When You Arrive, Send Me a Postcard

10 Things I Would Tell My Younger Self

Living is hard.

How do we fill our endless numbered days? How do you make a life? What constitutes a good life? These are daunting questions at 23 and they don’t get much easier to answer at 54. My life looks nothing like what I imagined it would when I was 23. But I was mostly an idiot back then— an idiot with a debilitating amount of testosterone and a staggering propensity for magical thinking.

See, I’m already doing it, being an asshole. It’s hard to be kind to myself. I’m embarking on this essay as a practical exercise in kindness. Wisdom is too lofty a goal, but kindness is, I hope, attainable.

As my grown children toil through the gauntlet of their twenties, I can’t help but see myself. I’m reminded of how much I thought I knew and how outraged I was that the rest of the world had it wrong. I’m reminded of how scared I was that I wouldn’t find my life’s purpose or even be able to earn a living. If you don’t have kids maybe it’s easy to forget where you’ve been and who you were. Our footprints fade into the sand behind us as we walk.

I was told from a very young age how talented I was. My mom praised every scribble, every funny turn-of-phrase, every joke, every song, and every creative idea I ever produced. My dad coached my teams, taught me to throw a perfect spiral, helped me with my fastball, and cheered from the sidelines at every single game. The message I absorbed from their indulgence and unconditional love was: you are special and you can do anything. What a gift, right? They did their job and I’m forever grateful.

And yet.

I was woefully unprepared for the reality that I was actually not exceptional and I could not, in fact, do anything. It took me decades to work through these simple truths and I’m still prone to delusions of grandeur.

I don’t believe I’m a unique phenomenon. I think there are many people raised in relative privilege who have higher expectations of themselves and the world than are realistic. I know I likely raised my kids the same way, though they would argue differently. You see, the defense for someone suffering from my particular maladaptation is to overcompensate. This looks like self-deprecation, pessimism, criticalness, and downplaying disappointment. Like every parent who’s blessed to see their children grow into adults, I know with certainty how many ways I failed them.

So, why am I bothering to tell you all this? I think my goal in writing this essay is to take an inventory of what I’ve learned up to now and distill it. I can’t go back and talk with my younger self. I strongly doubt my kids will have an interest in this, though they might twenty years from now. But maybe it will be of some value to you, particularly if you’re pursuing a life in the arts. It’s easier sometimes to take advice from a stranger and I’m pretty strange. Here we go.

1. You might be unique, but you’re not special.

There’s a difference. Have the patience to learn yourself and understand who you are independent of everyone around you. The need to belong and to be liked is so strong for this tribal species that we are. Most people will file down all their rough edges just to fit in. Embracing what makes you different will give you a confidence and resilience few people have. But being unique does not make you special. Special implies you are somehow better, more deserving than others. The drive to be recognized as special will lead to a vacuous, disappointing, and lonely life.

2. No one is watching you so stop performing.

I’ve observed an embarrassing tick I have and I’ll share it to make a point. If I’m walking somewhere in public and make a wrong turn or maybe I forgot something and have to turn back, I will suddenly and with studied purpose, look at my watch or pull out my phone as if I just received some important message that has compelled me to alter my plans. Why? No one on the street gives a fuck. They are paying zero attention to me. I’m performing the role of a “normal” person for an audience of one. I have wasted precious time and energy in my life worrying about what other people will think of me. It’s a silly vanity and serves no purpose. I believe this advice holds even if you’re actually on stage in front of people. If you’re performing, you’ve already lost something vital and authentic.

3. You’ll never measure up so put away the ruler.

I played a few shows with John Mayer back in 1995 when he was just getting started. I was 25. He was still a teenager. By comparison, I was the sage musician, headlining shows at Eddie’s Attic — a high-water mark for any regional songwriter. Within 18 months, he would have a major label deal and be selling out theaters and I would be a new father armed only with a music degree to try to find some way to earn a steady income. For a decade John haunted me. We never spoke again but his presence was always there, a constant reminder of my relative failure. I was sad and bitter. I had other friends from that scene who went on to achieve commercial success and they haunted me too. I allowed that. For too many years, I quietly shit all over the gift of the life that I had because, in my mind, it didn’t measure up to the life I thought they had. There are few better shortcuts to misery than comparison. And yet it’s one of the hardest things to avoid in this life.