that day, and to start by being thankful for the people in my story that make my life as rich and meaningful as it is.

Pete Mockaitis
That’s awesome. Thank you. And do you have a particular nugget you share in your consulting, your speaking, your writing that really seems to connect and resonate, folks are maybe quoting yourself to you, that’s an authentic quote as opposed to a mythic quote that’s mistakenly ascribe to executives?

Ron Carucci
I’ve never said that. No, I think it’s a question that I ask people that it can be a little bit off-balancing. But I love to ask it when I’m about to start any one of our diagnostic works, when I’m about to go do my MRI on an organization. And I love to ask this, “So what am I going to hear?” Because I love to both test their predictive nature and their intuitive insight. But they love trying to guess before they get the data, “I wonder what they’re going to hear?”

And, of course, as they begin to presume what it is I’m going to hear, they’re forced to test the assumptions around, “Why do I think that? And I wonder what he’s going to hear, and how do I know?” And so I love to put people on notice to say, “Okay, let’s go see what actually you’re doing here.” But it forces them to test the assumptions they’ve taken for granted often of which is some of the reason they had to call me in the first place.

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

Ron Carucci
I’d love them to come to do a couple of things. One, on our website, Navalent, N-A-V-A-L-E-N-T.com. We’ve got a great quarterly magazine on leadership and organizations and teams and all kinds of fun stuff we’d love to have you subscribe to. It’s free. We have a really exciting virtual summit coming up called Leading Through Turbulence and, wow, what a lineup we’ve got.

We’ve got Jon Haidt and Dan Pink and Dorie Clark and Whitney Johson and Nilofer Merchant and Mark Haughey and CEOs of big companies and entrepreneur CEO startups, and thought leaders of all kinds, but 25 speakers in all. It’s March 5 through 9, so come sign up for that. It’s also free for the week of March 5 through 9. You can also, for a nominal fee, buy an all-access pass for you that gets you a free coaching conversation with one of us from Navalent and get you a free e-book and all kinds of stuff. So we’d love to have your listeners join us for that. That’s going to be a great set of conversations and really rich content.

We also have a free e-book. So if you’re facing some change in your life, and leading change of some kind is important, if you come to Navalent.com/transformation we have a free e-book on leading transformation that you would find, I think, interest in and enjoyable. So I’m also at Twitter @roncarucci, and I’m on LinkedIn as well.

Pete Mockaitis
And do you have a final challenge or call to action you’d issue to folks seeking to be awesome at their jobs?

Ron Carucci
Yes, go ask five people for feedback on how they experience you, and make them tell you the truth. Some of them will go, “Oh, you’re great. You’re great,” and say what you want to hear. But say, “No, really. What’s one thing I could do better to help you do a better job?” Go ask people for how they experience you as a colleague.

Pete Mockaitis
Now, I really like that. And so when you say how they experience you, could you give us a few articulations of that because my hunch is some folks would say, “Oh, what do you mean? I think you’re a cool dude, Ron. Thanks.”

Ron Carucci
So what’s the one thing I do that most annoys you?

Pete Mockaitis
Alright.

Ron Carucci
What’s the one thing I do that makes your life easier? What’s the one thing you think that if I improve could make my career better? What’s the one thing that everybody else is talking about me behind my back and rolling their eyes about that no one thinks I know?

Pete Mockaitis
Perfect. I love it. Well, Ron, thank you so much for taking this time. This is thought-provoking. It’s powerful and I’m really excited to put some of this into action myself, and some eye-opening questions and things to go after. So I wish you tons of luck with the book, and your consulting, and the summit, and all the cool things you’re doing there.

Ron Carucci
Pete, it’s been a real pleasure. Thanks so much for chatting with me. Good to be with you.

262: Conquering the Five Career Derailers with Carter Cast

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Carter Cast says: "You don't have to be good at everything. You have to know what you're good at and know what you're not good at."

Kellogg professor Carter Cast provides his research on career derailment–and how to prevent it!

You’ll Learn:

  1. Two questions to ask yourself to pinpoint your strengths and weaknesses
  2. Frequently-occurring risk factors to watch out for
  3. The two critical things that put you in the 98 percentile of your company

About Carter 

Carter Cast is a clinical professor at the Kellogg School of Management. Previously he’s played a pivotal role in building numerous iconic consumer brands including Tostitos Scoops and The Sims. He served as CEO of Walmart.com, growing it to the third largest online retailer in the world. Carter is also a venture partner for Pritzker Group Venture Capital, where he assesses potential investments and advises portfolio companies.

Items Mentioned in this Show:

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

Carter Cast
I’m happy to be here. Thank you.

Pete Mockaitis
Well, you had some pretty cool professional experiences in your life, but what I’d like to zero in on to start is you were working to launch the computer game The Sims. Tell us about that experience.

Carter Cast
Well, yeah, we knew, just from the early builds of the game, that this was going to do really, really well. People were so engaged and it was like they had their own little self that they were trying to take care of, so you can see the beginnings of the sort of obsessions with the game, so it actually did not surprise me too much when we saw that sort of success there.

The fellow who was the executive producer on it, Will Wright, also did Sim City, and so he’s a genius. So this was his brainchild, and my role was to help market it and make sure it was accessible to the public so it was an extraordinary game back in the late…no, this was probably ’98. Are you player? Do you play?

Pete Mockaitis
Well, I remember playing it, you know, back in the day, and I think they just kept iterating on it like many, many versions, and so I think I had an earlier one but it was still rather engaging. And, I don’t know, it just sort of gets you thinking about your life in different ways.

Carter Cast
Taking care of this almost sentient being.

Pete Mockaitis
Yes. I mean, did you have any insights into your own life as you were watching The Sims take shape?

Carter Cast
Yeah, what I noticed the most was how attached, I think, with time, you can become attached to activities. So you really do get invested in this, you know, game and also with the character you’ve created. And so I thought, “Oh, it’s interesting. It’s strange.” I know this is a non-sentient being but I’d certainly starting to…I’m feeling like it’s actually something that I needed to take care of, like an animal, like a pet, like a cat or a dog.

So when I saw that sort of—and I think that part of this is you commit that much time to something and it becomes important to you. So there was an interesting psychological component to that when we were creating the game and watching him develop it.

Pete Mockaitis
That’s fun. That’s fun. So I’m excited to talk about your book in which you’ve sort of laid out a lot of your career lessons learned over time. And so, tell us, what is your book The Right (and Wrong) Stuff all about?

Carter Cast
You know, in a nutshell the book answers two questions, “What about you could hurt you?” What about you could actually impede your career progress? And then, secondly, “What do high-performers, hotshots that don’t derail, what can be learned from looking at them?” But the genesis of the book was that, as a professor at Northwestern’s Kellogg School of Management, I’ll talk to these very smart people and they’ll be looking at this, “Should I take this offer from this great consulting firm? Or should I go to this startup?”

And I’ll say, “Well, those are two very different opportunities,” and then I’ll ask some typical questions like, “Where do your passions lie? What quickens your heart when you’re really absorbed into something and the time flies? What are you doing?” And then I’ll ask them, you know, “Where do you want to be in three to five years? And what are you good at? What are you really skilled at? Where do you raise your hand and always say, ‘I got this,’ because you have a natural talent there?”

And they’ll answer these very fluidly. But then I’ll ask them, “What about you could hurt you?” And I’ll get, “Huh? What?” I’ll say, you know, “What about what could impede your career progress if not watch carefully? Where are you vulnerable?” And, invariably, I would get these very sketchy or no answers. And so I started thinking, you know, the whole StrengthsFinder, the whole now discover your strengths and focus on your strengths, it’s great but I tried to write weakness finders, you know, the flipside of a strength is some area of vulnerability that we have to be aware of.

A matter of fact, 98% of people – this is a lot of research – have an overused strength that actually hurts their career. So you can be so analytical that you suffer from analysis paralysis or overly-skeptical and drive people crazy. Or you can be this great team player who actually has difficulty making the hard call, you know, being decisive.

So there are these themes of strengths hurting us, and derailment propensities that we have being unaware of their potency. So I started doing research in it once I would not receive these great answers from students, and it became more and more interesting to me because I realized that companies aren’t using any assessment or very few companies are using derailment assessment tools. They’re using tools that might help employees identify their competencies. But are they actually using tools that help them identify their weaknesses?

And so I came to this realization that the conversations aren’t being had inside companies that help people develop based on understanding where they need to improve or what areas they have to do less of that could be hurting them. So that ended up making me feel that it was, even though I teach and I do venture capital for a living, I decided to try to carve out the time to do the research and write this book because I just thought it was a conversation that has to be…we have to surface.

Pete Mockaitis
Yes. Well, you got me excited right now. I’m right with you, and it’s intriguing, it’s important, and, well, I want to dig into some of your top research findings. So, maybe, could you share, when you talk about derailment, what are some of the most frequently occurring risk factors to be on the lookout for?

Carter Cast
Yeah, I found… you know, I didn’t know what I would find. I didn’t know if there were, you know, a whole bunch of them. And I found, I interviewed, I talked to a hundred people who have gotten demoted or fired, talked to a bunch of HR executives, and headhunters, and executive coaches, and even CEOs, and looked at all the academic research. And there was a lot that has been done on this topic because there are 360 feedback forms where you can mine the data and see what are people that are struggling, what’s holding them back, and when people are doing really well that are deemed in the top 10% of their organization, what are they doing really well that the people that derail don’t do well?

So there was just a ton of data on this. So looking at all the data, I found five themes over and over. And to try to make the topic more accessible and less scary, I created these archetypes or characterizations.

Pete Mockaitis
Oh, I love illustrations.

Carter Cast
So, instead of saying, “Oh, I suffer from interpersonal issues,” you can say, “Oh, I have a little bit of Captain Fantastic in me,” and you can laugh about it. So my attempt to make it a little less heavy of a topic was by creating these five archetypes, and here’s what they are.

The first one is Captain Fantastic, and this is for somebody who suffers from interpersonal issues. So sharp elbows, the quest for the Holy Grail of the corner office, you know, bruising people on the way. And this person either suffers from sort of over and unbridled ego or poor listening skills. And this happens to a lot of people. As a result, they have poor working relationships with co-workers and when, inevitably, when the performance, when they don’t hit their numbers, as inevitably happens, they don’t have support.

Pete Mockaitis
Yeah.

Carter Cast
So that’s Captain Fantastic. Now what’s interesting is, you might say to yourself, “Well, I don’t have those Captain Fantastic tendencies.” But there might be an aspect of you that has, under pressure, a tendency that can be self-sabotaging. Under stress, they have a tendency, and the tendencies can be they move away from people, they get cautious, or reserved, and they move away, or they move against people by being aggressive like Captain Fantastic would, but they could also move towards people, under pressure, and be ingratiating.

So these three tendencies – moving against, moving towards, and moving away – are all common behavioral traits we have when we’re stressed out and under pressure. That can hurt us interpersonally with other people.

Pete Mockaitis
Okay. Thank you. So that’s the Captain Fantastic story. And then what’s the Solo Flyer and the others?

Carter Cast
Yeah, the Solo Flyer is very common ailment when really good individual performers get promoted into managerial positions, they get a team and they still try to do all the work themselves.

Pete Mockaitis
Alright.

Carter Cast
They are so good at what they do, they want to keep doing it. They get so much satisfaction out of being able to make that spreadsheet smoke with their analysis that they keep wanting to do it and they don’t teach the team to fish. They want to fish for their team so they micromanage, they over-manage. Very common, and one researcher said becoming a manager is almost a transformation of identity.

What got you here won’t get you there. You have to change and you have to learn to empower and oversee and coach, and you’re not the player anymore. You’re the coach. And that’s a hard transition for people to go through. And people that derailed have a difficult time letting go of doing the work and learning to oversee the work.

And one of the interesting parts of this one was that it’s not just about overseeing the work, but your job as a manager is to build bridges into other departments where your team has dependencies and you need to get resources. So a good amount of your time, when you’re a manager, is spent with other functions in the organization upon whom you have dependencies, making sure that you’re aligned with them and getting resources so your team can do good work.

Pete Mockaitis
Got you.

Carter Cast
So that’s a Solo Flyer, and often a very good performer. So all of these profiles are people that are talented. The question is, “Is there something holding them back?” In the Captain Fantastic case, it’s often ego and ambition. In the Solo Flyer’s case it’s wanting to micromanage and do the work themselves.

Pete Mockaitis
Understood. Okay. And how about Version 1.0?

Carter Cast
Version 1.0 has gotten really comfortable in his or her routines and they’re skeptical of change. So they’re resisting learning new skills that they really need that will make them adaptable in the rapidly-changing business environment we work in. So they might say, they might have a mantra of, “Well, if it ain’t broke, don’t fix it.” Well, you know what, you’re going to have to make sure you’re staying fresh.

How are you staying fresh? Do you understand artificial intelligence as it relates to your job? Do you understand machine learning and big datasets? Are you getting comfortable with cloud computing? Do you understand digital marketing and social media? In this time that we live in, the importance of staying fresh and staying externally focused of these market changes is really important, and this person has just gotten too comfortable and they end up becoming a dinosaur.

Pete Mockaitis
Got you. Okay. And it’s interesting, and I’m thinking in particular that sometimes the resistance to change, folks can come up with very articulate reasons why they should continue doing what they’re doing.

Carter Cast
Yeah, justification. Right.

Pete Mockaitis
But, really, it’s sort of irritating everybody else. It’s sort of like, “Okay, that doesn’t really hold up,” and they can kind of sense what’s going on, and so it’s sort of like you’re outed in that way.

Carter Cast
Yeah, you know, I say to people, “Can you identify your areas of innate resistance? Where are you saying, ‘Yeah, but’”? Yeah, but…Where are you automatically resisting instead of just staying open-minded, asking clarifying questions, and then saying, “You know, that’s interesting. Let me consider that.”

Pete Mockaitis
Perfect. Thank you.

Carter Cast
So that’s Version 1.0. And this happens a lot of time mid-career. This is a mid-career derailer very frequently. And even into your senior level, executives who aren’t staying close enough to all of the disruptions driven by technology and globalization. So the most common reasons according to the research I did, the most common two reasons people derail are Captain Fantastic, interpersonal issues, and Version 1.0, just not being adaptable enough to change.

By the way, the change doesn’t have to be changing technologies and changing environments. It could be changing circumstances like you get a new boss. And the new boss ain’t like the old boss. And the new boss has a different modus operandi than the old boss, and you don’t realize that the onus is on you to change to the new boss’ style and not for the new boss that comes in to learn your style.

And I suffered from this one, frankly. I did well under one boss at Frito-Lay and I got this new boss, and he was much more hands-on than the old boss, and I resisted that, and I ended up trying to go around him, and I ended up getting kicked off his team.

Pete Mockaitis
Okay. Ouch. Lessons learned.

Carter Cast
I derailed because I was not adaptable to a boss with a different managerial style than an old boss.

Pete Mockaitis
You know, I’m curious. In hindsight or retrospect, what would you have done differently dealing with a boss who’s hands-on and you didn’t like it?

Carter Cast
That’s a great question, and I thought about that a lot. I should have realized that just because I was the one with the tenure in the group doesn’t mean that I didn’t need to adapt. The new boss coming in, even though he had less tenure than I did, he was still the boss. I should’ve gone to this fellow and I should’ve said, “How can I help you get up to speed? How do you like to communicate? Do you like to communicate over email? Do you like to communicate one-on-ones? What’s your preferred method? And how can I help you be successful in your role? You let me know what you need me to do so you can be successful because my agenda is your agenda.”

And I think if I would’ve gone in there with that sort of olive branch and let him know that my job was to help him succeed, then we would’ve gotten off to a much better start than what I did which is I thought, you know, I’m performing well in my position, he should just let me run, he should just let me do my thing, and that was a terrible attitude.

Pete Mockaitis
Okay. Well, thank you for opening up on that.

Carter Cast
I have a funny caveat.

Pete Mockaitis
Okay.

Carter Cast
He found the book and he read, and he wrote me about four days ago.

Pete Mockaitis
Tell me more.

Carter Cast
Oh, my gosh. So the book has been out two weeks, right? And he found the book, he bought the book, and he wrote me this note, and it was so interesting. The minute I saw the name on it, I was like, “Oh, my gosh, this is 20 years ago, I reported to this guy in the late ‘90s.” He said, “Thank you for your depiction of me. You’re kind.” Which was nice of him because he knew how I felt at the time, so to try to write objectively, I think, was he appreciated that.

And then he said, “I appreciate your candor in this story because your ability to be vulnerable and tell the story is going to help other people because so many times you read books and people talk about all the things they did well. And when you’re writing about these things that you did poorly or you learned from, I think it’ll make it very accessible to people reading.”

So it was this really nice complimentary note, but also I’m going to Dallas in a couple of days to present. He lives in Dallas, and he said, “I’d love to get together with you.” So, you know, it’s the last guy in the world I would’ve thought wanted to see me.

Pete Mockaitis
That’s cool. Well, you know, he’s probably learned some things, too, you know.

Carter Cast
I bet you’re right. I bet he learned some things on how to manage just from sort of the situation we went through. So it’s really funny. Really funny.

Pete Mockaitis
Well, that’s awesome. Well, thank you for sharing that. That’s so cool. Well, I want to make sure we hit all five. So how about the One Trick Pony?

Carter Cast
The One Trick Pony is an interesting case because they are good at what they’re good at, maybe they’re the controller inside of a company. They know exactly what they’re doing. They’ve done it well. But they haven’t broadened so they don’t have…you know they haven’t been on taskforce, they haven’t taken lateral moves. And so what happens is they become so reliant on what they’re good at, their sort of signature skill, that over time, unbeknownst to them, they become one-dimensional and/or considered unpromotable because they don’t understand how all the pieces fit together in a business, and they sort of tap out.

So it’s an interesting derailer because One Trick Ponies have great careers and be very good at something. But if they want to get to the next level, they eventually tap out because they’re seen as being too narrow.

So one of the questions I get for One Trick Ponies is, “Well, aren’t you supposed to specialize?” And I’ll say, “Yes, it’s really smart to get really proficient in one area because that’s your career capital, but at some point, if you want to become more of a generalist or you want to keep moving, you have to make sure you broaden.”

So, for example, when I was at Walmart, I was a marketer and my boss said, “Hey, do you want my job someday?” And I said, “Yes, that’d be great.” And he said, “Well, you’re not going to get it.” And I said, “Well, why?” And he said, “Because you only understand marketing, and to be in retail you have to understand operations, store operations and merchandising.” You know, buying and merchandising, assorting the product line, pricing the product line. It’s not just about demand generation of marketing.

And he said, “So you’re tapped out.” And I said, “Well, what should I do?” And he said, “Are you willing to take a lateral move into merchandising?” And I said, “Yes.” So I was moved into a different function, and that broadening allowed me to understand the buying and merchandising and assortment side of the business, and then later on it allowed me to have career flexibility going forward.

So there are times that it behooves us to take a lateral move to get experience, and later on that’ll give us some headroom to get promoted.

Pete Mockaitis
Perfect. Thank you. And how about the Whirling Dervish?

Carter Cast
You know, it’s funny. So the Whirling Dervish, I have this assessment on my own website. So I put this, I put the assessment in the back of the book so you can see which of these five archetypes is you, and I built this assessment with the Center for Creative Leadership so it’s a rigorous assessment, but I also put it on my own website just for free you can take it if you want. So it’s cartercast.com. I think it’s /derailment, and you could take this test.

The Whirling Dervish, the one I’m about to talk about, was the number one reason people, in a self-rated system, the number one people claim they derail. And that is, yeah, that you have trouble delivering on promises because you feel overwhelmed. So the Whirling Dervish is running around with their hair on fire, late for the next meeting, and muttering to themselves about their workload.

They lack planning and organization skills, and are known to over-commit and under-deliver. And what happens is their bosses and their co-workers can’t count on them to complete their assigned tasks at the time they said they can. And, eventually, people start distancing themselves from this person. So the Whirling Dervish over-commits and under-delivers, and has trouble with time management, with prioritization, and with organizational and planning skills.

And the reason, my theory is, so much… I’m seeing that so many people are claiming that they feel like Whirling Dervishes. I think it’s because we’re just…all of us are so overwhelmed by technology and by social media and emails and texts. I think everyone walks around feeling like a Whirling Dervish so it’s so important for us to prioritize to be able to say no to things, to delegate where we can.

Pete Mockaitis
And I’m curious, in terms of, first of all, so from the data perspective so your research with the 360 feedbacks and such, indicated that some of the bigger things that came up most often, right, was that the Captain Fantastic and the Version 1.0?

Carter Cast
Right.

Pete Mockaitis
But with the self-assessments is the Whirling Dervish. You think that’s indicative of a newer development in the workplace or just that people feel stressed when they take your self-assessment?

Carter Cast
That is a very good question, and I’ve thought a lot about it. I think that, especially as social media is just becoming more and more part of our lives, and texts, people are expected to respond like Pavlov’s Dog, you know, within minutes. And if you don’t get back to somebody in an email within hours, I think, actually, the incident rate of Whirling Dervish is increasing. And I think it is becoming one of the major reasons people feel like they are derailing or they’re not doing a good job at work, is flat out they’re overwhelmed.

And so how can they compensate? How can they work with their boss to be very specific and crystal clear on their job accountabilities so they know what they’re evaluated on and they can actually work with the boss to pare the list, you know, their laundry list of things they have to do? How can people be more intentional about planning and prioritizing their work? How can they say no?

One of the favorite books I read, because I have a trouble, a little bit of trouble with Whirling Dervish, too, and my problem is I’m a pleaser so I say yes to things. And my wife said, “Carter, before you say yes, I want you to practice this sentence, ‘You know, that’s interesting. I’ll take that under consideration. Let me get back to you.’”

And, you know, my bias is, “Sure, I can…yeah, we can do that.” So I think the ability to be more deliberate for this Whirling Dervish profile, whose eyes are bigger than their stomachs and they’re full of creative energy, and they want to say yes, but instead of automatically saying yes, maybe you can say no with grace. Maybe you can do a five-minute favor for somebody.

You know, this case came up with me. I was asked to fly to San Francisco to present to prospects who are applying to Kellogg Business School. Now that would’ve been a two-day trip, and instead of automatically saying yes, I said, “You know what, I’m so busy right now preparing for my book launch. Could you give me the names of a couple people that are really good candidates in my area of knowledge, entrepreneurship and leadership, and how about I call them and talk to them about Kellogg?”

So that’s kind of the definition of the five-minute favor. Instead of taking two days to do this, I could take two hours by calling some candidates. That’s something that I need to do a better job of myself, is learning how to say no but with grace. Instead of being interviewed, what if I send you two good data sources? Instead of flying to California, what if I just call a couple of good candidates? So how can you turn that ask into a five-minute favor?

Pete Mockaitis
Beautiful. Thank you. And so I want to get some additional perspectives when you talk about feeling overwhelmed, inundated with expectations on social media and email and text messages, etc. It’s like sometimes in my own experience, and I’m working with teams and talking with them, you know, I’ve seen a number of times it’s almost like the emperor has no clothes. We sort of unmask an expectation that isn’t really there in terms of, “Is it essential to you that someone replies to your email within four hours?” They say, “Well, no.” It’s like, “If I needed an instant response then I’ll probably drop by their desk or give them a phone call or whatnot.”

And so I’m intrigued. How much of the expectation do you think is real versus perceived? And what are some best practices for how teams and organizations can address the matter?

Carter Cast
Yeah, that’s interesting because I do think you’re onto something with the profile of the Whirling Dervish is often somebody who wants to please others, somebody who is creative and wants to be helpful and they get themselves over-extended. And that personality profile may be more likely to feel like they have to respond to every request that comes in versus saying, “You know what, my first accountability is to deliver on these core objectives that I’ve set with my boss. And after I get those things done, I can respond to some of these other things.”

So I think that’s an interesting observation. You know, there could be a personality component to this which is us pleasers are more likely to be Whirling Dervishes, and we feel like we have to respond in a timely manner. But you know what? If that’s not core to our job, which is how we get paid, then we should put that on the backburner.

So some of the tricks or remedies for the Whirling Dervishes, I say this, don’t work in response mode. Approach your day in segments. You set aside sacred time when you’re really productive to do the strenuous intellectual work. So, for me, personally, I’m kind of weird because I get up really early. But my most productive time is from like 5:30 to about 9:00, and I try to safeguard that three-four hours to do a lot of my more strenuous work, and then I will turn and email and respond to others during more non-productive time.

So a lot of times I’ll do that in batches. So I’ll say to people, “Don’t work in response mode, responding to people every time you hear that little buzz of your text, or you hear that chime of an email. Respond to people during times that you want to in batches.” So maybe for an hour you do email, and then for two hours you do thinking work, or for three hours you have blocks of meetings, and then you go shut your door and you respond. But people that are not as productive often find themselves in response mode all day long.

Pete Mockaitis
Right.

Carter Cast
And they let the tail wag the dog instead of managing their work                  according to their priorities.

Pete Mockaitis
Okay. Well, so thank you. And I want to make sure we give a little bit of attention to the flipside. You know, what’s the right stuff? Are there some universals that everyone should bear in mind to continue career acceleration?

Carter Cast
Yeah, this was actually the most…I was surprised because I thought the most fun part of the book is going to be identifying these derailers and sort of talking about them. What actually surprised me most, probably in the entire book, is that people that do really well, you know, we might think, “Oh, they’re going to be really good at lots of things, or like a decathlete, you know, they’re good at running and jumping and swimming and throwing the javelin.” I realized that swimming isn’t in the decathlon, by the way, just FYI.

But what I found was that actually they’re only good at a couple of things consistently, they’re only good at a couple of things. They are – and this is, again, mining 360s and looking at the people that are in the top quartile of their companies in leadership effectiveness, what do they do well consistently, they are able to build strong relationships with others and enlist others to their cause.

So they are empathetic, they’re open-minded, you know, St. Francis of Assisi, seek to understand before being understood. Their ability to be empathetic, good listeners, open-minded, they’re able to enlist others to their cause. Second, they pursue projects to completion and they take accountability for outcomes.

So if they say they’re going to get it done by a certain time, they stay there until it’s done. They are all about driving for completion. If you have those two competencies, drive results and enlisting others, and most companies have, let’s say, 10 or 11, eight to 10, eight to 12 competencies, if you only have those two, the chances, in the research that I examined, the chances are 72% that you’re in the top, that you’re in the 98 percentile of your company in effectiveness if you just have those two.

Now, if you add on top of it, you’re self-aware, you’re aware of your vulnerabilities, you’re aware of your strengths, then that’s the lethal combination. You have self-awareness of where you’re good and where you’re bad, so you put yourself in the right position to be successful, and you build strong relationships and enlist others, and are good at driving for results, that’s the right stuff.

It isn’t like this laundry list of things to be great at. It’s you’re self-aware so you put yourself in the right position where you work on what you’re good at, and you minimize what you’re bad at, you find workarounds so you outsource it to other people who are more qualified than you. You enlist others because you build bridges and listen well, and you drive for completion. That’s the right stuff.

Pete Mockaitis
That’s fantastic. Powerful. You know, we talk about 80/20 a lot here, and there it is. Boom. Awesome.

Carter Cast
Yeah, it really is 80/20. This was the biggest part of the research that surprised me the most was to find out to have the right stuff you don’t have to be good at everything. You have to know what you’re good at and know what you’re not good at, but you do have to be good at building relationships with others, and you do have to deliver on what you say you’re going to do.

Pete Mockaitis
Awesome. Thank you. I want to make sure we touch on, you have a point about “you can’t count on the man” and it is important to hear.

Carter Cast
Yeah, this was really, really interesting. So I’m doing all this research, and I’m constantly finding that a big component of people’s derailment is that they actually were let down by their organizations. Their organizations are complicit in their very derailment. It isn’t only about the employee not performing well, the organization plays a key role when they derail, and their culpability is around four areas.

One, organizations move people too quickly especially talented people, and they don’t give them broadening experiences so you end up with the One Trick Pony. You get moved too quickly and you end up in a position and you don’t have the perspective to make, in a complex situation, you aren’t able to make good decisions because you haven’t had enough different types of experiences to draw from.

Second, they ignore bad behavior if short-term results are present, and this is Captain Fantastic. If you’re getting results but breaking glass along the way, they’re willing to turn an eye, turn their head. Third, they don’t require superiors to develop subordinates like they used to. And I think this is the 1099 problem.

When people are moving positions a lot, and there isn’t this social contractor used to be with employers, companies aren’t investing as much into developing subordinates as they used to, and so the onus has to be on us to develop ourselves because our superiors aren’t incented like they used to be in our development.

Back in the old day, P&G, you couldn’t make it to brand manager or group brand manager unless you had somebody in your team that was ready to take your old job. And you don’t hear about that as much, you know. That IBM model of development, or when I was at PepsiCo 11 years, that PepsiCo model of development, it’s just gone away because people switch jobs so frequently.

Pete Mockaitis
And you’d mentioned in your HBR piece, this was striking, that a Korn Ferry study put, of all the competencies, and there were many, right, amongst leaders that they sort of rank their how well they did upon them, that developing others ended up ranking dead last.

Carter Cast
Yeah, I mean, that was striking to me. There were 67 different competencies that…

Pete Mockaitis
This is the older version of For Your Improvement not the later one with fewer competencies, all 67, baby.

Carter Cast
Good for you. You got it, man. Lominger finally tightened that up, but they had 67 they’d identified and dead last in the research was developing others. By the way, this is self-reported by managers. This is managers saying, “These are the things that I’m not doing a very good job of.” And this was, I think, motivating others and confronting direct reports was also in the bottom 10 of what bosses and managers do well. So developing others was last, motivating others and confronting direct reports was also somewhere between number 57 and 67. So you get the picture.

Pete Mockaitis
Certainly.

Carter Cast
They’re not going to help so you’ve got to do it yourself. It’s like a DIY, you know, we’re in a DIY kind of career management orientation if that’s what you have to have now. Do it yourself.

Pete Mockaitis
And so you’re saying, given that, go for it, ask for the feedback, hire a coach, take the LinkedIn Learning course, whatever it takes.

Carter Cast
Yes, you’ve got to take…the onus has to be on you because it isn’t like when I was… you know, I’m 54. When I was young, the organization would sit down and they’d have these developmental conversations and say, “Okay, so let’s get you these experiences in the next few years to develop. Here’s your profile, here’s three things you have to work on with your profile, Carter. Here’s three strengths we want to give you, a chance to even work harder on these strengths to get them even better, more potent.” You just don’t see that as much.

If you get a boss that’s like that, and says, “You know, even though we’re having this performance review for an hour, let’s spend a half hour on the performance review but let’s spend a half hour on your development, and let’s talk about three things that we want to get you to do to improve and let’s look at three leverageable strengths you have that we want to make sure you even work on more.” If you’ve got that boss, you are a lucky employee.

Pete Mockaitis
Okay. So noted. So you’re laying out the ways that the companies are complicit in derailment, and we kind of zeroed in on the “you can’t count on the man,” and then what’s to be done about that. Is there some more?

Carter Cast
Well, the other one is that it’s in this not directly confronting direct reports. The research shows that managers shy away from having hard but necessary career conversations with employees. And so if you have this conversation once a year during performance review time, well, that’s terrible, right? You need to have conversations, developmental conversations the minute you see the need to.

So if your boss, the minute you finish a big presentation, or you come out of a big client meeting, on the way to the airport with your boss, that’s the time to say, “Let’s do a feedback session.” And it can be really simple. You can say, “Here’s one thing you did well, Jim.” Or maybe even start with, “Jim, what’s one thing you think went well?” And then you shut up and listen. And then you say, “Jim, here’s one thing I think you did well.” That builds confidence.

“Jim, what’s one thing you think you could’ve done differently?” And then you shut up. “Here’s one thing I think you could’ve done differently.” And that builds skills. So this real simple feedback model, one thing you did well, you let them say, then you tell them one thing you think he did well, one thing that you think they could’ve done better, and then you say one thing.

This, on an ongoing regular cadence, is the way you develop people. It’s not like some once a year occasion during performance review time.

Pete Mockaitis
Well, Carter, tell me, is there anything else you really want to make sure to mention before we shift gears and we hear about a few of your favorite things?

Carter Cast
Yeah, you know, when I’ve been out talking about the book, and I get this question of, “Which of these five derailers hits you in different stages of your career? And which of them hit men versus women the most?”

And so if I would say, of the five derailers I laid out, early in the career, it’s often Solo Flyer. You haven’t learned to leverage your team, you haven’t learned to teach your team to fish, you haven’t learned to be a good manager yet. Mid-career, it’s often Version 1.0. You get stuck and you get complacent, and you need to find ways to jumpstart your learning curve.

And later in career, a lot of times it’s Captain Fantastic. You know you’re good at this and you get overly confident, and you stop having that beginner’s mindset and asking for feedback. And so the Whirling Dervish happens throughout your career. I mean, that afflicts people whether they’re right out of college, or they’re 50, 60 years old. You’re older. That one afflicts people throughout.

So mid-career Version 1.0 often hits people with adaptability, early in career a lot of times it’s Solo Flyer. Now, men versus women, the number one derailer the research showed that hurts women – and this is going to make you cringe, it made me cringe – it’s being viewed as non-strategic. And I always say, “Well, geez, do you think fundamentally genetically women are less strategic than men? Well, of course not.”

This, I think, is a problem with access. You’re non-strategic because you don’t see how all the pieces fit together. You don’t have a perspective on the business, it’s broad. The way you get a broad perspective on the business so you’re not non-strategic is by having access to senior leadership, is by being rotated into different assignments, it’s by being put on different assignments. So this is an access problem.

So this is where the importance of having mentors and advocates, and raising your hand and being asked to be rotated on different assignments. Like my boss said, “Carter, let me put you on a new assignment to broaden you.” That’s the sort of opportunity that a person needs to be able to be viewed as, you know, to move past being viewed as non-strategic, because fundamentally, being non-strategic it’s not like a genetic, you know, there are strategic people and non-strategic people. But, no, it’s a problem with access; access to opportunity.

Pete Mockaitis
Perfect. Thank you.

Carter Cast
So that men versus women. Then the number one derailer for men, not surprisingly, is Captain Fantastic. It’s being unbridled egos, dismal listening skills, listening, by the way, that came up so frequently. Thinking you have the answer and talking too much and not being receptive to feedback, not asking for feedback.

Pete Mockaitis
This is so much good stuff. Thank you. Now could you share with us a favorite quote, something you find inspiring?

Carter Cast
You know, it’s funny, I think I kind of tethered the quote into what I was saying. One of my very favorite quotes is, “Seek to understand before being understood.” And I actually look back and I think it came initially from St. Francis of Assisi, you know, hundreds and hundreds of years ago.

Pete Mockaitis
And Stephen Covey just picked it up.

Carter Cast
He picked it up. But if you go look at… we could even Google it. If you look up St. Francis of Assisi and look at his beautiful prayer, I’m going to even try to find it.

Pete Mockaitis
Right. The “make me an instrument of your peace,” the one?

Carter Cast
That’s it. That’s it. That’s the prayer. “Lord, make me an instrument of your peace. Where there’s hatred let me sow love. Where there is injury, pardon. Where there is doubt, faith. When there is darkness, light. Where there is sadness, joy.” And he says in the next verse, “Oh, Divine Master, grant that I not so much seek to be consoled as to console, to be understood as to understand.” And I think a lot of people have taken that wonderful prayer and re-purposed it as, “Seek to understand before being understood.”

Because if you do that, you establish these strong relationships with people, and people then want to understand how they can help you too. So that begins this process of reciprocity and mutuality between people, and you end up having a group of people around you that are enlisted in your success and want to see you get ahead. And it’s not disingenuous. You try to help them get ahead, you show interest in their career and their projects, and they naturally will say to you, “How can I help you, Carter?”

Pete Mockaitis
Awesome. And you’ve looked at a lot of studies and research. Do you have any favorites?

Carter Cast
You know, my favorite book, it’s funny, I read so many articles and so much academic research while doing this, and the Lominger stuff is great. It’s dense. There’s just a lot of the FYI and developmental planner by Lominger. But actually there’s a book called The Extraordinary Leader and the authors are Zenger, Z-E-N-G-E-R, and Folkman, F-O-L-K-M-A-N.

They were the ones that looked at… so mining, mining all these 360s and finding these very specific competencies that successful people have and high performers have, and I found that to be incredibly useful. And then I would say Marshall Goldsmith who’s just a wonderful example of leadership researcher. His book What Got You Here Won’t Get You There was wonderful in showing that, as we move on and get promoted, we have to let go of our old behaviors and embrace new ones.

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

Carter Cast
Reflection. The most important thing I think I do is, in the morning, I sit down with a cup of coffee when it’s quiet at 5:30 and it’s dark out, and I journal and I read something that’s either philosophical or spiritual or social psychology, and I reflect. So it’s like wisdom from the ancients, or wisdom from people smarter than I, and I reflect on it, and then I journal.

And I think about, how do I want to model this? Or how do I want to take these nuggets and bring them into the way I live and the way I behave? So, for example, I’m reaching into my backpack right now, and the book I’m currently reading is Anam Cara, A-N-A-M C-A-R-A. It’s a book of Celtic wisdom by John O’Donohue. And it’s just this lovely book on friendship and love.

And I find that if I get up and I immediately start my day, even before I work out or do anything, I read something that is really well-written by someone that’s very smart, and then I think about how I want to use that or incorporate that into my life. To me, it’s a great way to start the day, and I do it every day. Even if I read for 20 minutes, it’s become a practice of mine.

Pete Mockaitis
Beautiful. Thank you. And is there a particular nugget that you share, either in the classroom or when you’re coaching folks, that really seems to connect and resonate, and folks sort of quote it back to you, or they spread it far and wide?

Carter Cast
Yeah, there is actually, and it’s going to sound…I hope it doesn’t come off wrong. But I say often, in the last lecture I give in my class at Kellogg, don’t worry about what people think of you because they’re not thinking of you. They’re the protagonist in their own play, and they’re worried about their own lives. And if you realize that they’re not obsessed with how you’re behaving, that actually is empowering. It gives you freedom to do what you want to do with your life or your career instead of doing what you think others want you to do.

So another kind of companion phrase is, “Your opinion of me is none of my business.” I really do think that a lot of times we’re working so…we’re so worried that we’re being judged that it can stifle our creativity or make us make certain decisions about our career based on the safe path. But it really helped me to change careers eight years ago and go into academics and go into venture capital by saying, “You know what? I don’t want to be a CEO anymore. And if people are going to judge me because I’ve moved into this less ‘fancy’ career, then they can judge me.”

And what happened was I realized that nobody was judging me at all. It was my own misconception that people were more interested in my career than they were. They’re not interested in it. They’re worried about their own hide.

Pete Mockaitis
Certainly. That’s so good. Well, Carter, if folks want to learn more or get in touch, where would you point them?

Carter Cast
Well, for the book that I wrote I created a website that’s just my name CarterCast.com, and on that site there’s a whole bunch of information about the book, and you can take the derailment test. But also, I loaded it with resource just to try to be useful, so I’d point them there.

Pete Mockaitis
Awesome. And do you have a final challenge or call to action you’d issue to folks seeking to be awesome at their jobs?

Carter Cast
Yes, I would say every day when you reflect on the day, what’s the nugget you’ve picked up? Try to capture it because so much of what we learn we don’t codify and capture. So I think one of the challenges as we live in this fast-paced lives is taking the time to reflect and capture your learnings. So whether your journal or Dictaphone, some Evernote, whatever some app, whatever tools you use, I personally like the feeling of a pen and a piece of paper so I’ve gone through about, I think I’m on my 23rd journal now.

I just like to capture what I’m learning and then figure out a way to codify it into a behavior of some sort. So I would challenge people, what have you learned today, capture it some place so it doesn’t escape into the ether.

Pete Mockaitis
Beautiful. Thank you. Carter, thank you so much for sharing this perspective. I just have so much to think about. It’s like I’m quieter than normal because this so much good stuff to chew on, so thank you for bringing it. and I wish you lots of luck with your book The Right (and Wrong) Stuff, and your teaching, and investments, and all you’re up to.

Carter Cast
Well, thank you very much. I really appreciate it.

258: Doing the Work You Do Best with Ken Coleman

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Ken Coleman says: "Our sweet spot is at the intersection of our greatest talent and greatest passion."

Broadcaster Ken Coleman guides us in discovering what we’re created to do… and how to see that dream become a reality.

You’ll Learn:

  1. The litmus test for your passion
  2. The “nuclear option” for dealing with a difficult teammate or boss
  3. What to do when you’re burnt out at work but can’t leave just yet

About Ken 

Ken Coleman is host of The Ken Coleman Show and EntreLeadership Podcast, and author of One Question: Life-Changing Answers from Today’s Leading Voices. Ken is an acclaimed interviewer and broadcaster who equips, encourages and entertains listeners through thought-provoking interviews, helping them grow their businesses, pursue their passions, and move toward a fulfilled purpose. You can follow him on Twitter at @KenColeman, on Instagram at @KenWColeman, and online at kencolemanshow.com or facebook.com/KenColemanHost.

Items Mentioned in this Show:

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

Ken Coleman
Thrilled to be on. Thanks for having me, Pete.

Pete Mockaitis
Oh, yeah. Well, I’m looking forward to it. It’s so funny, I’ve seen your name many, many times in the iTunes Careers podcast charts, and now you’ve got two of them sort of surrounding me in the Top 10, which is not that rankings matter. It’s quite a mystery how they arrive there. But it’s fun to be talking to you like live, like you’re a real person and here we are chatting.

Ken Coleman
Yeah. Well, you know what, I am live and I’m a real person so that’s very exciting.

Pete Mockaitis
Two for two. So, I’d love it if you could dispel something I’ve been wondering about for quite a while when I see the EntreLeadership podcast logo. What does the word EntreLeadership mean, because I’ve got my own conceptions but I’d like to hear it from you? is it a state of mind, or a precise definition, or a brand? What should I think about this word?

Ken Coleman
Yeah. Well, Dave Ramsey is the founder of Ramsey Solutions, the Dave Ramsey Show, and the author of that New York Times bestselling book EntreLeadership, and the word comes from Dave’s desire to train internal leaders many, many years ago just as his company was beginning to grow in the 20, 30, 40 team member range, just training his own internal leaders.

And he began to think through, “Now, what does a healthy leader look like in an organization? We certainly want them to have all of the traits of an entrepreneur, but we also want them to be solid leaders as well and not all entrepreneurs are great leaders.” That’s a real combination, if you think, your audience, they can define what an entrepreneur is and then what a leader is.

And so, he smashed two words together, he goes, “I want leaders who are solid and can lead, but also have an entrepreneurial spirit, an entrepreneurial focus,” and so the word EntreLeadership, together, came into a teaching curriculum; internal. Then people started coming in from outside the walls of Ramsey Solutions and, over time, eventually it became a division and a bestselling book. So, that’s what EntreLeadership means. It just means an entrepreneurial leader.

Pete Mockaitis
Okay. Understood. I’m with you there. And so, now, you’ve got a newer show here The Ken Coleman Show which is cool. So, it’s all about – as I read from the description and listened to a little bit – folks who sort of feel often stuck in their jobs. Could you give us the broader picture for what that show is all about and a fuller picture for the problem of folks who are stuck in their jobs?

Ken Coleman
Sure. The Ken Coleman Show is completely focused on helping people discover what it is that they were created to do. And then once they discover that, well, then, “How do you make a plan to see that dream become a reality?” That is, in fact, what’s is about. So, you got people across the spectrum, we have people who call in on the show and they’re not sure what it is that they want to do with their life or what it is that they were created to do. No clues. They just need some sounding board to begin to look internally, and I’ll get to that in a second.

Then we have people who are confused, so they have a good sense of what they may be passionate about but they’re not sure how their talent intersects there. Then you have a large group of people that are stuck, and these are people who are actually good at their job, they have great talent, but they’re doing something that has zero passion.

And so, these all comes from a very simple analogy that a mentor gave to me many, many years ago when I was in my 20s, and the idea that is we all have a sweet spot. And our sweet spot is at the intersection of our greatest talent and greatest passion. So, in other words, we are living and working in our sweet spot when we’re using our top skills, top talents, the things we do best to do the work that we’re passionate about, the work that we love.

Then when you throw values on the backend of that, so I use my great talent to perform my great passion to see the results that I care most about; that’s talent, passion, values. When those three can intersect in that type of a purpose sentence and we live that out, we’re in our sweet spot. And everybody gets that analogy from sports.

If you’ve played any type of sports, whether it be baseball bat or a tennis racket or golf club, when you hit the ball perfectly in the sweet spot of that instrument it’s almost as if you cannot feel the contact of the ball, it’s such a clean crisp hit. And this isn’t just a homespun metaphor. There’s a guy by the name of Mihaly Csikszentmihalyi, you cannot spell it, you have to look it up.

But he’s a Romanian psychologist, that’s right, and he’s done 30 years of work on this idea of flow. And what he describes is essentially the same process of striking a ball with a club or racket or a bat, and that sweet spot it just feels as though it’s effortless. It’s almost as if time begins to stand still and disappear. So, there’s great science behind this.

And so, Pete, we’ve thrown this out there, we put it out there three months ago, and the response has been fantastic because people need a sounding board or need help walking through what their top talents are and what their top passions are and how those intersect, so that’s what we do everyday, one caller at a time.

Pete Mockaitis
Okay. Very cool. So, there’s so much to dig into there, and so I’d love to get your take on, so I guess, a role that matches your talent, your passion, and your values. And I guess, in a way, this isn’t quite binary in terms of, “This matches my talent. This does not match my talent. This matches my passion. This does not match my passion,” but it’s sort of like a spectrum, or zero to 100% range associated with a given role and how well it’s fitting into that sweet spot.

So, I’d love it if maybe you could orient us a little bit to what does something that’s kind of in your talent or your passion or your values sweet spot look, sound, feel like in practice versus something that is awesomely on track in your talent, your passion, your values? So, I imagine you’ve had many listeners and many callers and many clients and such that you’ve explored and assessed that.

But I think it’d be great if you could paint that picture for listeners so that it’s a little bit of a, “Oh, I thought I was doing okay, but, wow, there’s a whole lot more out there for me.”

Ken Coleman
Sure. Well, I think the easiest way to describe what you’re asking me to describe is, “What does it actually look like and feel like when I am doing work that I was created to do?” And, again, it comes down to the simple scale of, “Does the work that I’m doing right now, does it fire up my soul?” Because if it doesn’t, now we know, well, there’s reasons why.

But it’s the idea that when you are engaged in work that you truly love, that you’re passionate about, it’s because you’re actually good at it. Very few among us, I’m sure there’s some freaks out there who like to do things they’re terrible at. The only thing I do like that is golf. Like I play golf but I’m terrible but I enjoy the camaraderie.

And so, the reality is most of us don’t want to do anything that we’re not good at. And so, you can test your passion level. So, do you feel yourself alive and excited? Do you get a bit of a rush? Do you feel the juice? You’re just like, “Man, this is so much fun. I enjoy this. I get so much out of this work. I don’t want to stop. I find time just” as I said earlier, “beginning to slip away before I realize it.”

Passion is the great indicator as it relates to work that I love and work that matters to me, that’s values. So, if you don’t feel that and sense that, I can just tell you, it’s the greatest indicator and it’s the simplest indicator, then something is off. And most likely, what we find is, is that you may be good at doing what it is that you’re doing but there’s no intrinsic connection for you, there’s no heart connection, there’s no soul connection.

And so, that’s what you’re always looking for. Now you can flip that and you can see where people get confused and spend decades feeling like they’ve not caught an opportunity. So, this is the flipside of the question you asked me, “What does it look like when you’re not in the sweet spot?” What we see a lot of times is people pursuing something that they are very passionate about.

So, a lot of the emotion and devotion towards some work, but sadly they’re not aware that they don’t have the talent to pull it off. Something is missing and it’s in the talent/skill section. Maybe sometimes it’s just something you need to learn, but you’ll spend so much time pursuing something you’re passionate about but you don’t have the talent to pull off.

I run into this on the show a lot, Pete, with people who have tried so many different entrepreneurial opportunities and it just never click for them. And then when you begin to break it down, you realize they didn’t have the skill to pull of what they were trying to pull off. They loved it.

And so, a personal example, to pick on myself. I love the game of basketball. I absolutely love it. I love to consume it, I like to play it, but I’m 43 years old and I’m 5’9” so if I tried to make a living playing basketball or coaching basketball it’s just simply never going to work. And so, you have to be able to understand, “Wait a second. Do I have the necessary talent and skill to perform this function that I’m passionate about?”

And if not, it’s just about dialing it back and getting into a space of self-awareness to go, “Okay. This might be something that I do as a hobby or engaging hobby, but I can’t pull it off at least in this function.” So, I would work with somebody on the phone and say, “Okay. What do you love most about this type of work?”

And then you get to understand what it is they love the most. You go, “Okay. Now, what are your top talents? Can you pull it off? Because maybe it’s just a redirection and it’s a different perspective, a different avenue of performing work that you care about.”

So, again, it’s back to, “Am I having a hard time getting to work on Monday morning?” If that’s an issue of burnout. And if you’re passionate about something, you never burnout. You might get really, really tired and you need a break, but you don’t burnout.

Pete Mockaitis
Okay. That’s a helpful picture. Thank you. And so, now I’m thinking a little bit about some of the tricky issue. I think that it’s quite possible that you could be in a role where you got the talent, the passion and the values, and yet it’s not profitable. You talked about entrepreneurial things, I thought, “Well, they might just not have a product-market fit in terms of like the actual good or service that they’re bringing to the market, and no one really kind of wants it badly enough to buy it,” which I’ve seen and lived numerous times in my entrepreneurial failures.

And then, also, I think outside of entrepreneurial land, if you’re enmeshed in an organization with people and politics and teams and all that, I’m curious to zoom in there because I think there are many folks – and I’m thinking of a few right now, those close me – who, they got the talent. They really great at doing the thing. They got the passion, they really believe in what it’s all about and think it’s really cool to advance it, and they’ve got the values in terms of that’s really meaningful stuff that they’re working.

Let’s talk about the healthcare industry, for example. And yet there can be some challenges with regard to difficult co-workers, employees, bosses, politics, meetings. It’s sort of like the external kind of surrounding stuff that kind of diminishes the beautiful fit that we found here and brings it down so the experience of work is not delightful and awesome. What are some of your perspectives for dealing with those just difficult things that get in the way there?

Ken Coleman
Well, you gave me two scenarios so I’ll try to address both of them. Let’s go to the last scenario which is that lines up, the work lines up with their passion, their talent, and their values but it’s not fun anymore because they got a difficult leader or they’ve got difficult team members or the culture itself is really unhealthy, and we have that all the time on the show.

But, again, you’re in your sweet spot but this idea that life is a yellow brick road where little people are singing to you – like in the movie The Wizard of Oz, as you move along the journey – that’s just not the reality. So, I would say to that person, “You’re doing the right thing but you’re in the wrong place.” So, there’s no confusion, you’re doing the right thing but you’re not in the right place, because if you can’t fix the culture and you got difficult people then you need to get out.

Again, Pete, I have that call pretty regular. I’d say I probably get that call five or six times a week, and it confuses us and rightfully so, because you’re going, “Wait a second. I’m dreading going into work. I must not be in the right industry. What am I supposed to be doing?” And when I ask a follow-up question, you find out, “No, you’re just in the wrong place, in an unhealthy environment. Get out.”

Pete Mockaitis
Well, yeah, that’s really what I want to zero in on, so get out. Like, how do you navigate a little bit of that tricky zone in terms of you could sort of get out right away, you could try to change, to adjust, to influence things, to provide some feedback? How do you think about that world? If folks are right there, right now, it’s like, “Hmm, I am doing the right stuff but I am in the wrong spot,” what would you say are kind of like the immediate next step actions?

Ken Coleman
Well, the first thing is, can you do anything to make it better? What can you do? Before you pull the eject string there or hit the eject button, what can you do to make things better? Is there anything you can do? So, for instance, if you got some difficult teammates then I think there are some real healthy confrontation, you need to go to leadership and you need to go directly to them and you work on them.

I certainly believe in redemptive power. I believe in redemption, that people can learn so I’d start there. You just don’t throw your hands in the air the first time you deal with a difficult person. So, after that, if there’s no resolution after you’ve handled yourself well on a peer-to-peer basis and then you’ve taken the problem to leadership, and if the problem doesn’t get better then you’re immediately going, “Okay. What’s my plan? What’s my plan to get out?”

And when you think about a plan, you’re always going, “All right. Where is it that I want to jump to? How long is that going to take to get in a position where I can jump? Is there some additional qualifications, education, things of that nature that I’m going to have to do, some networking, relationshiping?”

And you don’t just jump. I never recommend unless you are in physical or mental danger. If it’s that serious then you leave that day. I don’t want to minimize that because that happens. However, most of us can put up with difficult people. Most of us can put up with a difficult leader. And so, I want you to be strategic about it, and you’re thinking through, “Okay. Where is it that I want to land? How am I going to get there? How much time do I think is that going to take?”

And it’s just like creating a plan for anything else. If you’re planning a vacation, you’re planning a workout routine, same kind of mindset so that you can move forward, but move forward in control as much as you can and you’re not putting yourself in financial danger or putting yourself out there with nothing to jump to.

Now, the only caveat to that is if you’ve got a substantial emergency fund, you got a lot of savings out there, or you have zero debt, and you’re well below your means then, hey, I would say eject because there’s no stress or pressure on you and you can get out right now. But outside of that I’d want you to come up with a plan.

Pete Mockaitis
Okay. Cool. And I love the phrase that you dropped there, redemptive learning, which is – speaking to my Christian roots over here – I dig it.

Ken Coleman
Sure.

Pete Mockaitis
So, I want to talk about that because I think that it’s easy to assume that someone, “That’s just the way they are. They don’t care. They’re checked out. They don’t like me. They’re not into coaching and growth and learning and development. They don’t value the same thing.” When I think it’s easy to say, “That’s just the way they are,” and sort of almost like writing them off.

And I think part of that comes from maybe folks have tried a couple times and haven’t seen much traction in terms of bring an issue up, or maybe it just comes from sort of a voice of fear justified, like, “Oh, that sounds like a really tough conversation. Well, it probably isn’t worth it. It wasn’t going to do anything anyway.”

So, I’d like to get your pro tips on, in practice, how do you engage in some of those difficult conversations and embark upon bringing about some redemptive learning?

Ken Coleman
Yeah. Well, before I give you some tips, we need to acknowledge something that most of us are terrified of confrontation.

Pete Mockaitis
All right.

Ken Coleman
And that’s a natural thing. It’s not fun, and especially in a work environment to sit down with somebody and go, “Hey, you’re a jerk,” but you’re not going to say it that way, but that’s essentially how you feel you’re going to come across. And the idea that is just insane, “I don’t want to put up with this. This isn’t even worth the stress of thinking about a difficult conversation,” otherwise known as confrontation. So, a lot of us are really terrified.

Now, there are certain people, I happen to be wired this way – if you’re familiar with enneagram – I’m fine with confrontation. Confrontation, to me, is kind of like it’s a sport, it comes along with life and I’m cool with it. It doesn’t mean you have to enjoy being mean. It just means you don’t mind a difficult conversation.

So, if you’re going to get in a situation like that and you’re at a point where you go, “This has got to be fixed. It’s got to change or I’m out,” then this is all about how you posture yourself. You sit down, and I would never do a one-on-one, I would have a leader involved just because I feel like, in this day and age, you just seem to have a witness there that, “Hey, this is how this went down. It was handled professionally.”

But I would have that sit-down with that difficult person and go, “Hey, this is how I’m feeling,” and that’s not accusatory. You’re putting it all on you, you’re saying, “Hey, this how I’m feeling. I’m perceiving you this way. And I want to ask you, is that reality from your point of view? Do you see it that way? Do you understand why I feel that way?”

And what’s happening there are two little tips that you asked for. Number one is you focused on the way you are perceiving it. You didn’t present it as a fact so, therefore, they have less chance to be defensive. The second thing you did, which also disarms in this, you ask them if they see it that way. So, now, you’re asking, and that interrogatory little tool there of a question, again, keeps them from feeling under attack.

Now, again, full disclosure, if a person is insecure and naturally defensive, no matter how you say it they just don’t like being called out on anything no matter how sweet and kind you are. But I would lead with that, and then I would say, in the course of the question, “Hey, I’ve sat down together today, and I ask you these questions and I put this out because I want us to not have this tension and I’m sensing it.”

And if they agree there’s tension, then, “Hey, what can we do? Because I’m here for this reason, and this is what I want to be, and I want to have a great relationship with you, and this is causing,” whatever, whatever, whatever. Very honest and extremely clear. Don’t beat around the bush. The more ambiguous you are the more defensive and insecure the person that you are confronting is going to be. And clarity may not be fun. It may be a little awkward but it is, as human beings, we crave clarity.

Is there anything worse than being unclear in confrontation? If the person that you’re confronting is going, and what they’re doing is they’re going, “Why don’t you just shoot me straight? What’s really going on?”

Pete Mockaitis
Oh, absolutely.

Ken Coleman
And you’re creating more tension. So, clear, clear, clear but very kind.

Pete Mockaitis
And actually it really amplifies the uncomfortableness.

Ken Coleman
Oh, sure.

Pete Mockaitis
Discomfort. That’s the word – discomfort. When you’re there, in terms of like, “What exactly are we talking about here? I think that something heavy is on your mind but I don’t perfectly know what it is yet. And I’m kind of spooked and just sort of waiting for the shoe to drop.” So, I love that tip about being super clear, and I love that sentence associated with, “I want us to not have this tension. I want to have a great relationship with you.”

And I think, boy, even the most, I don’t know, hardcore, purely task-result oriented, Grinch, heart of stone human being, I think if you hear that, I think just everyone will say, “Well, yeah, I’d like that too. It may be hard because of all these things you do that drive me nuts, or I might not think it’s in the cards because you are so wrong so profoundly in these ways that disrupt me.” But I think that that is something that just about everyone can agree to, which is cool.

Now, I want to zero in, I’m a little fixated though on you brought up getting a witness. And I think that, in a way, that makes awesome sense in terms of you don’t want things misconstrued, “I didn’t say that at all,” right? And it totally can happen. But, at the same time, having an observer present changes kind of the vibe, the dynamic. It’s almost like, “Uh-oh, I’m in trouble. This is serious hardcore stuff.”

And so, yeah, it sounds tricky. So, let me know more of your philosophy there.

Ken Coleman
No, it’s not. It’s not. There’s no trickiness about it. In fact, having a third person in there that is objective and in leadership or on the same level as both of you.

Pete Mockaitis
Oh, sure. Sure.

Ken Coleman
So, they’re investors. So, this is not somebody that would be below them. Ideally, it’s a leadership position. And I probably did not stipulate that, so let me be very, very clear. That’s what I’m suggesting. If this is a serious confrontation, this isn’t some just little, “Hey, listen, you said this the other day in a meeting.”

No, this is like, you gave me this scenario, Pete, of like you’re not happy, you want to get out, so this is the last resort. So, that’s when you get the third, that’s what I’m talking about. And it’s not tricky at all. Because it actually does what you said it does, which is it takes a whole another level of seriousness, like, “Okay. What’s going on here?” Especially when you’re letting them know what the meeting is about, and then they realize that person is in there, that leadership is in there and it just got real. And that’s what needs to happen. This is serious business.

Number two, it’s not just about having a witness so that things cannot be misconstrued and that you’ve got all that kind of stuff for HR and for the record, but it’s also so that you’re in check as well. You’re not going to come at somebody with a machine gun of charges and blare them out in front of a leader either unless you’re completely tone deaf, so it also keeps you in check and helps your posture stay in a place of gracious confrontation, “Hey, this isn’t about being angry. This is about let’s get some resolution here.” And so, it becomes less personal when we have another person, especially in leadership, that is observing.

The third thing is that person is objective. So, when it’s all said and done, it’s good to have that leader speak into the situation, even one-on-one with each of you afterwards, or right then and there, or later. But I absolutely think if you’re about serious redemptive confrontation you need to have a third-party person. I mean, that’s exactly what the Bible prescribes. And I think that if you’re going to confront somebody, you go right to them, but I think in this type of work setting where it’s really ugly, I would have a third party involved.

Pete Mockaitis
Okay. Got you. So, I think that’s helpful that we’re aligning in context right here.

Ken Coleman
Again, I think healthy confrontation, you get a leader involved and you get on the same page, in that way they realize, “Hey, we’re not coming after you. I’m not taking a shot at you. We need to fix this. This is not acceptable behavior.”

I just don’t see any problem with bringing in a leader especially if you’ve talked to the leader ahead of time. Now, if the leaders says, “I’m not comfortable. Handle it one-on-one,” then go for it. But I’m giving you what I think is the best way to handle confrontation in the workplace, I mean, serious confrontation where it needs to stop, behavior needs to change. If this was a misunderstanding, Pete, then I’m fine with just one-on-one go to lunch. But I think if a behavior needs to stop then it’s got to have a third party involved.

Pete Mockaitis
Here’s my resistance point, it seems like bringing the leader in, like it definitely brings with it a set of awesome advantages that you’ve laid out. I think the disadvantage, that I used the term tricky not to mean like politically sneaky in the sense of the word tricky, but tricky as in, “Ugh, the person on the receiving end of this may get seriously enraged that I “tattled” or told or brought the hammer of authority upon them in a way that it’s sort of like diminishes their reputation, good name, whatever you want to call it.” And so, I’m thinking that you could get a little bit of a backlash or a negative response just from the fact that that has happened.

Ken Coleman
Yeah, again, you’re not bringing authority down on them. You just have somebody that is either an equal peer on the same level who is just somebody who cares about both of you and wants to help with the resolution, or a leader is involved because, again, the behavior needs to stop, so I’m really not worried about them getting enraged.

And you’re not doing it publicly; you’re doing it in a private setting with leadership. I just think that’s a healthy, healthy environment when you can do that. So, we may have to agree to disagree. This is not my particular line of expertise. I’m not an HR consultant, but that’s my answer to that question.

Pete Mockaitis
Ken, what I’m loving here is that you have introduced something wholly new to my brain in terms of like, “Oh, that’s a fine thought,” and I am playing it every which way in terms of the pros and cons and implications and repercussions. And, of course, listeners will make their own judgments. And so, I’m digging it, and I’m thinking that this tool absolutely has its place in the toolkit so it’s been expanded in my brain which I like. It’s almost like a video game power up noise.

Ken Coleman
Sure. And understand that that’s how I think confrontation should be handled when something needs to stop. We’re not going to be sweet and soft about it. We’re going to be kind and respectful, but extremely honest. And, to me, there’s no sense in having four or five processes and setup. So, yeah, I get that. I may be uncomfortable over some but I can tell you this, if you try it, it’s the beginning of the end of that behavior one way or the other.

Pete Mockaitis
Cool. Okay. Well, so we covered that in great detail. So, moving on to new topics. I’d like to get your view for if folks are right here right now feeling some burnout but not yet ready to make the leap because of financial or other sorts of considerations, are there any pro tips for what can make the experience of work life suck less right here and right now where you are?

Ken Coleman
Sure. Yeah, I think it’s about progress. So, you’re in a position where you know you want to leave where you’re at but you can’t, and so it’s about mindset. And what we know about the human condition, there’s all kinds of science out there on this, is that when we are making progress towards our goals, even if it is incremental, so it can be the slightest amount of progress, it does motivate us further and it keeps us engaged.

So, engagement is many times about making some progress, so that could be a multitude of things. If somebody calls me on the show and says, “Okay, Ken, this is going to take me three years to get out of debt, and so it’s going to take me at least that plus then I’ve got to go to school to get where I want to go.” I had a caller the other day, he said, “It’s going to be about five, six years. What do you suggest I do in that time?”

And so, we broke down where he wanted to go, what he wanted to do. And so, he eventually wanted to be a physical therapist. He’s only got so much he can do, so what would he focus on? Well, the fact that he’s knocking off his financial goals, that’s going to fire him up because every time he pays off a debt he’s getting that much closer to freedom. Freedom to pursue what it is that he wants to do.

So, there’s some financial goals that if you begin to change the perspective that it’s not just paying off some stupid decisions that you made years ago, it’s, “Wait a second. Every time I pay something off on a monthly basis I’m getting closer and closer to my goal.” That’s a mindset switch and it really will help you.

But then, specifically, I told him, I said, “Hey, what are some things you can do because, at the end of the day, you really love the idea of helping people and through therapy and things of that nature. So, what about massage therapy or could you go work for a physical therapist 5, 10, 15 hours a week so that you’re at least in the space of the work that you want to be doing?” He lit up like a Christmas tree. He’d never even thought of that.

So, there’s a guy that if he goes and he just starts working part-time for a therapist, or he starts working for a spa or something like that, and he’s engaged in the work that he wants to do long term, he’s getting a little taste of it. And so, what that’s doing is I liken passion to an appetite. If you want to get a healthy appetite, a nutritionist is going to tell you you’ve got to put the right stuff in your body at the right times, and so that’s three, four, five, six meals a day, whatever.

So, you can do the same thing while you’re in the waiting. What little things can you do? What can you read? What classes can you take and in the space that you want to be in? What you’re doing there is you’re feeding your appetite and you’re keeping your passion not only alive but you’re actually growing your passion, and you’re keeping everything kind of going and it allows you to get through what you need to get through the whole idea of doing what you have to do so you could do what you want to do.

And, many times, what you’ll find is that you’ll get there faster because your passion is motivating you. So, it’s all about getting as much as you can while you can. You’re not going to get it all but get a little bit, get as much as you can, and you’ll find that time flies and you get where you want to be before you know it.

Pete Mockaitis
Oh, that’s good. Well, we’re entering the sort of final phase of these questions. I’d love to hear, you’ve asked many questions in your podcast and your book One Question: Life-Changing Answers from Today’s Leading Voices. What are some of the most exceptionally useful tidbits, if you could just give us a bullet or two or three, that you’ve gathered from these folks that are particularly applicable to working professionals?

Ken Coleman
Yeah, that’s hard to choose from, but I think two that popped to the top of my mind, one was from Jim Collins, the author of Good to Great, arguably, the greatest researcher in business sort of relates to great companies, what makes them, what breaks them. And I asked him, actually, in my book One Question I was coming at him on this idea of we all love greatness. Think about it, we love to go to a great restaurant or to a great concert or cheer for a great team, but, sadly, when we look at the numbers, most of us are okay with an average life. We don’t pursue greatness in our personal lives.

And I was asking him, “Why is that?” And he said something that I’d never thought about before but it’s so brilliant, he said, “It’s not that we’re risk-averse; it’s that we’re ambiguity-averse.” And I’m going to say that again because it’s so heavy. He says people don’t pursue greatness because they’re worried about the risk. They don’t pursue greatness because they’re worried about the unknown.

So, for instance, Pete, if I say to you, “Hey, we’re going to do some action sport,” and I say, “There’s a couple of risks. You might break an arm at the very worst but you’re going to get beat up a little bit. It’s going to be a lot of fun.” I’ve told you what the risks are, and you go, “Okay. Great.” But if I say, “We’re going to go do something, and we have no idea how it’s going to turn out,” that can literally paralyze a person. And it’s true; science shows all kinds of data there.

The number one thing that humans are afraid of is the unknown. So, that speaks, by the way, into the stat that many people have heard, that people are more afraid of public speaking than death, because with death we kind of go, “All right, I’m dead.” While public speaking, “I don’t know if they’re going to like me or go throw tomatoes at me, they’re going to laugh at me,” whatever it is. This ambiguity is what paralyzes us. So, that was really, really strong.

And then the other piece is I interviewed Coach K, the Hall of Fame Duke Basketball coach. It was the first interview I ever did. It’s crazy story. Unbelievable how I got to do that interview. But he said something to me at the time, and I had little ones, they were all, I think, under three. And he said something about some of these point guards that he’s had in the past, and he singled out two specifically: Bobby Hurley and Tommy Amaker.

And he said, “Both of those guys were very, very different, and I coached them different.” And he said that, “I had to learn how to let them be who they are in the framework of the system.” And then he went into another story, he said, “I’m the same way with my program in general. I don’t give much leniency at all with freshmen. For instance, if a freshman misses the bus by five minutes we’d leave him there even if he’s an All-American. But if a junior or a senior is five minutes late, we’re going to hold the bus.” He goes, “I call it fair but not equal.”

And it was a great piece of parenting advice and leadership advice that has stuck with me. It’s really, really true. As leaders, as parents, we’re going to have to really understand this idea of fair but not equal. You can’t treat everybody equally. And we live in a day and age, Pete, you know this in 2017, almost 2018, where it’s all about fairness, fairness, fairness but what it’s really about is equality. And there is certain equality that has to be in place.

We just talk about rights, but I’m talking about in a workplace. You’re going to have to treat certain people differently, and you can be fair but you can’t treat everybody equally as it relates to in the business and what they’re doing, the function they’re doing. They have differently personality so you’ve got reward them differently, you recognize them differently, you reprimand them differently. Same thing with parenting. It’s a really brilliant thought and it’s something that I think about on a daily basis as a dad.

Pete Mockaitis
Those are nice clear distinctions. I dig it. And, then, to sort of swap it a little bit, you’re often asking many people many questions. I’d love it if you could share a couple transformational questions that you’ve been posed or asked of and that have been particularly transformational for you.

Ken Coleman
Well, that’s a very interesting question. I don’t recall that I’ve had any guests that I’ve been in an interview format who’d turned the tables on me and asked me a transformational question just by nature of what we’re doing. But I certainly think of some transformational questions that I’ve had mentors ask me.

I had a mentor who was mentoring me in the area of marriage when I was in my 20s, and he said something to me that I’ll never forget. He said, “The next time that you’re going to express disappointment or anger or whatever with Stacy, I want you to ask yourself this question first, ‘Is it going to matter 25 years from now?’”

And I remember going, you know, I’ve probably been married like three or four years at the time, and it was so revolutionary to me, and not just in my marriage but in general. And I think that that’s something I’d pass along. That’s probably one of the most powerful questions that I’d ever been asked by somebody, was that right there.

Because, I think, many times we react in the moment, and then it’s the type of thing that if we put that kind of filter on it, think of the lack of confrontation, think of the dumb tweets that we wouldn’t tweet, or think of whatever it would be. But to put that lens on, it is really important, so I guess that’s probably the most transformational question I’ve ever been asked by anybody.

Pete Mockaitis
Awesome. Cool. Well, Ken, tell me, anything you want to make sure to mention before we shift gears and rapid fire and hear about some of your favorite things?

Ken Coleman
Oh, no, man, this is your show so I’m just here to answer your questions. I’m enjoying this.

Pete Mockaitis
All right. Cool. Well, then, let’s do it. Can you start us off by sharing a favorite quote, something you find inspiring?

Ken Coleman
Yeah. Well, I share this one on The Ken Coleman Show all the time. I probably share it once a week, and it’s by W.H. Murray, and this is a Scottish mountaineer who was also a writer. And you got to think of this, as I’m sharing this, as a guy who made his living on these daring expeditions. But he once wrote, “Until one is committed, there is hesitancy, the chance to draw back. Concerning all acts of initiative, there’s one elementary truth, the ignorance of which kills countless ideas and splendid plans; that the moment one definitely commits oneself, then Providence moves too.”

“All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favor all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamed would come his way. Whatever you can do, or dream you can do, begin it. Boldness has genius, power and, magic in it.”

And here’s my favorite three words, “Begin it now.”

Pete Mockaitis
Awesome. Thank you. And how about a favorite study, or experiment, or bit of research?

Ken Coleman
Favorite experiment, a bit of research. I think some research by the University of Michigan. I reveal this in my book One Question and it’s in the last chapter, talking about how to re-attain this habit of inquiry that we all are born with. As little kids we ask hundreds of questions a day. And the University of Michigan did some research on that premise, and so they found that toddlers sometimes can ask as many as a thousand questions a day, hundreds and hundreds of questions a day, up to a thousand questions a day.

But, by the time the average American reaches the eighth grade, we’re asking three questions a day. And that research fueled me to write that last chapter, and I just was so really, I think, despondent at the time. It’s such a strong word but when I read I was like, “What is going on?” In life and our Western education system is beating the curiosity out of us.

Think about this, Pete, we’re becoming trained to be test-takers instead of pathfinders. So, it’s all about, “Hey, get ready for the test. Get ready for the test. Standardized test.” It’s all about taking tests and having the answer as opposed to knowing how to ask questions. And I think that curiosity is the great key for life. It’s going to unlock so many doors for you. So, that research, for me, I got lost in that. It was pretty interesting stuff.

Pete Mockaitis
Oh, cool. Thank you. And how about a favorite book?

Ken Coleman
Favorite book. I think right now that could change within the hour, if you ask me that again. I would say The Art of Power by Jon Meacham. It’s about Thomas Jefferson. He’s one of the great thinkers the world has ever known. I’m a big Jeffersonian, fascinated by the guy. But it’s a book largely written from the letters that he wrote, so I would say that’s probably my favorite book.

Pete Mockaitis
And how about a favorite tool that helps you be awesome at your job?

Ken Coleman
That would be feedback.

Pete Mockaitis
Right on. And how about a favorite habit?

Ken Coleman
Quiet time in the morning. I’m up before everybody else. It’s dark. It’s quiet. And I’ve got a little routine with music, and reading, and meditating, and thinking, and breathing. I would say that with a great cup of coffee is my favorite habit.

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

Ken Coleman
I think the thing we hear from the audience the most they quote is the proximity principle, and that says that in order to do what I want to do I have to be around people that are doing it and in places that it is happening. And this is a game-changer when you realize that and you just get where you need to be. You’re observing, you’re learning, you’re watching. So, we’re hearing a lot of that. I think that’s kind of the thing right now; the axiom.

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

Ken Coleman
Yeah, KenColemanShow.com, and love for them to check out the show. If they don’t have Sirius XM they can get it. It’s a daily podcast on iTunes or Google Play. We’ve got a great free resource. In fact, that Jim Collins answer that I mentioned to you, that’s actually available on my website KenColemanShow.com, it’s absolutely free on the homepage. I forgot to mention that. But that’s such great, I love that so much. You can get that audio chapter for free from the audio book. But then check us out, subscribe, and share on iTunes. And, again, Sirius XM Channel 132.

Pete Mockaitis
Oh, cool. And, Ken, do you have a final challenge or call to action you’d leave folks who are seeking to be awesome at their job with?

Ken Coleman
Yeah, I think that the thing you need to remember on a daily basis, and you need to find a way to remind yourself and make this come alive, but if I could record a little audio bite that everybody would listen to every day it would be to say you matter and you’ve got what it takes. You really do matter. There is something that you were created to do, a very unique role.

And it doesn’t necessarily have to be tied to big dollars. It doesn’t have to necessarily be tied to fame or power, but it is tied to significance, and you do matter. And that’s the first thing, and then you do have what it takes. You have within you what it takes to do what it is you were created to do. So, now, it’s just about doing it, you believe that. And if you truly believe it, then you’ll become it.

Pete Mockaitis
Awesome. Well, Ken, thank you so much for sharing this time and perspectives. This has been a real treat. I wish you tons of luck with your shows and books and speaking and all you’re up to.

Ken Coleman
Thanks, Pete. I really appreciate you, man. Thanks for having me on.

251: Taking the Leap Into your Dream…the Smart Way with Mike Lewis

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Mike Lewis says: "People... want to help way more than you realize, but you have to tell them what they can help with."

Mike Lewis shares his journey from professional private equity to professional squash and provides perspective on how/when/why to jump into what you really want to do.

You’ll Learn:

  1. When it’s time to jump
  2. The right mindset for taking your jump
  3. Actionable ways to tune into your internal voice and deepest desires

About Mike 

Mike Lewis is the Founder and CEO of When to Jump, a global curated community featuring the individuals, stories, and ideas relating to leaving something comfortable in order to pursue a passion. Launched in 2016, the platform has attracted millions of impressions through digital and print media, in-person experiences, and collaborations with leading brands including Airbnb and Lululemon. In January 2018, his book, When to Jump: If the Job You Have Isn’t the Life You Want (Henry Holt Macmillan) releases worldwide. The book features over forty case studies with insights, frameworks and guidance around when to pursue a passion.

Items Mentioned in this Show:

Pete Mockaitis
Mike, thanks so much for joining us here on the How To Be Awesome At Your Job podcast.

Mike Lewis

Great to be here, thanks for having me.

Pete Mockaitis

Well, I’d love it if we could start… It’s fun that this is not only a fun fact but a key part of the story behind your wisdom. But could you tell us the tale behind you becoming the 112th best squash player in the world?

Mike Lewis

Sure, absolutely. And thanks again for having me, it’s a real treat to be on. I grew up in Southern California, my dad was a squash player. For those who don’t know squash, you’re in the majority. It is a sport like racquetball or even like tennis indoors, but west of New York City there really aren’t many players who compete at the high levels, particularly as a junior, as a kid.
When I was 14 years old and discovering the sport, my dad had obviously played it before. Like I said, he had played on the East Coast as a naval surgeon, and our family moved. I was born in the city, but moved to the South and then to Santa Barbara. And when I was 14, came across the sport on my own actually, ironically, at the one gym that had four courts or five courts within 100 miles from our town, and it just happened to be down the road.
So, I fell in love with it and I think I loved the idea of the adventure behind it. The idea that I could really create my own story from playing the sport, and really go my own path with it. So, at that point I thought, “I’m going to do this someday”, I just didn’t know exactly how that would happen. There was probably five of us, like I said, west of New York City, who were competing as kids. And first I had to get better to play in college and at some point I’d say, “Well, if I could do that, maybe I could get even better.”
And shortly after I started playing, there was a traveling pro who was coming through town for a tournament we hosted at our local club. And I remember I was around 14; he was I think just 5-6 years older, but described this adventure of playing a sport we both adored and using it as a way to see the world – playing on mountains in Brazil and cities in Asia and towns that dotted the Pacific. And I just knew at some point I would do that.
So, like I said, I found a way to get to play in college, I got to play for four years, I was the captain of the team my senior year, and then while I was in the working world for several years going forward after graduation I just kept it up. And I said to myself, “If I can just keep going and find a way to get better and eventually get sponsors and maybe even compete part-time, I’ll be able to maybe someday be able to do this full-time for a bit.” So, long story short, which we can get into, but I was able to do it and get as high as… And my goal was to rank 200 in the world, and I got to 112.

Pete Mockaitis

That’s good. It’s so funny – as you relate the story, it’s like I want to play squash and travel the world. It sounds awesome.

Mike Lewis

It really was awesome.

Pete Mockaitis

And so, now I’m just so curious. What fascinates me when it comes to professional anything, and sports I think is interesting in that world, particularly because I think if you’re like the 122th best basketball player or American football player, there are huge financial rewards. Can you enlighten us what sort of compensation does a 112th best squash player in the world see?

Mike Lewis

Well, the short answer is, not a lot. The pro squash tour is like the pro tennis tour, but the ugly stepsister, almost. So, you’ve got your Wimbledons of the world, but because we are a lot less popular, invisible and don’t have the marketing dollars and the brand sponsorships or the TV deals, there just isn’t that much money.
So, Wimbledon has several million bucks for the men’s and women’s champion; the Wimbledon in our world, the champion might bring home 50K at most. There is money in endorsements and camps and other stuff, but largely there’s just not much money. And then where I play, 112th in the world at my peak… You have to remember I started I think at 380 or something. You really are getting off the bottom in what was akin to the AAA Satellite tour – our version of Bull Durham and the minor leagues. And it’s nothing against those tournaments, but those were 16, 32 guys in a draw splitting $5,000.

Pete Mockaitis

Right, okay.

Mike Lewis

And yeah, you just wouldn’t bring much back from that. So, largely what the opportunity provided was exposure. You could get better, you could get yourself off the ground and get up the ladder a bit, but also it was the experience. A lot of these tournaments offer to pair you with host families, just like how we hosted that gentleman coming through town when I was a kid. That’s how I spent nearly every night of my 200,000-mile, 50-something country, nearly 2-year adventure. I was with other people along the way.

Pete Mockaitis

I don’t know why the first question that comes to mind when you mention all these different host families is, what have you settled in on as optimal mattresses and pillows, since you’ve tried them all?

Mike Lewis

You know what? It depends on the country and the continent. Some places I was just lucky to have… I remember my first place I stayed was right before I left Bain Capital, where I was working, I ran into a woman right nearby. I was going back to work after going to the gym, and she had told me, “Oh, you’ve got to play in the South Pacific.”
And I Googled when I went back to my office “squash in Fiji”, and a squash tournament in Tahiti popped up. And like two weeks later I was staying with the organizer of the tournament under a mosquito net in his daughter’s former childhood bedroom. It was decorated with princesses and glow-in-the-dark stars. And that, I can tell you, is not the Ritz-Carlton, but it was what I was hoping for. We picked the daughters up from school, we went to family outings, there was a birthday party at their neighbors’ that I went to, I sang karaoke. It was so much more than just the squash.

Pete Mockaitis

That is so cool. Okay, alright. So then, for everyone salivating, wanting to have their own sort of adventure in their own kind of a way, why don’t you lay out for us what’s When to Jump all about and can we hear who it’s for and why it’s important now?

Mike Lewis

Yeah, absolutely. So, When to Jump really came out of my own personal struggle to figure out when I was supposed to chase this dream. Like I said, it had been years, a decade since I first had this little voice in my head. And I was going about my job every day and I’m sure folks listening to this show can relate – you start to get a sense of circularity to your life. I knew what I had to do at work, it was fine. There was nothing too treacherous I could mess up. I kind of knew the playbook like the back of my hand. And on the other side there was this thing I really wanted to do.
So, I first Googled “when to chase dreams”, because I was like, “When do you do it?” And what I found was stuff that’s either too prescriptive, too self-helpy, or too inspirational where it’s almost just lost in the fluff of what you’re actually supposed to apply to your own life. And so, where I came out on it was, “What if I just talk to people who left something comfortable to go do what they cared about?” And I collected their stories and those stories could become proof that it wasn’t totally insane for me to do this.
And that’s what I did – I just started reaching out to people – first friends of friends, then colleagues, then passengers on the bus next to me, then a bartender down the street. And then all of a sudden as you start to peel back the layers, more and more stories became available.
And what was fascinating was that I wasn’t getting just that sexy, glossed-over photo, scoop or snapshot of the update from LinkedIn that only talks about the good stuff. This was the nitty-gritty, unsexy steps that come with chasing your dream. And people were giving highly vulnerable, real honest versions of what that looks like. And so, to me that’s what I wanted, that’s what made it feel realistic. They talked about the middle of that journey.
And so I remember speaking to a woman who was a Wall Street banker turned cyclist, and she had left Wall Street to try being a cyclist. And had largely failed for a while, but ended up making, after years and years, the Olympic team, and competed in London and then in Rio. And the conversation I thought would go something like this: “How was it to be a cyclist?”, “It was amazing, I made the Olympics.” And that would kind of be it. And instead it was: “How was it to be a cyclist?” And she was saying, “Well, here’s the hardest conversation I had with myself. Here’s what I was most scared of. Here’s what failure tasted like. Here’s why I kept going anyway.”
And when I hung up – this was January 2013 – I sketched a cover page to what I would call When to Jump. And I wanted to make a book of these stories with ideas and insights, but also to be able to create a space and a community where people could come together, have good drinks and snacks and food, and share ideas and stories with people in real life in a non-awkward, weird way, and come together.
And so, that was the idea. I told a buddy of mine I would make this someday. I put it on the back burner, I collected… I think I had one story from the US Senator from Maine Angus King – that was the one I had in the can, and then I kind of put it on the back burner, like I said.
And a year and a half later I had collected these stories totally really to give myself permission to jump. I had trained nights and weekends, I’d collected sponsors, I’d played anywhere I could, whenever I could, took sick days and holidays and half days. I had collected some sponsors using some material I’d put together at work on our own slideshow deck presentation templates, and all these different things, where all of a sudden the jump became more real.
And so, I left; I moved to New Zealand. Like I said, six months turned into nearly two years, and sadly while I was gone, my buddy, who was next to me at work, who I’d confided in around this idea of When to Jump, passed away in an accident. And at that point I said, “I need to finish this project.” And fortunately had the support of his brother and sister, and we talked and I was able to dedicate the project to him.
And over time, more people came forward with stories, from Michael Lewis, the finance author who wrote Liar’s Poker and Moneyball, The Undoing Project, to the second baseman for the Cubs who left the Cubs to go to college, all the way to the first female bishop in the Anglican church, who left PR to go into the Church.
So I had all of these interesting stories and slowly I was able to create a framework from the themes that I saw that kept coming back up again and again. And I came back in the end of 2015 and was approached by book folks, signed a book deal of this book that’s now coming out January 9: When to Jump: if the Job You Have Isn’t the Life You Want. And it’s 44 of my favorite stories with a framework that I call “the jump curve”. And it follows you through the different phases of taking a jump.
And what I found is that jumping can be for anybody. Some of us think that jumping is about changing jobs and moving to Bali and starting a company and doing drastic things. But what I found is that a jump is really having agency over your life. It’s about saying, “Okay, I want to change something, whether it’s the way that I commute to work, whether it’s a hobby that I want to develop or a new language I want to learn, or moving cities with my job, going for an internal promotion.”
But I think there’s this idea that you can do it; it just might not be pretty. And When to Jump exposes that through our community. And so when I signed the book deal, I ended up using the money to bootstrap a platform, and the platform has a bunch of different facets. We have a festival every year called Jump Club, which is part music festival, part beers with friends, part speaker series. Sheryl Sandberg keynoted our first Jump Club last year. She wrote the foreword to the book. Our festival grew nearly double to a weekend this year in New York, and I think we’ll be in London next year in October of 2018.
We started working with brands and we started to curate stories and we launched a podcast that’s now a top 10 business podcast on iTunes, all around these conversations. And so, what I found most, I think compelling, is that there isn’t one way to jump; everyone’s got their own jumps to make. But it really helps to know that you’re not alone, and that everyone goes through these hardships when they decide to make that step into the unknown. And often times the unknown is what will deliver the best parts of your jump.

Pete Mockaitis

Alright, this is juicy stuff. And I want to go in deep on the jump curve. But I want to maybe first say, I’m thinking maybe this is Step 0, if you will, but the decision that a jump is worth doing in the first place – not so much how, but whether to jump. And so I’d like to start by getting your take on, how do you go about framing up and thinking through that very initial part of the equation?

Mike Lewis

Well, the first piece of the jump curve talks about, listen to the little voice. And I think like you said, Step 0 would be to just acknowledge what you’re thinking about and what your feelings are that keep coming back, because our body doesn’t lie, as former NFL running back Rashard Mendenhall told me when I interviewed him about his jump from football into writing.
When you find yourself going to certain interests or ideas or spending your time in certain ways, those are usually telltale signs that there’s something boiling up within you. So, I don’t think there’s a perfect way to jump; I just believe that there are things you can do that will make sure it’s a positive, worthwhile experience. Because you really don’t know how it’s going to end, but you know how it can begin, and that I think takes planning and being thoughtful and following this jump curve.

Pete Mockaitis

Alright. Now when it comes to listening to the voice, can you elaborate a little bit, in terms of, what are some telltale ways that the voice or your body speaking tends to materialize? The symptoms, if you will.

Mike Lewis

Yeah, so it’s actually listen to the little voice because it’s that little voice that you hear when you go to sleep at night or wake up in the morning, thinking about. It’s something that’s kind of nagging at you, but you’ve always ignored. And I think for me, I knew that that fear of not listening to it would ultimately be more scary of having to deal with it, just echoing and echoing and sitting there for years and years. Then if I tried it – if I planned and proceeded forward with my jump – even if it didn’t work out, if I did it the right way, if I took the right steps, it would be close enough to saying, “Hey, I tried. It didn’t work, but I did it.”
And I think that often times that little voice is right, and we do a lot to drown it out, whether it’s through staying super busy, through working late unnecessarily, through making our calendar super jam packed – there are a lot of things we do to try to drown out that noise. And so if you can just find some silence in your day – I know that sounds really cheesy – I am in San Francisco, we have to be pretty crunchy out here. But I would say if you can wake up and say, “Okay, for five minutes today I’m just going to sit and be bored.”
There is a reason that we come up with our best ideas in places like the shower, where we can just sit and have nothing to do but let ourselves think and unwind. Our brains aren’t programmed to be stimulated to the extent that social media and smart phones and notifications demand of us. So if you overwork them, they don’t have the chance to start to loosen and let different juices flow. And I think that’s where you get that little voice. That’s where you can really start, is to say, “Okay, let’s try to take out some of these noisy distractions, let’s lower some of the other voices and let’s listen to what this little one has to say.”

Pete Mockaitis

Okay, that’s awesome. Alright, so then what’s the next step?

Mike Lewis

The next step is to make a plan. So we go from the aspirational to more the pragmatic. And within that step there are three pieces. One is financial planning – obviously you want to make sure that you’re jumping with some sort of cushion to really give this a go, and you don’t want to jump before that’s prudent.
The second piece is pre-jump practice, and that means really understanding what your jump is before you go. So, if you want to go start a furniture shop and selling furniture, you’ve got to learn about how to open a business. Maybe you should talk to small business owners. You’ve got to probably shadow or learn from a master handyman or a furniture maker. Maybe you start by watching YouTube videos. There’s a lot of things you can do just to start preparing for that step well before you have to jump. And that’s the pre-jump practice.
And then the third piece is safety net sewing. So I worked at Bain Capital for many years before I left to play squash, because I knew that if that jump didn’t work, and even if this jump doesn’t work, I would have a foundation. I had good reputation I think, decent enough; I worked on good projects and interesting deals; I got along with my superiors and others. And so, doing that type of legwork is actually really important, because I think for me at least, I’m not courageous enough to just drop everything and jump. I really need to feel like I’m supported, and Bain was very supportive when I ultimately decided to go. So those are the things that at a high level go into making a plan.

Pete Mockaitis

Oh, I really dig that. And so I’d like to get into a bit of detail with some of these here. Now when it comes to the financial plan, different people prescribe different sort of metrics or X month savings. What’s your take on what is financially cushioned enough?

Mike Lewis

Well, it’s funny. I think that it really is interesting when you peel back all the layers of what you actually need to live. You’ve got electricity, you’ve got water, probably let’s say that you need to have the Internet, you’ve got grocery bills, you’ve got your rent or your mortgage. You’ve got to have some sort of miscellaneous for external spending purposes, but what is that – five categories? Those are not 30 categories, those are not, “I want to dress in this certain way or drive this certain car or get this certain latte after work.”
And so, people think that financial planning is actually tough. What it is is really just being disciplined; it’s actually just cutting stuff rather than trying to say, “I need to go extreme and not spend a dollar.” You have finite fixed, hard costs – that’s not what we’re saying to change. It’s more like, on the margin, what can you start to tuck away? I’ll give you an example: If you cannot get a latte every day, you save $4-$5 each day for a year – that’s nearly $2,000 in your pocket. That’s a pretty good cushion to start your jump on.

Pete Mockaitis

Okay, cool, thank you. And when it comes to safety net sewing, I’d love to hear your take on, I guess the opposite point of view, which is, I don’t know – who was the famous general – the “burn the boats” guy. It’s like, that’s what made the soldiers fight oh so fiercely, is they had no option of retreat. And you’re proposing just the opposite – don’t burn those boats. Nay, craft an excellent boat. How do you think through these two sets of ideas on that?

Mike Lewis

Well, it’s funny because when we get going a little bit, it will actually be a little bit of both, and I’ll explain that to you when we talk again soon on the next steps. But the “burn the boats” piece is actually right to some degree. And like I said, there’s a part of that that’s true. But first you should make that boat really, really nice, and I’ll tell you why – because there are going to be people from your old life and your old jump that will come in again and again – references to you as you go for a new job, potential investors in your company or idea, customers of your new products.
And so, it just behooves you to not say, “Well, screw it. Guns blazing, middle fingers up, I’m out of here”, because the world is small, especially if you’re going to, let’s say, leave a cafe or a restaurant to start your own restaurant – you might want to hire someone from there eventually, you might want to get reviews from that person who runs the restaurant that you’re leaving, you might want to get tips on suppliers to buy from. So, there’s just a lot to do in terms of really maintaining a great relationship.
And I’m not saying that you will cross paths with those people and I think we’ll get to why it’s important to only look forward when you jump and not be half-in, half-out, but I think it will give you a piece of mind to feel like, “Maybe I’ll never run into these people again, but they all know why I’m leaving. If they were called by someone at some point needed to show a reference for me, they would say, ‘You know what? Mike’s a good guy. He’s not all over the place. He didn’t just show up one day, give us the finger and quit. He told us what he wanted to do.’”
When I started to play squash tournaments on the side, I told everybody because they got bought into it. And so later when the squash tour became a real possibility, they knew that I was looking towards doing that, they knew it was something I cared about. It would have been a lot harder to massage that story if I just brought it up on everyone one day. And sure, I could have done that, but now I look forward and the people that I let really understand my journey are folks that are still trying to be a productive piece to this next jump. And so I think that’s why you want to be able to sew the safety net.

Pete Mockaitis

Okay, cool. Alright, so have the Step 0 and Step 1, and what comes next?

Mike Lewis

So, the piece after that, which is really the hardest part, is to say, “Okay, you’ve planned as much as you can. Now you just have to take a jump and let yourself be lucky.” So that’s Step 3. And that’s a quote that Michael Lewis, the finance author, gave, which is, “If you look for luck you’ll actually find it.” It’s like when he described looking for money on the ground. Grown-ups leave it everywhere. You can find it, you just have to be open to it.
And the same goes for making a jump. If you look for those opportunities, if you make the plans, if you put down the pieces to what I call “let yourself collide with other people and things” – your odds are you’re going to find that luck. You just don’t know it until you jump. And obviously that’s just tough, because we as humans I think are rational to some degree, and when you leave a job you know what you’re giving up in salary, benefits, comforts, etcetera, but if you don’t know everything you’re getting in return on the next thing – that’s super hard.

Pete Mockaitis

I hear you. So you’re leaving a very clearly known, quantifiable piece for a quite unknown, unquantifiable upfront piece. So, could you give us some examples with regard to finding money lying around or colliding with people and opportunities? How does that appear in practice?

Mike Lewis

In what it looks like?

Pete Mockaitis

Right.

Mike Lewis

I think that what it is is, you don’t know what you don’t know. So, it’s really putting out a voice to it. It’s kind of going back to that little voice – you’ve now turned the voice up a lot. And so you’re saying, in my example, “I’m leaving, I’m moving to New Zealand. Everyone knows I love squash. Would love anyone’s thoughts”, etcetera. And the classic thing is, what happened?
Someone said, “Well, you should stay when you’re in Australia with my good friend who used to belong to my gym and he just moved with his family down there.” And then when I got down there, I met up with this gentleman and stayed with his family and they said, “Well, we have an extra apartment; we just moved. It was a corporate housing thing. Do you want to stay there?”
So all of a sudden I’m staying at no extra cost to stay with this gentleman and his family, and then he says, “Well, you should meet a friend of mine, who’s got a great podcast.” And it was Rob Bell. And I go on Rob Bell’s podcast last year as I was developing When to Jump, and through that podcast I received stories that are now in the book that’s coming out January 9 from people that were listening, and received amazing help from friends of mine who I would never have met, except for that they were listeners to Rob Bell’s podcast. And Rob Bell once surfed with a guy that I stayed with because our mutual friend heard my story in the gym locker room in Boston two months before I left.

Pete Mockaitis

I love that.

Mike Lewis

That could go on forever too.

Pete Mockaitis

Oh yeah. And it feels like an adventure. You think about the great sort of fantasy novels or movies of our time – that’s what happens. You go forth and then something happens, which leads to something else, which leads to something else, and it’s kind of unpredictable and cool and exciting. So, I dig it.
So, all you really did was say to the whole world, “This is what is happening, this is what I’m doing. Would love your input.” And then away it goes. And so, I think it’s pretty cool. It seems like there’s value in doing that, both in the broad and general “Hey everybody” Facebook, LinkedIn world – “This is what I’m doing”, as well as in the particular, like, “Hey, you lived in New Zealand for a little while. What do you know?” And so, kind of going in both directions there.

Mike Lewis

Absolutely. I remember having a spreadsheet where I’d just fill in anyone who had an idea for me once I said I was leaving. I think the thing that people really miss in a lot of this is telling other people about what you want to do, because people want to help. And they want to help way more than you realize, but you have to tell them what they can help with.

Pete Mockaitis

I love it. Okay, next step.

Mike Lewis

So the last one is, and this is the fourth and final step – don’t look back. And so that is the “burning the boats” one, is you don’t just kind of say, “Well, if this doesn’t work, I’ll always go back, or maybe I’ll do this three days a week, then two days here, and I’ll do this nights and weekends.” Because at some point you’ve just got to be all in.
And that’s what “don’t look back” means, is once you say you’re in, don’t look around and say, “I wonder if this is really what I should be doing. I wonder what my friends would think. What if this doesn’t work?” You just have to be all in. And I know it’s really hard, but when you jump you can only look straight ahead.
And we’ve got in the book cases of failures and jumps that didn’t work out, and I think that’s what makes it real and understandable to say, “It might not be what I thought it would be, but it’s still going to be productive because I’m doing along the lines of what I enjoy.” And I think that’s super important, is when you jump to say, “This is going to work and I’m not going to second-guess myself twice.”

Pete Mockaitis

Now it’s interesting, as I’m thinking about my own jump, leaving Bain Consulting this time, not Capital, which you were talking about how everyone confuses them. But when I left and said I want to do training stuff, speaker stuff; learning and development is what fires me up the most… So I guess talking about “don’t look back” – I had a spreadsheet talking about the financial planning piece, and I suppose I had some standard in which I say I will quit at this point.
And I guess my standard might be somewhat extreme or aggressive – it’s like, “I will stop this if I have $0. I will not go into sort of insolvency or a negative net worth, but I am going to spend every dollar I have.” And so, I guess in terms of “all in”, you can call that 100% but not 120%, in terms of my “all in” this. And so, I’d love to get your perspective on that. Are there any sort of parameters or rules or tripwire covenants? I can think of “all in”, even though it sounds absolutist, still, on a bit of a spectrum.

Mike Lewis

Yeah. There’s a great line that Ethan Eyler, who invented the Lyft mustache, if you remember that. He was a videogame marketer before he invented this mustache that could go on cars. And he says when you’re taking a jump – he’s actually featured in the book too – he says there is this “van down by the river” fear. I think that’s in a book called Cubicle Nation that talks about it, where you think that you’re just going to be a failure living in a van down by the river.
And that never really happens. It does in some cases, but that’s pretty rare, and it’s mostly in our mind of like the biggest failure possible. So, I think what you described is the right one, which is, “I’ve made a plan-ish. I’m as sure as I can be, and now I’m going to go for it.” And I think that’s the way you’ve got to be; otherwise then why jump?

Pete Mockaitis

Alright, I’m with you. And I love it; I think that you’re right with the van down by the river. I remember I was thinking, “What happens if I spend my very last dollar?” And I thought, “Well, it’s not like I’m going to be homeless on the streets. It’s just I’ll have to pick a job that I might not find so interesting.” I always told myself that I would be doing cheese strategy, like some job at a giant corporate consumer packaged goods company like Kraft, doing cheese or something. I’m not passionate about, but I’m sure probably is interesting in its own ways. It just says optimization is intrinsically interesting for me and working with smart people, but it doesn’t light me up at the core. That’s really what is it stake, is, “Either we’re doing this or we’re doing cheese strategy. You’re not dying in the gutter.”

Mike Lewis

Right, exactly. You’re not going to die in the gutter.

Pete Mockaitis

Quote it! That’s the big quote for you: “You’re not going to die in the gutter.” Cool. And so then, a lot of these jumps have been in the career context. I’d love to get your perspective – you mentioned that sometimes when you’re referring to jumps it’s about hobbies or learning something new. How should we think about jumps in those contexts, where you can totally just keep doing the same job, but you’re still experiencing that adventure and that jump commitment action?

Mike Lewis

Yeah, I call it “internal jumping” and I think there’s three ways you can mix things up through the city you’re in, the office location, especially if you’re with a beer company. If you’re at the cheese company, you could do cheese marketing in Wisconsin or in France. You can change products – you can go from cheese to detergents if it’s a consumer packaged goods company, or maybe you could go from selling cheese and marketing it to the product and engineering of it. And so, that’s kind of like a role and type of jump switch.
And so, I think those three things or any combination of them would really lead to something that would be stimulating, because it changes that circularity. I interviewed on our podcast – I think it comes out in a few weeks – former CEO of eBay John Donahoe, who’s actually the former CEO of Bain as well. And he talks about this product or this concept, and I’m not going to remember the guy’s name, but he calls it “repotting”, which is this idea that every 10 years or 7 years or so you want to repot – take yourself out of one pot, put into another and let roots grow again.
And John actually, if you look at what he did at eBay, they would regularly switch cubicles of folks so that people can mix up and meet other people. And I think there are just things like that. Even going to work a different way or talking to the person on the bus next to you – that type of thing can mix things up and it’s a super incremental micro jump.

Pete Mockaitis

That’s good. So, Mike, tell us – what do you think would be the very first step if someone is having a little bit of that little voice going on? And is it just a matter of making time for the silence and the boredom, or what would be the very first thing you do?

Mike Lewis

Yeah, I would say, absolutely. The thing that’s no-stress, low-touch, light-weight, easy to do would be – and I do this every day – take five minutes in the morning before you look at technology, write in a journal, or maybe just make a Google doc or Evernote or whatever it is, and write down the things that you thought you did well yesterday. Get yourself into a mindset to be thinking of the positives.
And then if you want, start with one thing a day you’re going to get done, like a 24-hour goal. That stuff’s really easy. The CEO of 1-800-GOT-JUNK? told me about that – Brian Scudamore. And you can be as bite-size as, “Okay, I’m going to research things I’m interested in today” or, “I’m going to talk to a musician.” Something that just makes you curious. And I think if you give that 5, 10 minutes to yourself each morning, you’re going to get a little bit closer to that thing and that’ll get you on that curve. It’ll get your voice to kind of grow a bit. It’ll tune it up rather than tune it out.

Pete Mockaitis

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

Mike Lewis

Yeah, I would just say if you want to learn more, our website’s WhenToJump.com. Our podcast is also called When to Jump, and you can find it on our website, also on iTunes and all that good stuff. We have a newsletter where we keep our community up-to-date once a month. Actually we just sent out our monthly one this morning. And then of course the book comes out January 9. So, I spent the better part of several years putting what I hope will be together the resources, the tools, the ideas and the people that give people a sense of permission. And I hope people enjoy the book, and obviously I would love to hear from you if you end up reading it.

Pete Mockaitis

Cool. Alright, now could you share with us a favorite quote, something you find inspiring?

Mike Lewis

I would say I’d have to quote my cousin Sheryl Sandberg, who wrote the foreword to the book, and to paraphrase her it would be – a question that I go back to, that she goes back to again and again is what she would do if she wasn’t afraid? And I think that’s the most important question we can ask ourselves.

Pete Mockaitis

Okay. And how about a favorite study or experiment or a bit of research?

Mike Lewis

I thought that Manoush Zomorodi, who wrote the book Bored and Brilliant basically found a way to see if we could lower the interactions we have on our cell phones and social media and all that, and see what kind of result that would produce. And it turns out that it makes us happier.

Pete Mockaitis

Oh, perfect. And do you have a quick tip, a bit from there, in terms of if we wanted to get a little piece of that value, what should we do?

Mike Lewis

Yeah. One thing that you can do that’s super easy, which was amazing is, when you commute to work, try not to have your phone on you. So not even in your pockets – put it in your backpack or purse. It does wonders. I actually now leave it when I go to the gym. And it’s little things like that to disassociate; it really will rewire your mind and let you be bored.

Pete Mockaitis

Oh, cool. And how about a favorite book?

Mike Lewis

Memoir-wise I would say Shoe Dog by Phil Knight and his story of starting Nike – the ultimate jump start in many ways. And then in a more serious and kind of meaningful tone would be Man’s Search for Meaning by Viktor Frankl, a holocaust survivor and an absolutely extraordinary man. I think everyone should read that book.

Pete Mockaitis

Okay. And how about a favorite tool?

Mike Lewis

I really like the microphone I use when I travel for podcasts. I know I don’t know what this one is I’m using now, but when I travel I have an H1 microphone and recording set. And it’s just awesome; it’s really simple and small and you can actually have a lot of fun with it. You can record yourself and notes to yourself, you can record conversations, podcasts, interviews. It’s very cool.

Pete Mockaitis

Oh, excellent, thank you. And how about a favorite habit?

Mike Lewis

It’s funny you ask that. Last night I actually for the first time looked back at how many mornings I’ve written in my journal to start the day. And I just write. I don’t really read it again, I just write down yesterday’s synopsis – kind of what I said earlier. And I knew I started January of 2015, I’m wrapping up my third year, and this year and last year I’ve written 140,000 words each, which is pretty surreal to me.

Pete Mockaitis

And so, are you saying that you’ve got pretty nice consistency, in terms of every single day rocking out there?

Mike Lewis

Every single day. It doesn’t even occur to me not to do it now. So it’s just habits.

Pete Mockaitis

Cool. And is there a particular nugget or piece that you share that seems to really resonate with your audience and community, and it gets them kind of retweeting and quoting it back to you?

Mike Lewis

Yeah, I think that it’s, “Think of when you’re 80 years old and you look back on your life. What are you going to be most proud of? What stories will you make for yourself?” And I think that’s what drives people to jump.

Pete Mockaitis

And if folks want to learn more or get in touch, you say WhenToJump.com is where it’s at?

Mike Lewis

WhenToJump.com – it’s the home base for us. Our newsletter sign-up is on there, podcast, you can pre-order the book. And starting in February of 2018 we will have a Jump Ambassador program, which will be a 10-week intensive online course for people who want to meet 19 other RAD applicants that have been selected from around the world, and get closer to their jump. So all that can be found on the site, WhenToJump.com.

Pete Mockaitis

Oh, RAD makes me think of Silicon Valley.

Mike Lewis

Yeah.

Pete Mockaitis

Oh, boy. And do you have a final challenge or call to action you’d issue to folks seeking to be awesome at their jobs?

Mike Lewis

Well, I would just say, write down what your goal is. It’s a perfect time to say, at the end of 2018, what does your job look like? What are you doing? How are you crushing it, to say it in Silicon Valley terms?

Pete Mockaitis

Okay, cool. Well, Mike, thanks so much for taking this time and sharing the goods. I wish you and all of your jumpers lots of luck in their adventures!

Mike Lewis
Thank you for having me. It’s pleasure to be on. I hope this was helpful.

230: How to Get an MBA Education (and more!) for Under $1,000 with Laurie Pickard

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Laurie Pickard says: "What's amazing... is that you can be learning pretty much constantly."

No-Pay MBA guru Laurie Pickard explains Massive Open Online Courses (MOOCs) and reveals precisely how to get quality education for under $1,000.

You’ll Learn:

  1. All about MOOCs! What they are, where to find them, and how to pick the winners
  2. How to use Loss Aversion to avoid quitting online courses
  3. How to build a prestigious network without going to a prestigious university

About Laurie

When some of the most prestigious business schools in the world began providing free versions of their courses online, Laurie Pickard saw an opportunity to get the business education she had long desired, at a fraction of the typical MBA price tag. Her “No-Pay MBA” project (NoPayMBA.com) has appeared in the Financial Times, Poets & Quants, Fortune, Entrepreneur, CNN/Money, and the Wall Street Journal. Don’t Pay For Your MBA is her first book.

Read More