Right About Now - Legendary Business Advice
How to Build a Career That Can Survive Drastic Change | Jason Feifer
12 Jun 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: Why is waiting to be chosen a losing strategy?
A lot of times we think about how hard this is going to be, what a terrible road this is going to be. But most of the time, sticking your neck out just means putting in some effort without knowing how it's going to be rewarded and then enduring a lot of non-reward. And if you can do that, then you can put yourself in a position to learn. Do it over and over and over again.
Fail, fail, fail, fail, fail. Eventually you will get somewhere.
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Hey guys, what's up? We're talking with the champion of change today, my friend, Jason Pfeiffer, editor-in-chief at Entrepreneur Magazine. What's up, Jason? I appreciate the enthusiasm by which I was just introduced. Hey man, we all have to do something well. Welcome to the show. Great to have you. I study all my guests and from afar, been a fan, been listening to your show.
Certainly have heard of the little magazine you write. Host of Build for Tomorrow. You've got your podcast and stuff. You've done a lot of interviews. A lot of our listeners enjoy hearing that professional journey. I'd love to give everybody a little taste for yours. I started not having any idea what it is that I wanted to do, but I knew that I like to write.
I knew that as a reporter, people will just tell you stuff. It's kind of amazing, actually. You just go out and you say, I would like to interview you. And they say, come on into my home and let me tell you all the things. That was a pretty... unbelievable experience. I started as a community newspaper reporter. It was just the only job that I could get.
The very, very beginning, I was at Gardner News, Gardner, Massachusetts. Tiny little paper, North Central Massachusetts, covering nothing because nothing's going on. I did it for about a year. It was a grumpy year for me because I felt I'm too good for this place. I have all these ambitions and I should be writing for the New York Times. Two things about this. Number one, What a jerk.
Because the thing is, if I was too good for that place, I wouldn't have been at that place. We need to stop wherever we are and say, what can I learn from this experience right here, right now? Instead of wishing that I was somewhere else, why don't I work towards that somewhere else by starting right now? Bloom where you're planted. There you go. That's a nice cliche. That's for a good reason.
And then number two is that I, after a year, thought to myself, all right, well, look, if I'm really serious about this and I'm not just grumbling, what does it take to go somewhere else? What does it take to work at these large publications?
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Chapter 2: What did Jason Feifer learn from starting at a tiny local paper?
Never, ever wait for somebody to come to you with an opportunity. They never, ever will. You go to them. I love it. A lot of lessons, a lot to unpack there. And as I was listening, I was saying, I joked about the balloon, not even joked, but just stated the balloon where you're planted. But then you just expanded from there.
It's funny, people, there's a lot of talk now about manifestation and all those things. And I buy some of that, but there's still an action that has to take place. It doesn't just happen. I love that notion of just sticking your nose in it. I don't know if like enough people have the grit to do that, but that's really what I'm hearing. Yeah, that's right.
The funny thing is it doesn't take that much grit. Literally, what was involved in the grit of me trying to write for these publications that didn't take me seriously? Well, I had to go out and find some stories. You do some research, talk to some folks, you find some stuff. You learn how to pitch, go out, buy a book, learn some stuff, figure out some people's email addresses, send it off.
What's the worst that could happen? I'll tell you. They ignore you or they say no. That's the worst. Can you live? Can you survive that? I could. Turns out it's not that hard. You get a rejection, you move along. This is the thing. I mean, a lot of times we think about how hard this is going to be, what a terrible road this is going to be.
But most of the time, sticking your neck out just means putting in some effort without knowing how it's going to be rewarded and then enduring a lot of non-reward. And if you can do that, then you can put yourself in a position to learn. Do it over and over and over again. Fail, fail, fail, fail, fail. Eventually, you will get somewhere.
Ryan Reynolds once told me that in order to get good at something, you have to be willing to be bad. And I love that line because it is so truthful. Very true. You bringing that up. If you're like me, you probably spend a lot of time paying attention to what's happening in the world. Markets, business, crypto, interest rates, sports, politics, all of it.
I'm always looking at headlines thinking, okay, what happens next? That's honestly why I've been spending time on Gemini predictions. What makes it interesting is instead of just watching stories move the market in real time, you can actually trade on the outcomes of real world events.
Maybe it's oil prices, what happens with the Fed, crypto movements, major sports events, or broader world headlines. There are live contracts across all kinds of categories. And what I like is it feels built for people who already think this way.
If you naturally pay attention to trends, follow business news, or spend your day analyzing what's happening in the economy and markets, this gives you a completely different way to engage with it. The platform itself is also really straightforward. Everything runs directly through the Gemini app. The interface is clean, and there are new markets opening every day.
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Chapter 3: How do self-limiting plans close off better opportunities?
Make picks. Win money. Must be 18 plus, 19 plus in Alabama, Nebraska, 19 plus in Colorado for some games, 21 plus in Arizona, Massachusetts, and Virginia, and present in a state where underdog fantasy operates. Terms apply. Concerned with your play? Call 1-800-MY-RESET or 1-800-GAMBLER or visit www.ncpgambling.org. Arizona, 1-800-NEXTSTEP. 1-800-639-8783. Or text NEXTSTEP to 53342.
New York, call the 24-7 Hope Line at 1-877-8-HOPE-NEW-YORK. That's H-O-P-E-N-Y. Or text H-O-P-E-N-Y-467-369. I've seen you answer this, and you can Google this, and you'll find Jason's answer to this. I'm going to lead him down a different road, I hope. You're now both an entrepreneur, I'm sure, at Fast Company, others.
You've been around and interviewed and told stories about a lot of successful people. So I'm going to stop short of saying, what's the formula for that? I'm going to stop short of that because you've talked about it. But more importantly, maybe have you narrowed in on a characteristics of certain guys like Ryan Reynolds or Jimmy Fallon?
Is there a single characteristic or trait or two that might be not something people would expect that you've seen? The usual answer is adaptability. This is the number one thing that I see. It's the reason why I wrote the book that I did, which is called Build for Tomorrow, because it's all about how to see change as opportunity.
That Ryan Reynolds quote that I just used came in the context of us talking about how he moved from one kind of career to another and from being an actor to running an ad agency. He didn't intend to do that. What had happened was that he could barely get anybody to take Deadpool seriously and And so he basically did the marketing himself with a guy that he met at the studio.
They did all this crazy, wacky stuff. This is all stuff you would really appreciate out of basically no budget. It drove so much interest that it made Deadpool one of the highest grossing movies. It was very, very successful. How do you do that? Well, the answer is that you're willing to be bad.
You are willing to go through the transition where you're in an uncomfortable place and you don't exactly know what's next, but you just have the commitment to know that moving forward is literally the only way to get to something better. I see that. see people do that over and over and over and over again.
They have an ability to get past the barrier that I think most people slam into when there is some kind of change or they're trying to do something that they're not familiar, which is that they panic. That's the first thing most people do is they panic. I've panicked. I'm sure Ryan Reynolds panicked. Jimmy Fallon definitely panicked. We talked about it.
Then you get to a place where you say, all right, there has to be more than panic. There has to be more than this. And the people who are able to get through that first wall are the self-selected group of people who can build something that is successful. I love it. And you know what? I almost lump it in because I get asked that same question sometimes. And I almost lump it in.
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Chapter 4: What is the audience-first framework for storytelling?
Talking with Jason Pfeiffer, editor-in-chief of Entrepreneur Magazine. I really like this quote, one of your latest articles. When you narrow your path, you limit your chances of finding what will make you happiest. I want you to expound upon that a bit, if you don't mind, for everybody listening.
The very first time that I noticed people do this was years and years ago when I was still mostly identifying as just a kind of pure magazine guy, journalist. And I would be invited to come speak in journalism classes as I talked to these college kids who all aspire to work in magazines.
And they would inevitably, every class, one or two kids would raise their hand and they would say something along the lines of, my goal is to work at Entertainment Weekly. What do you think I should do to get to Entertainment Weekly? I just think that this is a terrible way to think. This is just an awful way to think because fine, you have a goal of working at a place. That's good.
Having a goal is great. Having some direction to move in simply so that you can start moving is wonderful because we got to move somewhere. We got to go somewhere. but do not limit every decision that you make based on an ultimate goal because you don't know if that goal is actually going to be any good. You could get to Entertainment Weekly and it could suck. And I will tell you something.
I have so many friends who aspire to work at certain places and they got there and it was not at all what they expected. You cannot limit yourself like that. When you limit your options along the way, All you are doing is turning down all these amazing new opportunities to learn, to grow, to discover a path that you didn't know was available.
One of the reasons that those kids are saying, I would like to work at Entertainment Weekly is because they only know of a certain number of outcomes for their career. They're only aware of a few. And I'm going to hazard to guess that
that although a small number of them may have landed at their dream job that they aspire to do, the vast, vast majority of them, and I include myself in this, ended up somewhere that they could not have possibly predicted and that, frankly, they may not have even been aware of. When I started my career, I'd never heard of Entrepreneur Magazine. What the hell is that?
But eventually, because I made enough choices financially, throughout my career, choices that were based not on one ultimate goal, but rather of seeing something and saying, I wonder what's over there. Maybe there's something that I can learn. I got to a place where I had the necessary skills to take over a magazine called Entrepreneur and then see what else was available to me because of it.
Speaking, book writing, podcasting, going on TV, all this stuff. This is not stuff that I ever thought that I was going to do. It would not have been possible unless I took those unexpected paths. And that's what we all need to do. We cannot close ourselves off to those. That's where the real opportunity is. I like that a lot. And there's a couple terms I use.
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Chapter 5: Why do problem-solving stories outperform generic success stories?
The answer is because putting a celebrity on the cover of a magazine is a much better way to sell a magazine than putting a piece of fruit. You are a business. You're trying to sell copies here. That's right. And there's nothing wrong with that. Nope. I want to make sure that it's valuable to people. It can't just be Jimmy Fallon for the sake of having a photo of Jimmy Fallon.
It's got to be valuable. Jimmy Fallon does a thing that most people do not do and never will do. The level of success that he's had, he's hosting the Tonight Show. Most people are not going to do that. In some ways, the basic outline of Jimmy Fallon is very unrelatable. I have to start with, why does somebody pick up a copy of Entrepreneur Magazine?
Well, the answer is because they are looking for some kind of growth and insight for their careers or their business. That's why they're picking up the magazine. What could they want from Jimmy Fallon? First of all, I've made a selection of Jimmy Fallon because I think that they can get something out of Jimmy Fallon. And now I got to go in and I got to deliver on that.
When I go in to talk to Jimmy Fallon, I am talking to Jimmy Fallon about Jimmy Fallon, but I am really mindful of the reader. And I'm mindful that people don't care about Jimmy Fallon's career arc. They could find that somewhere else. What is the story that I can tell? What is the unique value proposition that entrepreneur has because it understands its audience?
And to me, the way that I approach these stories is that it never really can be about the person who I'm writing about. It is, but it's really about something else, something unique, something that anybody can learn from this person because this person is actually a great representation of and they have thought through this thing.
For Jimmy Fallon, it was a story about finding your why, finding your mission and your purpose, how to identify it and how to put it into action. That's what that story was about. And every question that I asked Jimmy was in some way pushing him to articulate that, to identify it, to dig into what it was like for him as a way of helping Thank you so much for joining us. We'll see you next time.
saying, stop wasting my time. Whenever you're telling a story, have that in your head. And a chorus of people, a Greek chorus, were basically singing, stop wasting my time. And you better not waste their time. You know what everybody's favorite radio station is? WIFM. What's in it for me? That's what you just described, brother. It's true, though. It is. What's in it for me? That's fine.
I don't begrudge people that. Why would I begrudge people that? Because that's what I'm doing. What's in it for me is how I consume things, too. I don't have time for your random crap. When I was in my teens, we just wanted to burn Saturday nights going to the movies. I'll watch anything. But boy, as we get older, we don't have that kind of time anymore.
You got to understand what is in it for your audience and deliver on that relentlessly. The days of showing ex-celebrity and the mansion they live in and the Porsche that they drive or whatever. I'm not saying there's not a time and a place for that article. This is what I love about what you guys are doing. An entrepreneur is more of that aspiration motivation.
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Chapter 6: What are the four phases of change in building a career?
TikTok for the masses. We were in the 15 to 20 year old stage. We're in the 25 to 35 stage. Is this going to be a mass, mass, mass player? Is it always going to be niche, i.e. Snapchat? All right, I'm going to go simple on that one. Rad. NFTs. Oh my God, I'm going to get a lot of hate for this answer, but I'm going with fad. The... Technology behind NFTs is exciting and interesting.
What you're seeing in the marketplace right now is unsustainable and is probably a lot of garbage anyway. People buying their own NFTs to pump the numbers. I just don't think that that lasts. You're a smart man, my friend. Where can everybody keep up with Jason Pfeiffer? I'm on social at HeyPfeiffer, et cetera, et cetera, podcast built for tomorrow, just like the book.
But if you go to JasonPfeiffer.com, J-A-S-O-N-F-E-I-F-E-R.com, and you click that button that says free training, what you will get is an hour long free audio course that I put together about how to become more adaptable, how to feel more comfortable with change. I have heard from so many people who have gone through it and who have really appreciated it. It is there for you.
Please go and check that out. I love it, brother. Adding value left and right. Editor-in-chief of Entrepreneur Magazine. The biggest, the best one was Champion of Change. I just wanted to call you that. Thank you. I appreciate that. It's funny. You put something in your social media bios and people just start using it. It's a funny thing. Yes. You need a jersey. Champion of Change.
Get you a ring. Nice bling. I need some bling. This is our gold chain. Yeah, I don't have enough of that. I don't know if I can pull it off either, brother. I really appreciate your time. Thank you. I appreciate yours. Hey, guys, you know where to find us. Search for Champion of Change. You'll find all the content from today. We really appreciate Jason Pfeiffer. We'll see you next time.
Here's the truth.
Information doesn't change your life. Execution does. So don't just listen to this episode and move on. Take the idea. Make the call. Launch the thing. Fix the problem. Build what you keep talking about building. For more, follow Ryan Alford on Instagram, at Ryan Alford. And watch or listen to every episode at RyanIsRight.com. This is Right About Now. Now quit waiting. Go win.
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