Leap Academy with Ilana Golan - Entrepreneur Magazine’s Jason Feifer: How to Build a Career Beyond Your Job Title | E159

Episode Date: May 19, 2026

Jason Feifer started his career writing about middle school dances at a tiny local newspaper, frustrated and convinced he was capable of more. Stuck in a role that wasn’t moving him forward, he quit, sat in his dumpy apartment next to a graveyard, and began cold-pitching major publications with no connections. That decision transformed his trajectory, eventually leading him to become Editor-in-Chief of Entrepreneur Magazine and a leading voice on career growth and adaptability. In this episode, Jason chats with Ilana about why doing only what’s expected of you slows your growth, how to identify opportunities, and steps to take control of your career in an unpredictable world. Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a podcast host, book author, and keynote speaker who helps people build careers and companies they love by sharing lessons from the world's top entrepreneurs and leaders. In this episode, Ilana and Jason will discuss: (00:00) Introduction  (03:48) Cold Pitches From a Bedroom Next to a Graveyard (06:41) Developing an ‘Opportunity Set B’ Mindset (09:51) Building Skills Strategically Across Jobs (12:58) Renting a Title vs. Owning Your Name (17:02) The Mission Statement That Survives Any Job Loss (24:22) Why Jason Walked Away From His Biggest Hit (31:51) How to Test Multiple Ventures At Once (34:31) How a Lawsuit Accidentally Built Jason’s Success (40:00) The Danger of Labeling Yourself (47:47) Q&A: How Do You Become More Adaptable? Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a role he has held for over 10 years. He is the author of Build for Tomorrow, host of the podcast Help Wanted, and a sought-after keynote speaker who has spoken for companies including Pfizer, Alibaba, Clorox, and more. Jason also advises startups, sits on multiple advisory boards, and writes the weekly newsletter One Thing Better. His work centers on adaptability, personal reinvention, and helping individuals and organizations thrive through change. Connect with Jason Jason’s Website: https://www.jasonfeifer.com  Jason’s LinkedIn: linkedin.com/in/jasonfeifer  Jason’s Instagram: https://www.instagram.com/heyfeifer/ Resources Mentioned: Jason's Newsletter, One Thing Better: https://www.jasonfeifer.com⁠  Jason’s Book, Build for Tomorrow: An Action Plan for Embracing Change, Adapting Fast, and Future-Proofing Your Career: https://www.amazon.com/dp/059323538X Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

I was sued by a vindictive person with a lot of money, and the lawsuit was really scary. I mean, I didn't know. Was this going to bankrupt me? It told us that we should consider getting divorced to shelter the money with my wife in case this destroys me. Like, it was scary. Life is not linear. Life is reactive. Because of a bad thing, we make decisions that are different than we would have before. As the editor-in-chief of Entrepreneur Magazine, Jason Fayfair, talks to hundreds of entrepreneurs every single year.

He sees exactly how they navigate change, how to overcome failure to build for the future. He's also an author of The Incredible Book, Built for Tomorrow. In a world of AI where everything is slop, the only thing people are going to trust are other people, the authenticity of other people. I think a lot of our listeners lost that title or they... were laid off or whatever happened, their identity is attached to that title. They don't know who they are without it. We need a different way to understand our identity.

And here is my challenge to you. It's going to start with I and then... Welcome to the Leap Academy with Ilana Golan Show. I'm so glad you're here. In the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures, and countless lessons.

So lean in. This episode is going to be. amazing. I'm in a mission to help millions reinvent their career and leap into their full potential, land their dream roles, fast track to leadership, jump to entrepreneurship, or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams. And with this podcast, we can give this career blueprint for free to tens of millions. So please help my mission by sharing this with every single person you know, because this show has the power to change countess of lives.

Deal? Okay, so let's dive in. Welcome back to the Leap Academy podcast, today's guest. Ooh, I've been following him for a while and you guys are going to enjoy it so much. Look, he has a front row seat to the minds of the most successful founders on the planet as the editor-in-chief of Entrepreneur magazine. Jason Fayfair talks to hundreds of entrepreneurs every single year. And he sees exactly how they navigate.

get changed, how to overcome failure, to build for the future. He's also an author of the incredible book, Built for Tomorrow, and a host of his podcast, Help Wanted, and speaks on stages about adaptability, which is so aligned with everything we talk about here in Leib Academy. So get ready to take some notes. It's going to be so fun. But I will also remind me one more thing. Every week, we select a question that you put on our YouTube channel and we answer it at the end of the conversation. So in this case, Jason, I might be putting you on the spot, but I think you're going to like it. I found a question from Omer, which is perfect for both of us to answer together. And it's all about what is AQ adaptability and how do you become more adaptable as an individual, as

organizations? So well, Duffy, like if you're okay with it, Jason, can we geek over that question at the end of this? Oh, of course. We can do whatever you want. I am here to serve and I'm delighted to be here. So fun. So Jason, this is so cool. And by the way, if you have not signed up to his newsletter, look up on LinkedIn, like, oh my God, so much and so many nuggets, Jason, I'm learning from you every single day. But I want to actually take you back in time because it's going to be a little bit about your career. You start as a reporter. But talk to me about those early days. You're sitting, you're doing these cold pitches. You're just trying to get off the ground. Take us back in time a little bit. First of all, thanks for having me. It is so great to be here. Thanks everyone for spending some time

with me and us. So I have been the editor-in-chief of Entrepreneur Magazine for 10 years now. And in that time, I have grown quite a lot and transformed myself in many ways. I now, in addition to Entrepreneur, as you said, have a thriving business in which I give corporate keynotes. I also advise it on a lot of advisory boards. I work with a business community in New York called Uncharted and a juggling a whole bunch of other things. But at the very, very beginning, I was a community newspaper reporter, and I got my start at a newspaper called The Gardner News in North Central Massachusetts. At the time, which was 2002, it had 6,000 subscribers.

So super tiny. I was writing about middle school dances. It was a big ego blow. And I really was a jerk at that publication. And the reason was because I was. fresh out of college. I had big ambitions for myself. I thought I was very talented. And I was frustrated that I wasn't moving fast enough in my career. And I was taking it out, frankly, on the place that employed me. And so I definitely showed up a little holier than now.

And I eventually got a big talking to from the boss. And I decided to quit. And there are two things that I learned from that moment. Number one is going to be especially relevant to people at the earlier stage of their career, but number two is relevant to everyone throughout their entire career. The first was that I realized that I needed to balance, and I didn't have the language for this at the time, but in retrospect, I needed to balance impatience with patience,

which is to say that I think that impatience is a really valuable thing. It pushes us. I do not want to be content with where I am at any point in time. I don't think that that's a problem. I think that that is what motivates us to wake up every morning, wanting to build and do better. So I like impatience. But I needed the patience back then to recognize that if I was as talented as I thought that

I was, then I would be somewhere else. But I wasn't. I was where I was because that was actually my level at the time. And I needed the patience to recognize what I did not know and the skills that I needed to develop in order to actually get to the place that I thought I belonged in. And so you need that balance of patience in impatience to push yourself, but also to recognize what you still need to grow. That was number one.

Number two was that I realized that in front of me at that time, in front of me right now, in front of you, Ilana, in front of everybody who's listening. There are two sets of opportunities. Opportunity set A, opportunity set B. Opportunity set A is everything that's asked of us. So we show up at our jobs and we have expectations and there are KPI's and we are being measured. And we got to do a good job at those things. That's Opportunity Set A.

Opportunity Set B is everything that is available to us that nobody's asking us to do. And that could be anything that could be at your corporate job where you decide to volunteer for a new team or take on some new project or whatever. but it could also be something outside. It could be that you like podcasts and you decide to start your own podcast or you start to take a course in something, whatever the case is. But here's the thing. What I realized back in that moment at that newspaper was opportunity set B, do the thing

that is available to you that nobody's asking you to do is always more important, infinitely more important. At the time, what that meant for me is that I realized that if I sat around at that newspaper and just did the thing that was asked of me, my career would advance very slow. But you know what nobody was asking me to do? What nobody was asking me to do was to come up with ideas and pitch them to national publications who were not going to hire me because I wasn't skilled enough. But maybe they would consider one idea of mine and be willing to let me write one piece

and prove myself. I quit that job. I sat in my bedroom in a dumpy apartment in central Massachusetts next to a graveyard. I mean, it wasn't quitting that much. My job paid me $20,000. So I wasn't giving up that much. And I just started cold pitching. I started cold pitching.

and that is how I got into the New York Times and the Washington Post and the Boston Globe and how I started to really advance my career. And ever since, I am obsessed with the question of what is Opportunity Set A and what is Opportunity Set B? And I continue to do that today. I listed off all these other things that I do. I know I'm going to show up in a second. This is the longest I will talk the whole time. I know I promise. But I'm at Entrepreneur Magazine.

I do all these other things outside of it. Those are all Opportunity Set B's. Those are going to be the thing that define the next phase of my career, not what I happen to do with the next issue of entrepreneur. magazine because even though that's what's being asked of me and I have to do a good job, that's not where growth comes from. I love everything that you just said because it's exactly, first of all, yes, there's portfolio career that you want to build. And honestly, this is where the future is going. And you have a classic portfolio career with your speaking in the podcast. And what beautiful about what you're doing, and we'll eventually talk about this because

it's not about throwing spaghetti on the wall. It's about getting very intentional and strategic with who am I, what do I want to be known for, and how do I experiment, but also how do I create ripple effect? So I do want to eventually talk about this, and I like that you said patience and impatience, because I am a very impatient creature, but you're right. Also, some of these things just in general take time and playing in the hidden market. A lot of these opportunities are going to come from a hidden market, and that's going to take time, right? So there's a little bit of that. But we will talk about how do you decide when to be intentional and proactive. But I'm still taking you back in time for a second. So you're reaching out to the New York Times in the Washington Post.

And in general, I'm sure there's a lot of nose or ghosting and eventually, suddenly it starts working and you starts adjusting the story. Do you feel like you're just getting better? Do you feel it's a numbers game? Do you feel there's a lot of learning from doing this? What eventually helped you? Back then, I had a specific goal, which was originally to work for a national newspaper and then I shifted it to work for a national magazine. And so what I had done was break down what I needed to know to get there. And I realized I'm missing a whole lot of things. I was missing connections. It's a very who you know kind of business. I was also missing multiple levels of skill. I was realizing that, okay, well, most junior editors come in and they edit what's called the

front of book section, these kind of smaller items. I don't even know if that's true anymore. because the industry is completely collapsed. But back then, that's what it was. And then I'm going to need to learn feature writing and feature editing, which is the longer form things. And then I'm going to need to learn management. And so I just created this list of things that I was going to need to learn. And then I started to seek out opportunities that would allow me to knock those things down

one by one. So the earlier part of my career before I completely reinvented myself into more of an entrepreneur person, but back then, every step of, of that journey, if you don't know me and what I was thinking, doesn't look like it makes any sense. I was at Boston Magazine. Then I went to Men's Health. Then I went to Fast Company.

Then I went to Maxum, right? I'm like bouncing around between local and business and men's stuff. But I was taking those jobs not because of the subject matter. I was taking them because of the specific opportunity that they were going to provide to fill in one of the gaps and skills that I had recognized that I needed. So I took the men's health job because it allowed me to do short form editing at a national level.

I took the fast company job, not because I cared about business because I didn't at the time. It was because they were allowing me to work on long form. And then I took the Maxim job, not because I cared about Maxim. I definitely didn't. It's a crappy men's magazine. But I took it because it was the first management role that I was able to get. And when I got to entrepreneur, honestly, I just saw it as the opportunity to execute a vision in a way that I hadn't before. and the major turning point was when I started to get interviewed on podcasts and on stages,

and people started to do the thing that you have done here today, which is to treat me like an authority, to introduce me as an authority. I can live up to that now. I feel very confident, but I did not back then at all. And yet I recognized that there was an opportunity. There was a gap between what people perceived me to be and how I felt about myself. And if I could bridge that gap, which would be, which would be, require reinventing myself and becoming the person that everyone thought that I was,

there was probably massive opportunity there. And that was what prompted the next reinvention. Oh, I love that because, again, you wanted to step into that identity because it's true. I think about a decade ago, and we will talk about the change because I think there is a big shift in how you get to people versus, but at that point, it felt like the entrepreneur magazine is your ticket to success, right? That was like the gateway. If I make it, I can be famous, right? There's a little bit of that feeling and you're that gateway, right?

So talk to me about your coming to Entrepreneur Magazine. You're starting to feel like, okay, there's a lot of weight on my shoulders. How do you start stepping into something bigger? Is it just a bunch of experiments? Is it mentorship? It's like, how do you start doing that? It's a bunch of experiments that are driven

by a specific anxiety. And that specific anxiety is really around that thing that you just said a second ago, you said, Entrepreneur Magazine is my ticket to success. What I was very attuned to at the time, and I'm very attuned to now, is that I have a really cool title, Editor-in-Chief of Entrepreneur Magazine.

I rent that title. I don't own that title. This is not my company. I rent it. I'm renting a position of authority right now. And it will not be mine forever, and I don't. don't actually have full control over how long I have it. So I realized that the opportunity

available to me, the gigantic opportunity available to me, was to somehow figure out how to transfer myself from renter to owner. And I cannot own the title of Editor and Chief of Entrepreneur Magazine because I don't own this company and I never will. But I can own Jason Fyfer. So if I can turn Jason Pfeiffer into a asset going from random guy who you don't know his name, but you do know his title, to a guy whose name you know and also, oh, that title is cool, that is power. I have come to be obsessed with this word, which I will tell you. And the word is singular. The more singular you can make yourself. higher your value is. It is that simple. We live in a supply and demand world. And if there are a lot

of people like you, people who all do the same thing or who at least seem fairly interchangeable, unless you spend a lot of time getting to know each individual person, which a hiring manager is not going to do, then you are not singular. You are one of many. Your market value is low. the more in which you can present yourself as singular, where it's not, I need an editor of a magazine. No, I need Jason Fiverr. I need that guy. I need that guy on the stage. I need that guy on my advisory board. I need that guy in the room. The more in which you can create a perception of singularness, the more you create a scarcity in the market for yourself. And then your value goes way up. And that has been the project of the last 10 years for me.

I want to tap into that because at least for me, it took me decades to understand that at the end of the day, I am the product. Yeah. Because I was not the product. I was the engineer. I was the VP. I was whatever. Like you said, I was renting the title, but my identity was attached to the title. I think a lot of our listeners, you know, if they, God forbid, lost that title or they were laid off or whatever happened, suddenly for the first time, their identity is attached to that title.

They don't know who they are without it. And again, I'm a big believer that today everybody needs to become their own economy. It's a big piece of what we teach. But how do you start creating your identity as Jason? Because that's a very different thing. Because, again, most of us needed a big slap in the face to realize that we need to do that. Yeah. Yeah.

So there are two ways that I'd like to answer this question. The first is by talking about crafting a mission statement for yourself. and the second is building authority publicly. So let's do both. You are correct that we tie our identities to our tasks and to our roles. And that is fine in theory, except that those things are super changeable. So if your identity is anchored to your tasks or your roles, which could sound like, I am a magazine editor, right?

that is an identity tied to a task and to a role. But all it takes is one phone call, one phone call telling me that actually I'm fired. And then that's not just a change to my work. That has become a change to my identity. Very scary. And it causes us to either want to hold on to what came before or to not be open to considering what's next. So we need a different way to understand our identity. And here is my challenge to you. You need to come up with a personal mission statement, which functions as your identity. It is what I call the thing that does not change in times of change. It is going to be a single sentence. It's going to start with I, and then every word is carefully selected because it is not anchored to something easily changeable. So it is the difference

between I am a magazine editor, deeply changeable, and I tell stories in my own voice. which is not changeable. That is an identity. That is an identification of my transferable value. And when you recognize what your transferable value is and you can live inside of that, then you recognize that actually every change is just a new opportunity to do the thing you already do best. This is part of a whole big exercise that I do in front of corporate teams. I run them through this exercise to get them to this mission statement. And then I literally hop off the stage and run through the audience and I ask people to share their mission. statements. It is so cool. I hear people say, I solve the most complex problems. I help teams achieve

greatness. I tell them, look, you know when you've got a good mission statement when you are saying something that people always need. Do people always need someone who can solve complex problems? Do people always need someone who can help teams achieve greatness? Yes, great. Then it doesn't matter if your job disappears because you have value that you can take somewhere else. This is the anchor. This is the most important thing that you can do for yourself so that you understand that your value is not tied up in the way that you happen to execute some specific tasks at some specific company at some specific moment in time. But you have transferable value that goes way broader than that. We need to pause for a super brief break. And while we do, take a moment and share

this episode with every single person who may be inspired by this because this information can truly change your life and theirs. Now, I want a check in with you. Yes, you. Are you driven, but maybe feeling stuck in your career or a fraction of who you know you could be? Do you secretly feel you should have been further along in your income, influence, or impact?

Do you ever wonder how to create not just a paycheck, but the life you want was a paycheck? The thought leadership, the legacy, the freedom. Because that was me, and that's exactly why I created the Leap Academy program, which already changed thousands of careers in lives. Look, getting intentional and strategic with your career is now more important than ever.

The skills for success have changed. AQ, adaptability, reinventing, and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures are no longer a nice to have. It's a must have, but no one is teaching this except for us in Leap Academy.

So if you want more from your career in life, go to leapacademy.com slash training. Check out this completely free training about ways to fast-track your career and you'll even be able to book a completely free strategy call with my team. That's leapacademy.com slash training. Too many people finish their workday, feeling frustrated, drain and unfulfilled. The good news is it doesn't have to be that way. and you don't need necessarily a new job to fix it. Patrick Lentioni, also of the five dysfunctions of a team and more than a dozen other bestsellers,

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And really find greater joy in what you do because confidence isn't about pretending that you're good at everything. It's about knowing where you're truly gifted. So take the working genius assessment today, get 20% off with a code leap at working genius.com. That's working genius.com. You'll be glad you did. I'm a big believer in the mission, right? And I'm a big believer in the mission, right? And I do believe that, especially now, you know, and I'm curious how you see that, when everybody can sound the same, especially in the era of AI, everybody can be average. Yes. In fact, if you're not even average, you can't bridge a gap. But the problem is to rise above the noise is just become exponentially harder, which probably ties also into how do you build that authority?

Because that's not enough anymore. Like a really good mission statement, you need it for yourself. But then I want to make sure that you can run. above the people pile because it's brutal out there. Yeah. Well, so first of all, the thing about the identity that becomes really profound is recognizing that the thing you do goes deeper than you think. So I got that idea by listening to entrepreneurs and just hearing this repeating thing where the CEO of a baking mix company would say, we don't make baking mix is what we do is we bring joy to people with sweet baked goods. And the president of a cosmetics company who said,

I don't sell cosmetics. I help people reclaim their sense of self. And I'm like, ah, you are understanding the value that you play in people's lives such that if the market shifted, if people didn't want baking mixes anymore, that's okay because you're not in the baking mix business. You're in the business of bringing joy to people with sweet baked goods. People will always need joy. They will always love sweet baked goods. You figure out what they want next, right? And you can do that for yourself, too, and it becomes an incredibly powerful. orienting tool. This doesn't mean that if you walk into a party and someone asks what you do, you're like, I tell stories in my own voice because what the hell does that mean? That doesn't mean

anything. This is not about external presentation. This is about understanding yourself. For me, the ground shifting insight was that telling stories is a much broader application skill than I thought it was because I used to think all I can do is tell stories in magazines. But no, because first of all, I have already told you stories today. And I built my newsletter and my book off of telling stories. And also, when people hire me for corporate keynotes, I tell a lot of stories on stage. And when a founder who I'm on the advisory board of calls me and they have a problem, you know what I do?

I usually say, ah, you know what? That reminds me a lot of something that I learned from that other person. And I tell them that story. This is my skill. And it is broadly applicable. And I have given myself permission to define it broadly. and to understand that I have value anywhere. Now, the next thing is, yes, you're right.

We live in a world of AI, and that's a noisy world. But you know what? It's also a world full of crap, and it's actually pretty easy, I think, to rise above it. So what you need to do now is you need to understand what your value is, and you need to build external authority around it. If you are not posting every day on LinkedIn, then you are crazy. You are just fully missing out on the ability to present yourself to current partners, and future partners as the authority that they need. Look, there's skills, but everyone has skills.

But what makes you singular is perspective so that you have the insight that other people don't have. That is what makes you singular. Unless you truly are the literal best at what you do, LeBron James is singular because he just happens to be the best basketball player. It doesn't really matter what his perspective on basketball is. But you know what? there's only one of him. But everybody else, perspective matters and relationships matter and the ability to present yourself matters. And just having proven authority matters. I have 250,000 followers on LinkedIn right now. You better believe that people think that I'm smart because I have that number. Am I smart? I don't know. But people think it because it's been validated. So you need to get

out there and do that and build a newsletter, start a podcast, do something so that you are a distinct authority in your area and not just one other person who does the job. I absolutely love that. Again, I've been following your LinkedIn for a while. Your ability, many, many years, actually, a while means many, many years. Thank you. And your ability to tell stories through your LinkedIn post, you don't just post whatever. You have interesting ads that you found and interesting journeys.

Like, you have some really interesting nuggets, which is all tied really well together. to your storytelling because you're telling us stories and your newsletter. And so that path is really, really cool to see. But I actually, I think you have a gift and I would like to take you back in time because you kind of understand a little bit what goes viral, right? And I think you had this really funny selfies and funerals.

Oh, yeah. Oh, my God. That's a little bit. So take me a little bit because you understood virality and human psychology. I think almost way before any of us maybe understood even that it's important to understand. I really appreciate that. It is rare these days as somebody says the phrase selfies of funerals to me. But oh my God, it was all I was hearing about in like 2013.

So I had so thank you. If you're listening right now and you know what selfies of funerals is, you're like, oh my God, I remember that. Please email me. I would just be delighted to know. So there was quick internet history is around 2012, 2013. A big thing on the internet was what was called. single topic tumblers. So Tumblr, which was this micro blogging site, which I think still exists in some form, people would make these tumblers, these blogs, for a very hyper-specific,

sort of comedically hyper-specific purpose. So one of the first big ones to go, pop, was women crying while eating salad. And so the website was women crying while eating salad.tumbler.com. And it was just a compilation of all the stock photography that had been taken for the you could fine on Getty and eye image and whatever. Like, that was just women crying while eating salad. You know, and it's like the funny thing is like, why? Like, why is that a thing? Why is that a thing that we culturally want?

Like, there's a demand for that clearly. And that's why people are using the, but like, what is it communicating? And it's just really funny. So there were a whole bunch of them. There was another one where this guy created a thing called Reasons My Son is crying. And it was just like photos of his toddler like bursting into tears and like the ridiculous things that the kid was crying about. They were great.

And so I created a series of them. The first one was called selfies at serious places where I scoured early social media and found all these selfies that these mostly teenagers had posted in places where it's just kind of weird to take a selfie, you know, like Auschwitz and the 9-11 Memorial

and, you know, just like Chernobyl, just like really strange places. And that got a bunch of attention and there was one or two selfies at a funeral in there. And I thought, hey, you know, I should probably do like a spin-off just of that because there were so many of them. So I created selfies at funerals

and it was, I've never experienced anything like it. I made selfies of funerals. com. I hit publish on it. I was sitting at my desk at Fast Company at the time and then I like walked away to a meeting or something and I came back to my desk

and it was already global. Like somebody at Business Insider had seen it and made a post about it. And that ignited two years worth of reporters, calling me, asking me about selfies, and every time something big would happen in the selfie world, I remember Obama took a selfie at Nelson Mandela's funeral, and like, I'm getting reporter calls. It was wild. I've never experienced anything like it. I was on international TV and radio, and it was so weird and funny. Looking back on it, first, I never made a dime off of that,

and then I made some other tumblers, but I never made a dime off of that. And that was in part because I consciously thought, I mean, I had this conversation. with my wife. I was like, do I want to be the selfie guy? I don't think so because that anchors me. Like, we're going to stop talking about selfies in like three seconds. And I don't want to be anchored to this thing that then becomes really old. And also it's just not where my passion is. I don't know that it leverages my skills that much. But it definitely also taught me that virality is about creating something that is recognized. as something that we either do or have anxiety about or are already thinking about.

It is putting either words or images to something that is in everybody's heads, but hasn't been articulated the way in which you will. And the reason why Selfies at Funerals really worked was because it tapped deeply into this anxiety about how technology is changing. young people. And I actually think that technology is largely not changing young people. I think that we just have this recurring narrative across all generations that technology is ruining young people. But like our version of this story is not any different than any previous version of this story. But it hit the nerve there. And that's why people wanted to talk about it, because it was a small

thing about a large thing. And that is ultimately what I think you need to do when you create something for the masses is you need to create a small thing that's about a large thing. I mean, think about every movie is a small thing about a large thing. It's a story, but it's about something bigger. It's about a human emotion or experience or something. And every story that I write is a small thing about a large thing. It's maybe I'm profiling one company, but what I'm really doing is I'm writing about a bigger idea about business.

If you can bring people in by simplifying a smaller concept, but also give them a way into a larger concept, especially something that they want to talk about. they will engage and sometimes globally. And I want to tap into what you just said before because the fact that you were good at it or it went well doesn't necessarily mean that this is what you want to be known for. Right. And I think that's also another distinction, right? A lot of times we tie yourself to something that worked out.

Like I worked in cloud data centers or whatever, right? Like you're tying your identity to something that you're okay at. But it doesn't mean that this is all you want to do in your life. that doesn't mean that this is what you want to be known for. And I think that distinction is really interesting how you basically just said, okay, this worked really cool, but this is not where I want to be. I don't want to run for cover. To me, that's running for cover.

That's you're out in the rain and you want to find the nearest roof and just get out of the rain. It's like, oh, that works. Okay, let me get over there. And then you're like over there, right? That's not what I want, right? The selfies thing worked. And at the time, yeah, I had a lot of big questions about what I was going to do with my career. and then I had this hit.

But I don't want to take shelter under that roof just because it's the roof I happen to find. I don't think that it was a good roof. I think that it would have gotten leaky really fast. And I think that it would have been embarrassing to try to ride it. What would I have done? Like, I don't even know what I would have done.

I guess it's possible that I could have faked my way into presenting myself as some kind of youth marketing expert. But I don't know. I didn't have enough to say about it and I don't really care. I've felt that way. and I think that many people anchor themselves to the thing that happened to work

without thinking through whether or not it was the thing that they actually want. To me, great success is finding the intersection of the thing that you're really good at and the thing that you love. There are a lot of things that I'm good at that I don't love. At this point, I'm really good at magazine editing. I'll be honest, I've edited magazines for decades now.

I don't love it. I don't care. Like, I just don't care. I've edited so many magazine stories. It does not fuel me. But I'm good at it, you know. And then there are things that I love that I can't figure out any way to make money off of.

So I need the intersection of the thing that I love and that I'm good at. And that is where success is. And I want to tap into something for a second, Jason, because sometimes, and I think we see it a lot, when somebody is reinventing themselves and you started different things, you started a podcast.

You don't know if you're going to love it. yet, right? You don't have enough evidence. You're trying different things. You're experimenting with different things, but you don't necessarily have the notion of, oh, my God, this is going to be it. So how are you taking experimentation? I'm big on experimentation, but I mean, you still don't have the evidence that you're going to love it or is they going to become your passion. How do you look at that? So I usually go into something with a theory. And the theory is this is going to be valuable because this is going to teach me something. This is worth doing because it'll build this relationship, this seems like it's a pathway to new revenue, then I want to test the theory.

I need to go into it not knowing exactly what the ROI is, but certainly knowing what I think the ROI is. Then you essentially need some kind of trigger point at the end to test this. I frequently test whether or not I was right about trying one experiment by simply trying another experiment, which is to say that I will say yes to another thing. And when I say yes to a new project, it forces me to reconsider how I'm doing everything else. How is my time being spent? Is my time on this project valuable? Okay, well, we've given this two years. Is it producing what it should? No. Do I see a great pathway to clear growth? No. Well, okay, then I think it's time to make the hard decision that that has concluded. This goes to my theory about time, which is that I believe

that time expands under pressure. Like the way in which to get more time in your life is to add more things to your life, which then forces you to figure out how to become more efficient with the things that you're doing or drop some things that aren't nourishing you in the right way. I am not the world's most strategic person, so I do this in a kind of scattershot way, but it has worked for me. And that is also because I don't define success by one specific metric. I kind of define success by, am I doing a lot of interesting things that I find challenging and rewarding? So as long as I'm doing that, then I'm on the right path. I think you talked about assets and rent a title and become the owner and the assets. And I think a lot of it is tied for me to freedom.

And the freedom is freedom of choice. It's not necessarily sitting and drinking margarita all day. but it's really the freedom of choice to decide what you want to say yes to, what you want to say no to, which I love what you're saying. But can I ask you something? So each person usually have some moments that define them and pushed you into a whole different direction that maybe you didn't perceive or didn't expect I needed to be kicked out of my own company, you know, right after we raised capital. Like what are some like a moment or two that kind of really defined your career? Yeah, well, I mean, I told you one of them, which was getting into the role as editor-in-chief and then it pushing me to reconsider who I am.

There's a moment just before that, which I'll share, which is like the heavier moment, which was that I was sued. This was 20, I don't even remember. It was something, 2015 or something. And I was sued by a vindictive person with a lot of money. you know, one of these people who just can use the court system as a weapon. If anybody's engaged with the court system, then you know it basically just is a weapon for wealthy people. And like, nobody in the court system, including the lawyers and the judges, seem to care about that.

They just don't seem to care that they're being used as a weapon. In fact, they prolong it. It's the craziest thing. And it makes me very afraid that this is the undergirding of our society. But I was sued and it was awful. And at the time, I was, was in the middle of executing a big shift. I had actually decided to leave magazines, and I was going to try a couple different things. I was going to try some consulting, editorial consulting work, and I was going to become a celebrity ghostwriter.

And I had gotten my first celebrity ghostwriting contract, and my first child who had just been born. And so a lot was happening. And then the lawsuit. And the lawsuit was really scary. I mean, I didn't know, was this going to bankrupt me? My wife's friend, who's a lawyer, told us that we should consider getting divorced to shelter the money with my wife in case this destroys me.

Like, it was scary. So I decided I needed, you know, talking about running for cover. At that point, I really did need to run for cover. And one of the freelance jobs that I had set up at the time was that I became a freelance editor at Entrepreneur Magazine. That was actually my start. and they had asked me if I wanted to come on staff and I had said no. But then I got sued and I felt like I need health insurance, I need a steady paycheck.

I cannot execute a career pivot with a new child and a lawsuit. So I went back to Entrepreneur and I asked if I could join the staff. And they said yes. And that is how I became the executive editor of Entrepreneur Magazine. and then nine months later, the editor-in-chief left, and then I made a play for the job, and I got it. And then I faced that big question that I told you about in which I transformed myself

and led into the person that is in front of you right now. And so when I look back at that moment, what I realize is that life is not linear. Life is reactive. So we think that bad things are bad because we think that the next thing that happens, also be bad. This bad thing will lead to that bad thing, will lead to that bad thing, will lead to that bad thing. And it will be a linear progression of bad. But actually, what happens is that because

of a bad thing, we make decisions that are different than we would have before. We react to them. And when we do that, we take ourselves on a different path that can ultimately be so much more productive than the original path that we were on. And I try to remind myself of that every time something bad happens, because I now understand that when the unexpected happens, I will make what would have been seen before as unexpected decisions. And that will propel me in ways that I cannot imagine. Oh, this is so powerful. And I want people to hear this. So this might be what you all need to here right now because the truth is the worst part is not a bad career path because that's screaming at you, get out, get out. It's actually a good career path that isn't yours, right? And I think there's a lot

around like your comfort zone will just kind of keep you going. And sometimes you need that moment that you or that slap in the face to say, oh my God, I need to make different decision. And suddenly it takes you on the better path. I love how sometimes it is darkest before the sunrise, right? Yeah, and you just don't know how things are going to play out. I have great friends, Peter and Kelly, very accomplished. And they told me that whenever something bad happens in their careers, in their lives or something, the thing that they tell each other is, we don't know whether this is good or bad. It feels bad now, but we don't know how it will ultimately play out.

And there is a chance that it's going to play out in a very good way. And that is certainly true for me. when I think back on all the bad things that have happened, it's not like I want them to happen. It's not like I wanted that lawsuit. That lawsuit was awful. If I had to do it over again, I would not ask for that lawsuit.

But it ultimately produced good. And I could not have expected that at the time, but it's important to remember it. Oh, so powerful. And you're talking to hundreds or thousands or whatever, some of the most incredible entrepreneurs in the world. I bet you're hearing some of these all the time. But, you know, I'm actually curious, what are some of the biggest lessons that you've heard kind of more repeated or some of the biggest takeaways that you've taken from some of these conversations?

You know, a lot of my work and the speaking work in particular is around adaptability. And that's because that's the pattern that I saw when I talk to people about success. Going back to that early time in which I was trying to figure out who I can be in this world of entrepreneurship and how do I reinventing. at myself, I came to a realization which was, if you listen to the questions that people ask you, you will see that what they're really doing is telling you what they think your value is to them. And the more you can understand what people perceive as your value to them, the more in which you can lean into it. So I was getting the question all the time in those early days when nobody knew what to ask me because I hadn't built a profile, there was no body of work

to build off of the way in which we're having the conversation today, they would just ask me some version of what are the qualities of successful entrepreneurs? That's what they wanted to know. And I thought, why are they asking me that? Why is that the question that I'm always getting? And I realized it's because what they're really saying is you have access to everybody. And so you are a pattern matcher. We perceive you as a pattern matcher. And so, So you can tell us the patterns among all these people. And I thought if I could figure out what the patterns actually are, because I didn't know, then I probably would have a good business.

And that is what led me into thinking about this kind of stuff. And the answer that I came to was adaptability because it's true. I see it everywhere. I also feel it to myself. It is the thing that just driven me. And what I see is that the most successful people truly are the most adaptable. and I hear it in so many different ways from so many different people.

I have all these quotes in my head from people who I've talked to who have all said some version of the same thing. I'll just give you a couple examples. Malcolm Gladwell said to me, self-conceptions are powerfully limiting. I had asked him about how he perceives a Malcolm Gladwell project to be.

Like, what are the qualities that have to be inherent in the project for him to say, yes, this is a Malcolm Gladwell project? He had said, I really try not to think about it like that. because self-conceptions are powerfully limiting. The more in which you narrow your definition of self, the more in which you will turn down all the other opportunities available to you

that might be bigger than the narrow version that you have. So I loved that. But that is not really any different from Ryan Reynolds saying to me, to be good at something, you must be willing to be bad. I love that. To be good at something you must be willing to be bad? So good. true because the thing that divides successful people from unsuccessful people is not whether

you're good at something at the start. It's whether you're willing to tolerate being bad long enough to get to good. And I've just heard versions of this from everybody. It's a different articulation, but it's the same insight. And that has been powerful. And I'm finding that there's a lot of hunger out there, even though people understand there's a lot of hunger out there and understanding, well, how do we tactically approach that? And so that's how I've built a lot of my work. I love this quote, by the way. I wrote it down when I heard it. I was like, this is so good because it's true.

You get the first time, whatever you're going to do, you're going to suck at it. Like, you know, the second time, you're going to suck a little less and then you're going to suck a little bit, right? And then eventually maybe you're going to be decent or good. And, I mean, it's really more about just keep on getting up and doing it. I do want to take you, though, a little bit towards how you see the media changing because you're adapting a lot and everything is adapting. I think we're still trying to figure out, what is traditional media? Should we just post on YouTube? When you talk to people, what do you say to them?

How do you see we're pitching entrepreneur magazine? We would love to be, you know, but still. But I think there's also a lot in terms of just be out there, be on LinkedIn, be on YouTube, be on Instagram. So how do you see it today? I do not say this to undercut myself or my company, but I do not think that traditional media has the weight or relevance that it used to, and I don't think that it's ever going to regain it.

There's good reason for that. It is because the means of distribution are no longer owned by traditional media. So it used to be that if you wanted to get your story out there, you needed to get a traditional media outlet to pay attention to you because they owned the means of distribution. And they don't own the means of distribution anymore. The means of distribution are totally flat, which means that if you open up Instagram right now

and you start scrolling on reels, then Entrepreneur Magazine, which has been around for nearly 50 years, gets the same amount of space as a random person who just posted a video. So that is a democratization of information and access, and it is a real challenge to the positioning of traditional media. Now, that's not to say that traditional media doesn't have its place. It is building off of decades of trust, and it has to be a good steward of that trust. And I think that different media companies are doing varying degrees of good or bad work at maintaining that trust.

And I think also that those traditional media brands still carry some kind of validation in a marketplace. So if I have a new beverage brand, it would be really, really great to get Bon Appetit or food and wine to say a nice thing about me so that I can put that logo on my website and it conveys some kind of authority. But here's the thing. If you're an average person and you're just trying to get your story out there, traditional media is a pretty bad way to do it. There are fewer outlets. There are fewer people working at those outlets. They are. producing less work and that work is reaching fewer people. So what you should instead be doing is not waiting on someone else to tell your story. You should be telling it yourself. And that's

the reason why I advocate for getting on LinkedIn, starting your own newsletter. You own the means of distribution as much as anybody else. And that is powerful. It has created a kind of chaos of information, but I do believe that there's a massive opportunity for anybody. I mean, look, just who are the big names right now who are competing against Forbes, Fortune, Inc. Fast Company? The names are not other media outlets. The names are Stephen Bartlett. The names are Gary Vaynerchuk. Individuals who can build trust with audiences, frankly, faster and easier than a brand can. A brand is a faceless entity. An individual is someone you can build a relationship with. It is very hard, I think, today for any brand to compete against an

individual. And in a world of AI, where everything is slop, the only thing people are going to trust are other people, the authenticity of other people. So that is your opportunity. Ooh, slam dunk. Mic drop. Jason, I love that. I would love to actually do something fun with you, which we usually don't do, but I think it's going to be fun. So what we do is every week, we choose a question from our YouTube channel and we answer it. And usually I answer it after the episode. But because it's so classic for both of us to answer, would you mind doing it? I think it's going to be fun.

Let's do it. Okay. So it's Omer's question. And he basically says, what is adaptability? Which we talked a little bit about, but maybe dive into it a little bit more. And how do you become more adaptable as an individual and as an organization? And I would love to geek this out a little bit, Jason. What do you say?

Thank you, Omer, by the way, for the shout-out. So let's go. Jason, let's have some fun. Let's do it. All right, well, we're both answering this, right? So I'm very interesting what you have to do. We're both answering. Okay.

Let me tell you a quick story, which really captures adaptability to me. March of 2020, the last social event that I went to before COVID shut everything down was my friend Nicole Lapin's birthday party. She got a bunch of friends together and we all went out to dinner. It was very nice. So I was sitting next to a mutual friend whose name is Megan Asha. Megan at the time was building and running

a company called Founder Made, which was a trade association. It's been since acquired. It was a trade show for the natural CPG space. And I had spoken at Founder Maids before, a really great event. And I said to Megan, I said, events seem to be shutting down, right?

COVID is coming. We don't really know what was going to happen. Events seem to be shutting down. You're a live event. business, are you freaked out about this? And Megan said to me, you know, I'm actually excited. And the reason for that is because we've had all of these ideas about new lines of revenue for founder made. And we never really get to explore any of them because we're always so busy putting on the events. But now, with the events on hold, we'll be able to explore some of these

other ideas. And at the time, I thought, that is a woman with no fear. It was just a fearless person. But as COVID went on, as I started to talk with more people who had similar ways of thinking, I realized, Megan does not have no fear. Megan has the right kind of fear. There are actually two kinds of fear. There is the fear of losing what you had. And then there is the fear of not figuring out the next thing fast enough. And the fear of losing what you had is a fear that is backwards looking, and it forces you to want to hold on to what came before. And the fear of not finding the next thing fast enough is a fear that is rooted in the belief that there is a next thing. And it is actually a forward-looking fear. It propels you. It is the impatience that we were talking about at the

beginning of this episode. And I realized that Megan just had the right kind of fear. She understood that there would be new opportunities, and she needed to figure out what they were fast enough. And that, to me, in a nutshell, is adaptability, which is to say it doesn't mean that you are unafraid, it doesn't mean that change is easy, but it does mean that you go into change with a belief that you can solve it and that there are new opportunities ahead,

and that all you need to do is figure out what they are. And if you can keep that mind, set clear while every crazy thing is going on around you, you're going to be fine. Oh, this is so good. This is so good. I love that I got to do this with you. This is so fun. And I'll tap into that because I didn't think of going all the way to COVID, but I think

it's a beautiful example. There was actually a beautiful research, and I wish I could quote that. And maybe if I find it, maybe I'll put it in the show notes. But there was a beautiful research during COVID. And basically, they were talking to all different CEOs about how they're going to adapt to COVID. And the research was really, really interesting. So there was like, there's a group of CEOs that were basically just ignoring, like initially, like, oh, this is going to be nothing. Nothing's going to happen. It doesn't matter. And it was interesting because a lot of these

companies died later because they didn't adapt. They just ignored the thing until it was too late. There was another group of people that were just freezing, right? They were just like so frozen from the fear that they were not able to adapt. They were just like busy, you know, looking at the news and being frantic about it. But then there's a smaller group that basically, like you said, like they were just like, okay, then let's dive in. Like I just talked to Julia Hearts from Eventbrite, speaking of. Oh yeah, I love Julia. She's great. Right. And I mean, yeah, like you said, all their business shuts down overnight. You have to get a little scared of it, but it's also like an incredible opportunity. So what I would say to people right now,

First of all, the big thing is to learn as much as you can, as fast as you can. Done is better than perfect. You're never going to be perfect at any of this. So just learn as much as you can. Learn experiments. Try different things. Experiment different things. Get your hands dirty.

And then you're just going to adjust your story every single time. Experiment. Adjust your story. Build a load of a brand. And just decide if this is the right avenue for you or not. But I think that agility is just going to be so critical today, than any other time that we've seen today. So Jason, maybe last words,

like if you're taking yourself back in time and maybe you're meeting yourself a few decades ago or whenever or one of those hard moments, what would you want to say to yourself? You know, it's funny. I've thought about that scenario because I'm prompted by a question every so often. And I think the honest answer is that I wouldn't have listened to myself.

You don't listen to the people who have made the mistakes and are telling you what to avoid because you don't think that they're right or because they don't understand you or okay, old man. And I think truly that the mistakes that I made along the way are the thing that shaped me into what I am. And so I don't know that I could have gone back

and, like, said anything that was, would have been all that meaningful that the younger version of myself either believed or didn't already know. I could say, don't worry about the path. It will reveal itself. But it's like, okay, I guess I sort of already knew that inherently. So every phase of our life has a certain role. I think of my time on this earth so far. I'm 45 as being divided up into some specific segments, which I tend to like to do by decade. So my 20s were all about setting things up. And then my 30s were all about executing things. This is how I think about like I theme my decades. And then my 40s are doing things on my own terms. So that is roughly how I comport myself. Like what are

the opportunities that I'm seeking right now in the middle of my 40s? They are all about doing things on my own terms. And they're all about making sure that by the time I get to my 50s, it is all on my own terms. And I don't know what the theme of my 50s will be. People who are in their 50s tell me that the theme is that they don't give a crap anymore. That sounds good. But I'll get there when I get there.

And in the meantime, I'm just not sure that like there's enough that one decade can learn from the other except in linear order. Oh, this is so true. I wish I'd listen to myself because I have so many good nuggets to myself. But you're right. I probably wouldn't. But that's a really good point. So Jason, where can they find you?

Obviously, we'll have your newsletter and LinkedIn, but maybe summarize it for them. Sure. Well, thanks for spending this time. I really appreciate it. I'll give you really just one thing to do, which is that I have a newsletter. It is called One Thing Better. Each week, one way to be more successful and satisfied and build a career or company that you love. A lot of the stuff that we talked about today either comes from the newsletter or is reflected in the newsletter or is something that I said that I then

thought to myself, oh, I should write about that in the newsletter. Like, I haven't done singular yet in the newsletter, but I really have been meaning to. So it's a great way to get a kind of steady dose of guidance and insights that I'm learning from the world's greatest entrepreneurs and also just from my own experiences. And so you can find that at one thing better. Email. So the newsletter is called One Thing Better. And the web address is One Thing Better. Email.

So I would love if you subscribe to that. Also, I know we've got a lot of corporate listeners here. I do keynotes in the last year. I spoke for Pfizer, Alibaba, Dick Sporting Goods, Clorox. My mind is a mush because I'm traveling a lot. But I love these kinds of engagements and getting out there and helping people feel more adaptable and helping organizations grow. So you can get in touch with me really in any way.

Instagram, LinkedIn. My website is just jasonfeiffer.com. You can find a speaking form there, but I would love to come and say hi. So fine. We should have had you on LeapCon last week. But that's okay next time. But it's so good, Jason. You are the best.

You're the best. That was so cool. Thank you. Remember this episode. It's not just for you and me. You never know whose life you are meant to change by sharing this episode with them. And if you love today's episode, please click the subscribe or download button for the show and give it a five-star review. This really means a world.

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