Advice for the Class of 2025
Top Substackers share words of wisdom for new graduates—and, honestly, everyone
Graduation has always marked a transition from one phase of life to another, but rarely have new graduates stepped into a world where everything else seems to be in transition, too. The economy, media, politics, art, technology—there’s a lot of uncertainty about what the future holds.
We reached out to a broad cross-section of writers, creators, philosophers, artists, and technologists on Substack to share their hard-won wisdom with the Class of 2025.
“Shoot first, aim later”
One thing nearly all of our contributors agreed on: it’s time to reconsider the old playbooks of success.
Cultural critic Ted Gioia of The Honest Broker had some stark advice for college students: leave. “If you haven’t graduated yet, there’s still time to drop out of college. Don’t laugh—the most successful people from many colleges are the dropouts. Maybe you should leave campus before they hand you that diploma.”
But if you’ve already crossed the commencement stage, all is not lost. “You will have other chances to rebel in the days to come. And rebellion really is your best long-term strategy. So don’t work for the system—work outside the system. Don’t follow the rules—create better rules.”
Kareem Rahma, the creator of Subway Takes and Another New Thing with Kareem Rahma , echoes the DIY ethos. “Shoot first, aim later. Especially if you’re trying to break into entertainment. If you’re not out there generating your own ideas and executing them, you’ll be stuck waiting forever for someone to hand you an opportunity that may never come. You’ve gotta make your own. Do not wait! Write the script. Make the movie. Start the podcast. Whatever it is—just start.”
Ross Barkan, the author of Political Currents by Ross Barkan and editor in chief of The Metropolitan Review, recommends writers strike out on their own. “Start a newsletter and write in your own voice. Find a niche relatively few people are writing about or follow your greatest passion—better if there’s an overlap. Build your own audience methodically by publishing every month or, if possible, every week.” Not giving up is key, as is embracing rejection. “Every publication I’ve written for has also rejected me. Rejections are part of the hustle. You’ll succeed if you stay in the fight.”
“Pivot, pivot, and pivot again”
The “career ladder” is an anachronism, like horse-drawn carriages and phone calls. But there’s a freedom in that. “Prior generations were trapped by a rigid blueprint of success or tortured by its lack of achievability, but we had a blueprint,” said writer and philosopher Laura Kennedy of Peak Notions with Laura Kennedy. “You don’t. That's frightening and lonely. But in the midst of this unravelling of our conception of how things work and where we’re collectively headed, what you get—you uniquely—is autonomy. Freedom from the pressure to make one ‘correct’ choice. There is no correct choice. There’s just what you decide you value. Ignore other people’s blueprints—they depict a world we no longer live in.”
Caroline Chambers of What To Cook When You Don't Feel Like Cooking has firsthand experience embracing the career change. “Don’t be afraid to pick one path for now and then pivot, pivot, and pivot again. Just because you start your career in one field doesn’t mean you have to keep climbing that particular ladder… I majored in International Studies, started my career in advertising, pivoted to catering, then restaurant consulting, and now I’m a food content creator whose cookbook was on the NYT bestseller list for six weeks. As long as you work hard and are good and kind to the people around you, you will go far, pivoting your way around until you figure out where you’re meant to be.”
No matter how many pivots you make, though, you’ll still face choices. Author Gretchen Rubin of Secrets of Adulthood offers some wisdom there: “Whenever we choose one path, we must forgo other paths, so any choice may bring unavoidable regret… If you move to Boulder, you can’t also live in New York City. If you go to grad school, you can’t join that start-up team. Trade-offs and compromises are inevitable. It’s very reassuring to accept that we may have some regret no matter what we choose.”
Just be sure to make the choice, however difficult it may be. “Remember, not choosing is a choice. The more mindfully we make our decisions, the more satisfied we’ll be with our direction.”
“Get a life. A real one.”
Education doesn’t end after graduation; it just changes format. “I graduated from NYU in 2005 with a degree in journalism,” author Tao Lin told us. “One of the main messages I got from college—and public school—was that most things have been figured out, and so few mysteries remain. Since then, I’ve realized this isn’t true. Many questions remain unanswered or unasked, and much of what’s presented as foundational appears to be incomplete, misleading, or false. Reality seems to be far more mysterious, complex, magical, benevolent, and terrible than textbooks, mass media, and pop culture suggest... So I recommend viewing your post-graduate life not as the end of your education but as the start of a longer phase of it. One with no professors, tests, or grades—just you and books.”
Tina Brown has one of the most fabled editorial careers in living memory—leading mastheads at Tatler, Vanity Fair, The New Yorker, The Daily Beast, and, now, FRESH HELL Tina Brown's Diary—but she’s still learning from the greats. “A good primer for how to succeed at warp speed is Barry Diller’s memoir Who Knew, which I write about in Fresh Hell this week. When Diller worked in the William Morris mailroom at age 19, he spent every spare moment reading the files of past negotiations and learning about the business. Tough-skinned, ego-free, work-all-night willingness to do any job is so rare these days, it will instantly mark you out for promotion.”
Continuous learning and curiosity might even turn into a job. “Back when I started Exponential View,” Azeem Azhar said, “I wasn’t chasing a business model. I was looking for understanding. Writing publicly forced me to refine my thinking. That compounding curiosity became the foundation for a global audience and a new kind of business. You don’t need a newsletter, but you do need a place to test your ideas.”
And as Emily Sundberg of Feed Me notes, leading a curious life is—frankly—cool. “Get a life. A real one. Not just a following online or a job title that your peers respect—a real life. Have interests and then dig deeper into them. Attempt to become an expert at something. It’s cool to sit down at a dinner table and teach your friends something new. It’s cool to sit down at a dinner table with strangers and have some insight into what they’re talking about.”
“All flourishing is mutual”
Despite all this talk of individual paths and personal autonomy, success rarely happens in isolation.
“It took me more than a decade to learn that I am not an individual actor striving for personal success in a harsh world, but rather a node in a web of interdependence that defines the human experience,” Rosie Spinks, the journalist behind What Do We Do Now That We're Here?, told us. “We live in a time when storied institutions and the traditional metrics of success seem to be in collapse. That is precisely why investing your energy into building a network of strong relationships—not just online but in your personal life, your wider community, and the few miles around where you live—is becoming a more meaningful source of security than an employment contract. I invite you to reject the main-character myth, which is defined by scarcity, competition, and infinite extraction. And instead embrace the far more liberating truth that, as author and botanist Robin Wall Kimmerer wrote, ‘all flourishing is mutual.’”
Tina Brown notes how important interpersonal skills are in professional relationships. “In job interviews, avoid the construct of ‘me’ and ‘I’ and ask yourself, what can you do for the person interviewing you? Not ‘I’m looking for a way to be creative and show I can do whatever’ but ‘I’m so excited by what your company is doing with X and relish the chance to contribute to it.’”
As a self-confessed former asshole, author and podcaster Dan Harris says “the skill that you should work on is your ability to relate to other people.” Here, he shares instructions for a loving-kindness meditation, designed to help you feel more empathy and warmth toward other people (and yourself).
Rather than offering advice on re-creating his own meandering career path—a “historically specific exercise in luck through which my particular skills and neuroses were appropriate to publishing formats, funding structures, and business models that didn’t really exist before this century and seem unlikely to last much longer”—Max Read instead suggests a few “slick moves” designed to assure everyone you know that you are “a generous and classy friend”:
When you’re invited over to someone’s home for the first time, bring a tin of home-baked rosemary shortbread, specifically this recipe from Melissa Clark, which is delicious, sophisticated, and incredibly easy.
If you find out the hotels your friends are staying at on their honeymoon, you can send them a bottle of champagne to have waiting in their room when they check in.
For your partner’s birthday, send them to a spa for a day with a friend, and pay for the friend as well.
When your friends have kids, send food right after the birth (homemade pesto and homemade pasta is a good gift), and then again after 2 or 3 months when people have stopped sending things. Send a batched cocktail, too—St. Agrestis does boxed Negronis.
Always—always—tip over 20 percent. You will never, ever regret tipping well, in your entire life.
“Trust your feelings”
It’s age-old advice for a reason. Signull of signull vs. noise puts it succinctly: “Rationality becomes a cage when you’re constantly simulating instead of experiencing. And ironically, the more you ‘think it through,’ the more detached you get from the signal your instincts are screaming at you. The best compass is often what feels obvious but terrifying. Not what’s safest, or what’s most optimized. I would trust your feelings more than you otherwise would.”
Heather Havrilesky—of Ask Polly fame, and an expert advice-giver if there ever was one—gets to the heart of this transition: “The only way to become intimate buddies with an inky black abyss is by looking inward: hearing the voice inside you that feels connected to this gorgeous and scary world in spite of your fears, listening to the melody under your skin that tells you that you’re brilliant and strong and you can show the world your heart without fear. Every time this broken world destroys your sense of yourself, remember that this is how you find your true path, your deepest desires, your strongest convictions, your most enduring connections to beauty and love and happiness: You expose yourself to the world as it is. You embrace your new role as the boss. You won’t always want the job. That’s normal. But you’re the only one qualified for it. Trust yourself.”
“There is no better time to be uniquely human”
So far, we’ve danced around the topic on everyone’s mind: The AI revolution isn’t coming—it’s here.
Azeem Azhar cuts straight to the chase: “You’re graduating into a moment of deep transition. Beyond difficult politics, polarisation, and a climate crisis, is AI. It is the single most important change in a century or more, and extremely powerful AI is going to be a reality in the next couple of years... The world you’re graduating into is unpredictable, so become adaptable, not just employable.”
Knowing how to navigate the tech is key, according to Timothy B. Lee of Understanding AI. “Invest time experimenting with new AI tools so you can figure out how to use them at work. AI tools are poised to accelerate almost every white-collar occupation … if you become one of the first people in your firm to master a new AI tool, you’ll be far more productive than your peers.”
That said, remember who’s in the driver’s seat. Alberto Romero of The Algorithmic Bridge offers a crucial distinction: “AI is a tool, and like any other, it should follow the golden rule: All tools must enhance, never erode, your most important one—your mind. Be curious about AI, but also examine how it shapes your habits and your thinking patterns. Stick to that rule and you’ll have nothing to fear.”
And there’s opportunity in the disruption. “There have always been opportunities for independent operators and contrarian thinkers. I’ve learned a lot from studying them, and emulating them,” Ted Gioia told us. “But now is the best time ever for bohemians, outsiders, nonconformists, visionaries, and gadflies. That’s why we’re seeing a rise in alternative culture. That’s why we’re seeing the emergence of new indie channels (like Substack). Not even AI can stop this—in fact, AI will accelerate the shift away from the monolithic and toward the personal. The more individual you are, the more you will be immune to it. The more you will thrive. The more you will enjoy life.”
Animator Erik Winkowski of Paper Films agrees. “As generative AI gets increasingly sophisticated at making slick, spectacular, perfect art, I believe there will be a growing hunger for the imperfect—the human. Nothing is more alienating than perfection. Your so-called ‘imperfections’ may be the very thing that creates a connection with your audience.”
Nonagenarian writer, editor, photographer, and publisher Lloyd Khan thinks that AI will lead to a renaissance in practical skills. “Strange as it may seem, I’d recommend learning to work with your hands. I had a full-time job in the ’60s (insurance broker in San Francisco), but I spent every night after work and every weekend building a house.” And there are other benefits, too: “As a result, I’ve never had a mortgage, nor have I ever paid any rent. Learn to use your hands.”
Despite the name, energy, finance, and economy expert Doomberg delivers perhaps the most uplifting message of all: “Believe it or not, there is no better time to be uniquely human. The realm of banal mediocrity is flooded, but there is a life raft for those who approach their work with a commitment to excellence. The trick to success is that there is no trick: the trick is to be better. Yes, that’s right, quality execution builds a durable, valuable moat around any endeavor—a principle that applies to all types of work in any field and any industry. Good luck, and go make yourself indispensable!”
Lightning round
Hunter Harris: “Keep your student ID so you can use it for discounts. And back up the contacts of your .edu address too!”
Kareem Rahma: “Only work with people who you’d like to go on vacation with.”
Tina Brown: “Never utter the words ‘work from home.’”
Laura Kennedy: “Try not to neglect dietary fibre. Literally everything goes wrong without it.”
Ziwe: “My advice is to listen to Roy Wood Jr.”
Thank you to Alberto Romero, Azeem Azhar, Caroline Chambers, Dan Harris, Doomberg, Emily Sundberg, Erik Winkowski, Gretchen Rubin, Heather Havrilesky, Hunter Harris, Kareem Rahma, Laura Kennedy, Lloyd Kahn, Max Read, Rosie Spinks, Ross Barkan, signull, Tao Lin, Ted Gioia, Timothy B. Lee, Tina Brown, and ziwe. And a special thanks to Wendy MacNaughton for the beautiful art.
Reading this I understand why young people today are screwed: Every drop of wisdom here is pointless unless you are pursuing a career as a “creative.” Do we really need more podcasters, bloggers, YouTube celebrities or influencers? How about plumbers, electricians, pulmonologists and firefighters?
F*ck this was GOOD read