Right About Now with Ryan Alford - How to Build a Career That Can Survive Drastic Change | Jason Feifer

Episode Date: June 12, 2026

Ryan Alford talks with Jason Feifer about what it really takes to build a durable career in a world that keeps changing faster than people expect. Jason explains why he stopped waiting to be discovered, why every path carries risk, and why adaptability is often the trait that separates the people who keep growing from the people who quietly get left behind. The conversation also digs into storytelling, audience psychology, and what makes content genuinely useful instead of just self-congratulatory. Jason shares how he thinks about serving an audience, why he prefers problem-solving stories over simple success stories, and how that mindset has shaped his work at Entrepreneur and on Build for Tomorrow. By the end, the episode becomes a bigger conversation about how to think long term without becoming rigid, how to stay useful in changing markets, and how to recognize that every decision carries risk whether you move or stay put. It is a thoughtful listen for anyone building a business, a brand, or a career that has to evolve over time. Topics Covered Why waiting to be chosen is a losing strategy What Jason Feifer learned from starting at a tiny local paper Why every career path carries risk How self-limiting plans close off better opportunities The audience-first framework for stronger storytelling Why problem-solving stories outperform generic success stories The four phases of change from Build for Tomorrow Ryan Alford and Jason Feifer on reinvention, relevance, and growth Links Right About Now https://www.ryanisright.com/ Ryan Alford https://www.ryanalford.com/ https://www.instagram.com/ryanalford/ Jason Feifer https://www.jasonfeifer.com/ https://www.instagram.com/heyfeifer/ Build for Tomorrow https://podcasts.apple.com/us/podcast/build-for-tomorrow/id1104682320 https://open.spotify.com/show/2JWluwXrmvrgeogZCAIWVF

A lot of times we think about how hard this is going to be. What a terrible road this is going to be. 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. You don't win by following the playbook.

You win by rewriting it. 700 episodes deep with the people who actually. built something real. No theory, no fluff, no shortcuts. This is right about now with Ryan Alford. Hey guys, what's up? We're talking with the champion of change today. My friend, Jason Fyfer, 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're a 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 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 in garden. 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. It's a nice lechay. It'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? And I realized that, well, working at the Gardner News is not to get me there because at no time in the history of the world will somebody at the New York Times pick up a copy of the Gardner News read the story I did on the middle school play and call me up and say, you're bringing me up to the big time. It's like never going to happen ever, ever. I needed to go to them. I quit the newspaper and I sat in my bedroom, bird nine months and I cold pitched everybody. I didn't have any connections. I knew nobody. And I'm writing editors of the Washington Post and the Boston Globe and the Associated Press. Eventually, I start to land stories in these public it takes a long time. There's a lot of being ignored. And even when I do land a story,

as exciting as that sounds, I will tell you that the money that comes along with it is not that exciting. So I would bust my butt to get $500 out of the Washington Post or something like that. But after nine months of this, I had proven something. And what I had proven was I can work at a different level. And I didn't do it by just sitting around and grumbling and expecting somebody to hand it to me. I went out and I did it myself. I went to them. And that is a lesson that I've carried forward throughout my career as I then got into magazines eventually, moved to New York, worked at a whole bunch of different magazines, Maxim, that was a terrible decision, men's health, a better decision, fast company, a good decision, entrepreneur, a great decision. The lesson that I

always took was go to them. 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 stayed at the bloom 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 and you move along. This is the thing. I mean, at a lot of times, we think about how hard this is going to be, what a terrible road this is going to be. 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 true. Very true. You bringing that up.