Generation Hustle

Why Jeff Pearlman was right

Over the last week, the sportswriter Jeff Pearlman has become the new internet hate object. Pearlman, perhaps best known for writing a book about the 1980s Los Angeles Lakers that was turned into an HBO series, was caught doling out advice to young sportswriters who have been suffering through the full-scale collapse of print and online media. Pearlman was damned most for the following:

“The number one thing is, you have to make yourself indispensable; you just do. I told this to someone I know, but if you’re covering a team — let’s say you’re covering Wichita State basketball for some newspaper. Ask your bosses if it’s OK if you start a podcast too — a Wichita State sports podcast. Build up an amazing Instagram following, and start doing TikTok videos about Wichita State sports to the point where you’re known as the guy on TikTok for all things Wichita State. Find a million different ways; build up your Twitter following.

“It’s stupid, it’s annoying, but it’s the same kind of the way you survive as an author of books these days. You make it so that you have this built-in audience of people who are waiting for your book or what you have to say. You just have to become an expert. And you just have to do everything. You have to grind and grind and grind. Start a Substack that directs people ultimately to your work on your newspaper website. Come up with a book proposal, and come up with book ideas. And my advice to, if it’s a first-time book, is don’t make it about your uncle who is diabetic and his battle. Find something that is mainstreamish — the Big East in the 1980s, LeBron and Kobe’s relationship. Something big, something that works, something that would grab a publisher.

“You just have to find a million different ways to stay relevant. Stay on top of things, have a million different tentacles everywhere. I left Sports Illustrated in 2003 and honest to God, one of the reasons I did — besides wanting to write books and being tired of sports — is I just didn’t love the direction of where things were going. You just have to stay a little bit ahead. I know it sucks. It’s hard. It’s brutal. I apologize, but that’s my best advice.”

Pearlman was widely mocked on X, formerly known as Twitter, for suggesting young reporters had to make themselves “indispensable” by hustling on various online platforms. He was seen as blaming laid off journalists for their own fates and being, as a fifty-something sportswriter, deeply out of touch with the current crisis. It was pointed out, rightly, you can’t simply “grab a publisher” with a wonderful idea like interviewing the most famous basketball players on Earth, and that the concept of starting at a local newspaper and working your way up might be outdated, given the disappearance of these entry-level gigs. “Taking on more work for less money will not save you when the hedge fund in charge decides they don’t need journalists,” wrote the journalist Megan Greenwell. “And it’s deeply unethical for a self-appointed senior statesman to say otherwise.”

There’s nothing unethical, though, about dispensing advice. The better question is what, exactly, Pearlman said that wasn’t true in 2024. Ethan Strauss, the sportswriter and successful Substacker, said it best, and I will add a bit of what I’ve learned through the same era of tumult. Unlike Pearlman, who can be castigated for not having entered the industry in its period of terminal decline, I can speak exactly to what journalists are enduring right now. I have been fired. I have been forced to quit. I have spent the better part of a decade hustling up gigs, stringing together four or five or six different streams of income to pay rent in New York City. If you browse my CV, you’ll find I’ve worked for my share of publications that no longer exist. I’ve had publications fund me well one year and disappear the next. I’ve had cherished editors—the people shepherding my pieces into print, and getting me paid—laid off, my connection to a prestigious publication severed overnight. Entering the media industry today is nightmarish, but it was exactly this way in 2011, when I left college and the global economy was barely recovering from the worst meltdown since the Great Depression.

I’ll be blunt here, especially for the Gen Z journalists and writers who might be reading this: Pearlman is right.

He is right because there are only two ways to survive if you want a career in media today. You have to be very lucky. Or you have to be very good.

To be very good, you absolutely have to stand out.

Luck goes without saying. Luck is family wealth to support your bid in the most precarious industry in America. Luck is attending the right school, meeting the right people, or getting hired at the perfect time. Luck is finding an internship that offers a glide path to a full-time job with benefits.

Life, as my late father used to say, is luck and timing. To get anywhere now, you need both. Pearlman certainly was lucky. It’s better to be born in 1972 than 2002 if you’re attempting a career in media. If you’re twenty-one or twenty-two right now, you will never, ever have the opportunities Pearlman had, like working at a fully-staffed and functioning Sports Illustrated.

The very good element here is trickier. You can be extremely talented and still get laid off. Pearlman kicked off a firestorm because too many people wrongly interpreted his remarks to mean those who lost their jobs at SI, the Los Angeles Times, and Pitchfork somehow deserved it for not being good enough. Pearlman, who is otherwise a liberal in good standing, never meant that. He was simply offering a path forward through the chaos.

The path forward, by the way, has no guarantee of success. Aspiring to a career in the media or the writing field is a bit like wanting to make it in Hollywood or crack the roster of a Major League franchise. It is very hard and rather unlikely, though not as unlikely as Hollywood or MLB. I make this point simply to underscore that you can’t assume anything and you must have a fallback. Not everyone gets an acting career. And even those that do are waiting tables, teaching, or finding other ways to pay the bills.

To have a chance to survive (or even thrive), you have figure out how you can distinguish yourself in a brutal marketplace. The journalists and writers clinging onto sinecures at mainstream publications—those firmly in the macroculture—always seem to take most offense to this. You can’t be like everyone else. And you’ve got to find a way to convince some segment of the public to care about what you do and eventually pay for it. Substack has attracted all kinds of needless hostility from legacy publications and I am not interested in more meta-commentary on the subject, but I’ll note that it offers a golden opportunity for any ambitious person who wants to fill a coverage gap that the disintegrating mainstream media has left wide open. Do you write well on music? Do what Pitchfork did, and start reviewing new bands. Do you care about local news? Move to a cheap, underserved locality and start reporting there. Convince people you’re worth the investment. A guy who now clears $350,000 a year writes about basketball in the Pacific Northwest.

Can you be that guy? Probably not. That’s a lot of cash, and this Substack you’re reading doesn’t make nearly that much. But you can definitely make more than zero dollars and could, in time, replicate the salary of a staff reporter—except you’ll have all the autonomy and room to keep growing. Is this how I want the media to work? No. I want large, well-funded institutions. I want collaboration. I don’t want atomization. I’m also not here to tell you or anyone else what I want. I can only speak for the world in front of me. In a market with intense competition and few opportunities, you cannot afford to be mediocre. There are many people who had comfortable twentieth century media careers who, in this environment, would have washed out in their early twenties.

Now? You’ve got to outwork the competition. You’ve got to find a niche. You can’t be afraid to be weird. If you’re struggling with what to do, look out at the offerings and ask yourself what you can write that’s not like everything else being published. What can you add? I don’t love Pearlman’s advice about existing on three or four different platforms. Pick one and excel at it. If you’ve got a knack for podcasting, podcast. If you have writing chops, keep writing. If YouTube is your thing, enjoy that. You can always branch out and be a multimedia mogul, but you’ve got to get very good in one place first. Strauss, mentioned earlier, is a great example. He podcasts through his Substack but he made his name through the written word and it’s his posts that undergird his success.

The reality is that you can’t—unless you’re very lucky—hitch your career to one institution. You can’t hope the institutions bail you out. Newsroom unions are great, but newsroom unions can’t stop layoffs. Pearlman exhorts the young to find a “million different ways to stay relevant” and to keep a “million different tentacles everywhere.” I think this is right. It’s less about being a jack-of-all-trades and more about having backup plans, and backup plans for those backup plans. It’s also about that ability, almost ineffable, to stay ahead of what’s happening. Have a sense, if you hold a full-time job, where this is all going. Do you like the direction? The Messenger officially collapsed. Don’t work anywhere if you can’t readily identify a business model and how it might work.

And don’t be defeatist. It’s bleak out there, but it’s not impossible out there. Tenacity and talent still matter. They always will.