When I was younger, people were constantly telling me that they expected me to go on to do great things. I remember this coming from teachers, mostly, but sometimes other kids too; I was always hearing that I had big things in my future, that people were keeping an eye on me, that they looked forward to being able to say they knew me back when.

I know I wasn’t alone in this—there must have been a fistful of us in every school, a nationwide army of identical standouts. And I’m not even sure how many of the people who said these kinds of things actually believed them. I’m sure at least a few of my teachers really did think I was uniquely talented, but I also suspect that a lot of the time, telling a high school kid he seems like he might be famous someday is really just a more polite way of telling him he’s weird.

I’d certainly like to think I never believed any of it myself. Whenever anyone said something even remotely along those lines to me, I’d brush it off, look down at the ground, try to change the subject. I knew that I had a few attributes that looked impressive on the outside, at least from certain angles, but inside it just felt like I was being myself the only way I knew how. Besides, like all charming people, I try desperately to impress people and then, when I succeed, secretly suspect that I’ve somehow pulled one over on them.

But if I’m honest with myself, I know that on some level I absolutely did believe it. Have enough people tell a kid he’s special and it’ll be impossible for him not to think they must be on to something. Besides, even though I was decently popular in high school, and genuinely liked it, I always felt deep down like I was somehow different from everyone else. And when you think that, you have two options: you can feel like a freak, or you can tell yourself you’re special.

And the truth is that for all the journal entries I have from those days fearing that I would never fit in, it wasn’t really fitting in that I actually wanted: it was standing out. In middle school—when I actually was weird and unpopular, and when I was certain that no girls would ever like me—I remember looking at the cool kids and thinking not Why can’t I be like them?, but rather, Why can’t they value what I’m already like?

For a while, it was easy to find evidence that I really was special, because when you’re young and have the limitless expanse of your future stretched out ahead of you, the possibilities of specialness are everywhere. Throughout my college years I’d rack up small accomplishments—getting on Who Wants to Be a Millionaire?, winning the prize for best English department thesis—and each one would seem like further confirmation of the inevitable.

Being special wasn’t about being famous, or rich, or accomplished, though there was the chance that all of those things would come along as byproducts. It was about the same thing I’d wanted back in middle school—to stand out. To have a life that was made up of more than just whatever it was normal lives were made of. I didn’t know what that was, but that didn’t make me any less certain it was out there. I wanted the kind of life where when it was all over, people would read my obituary and think, what a ride.

And for a while after I graduated, it seemed like I was on my way. I moved to Detroit and bought this abandoned mansion with some friends and started a company that became hot shit for a hot second. We were in the news a few times and even ended up followed around by a film crew as part of a documentary. A girl I’d briefly dated at fifteen sent me an email to say she’d seen my face in a movie trailer, and a guy I knew from college told me that he’d heard me on NPR one morning and been so surprised he’d pulled over. And it felt like maybe, just maybe, it was all about to happen.

And then, of course, it didn’t.

It wasn’t just that my company failed (though it did), or that I moved out of the crazy Detroit mansion and into a normal apartment (though I did), or that I slowly, imperceptibly, grew up (though of course I did that too). All of a sudden I wasn’t the youngest person in every room I walked into and people stopped grading my accomplishments on the curve of youth. I’d aged out of precociousness and into regularity, and the “someday” that had been a far-off vision to anticipate had not only arrived but was threatening to blow right past me into the rear-view mirror.

The unexpected thing, though, was that I didn’t mind.

It took me months, maybe a year, to even notice. I’d made unquenchable ambition a core part of my identity for so long that I kept running in place for a long time before I even realized that I had never been in a race to begin with. I began to feel embarrassed about having been so ambitious for so long, began to understand that ambition by itself is worthless if it’s not pointed towards something meaningful. And as I slowly became aware of all the emotional development I’d failed to do when I was trying so hard to stand out, it started to seem shamefully out of touch to see myself as special. Special? I’d be lucky just to make it to normal.

But what really made me see how much I’d changed was how my perception of my parents changed. When I was younger I looked at the life they’d built for themselves—a life that was, by most people’s standards, quite successful—and I saw it as irredeemably limited. All my parents wanted a strong marriage, healthy children, meaningful work, and financial security, and they’d built a life that had it all, and though I loved them and appreciated my family, I dreaded a middle age that looked like theirs.

Whether out of privilege or willful naiveté or just because I was one of those kids who always had his head in the clouds a little bit, on some level I assumed that the life they’d worked so hard to build was the default that pretty much everyone ended up with. Or maybe not everyone—after all, I was surrounded by counterexamples—but certainly me. That stuff was just the base that would inevitably fall into place. Real life, the juicy stuff, would be whatever else I layered on top of it.

Now, after so many fuckups and failures that my first attempt to list them all made this essay unreadably long, I’ve figured out what a lot of smarter and wiser people than me understood long ago: that building a life that contains just some of those basic components, let alone all of them, is incredibly hard, and that many—most!—people never manage to. My youthful dismissiveness of the essential building blocks of a good life now seems almost too stupid to have been real, like the kind of thing that would appear in one of Homer Simpson’s thought bubbles.

The older I get the more I believe that real specialness is not an inherent property that only some things—or some people—have, but rather something you can learn to find anywhere, though I increasingly suspect that it takes a lifetime of practice to do so. I often think back to the silent meditation retreat I went on last year and remember how by the fifth or sixth day, when the so-called “real” world had started to seem like a long-ago dream, my mind became so quiet that I could watch a squirrel on a branch or a leaf in the wind for hours and never once get bored. And I remember how obvious it was that those things had never been anything less than special. I had just been too distracted to notice.

Although I still look back fondly on those years in my early twenties when it seemed like great things were about to happen for me, I’m also aware that those years were the most self-centered in my life. Now I try to see specialness as something to be found, rather than something that you have; something to create for others rather than just take for myself. If I am actually special, the true measure of it is how special I make the people around me feel.

It’s not like I’ve completely given up on ambition. I still try to do things that matter, in my work and my personal life and everything in between. And who knows, maybe I will end up doing something truly great someday—even though I’m not totally sure I ever even knew what that meant.

But I no longer care so much about how cool I sound in my obituary. After all, I won’t even get to read it.

Yours in admitting that after everything I just wrote, I wouldn’t be doing this newsletter if I didn’t still think I was at least a little special,


P.S. I was the featured “hot single” in this week’s issue of hotsingles.nyc, a newsletter about—you guessed it—single people in New York. Share it with the single women you know, but whatever you do, please don’t show them my newsletter.