A Letter to My 20-Year-Old Self
A while back, a friend asked me what advice I would give to my 20-year-old self. I love that question. I thought about three decades of mistakes, failures, and breakthroughs, and about the lessons I wish someone had whispered in my ear when I was that age. With two sons in their twenties and a daughter not far behind, I also thought about what I would want to pass on to them—and to anyone else navigating those uncertain years.
Our twenties are a sacred decade—the threshold between childhood and adulthood. I remember the restless energy I had during those years, always running hard without pausing to see if I was even on the right path. So often, I wasn’t. I poured myself into jobs that didn’t fit, chased relationships with people who drained me, and followed crowds toward cliffs I didn’t see coming.
I’m writing this not just to the younger version of myself, not just to my kids and other young people, but to anyone still searching for their footing, in their twenties or beyond. My hope is that these suggestions offer a bit of light, or at least a reminder that you’re not alone in finding your way.
Dear Graham,
I hope you’ll pause for a few minutes to read this. I know how heavy life feels right now—the endless assignments, the tests, the pressure to prove yourself. I would like to tell you that none of these things will matter in the long run, because, truthfully, they won’t, at least not in the ways you think they will. But they will matter in a way you won’t realize until they are long behind you.
It was never about the tests, company analyses, or papers per se. These tasks are really about shaping you into the person you want to become. In taking them on, you are feeling the difference between phoning it in and giving 1000%, between chasing something hollow and pouring yourself into something meaningful. These challenges, like most challenges you’ll face in life, are not the destination—they are helping you develop your identity.
I know you are most focused on your career right now, so let’s start there. The greatest goal of your twenties is not to seem successful—it’s to become formidable. Don’t just chase the warmth of the crowd, the paycheck, or the prestige of a brand-name firm. What matters most is whether you build real skill and courage, whether you become someone who can make a lasting difference in the world. That happens not through shortcuts, but by sticking with work that matters to you long after the excitement fades, and by getting back up when you’re knocked down. Most of all, it means having the courage to bet on yourself.
Don’t waste your twenties trying to look good; use them to actually become good.
“The greatest goal of your twenties is not to seem successful—it’s to become formidable.”
When you discover something that gives you energy, surround yourself with the smartest and kindest people you can find—and ask them to teach you. Two years with the right mentors will be worth twenty years in the wrong room. But remember, this only happens if you’re humble enough to admit you don’t already have all the answers.
Pay attention to who you let in. You will become the people you spend your time with—and that goes not just for mentors, but peers and partners as well. Take a moment to think about everyone around you. Do they share your values, hopes, and dreams? Are they going where you want to go? If not, you can lovingly step back. Don’t waste time chasing people, romantically or otherwise. The right people will see you and will appreciate you for who you really are. You will feel it and know it. Clearing space for these people may feel lonely at first, and you might have the urge to hang on, even when you know someone isn’t right for you. But letting go is what makes room for the people who truly light you up.
“Take a moment to think about everyone around you. Do they share your values, hopes, and dreams?”
The mind follows the body, so take care of yourself—especially your sleep. Sleep feels optional now, like something you can steal from for more hours of work or play. But it isn’t. Sleep is not wasted time. It is fuel. It restores your mind and spirit. As Vince Lombardi said, “Fatigue makes cowards of us all.” A good night’s sleep makes you braver, sharper, stronger. Your full power demands courage, and courage demands rest.
At least once a month, stop and ask yourself: “What would I do if I knew I could not fail?” Ask this question about your work, your relationships, and your health. Don’t just think about it—write your answers down. They will almost always reveal what your heart longs for, beneath the fear. Follow that path as best you can. This life is too precious to be lived by fear’s rules.
Once you get a glimpse of your bigger goals, break them down into small, daily steps. Each morning, write down three things you can do that day to move closer to your goals. Then go do them. This may feel tedious, even boring. But greatness rarely comes from big sweeping gestures; it comes from small, persistent steps repeated over and over. You will achieve more in three months writing down your goals daily than you would in three years without doing so.
Pay close attention to all your habits. It’s easy to dismiss them as small and insignificant, but over time, they become the architecture of your life. As the saying goes, “The chains of habit are too light to be felt until they’re too heavy to be broken.” You’ll watch friends start small habits in this decade—harmless at first—that will grow unchecked into full-blown addictions, taking over their lives. In the end, your habits—good and bad—will shape your happiness and success more than almost anything else.
Give yourself grace. You are not behind; you are exactly where you’re meant to be. Life is an epic adventure stretched over many years. What matters most is your commitment to keep growing, not how quickly you “arrive.”
“You are not behind; you are exactly where you’re meant to be.”
When you look back, the moments you’ll treasure most are not the ones where you easily crossed the finish line, but the ones where you struggled and grew alongside the people who mattered to you. Ironically, the hardest moments will enrich your life the most. Notice who stays around during those times. Hold them close. And when others are struggling, show up for them, too.
“Ironically, the hardest moments will enrich your life the most.”
Let me set you free from one of the biggest illusions you’re carrying: the belief that if you work hard enough, climb high enough, or prove enough, you’ll finally “arrive” at happiness and wholeness. You think peace is waiting for you on the other side of achievement.
Here’s the good news: you will reach many of the crazy goals you’re dreaming of right now. The bad news? Success isn’t going to deliver the peace you’re seeking. The future is not some magical destination; it’s simply more present moments, just like the ones you’re in now, inviting you to live in them. Don’t wish these moments away—they are your life.
Graham, so far, you’ve treated life like a race—always hurrying to reach the next milestone. And yes, it’s good to throw yourself in fully, to take things seriously, to give your all. But life isn’t a race. As Alan Watts says, it’s a dance. The melody you’re hearing right now won’t ever play again. Each chapter of your life is a song that will play only once. Don’t rush through it or try to skip ahead. Let yourself enjoy the rhythm. Laugh in the off-beats. Savor each song while it lasts.
If you take away only one bit of truth from this letter, the closest thing I have found to the meaning of it all is this: Each phase of your life is not something to be gotten through, it’s something to be savored. The whole point is to enjoy the dance.
Godspeed,
Graham