Jason Feifer shares the simple things you can do today to set yourself up for a more successful tomorrow.
- The mindset that helps you uncover hidden opportunities.
- Why real growth happens outside your role.
- The biggest career mistake professionals make.
Jason Feifer is the editor in chief of Entrepreneur magazine, a startup advisor, host of the podcasts Build For Tomorrow and Problem Solvers, and has taught his techniques for adapting to change at companies including Pfizer, Microsoft, Chipotle, DraftKings, and Wix. He has worked as an editor at Fast Company, Men’s Health, and Boston magazine, and has written about business and technology for the Washington Post, Slate, Popular Mechanics, and others.
- Book: Build for Tomorrow: An Action Plan for Embracing Change, Adapting Fast, and Future-Proofing Your Career
- Podcast: Help Wanted
- Book: A Heartbreaking Work Of Staggering Genius : A Memoir Based on a True Story by Dave Eggers
- Book: Quit: The Power of Knowing When to Walk Away by Annie Duke
- Book: Start with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek
- Past episode: 665: How to Make Lasting Change – According to Science – with Katy Milkman
- Past episode: 614: Making Smarter Decisions When You Can’t Know Everything with Annie Duke
- Past episode: 217: An Effective (but Rare) Strategy to Snag Your Dream Job with Kristen Berndt
Jason, welcome to How to be Awesome at Your Job.
Thank you for having me.
Well, I’m excited to dig into the wisdom of your book Build for Tomorrow: An Action Plan for Embracing Change, Adapting Fast, and Future-Proofing Your Career. But, first, I think we need to hear a little bit about you’ve been living without a sense of smell even way before COVID made that a more common thing for people. What’s the story here?
Yes, I felt like people were stealing my cool, fun fact when everybody started losing their sense of smell. The story is that when I was in college, I was dating a girl who had a very, very good sense of smell and taste. And for the first time in my life, she started asking me questions, like, “What herb is in here? Did you taste the rosemary in that?” or whatever, these questions nobody asked you when you’re in high school.
And I didn’t know what she was talking… I just didn’t know what she was talking about. I had no idea what she was talking about. And we realized maybe something weird is happening. So, we did a taste test, which was that I closed my eyes and she fed me different flavors of ice cream, like chocolate and vanilla and whatever, and they were all exactly the same. I had no sense.
And this was not a new thing, this was just the first time that I’ve realized that I had no perception of this at all. I’d gone through my life, up until that point, not aware that I was not perceiving things the way that everybody else in the world was. And I’ve since gone to a taste and smell clinic and done a lot of research into this and found that just an endless variety of things can impact your sense of smell, everything from nasal polyps to a brain tumor.
In my case, it was probably head trauma as a child. I fell out of a stroller when I was very little. This was what my parents told me as soon as I told them about this.
But they didn’t tell you before, Jason. They’re holding on that under the vest until…
Well, you know, it wasn’t that relevant a piece of information many years later. It was just I fell out of a stroller. I was in traction, apparently, but life moved on so I wasn’t aware of it. But once I told my parents the leading causes of this are…if something has come and gone, you can’t find some other active medical issue.
The leading causes of this are head trauma, chemical exposure, or an upper respiratory infection that just happens to get up into your olfactory nerve. My parents said, “Oh, my God, the head trauma.” And so, now we probably know. And, in the meantime, everything tastes exactly the same to me, which is it tastes like nothing.
Wow. So, I’m curious then, before you realized that this was going on, did you have any differentiation between, “I’m eating steak,” versus ice cream. I mean, there’s texture, but, like, the taste was just about the same to you?
Yeah, but I didn’t know that it was supposed to taste any different. You’re wearing glasses right now, and I wear contacts, which means that there was a time in your life where you put on glasses for the first time. Do you remember that time?
Do you remember your experience of that?
Well, it was fun, it was like, “Oh, wow, it’s like all the font became semi-bold. That’s kind of nice.”
Right. I remember the first time I realized two things. One, you can look at carpet and see individual fibers and, two, you can look at trees and see individual leaves. That was more information than I was ever getting before and I didn’t know that the average person got that information. And the same is true with this. I just didn’t know that this information was available to other people.
I thought, when people talked about flavors, they were talking about such insanely subtle differences between things that I probably just didn’t care about them. I didn’t realize that they are fundamentally different. And I still don’t really understand what it means. Like, wine is a funny thing to me. Every wine is exactly the same to me. So, I don’t know what people are talking about when they take a sip of wine, and they list off all these notes. It’s a complete foreign experience.
And I guess wine might also be the same to you as tea or water.
More or less. So, wine has alcohol, and you can feel the alcohol. So, there’s something that’s a little different there. And there’s a little quick science lesson, which is that, so let’s say wine, let’s say you take a sip of wine. This happens, functionally, simultaneously, but the first thing that happens is that the wine will hit your tongue. And that is the sensation of actual taste, which is just sweet, salty, sour, bitter. It’s just categorical.
Then odor molecules from the wine go to the back of your throat and up, and they’re read by your olfactory nerves, which is what controls your sense of smell. And that is actually what creates the sensation of flavor. Flavor is you smelling something inside of your mouth, basically. So, I can get sweet, salty, sour, bitter because my tongue works just fine. The problem is olfactory nerves so I can’t get flavor. So, it’s the difference between chocolate is sweet but it is not chocolate, and, therefore, vanilla and chocolate and strawberry ice cream are all exactly the same, they’re just sweet.
Okay. Well, Jason, it seems like you have adapted and functioned well despite this challenge. Kudos.
And, boy, what a metaphor, the idea of putting on glasses for the first time or realizing that your perception is different when it comes to other folks are picking up on flavors. Can you give us, we’ll put you on the spot, a segue for some lessons that are also similar, relevant, comparable, to those found in your book Build for Tomorrow?
It was a great setup for a segue, and I’m happy to take the challenge. So, I would say the transition here is that there is a way of learning how to think such that you see doors where other people see walls, in the same way that I saw blobs of green until I see leaves. And this isn’t, fortunately, something that you need to go out to a doctor to see, and it’s also something that everyone has access to, unlike me who cannot fix my sense of smell, because what it really requires is an understanding that we spend too much energy debating whether or not something should happen when it has already happened.
We spend a lot of time and energy trying to hold onto what we were comfortable with, and then trying to push back against inevitable change. And that’s counterproductive because if the change is happening then we have to deal with it. And the thing that I have learned from spending so much time, years and years, with entrepreneurs and innovative leaders is that there is a way to think about this experience.
There is a way to recognize your transferrable value. There’s a way to understand that the things that are in front of us are opportunities that when something changes, it just doesn’t change for us, it changes for everybody, which means that we are actually now in a situation where other people need new things, and we can rise up and serve them, and be the person who solves their problems.
That if we’re working in a job, that we can spend a lot of our energy figuring out how to be good at that next job even if we don’t know what that next job is. That the more that we build into the way that we just run our lives, the reality that a lot of the things that we do are going to change, the more we can start to prepare for it, and, ultimately, open up opportunities in the future.
Okay. That’s cool. And I love that notion of seeing doors where everyone else sees walls. And, boy, we talked about high school, this just brings me back to a high school memory in which I was in an organization that’s called the National Honor Society, and I think I was a junior, and we did very little in this organization, which I saw it was kind of silly. It’s like we’re honored, it’s like okay. But there’s supposed to be, like, service and such.
And I remember the advisor asked, “Who would like to organize the clothing drive?” and then nobody was volunteering. And I heard, “Who would like to be the National Honor Society president next year?” because it’s like, “If we do almost nothing, and then you do the one major thing that we do, then, in an election sense, you would win that.”
And at the time, I was very, I guess, ambitious, and resume-conscious, and thinking about college applications, and looking amazing, all that stuff, so, for me, that represented an opportunity, and I was sort of surprised that nobody was interested in it, and I felt like I needed to. And maybe I was a sophomore. I felt like I should hang back and let the upperclassmen take it but then nobody did after about seven seconds, I was like, “Well, I’m taking it now.” I raised my hand and, sure enough, I became the president.
Thank you. Yeah, I don’t know how much of a difference it made in my grand scheme of trying to look super impressive on applications or whatever, but I think that goes to show that I’ve had other times where I was at a podcast conference and someone showed me their app, and I was like, “Oh, my gosh, your app shows how many people are subscribed to a given podcast within that app?” And he’s like, “Yeah.” “Well, that means I could use these data to extrapolate against known podcasts audience sizes to estimate the size of any podcast, which is massively valuable when you’re assessing opportunities.”
And so, I think that really resonates in terms of when you see a door where other see walls, I have had those moments, like, I see something other people don’t see, and because of that, cool things are opening up. So, lay it on us, Jason, how do we get there?
How do we get there? A lot of different ways to get there. Those are good little stories. Let’s start with this. This isn’t something that you just do all of a sudden. This is something that you build towards. These are habits and ways of thinking that help you operate, make decisions, do something now that’s going to pay off tomorrow. I’ll give you a couple ways to think about it.
Number one, we’ll start with this. We should all be doing something in our own work that I like to call work your next job. And work the next job is this. Look, in front of you, Pete, in front of me, in front of everyone who’s listening to this right now, there are two sets of opportunities. You can call them opportunity set A and opportunity set B.
Opportunity set A is everything that is asked of you. So, you have a boss, and that boss needs you to do things, and you show up and you’re evaluated on whether or not you have done those things well. that is opportunity set A, do a good job. Opportunity set B is everything that’s available to you that nobody is asking you to do. And that could be at work, you could join a new team. You could take on a new responsibility.
It could also be things outside of work, like listening to podcasts then you decide to start your own. Whatever the case is, here is my argument to you. Opportunity set B is always more important. Infinitely more important than anything else. And the reason for that isn’t opportunity set A, doing the things that are asked of you, is unimportant. It is important. You have to do it or you will get fired. You need to earn money, but opportunity set B is where growth happens.
If you only focus on what you already know, you will only be qualified to do the thing you’re already doing, but opportunity set B is where growth happens. That is where you start to lay the foundation for payoff that you cannot even imagine, and you don’t need to know what the ROI is on it. You should just be doing things because you find them interesting, informative, because they create new skillsets, new opportunities, because you’re thinking about, “What do I need to learn? And have I learned it yet?”
I’ll give you an example for myself. When I was at Fast Company years ago, I was a senior editor at Fast Company years and years ago, and a senior editor is something of a misnomer. It just means you’re kind of a mid-level editor, and my job was to be on the print magazine. I was a print magazine editor. And then the company brought in the video department, launched a video department. Nobody asked me to be a part of this video department but I volunteered to stand in front of the camera and see if I could be a host, see if I could host some shows.
And I had some kind of raw instinct on it, and the director really helped me hone it, and I got good, and I wondered, “What is the point of this? Why am I doing this? Is someone going to offer me a television show?” No, nobody offered me a television show. But I learned a couple of really valuable things. Number one, I learned to talk the way that I’m talking right now, which is to say to be animated, to kind of fluctuate the way in which I’m louder and then I’m softer, and I’m just trying to keep your interest.
Also, I learned how to be good on camera, how to move, how to think, how not to say uh a million times, and that then translated into a bunch of other skills like standing on stage. And, as a result, years later, when I was interviewing to be editor-in chief of Entrepreneur magazine and I’m talking to the president and CEO of the company, one of the things that they really liked about me was that I could represent the brand well, that they knew that, in hiring me, they had a face of the brand who could go on TV and could go on stage, and that helped me get this role.
And then, once I got this role, I started getting invitations to come speak on stage and make money doing so, and now that’s a really nice business for me. All of that I attribute to standing in front of a camera at Fast Company when nobody asked me to do that, and to just start learning. I was working my next job without having any idea what that next job was. And you, right now, have that opportunity in front of you. There are things available to you, nobody is asking you to do it so you have to do it.
Well, that’s cool and beautiful. I guess my first thought in terms of that being challenging is there are a billion potential things you could go do.
Sure, there are.
So, how do we figure out which of these things are particularly worthwhile for us?
Well, the answer is that you cannot know so you’re going to have to take some bets, and you’re going to treat them as experiments. And this is important because something that we do too often is we think of every new thing that we try or do as a full commitment and, as a result, we don’t do them often enough. I was talking to two people who really informed my understanding of this. One is Katy Milkman who is at Wharton, and then Annie Duke who also has a Wharton connection.
Two fun guests of How to be Awesome at Your Job.
There you go. Well, I shall remind perhaps your listeners of things that they said, but Katy told me, we were talking about change and how to manage change, and I said, “What is the simplest thing that somebody can do?” And she said, “This is going to sound kind of like a pat answer, but the answer is experiment.”
And the reason for that is because most people do not. They think that everything that they do has to be a full-time commitment, and, therefore, they’re afraid to try it in the first place. But if we just go into everything, thinking, “This is an experiment, and I’m going to run it for a couple days, a couple weeks, a couple months, and I’m going to see if it gives me something.”
Well, then, you know what, even if it doesn’t work out, even if it’s not all that compelling to you, it is valuable. And it’s going to be valuable because you’re going to have treated it like an experiment, which means that if it doesn’t work, it’s not failure, it’s data. And that is a much more constructive way to think.
Annie, meanwhile, Annie has this great book called Quit, about why quitting is a great decision-making strategy. And she told me, and this really snapped this into focus for me, she said, “Look, imagine that you had to marry the first person you dated. What would you do? The answer is you would never date. You’d just never do it because you’d be afraid of making that commitment.”
The reason why we’re able to find the person who is right for us, hopefully, is because we are able to quit lots of other people before. We try and then we quit. And Annie said, “You have to just think of that for everything. We date ideas. We date projects. We date jobs. And we’re going to quit the ones that don’t work.”
So, to your question, “How do we figure out which ones to pursue?” I always start with, “What is compelling to me? What excites me? What builds upon, in some ways, the skills that I already have but takes me in a different direction? How do I think vertically, basically, instead of horizontally?” Entrepreneurs, I found, have this really magical way of thinking, which is vertical thinking, which is to say, “The only reason to do something is because it creates the foundation upon which the next thing can be built.”
Whereas, most people, myself included for a lot of my career, really think horizontally, which is to say I do something and then maybe I move along and I do something unrelated, and then I move along and I do something unrelated, and that doesn’t build, that doesn’t give me an ever-growing foundation so that I can level up, so that I can do more, so that I can accumulate people and connections and skills and insights that are, ultimately, all going to power whatever the next thing is that I do.
Okay. That’s cool. Vertical thinking, yeah. Can you give us some examples of that in practice? So, you shared your instance of communication then getting on camera. Any other examples to make that vertical thinking concept land for folks?
Yeah, sure. So, here’s something really simple. For years, my career has been in media. I worked in a number of newspapers and then a number of national magazines, and now I also make podcasts, write books and stuff, and I run a national magazine. And throughout much of that time, I really thought of myself as mostly a servant to the task.
So, when I was at Men’s Health, for example, I would write about this thing, and then I’d move along and I’d write about that thing, and anybody who I met along the way is sand through fingers. You meet people and then you move along. And when I got to Entrepreneur, I started to realize I am meeting all of these people and I’m not taking any care to how they can be part of an ever-growing and useful network because I’m going to be doing things in the future, not now, but in the future where maybe I need these people.
And, like, for example, a book. We’re talking, we’re sort of prompted by that I have this book Build for Tomorrow come out, and I knew, years from now, I will have this book and I will need as many people as possible who like me, and who have audiences, and who I can call upon. And so, if I’m thinking vertically, what does that mean?
That means that I must accumulate, that the reason to do something is because it is going to build a foundation upon which the next thing will be built. Every little interaction that I have can be part of that. I created a spreadsheet; it’s called Good Contacts. Everybody I meet goes in it. Everybody. It’s a Google Sheet, and it has a million tabs in it – investors, media, entrepreneurs. And I’ve been doing this for years and years.
And when I launched my book, the very first thing I did, or months before, was I went into this sheet, and I started going through everybody. Rather, years before, I kept going through that sheet and I would reach out to people and I would check in with them, and I would say, “Hey, I loved that thing you just did.” “Hey, is there anything that I can help you out with?” Why? Because when you gather people, the last thing that people want is to only hear from you when you need something from them, so you got to be warm, you got to treat it like a real relationship.
And this kind of thing is something that I now try to apply to everything that I do, which is basically, “How can I use today for tomorrow? What is it that I have right now, what thing am I building, what thing am I thinking about, what do I have access to, how can I make decisions where I’m putting my energy towards setting myself up for tomorrow even if I don’t exactly know what I need tomorrow? But what I do know is that today is an opportunity to do that, and I want to be mindful of it?”
That’s cool. All right. Well, now, I’m shifting gears a little bit, when you talk about change, you mentioned there’s four phases of change. Can you give us that overview picture and some pro tips on what do we do to change well?
Yeah. All right. So, here’s the theory that I came up. I came up with this theory that change happens in four phases: panic, adaptation, new normal, wouldn’t go back. Wouldn’t go back being that moment where we say, “I have something, some new and valuable that I wouldn’t want to go back to a time before I had it.”
And this came out of pre-pandemic. I had come to this conclusion that the most successful people that I met were also the most adaptable, and I wanted to understand what it was that they were doing and how they were thinking. And then the pandemic was a really fascinating experiment because what happened was you got to see everybody go through the same change at the same time and then radically diverge.
And some people moved forward, some people reinvented, others tried to cling as tightly as possible to whatever came before and whatever they felt like they were losing. And I wanted to understand what it was that the people who were moving fast and forward were doing and thinking. And they’re doing a lot of things but I’ll start by sharing this one.
Most of us make a mistake, and the mistake that we make is that we identify too closely with the output of our work or with the role that we occupy so that if someone came up to you at a party and asked what you did, your answer would be one of those two things. It would either be a thing that you make or the role that you occupy. And that’s fine, that makes sense. I would do a version of that, too, but it creates a problem.
And the problem is that those things are easily changeable. And if we anchor ourselves too deeply to the tasks we perform or the role that we occupy, then when those things change, and they will, then we will not just experience a change to our work; we’ll experience a change to our identity. And that’s what creates a total sense of disruption and panic. So, what’s a better thing to do?
Well, look, there’s a lot of talk, Simon Sinek had Start with Why, and then everybody talks about why, and I’ve always found that to be, honestly, a little bit of an abstract concept. And what I came to realize is that I think what we need is a mission statement in which every word that we select is carefully selected because it is not anchored to something that easily changes. What does that mean, abstract?
I used to identify as a newspaper reporter. Then I identified as a magazine editor. I stayed in jobs, newspaper jobs and magazine jobs that I disliked for way too long, becoming way too bitter. And the reason I did it was because I was a newspaper reporter or I was a magazine editor. The very idea of leaving those jobs and, therefore, giving up that identity was too challenging, and, therefore, I couldn’t bring myself to get out of bad situations.
Now, I have a sentence for myself, and that sentence is this, it’s seven words, “I tell stories in my own voice.” I tell stories. Story is a really important word for me. And the reason for it is because it is not anchored to something that is easily changeable. I don’t own Entrepreneur magazine, my boss can call me at any time, he has my phone number, and he can fire me. He could do it right now. And if my identity is “I am a magazine editor,” then I am one phone call away from losing my identity. That’s a terrible place to be.
But if I can think of myself as I tell stories and then in my own voice, that’s me setting the terms for how I want to operate, that’s me at this moment in my career. Well, now, when something changes, I have an understanding of the transferrable value that I have. I understand what I am, and I understand what I’m good at, and I know that it is not dependent upon one way that I used to do it. And when we have that understanding of ourselves, what we’re really doing is liberating ourselves from being stuck in one mode, in one job, in one task.
I’m intrigued by that notion, in your own voice. I’m thinking about Entrepreneur magazine, Fast Company, Men’s Health, each of them – well, you tell me, you’re the insider – has some guidelines, I imagine, associated with their voice, their tone, their style, their flavor. Are you able to tell stories within your own voice at each of these different outlets?
Well, I wouldn’t have said I tell stories in my own voice when I was at Men’s Health, and, really not even at Fast Company because I was at a different stage in my career at the time. The mission statement should evolve. When I was at Men’s Health, for example, I was in my late 20s. It was my first national magazine job. I worked at a couple local newspapers and a regional magazine before that.
And you had a shredded six pack.
And I had a shredded six pack, and I only ate vitamins. And I got there and I was, at the time, I was guided by this thing that I’m still, in many ways, guided by, which are these two questions, which is, “What do I need to learn? And have I learned it?” And so, I arrived at Men’s Health knowing what I needed to learn.
I needed to learn how to edit at a national magazine level, and, in particular, Men’s Health was really good at a kind of editing called packaging, which is lots of little bitsy items. It was very hard because you had to convey a lot of information in not a lot of space. And I wanted to get good at that. And a couple of years in, I had done it.
And so, when I asked my questions, “What do I need to learn? And have I learned it?” the answer is, “I knew what I needed to learn and I’ve learned it. It’s time to get the hell out of here.” But I’m not interested in what else someone tell me that I have to. Like, I need to go. And I did. I’ve never once in my career, and this is not career advice, you choose your own path.
But I’ve never once, like, gotten a job offer and then come back to my boss, and be like, “Oh, I got this job offer. Can you give me more money?” No, because when I’m out, I’m out. It’s time to go learn something else. That’s the thing that matters most to me. So, back then, I was writing in the Men’s Health voice, and the Men’s Health voice had a very, very particular style and a particular tone, and my voice was subsumed into that voice. But I also was younger and I didn’t have a stronger voice, and I didn’t have a stronger perspective, and I didn’t have something to tell people myself.
At Fast Company, it was roughly the same thing. I found a voice there but it’s very different from the voice I have now. I wasn’t as confident in it and I was still learning. I took that job because there was something else that I wanted to learn, which in that case was feature editing and feature writing and then eventually also video.
And so, I wasn’t really ready to speak in my own voice until much later in my career. Back then, had I gone through this exercise, and I hadn’t because I still just thought of myself as a magazine editor, I was anchored to my tasks, but back then I would’ve said, “My job is to be a good magazine maker.” The thing that I do is I take magazine jobs and I write really good stories and I edit really good stories. It was very limited because that’s how most people think.
Most people think that the thing that they are is the thing that they do. And it wasn’t until much, much later, after I’d gone through a lot of disruption in my own career, and I was trying to figure out how to feel a sense of ownership over myself, because when you’re just at the mercy of a company that you work for, you don’t have a lot of ownership over you.
But if you can spend some time thinking about what you are separate from that, and what value you have that can be brought to many different places, and people are lucky to have you, you start to feel more of a sense of ownership over yourself. I think that’s really important. And this exercise was a way in which I got there.
Well, tell us, when you talked about the exercises and the reflections and the key questions, any other powerful practices that help serve up these insights?
Yeah, I’ll give you another exercise to run yourself through, which is “What do I have? What do I need? What’s available?” I like the word available. Let me tell you what that was. Okay, my first job was at The Gardner News. I don’t even know if it still exists, but at the time it was like 6,000 circulation daily newspaper in North Central Massachusetts. I was a general interest reporter, fresh out of college, $20,000 a year.
And I hated that job. I hated it. And the reason I hated it was because I had these large ambitions and they were not being met, and I couldn’t figure out the pathway to meet them. I was at this tiny little paper, I wanted to do bigger work, and I couldn’t articulate it, and I didn’t have access to it, and I was really frustrated.
And as a result, I was taking the wrong path, because I was blaming the people I was working with for, like, holding me back. They weren’t holding me back. I was holding me back. But eventually I did this thing that I wasn’t doing it so consciously back then. But now that I look back upon what I did and kind of come up with a little framework, I realized that what I did was that I asked myself these three questions, which is, “What do I have? What do I need? And what’s available?”
So, break it down for that experience. What do I have? I have a job, and it’s not a very satisfying job but it is a job doing a thing that I want to do, but what I want is to work in a much higher level. What do I need? Well, the problem, if we’re being realistic, is that I don’t have the experience to prove to anybody at a higher level that they should hire me. I have nothing. I have nothing except for this small credential, which is that I’ve worked at this tiny newspaper, which The New York Times is not going to take seriously if I go apply in The New York Times.
What do I need? What I need is I need more experience and I need to work with editors who I’m going to be able to learn from because right now, I’m at a tiny little newspaper, and my peers are not much more experienced than I am, and I’m not learning from them. So, I need access to talent, and I need to be able to prove myself at a higher level.
What’s available? Well, this is the hard one because you can’t answer it with a fantasy. It’s not “What’s available is, ‘Oh, why don’t I just apply for dream jobs.’” It’s not “What’s available is, ‘Oh, maybe I’ll just kick the can down the road and we’ll try to figure it out in a couple of years.’” No. What’s available right now? Like, literally, if you’re stuck, something is available to you right now. Something. What is it? Find the door where you’re looking at a wall.
And, in my case, in that particular situation, I thought, “Well, okay, nobody’s going to hire me, The New York Times is not hiring me, but there’s another way in.” And the way in, in my industry, this is freelancing, which is to say that a lot of what you read in newspapers and magazines are written by freelancers. They’re independent contractors who generally pitch a single story and an editor had said yes to it, and then they go out and they report to that single story.
I thought, “Why don’t I start doing that?” So, I quit. I quit that first job and I just started cold-pitching. And I was going to them instead of waiting for them to come to me.
And, as a result, after many, many, many, many months of pitching and getting rejected or ignored, I got a piece in The Washington Post, I got a piece in The Boston Globe, and I started to build this freelance career that, ultimately, allowed me to prove to other publications at a much faster clip, that I could work at their level. And that was what ultimately helped me build the career that I have. It’s what jumpstarted things.
And I look back on it now, and I say the reason I was able to do that was because I thought through that transition, because I didn’t stay at that job. What I needed to do was figure out what was available to me, realistically so, and then put myself in a position to go get it.
Jason, I love that notion associated with it’s kind of like you’re stuck, but then something is available, and it’s the freelancing. And I’m thinking about someone else, actually, she was on the podcast, Kristen Berndt, her dream was to do, like, baggage operations for airports, which is fun, like, that’s her thing, and yet she had no opening there. She just literally started a blog all about this.
I love that.
And so, there’s one approach. You do some writing, either for the publications or on a blog or social media, LinkedIn posts, whatever, a podcast. You create some media such that it’s like, “Oh, look, this person is an expert and can do some stuff that’s good.” What are some other approaches if you feel kind of stuck? Like, what’s available is sort of hard to see from where you’re sitting.
And it started by asking, “What do I have and what don’t I have? And what don’t I even know I need?” I don’t know if you remember, but Donald Rumsfeld was the Secretary of Defense during the George W. Bush administration.
And, in the leadup to the Iraq invasion, a reporter asked him something, and he responded in this crazy, like, lyrical weird poetry thing that people made fun of him for, which was that he said, “There are known knowns. There are known unknowns. And there are unknown unknowns.” And people thought that was nonsense and it made for late-night joke fodder, but I was curious about it because I thought, “That’s not something that you just come up with on-the-fly. That has to be from something.”
And it is. It’s from a thing called The Johari Window, which is a self-assessment test, popularized in the 1970s, that then became very popular in military circles. It was actually a pretty useful way to evaluate a situation, “What do we know? What do we know that we don’t know? What don’t we know that we don’t know?”
And I realized that if we do a version of that for ourselves, we’d run ourselves through a little test like that when we’re feeling stuck, as you would ask, we get some interesting stuff. You can ask yourself, “What do I know that other people know?” All right, you’re at a job, you’re stuck, you’re feeling stuck, “What do I know that other people know?” “Well, here are the things you know.”
“What do I know that other people don’t know?” basically what is your competitive advantage. What are you really good at that maybe other people aren’t? “What do other people know that I don’t know?” Well, now, you can start to look around. You can see that people who maybe were your peers had taken radical interesting shifts, and they’re now doing interesting things. You can see that people are in fields that seem really intriguing to you, that you think you would be good at but you just don’t know that much about, and maybe it’s time to ask them.
And now the most terrifying question of all, of course, is, “What don’t I know that other people know? What am I not even thinking about? What am I not even looking at? What am I not even seeing?” And that should drive you to start to talk to people to explore what they have done, what path they took, what risks they took, and what were calculated risks that maybe seem crazy to you but actually seem pretty logical to them.
And what you’re doing, just to go back to Katy Milkman one more time, is you’re bridging what Katy told me, is called the false consensus effect. False consensus effect means that we tend to think that other people think exactly like us, and, therefore, we don’t think to use them as resources. But it turns out that people think pretty differently than us.
And when we ask them what they have done, and how they have done it, they will reveal to us all sorts of insights that we weren’t aware of. And those things can help us start to illuminate some of those unknown unknowns. And that will give you the path forward that you aren’t seeing right now.
All right. Beautiful. Well, now, could you share a favorite quote, something you find inspiring?
Yeah. I was interviewing Ryan Reynolds for Entrepreneur magazine, and we were talking about the career shifts that he’s made. He’s gone from acting into business, there’s a number of them. And he told me, “To be good at something, you have to be willing to be bad.” And I love that because it’s true, because we often assume that if we’re not good at something at the beginning, it’s because maybe we’re not going to be good at it.
But what Ryan is saying is that the difference maker isn’t whether or not we’re good at something at the beginning, but rather whether or not we’re willing to tolerate being bad long enough to get to good. That’s the thing that weeds people out, it’s that most of us aren’t able to tolerate that discomfort. But the ones who are, are the ones who get there.
All right. And a favorite book?
I, as a kid, read Dave Eggers’ A Heartbreaking Work Of Staggering Genius, which was a memoir. And the thing that mattered most to me about it was that it was written in a style and played with language in a way that I didn’t know was possible. And the things that I love consuming the most are the things that show me that the boundaries are not where I think they are. And that was, I think, the first time that I consumed something that really showed that to me.
And a favorite tool, something that helps you be more awesome at your job?
This is not going to be an exceptional tool, but I will tell you the thing that I live by, which is the native Reminders app on the MacBook and on my iPhone. They sync so that I can add something on the Reminders app on my phone, and there it is on my computer. And I look at that thing every 10 minutes, and every time somebody tells me something, it goes on there. And as I’m half falling asleep at night, I think, “Oh, crap, I didn’t tell that person that thing,” and it goes on that Reminders app, and I couldn’t leave home without it.
All right. And is there a key nugget you share that really seems to connect and resonate with folks; they quote it back to you often?
Yeah. I do a lot of speaking, and so I travel around and I talk to groups. And the thing that people always come up to me after my talk and tell me is their mission statement, the thing that I shared with you earlier. I have a whole exercise for how to get there, and I walk people through it. It’s in the book.
And afterwards they come to me and they tell me their mission statement, or they email me afterwards and they tell me their mission statement. And I think the reason they’re doing that is because it feels like a breakthrough when you’ve done that for yourself, and they just have to share.
Okay. And if folks want to learn more or get in touch, where would you point them?
I would point them to a couple places. Number one, my book is called Build for Tomorrow. I’d love for you to check it out. Also, you’re a listener of podcasts, I am a maker of podcasts. I have a podcast; it’s called Help Wanted.
I co-host it with Nicole Lapin, who’s a bestselling finance author. And what we do is we take people’s problems, often they’d call into the show, work problems, career problems, and we talk it through them in real time, or at least we take their questions, and then Nicole and I debate them and come to the right answer. And our goal is to help you build a career in a company you love, and you should check it out. It’s called Help Wanted.
All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?
Yeah, I’m going to tell you another quote, and I want you to spend time with it. And the quote is this, this is something that Malcolm Gladwell told me. We were talking about how he decides what products or what projects, rather, to take on. And he told me that he really pushes against trying to think of himself too narrowly, and to think of his voice and style and the things that he does too narrowly. And the reason, he said, is because self-conceptions are powerfully limiting.
Self-conceptions are powerfully limiting. That’s basically my call to action to you, is to consider what your self-conception is, and how that is limiting you because, the thing is, that if we define ourselves too narrowly, we turn down all the amazing opportunities around us that don’t meet that narrow definition. But what happens if we loosen the grip, that I think is where growth happens.
All right. Jason, this has been a treat. I wish you much luck and fun as you build for tomorrow.
Hey, thanks for having me.