The Joy of Not Finding Early Success

And the moderately tragic lives of those who do.

We all know those people who peaked in high school. Cheerleaders, football players¹, A students who won every award—lives that were in general gleaming with promise.

I wasn’t one of those. I mean, I had cool friends and did plays and went to lots of parties but I definitely didn’t feel like one of the Smart Kids and certainly wasn’t a star athlete.

Of course, we all know what happened to the high school peak-ers! We know because we see them on Facebook where they make us feel immensely superior since their lives are so utterly basic and ordinary. Whether it’s weight gain, baldness or lame-seeming lives, they tend to regularly make us feel grateful that we weren’t the Homecoming King or Queen.²

What we don’t realize when we enter adulthood is that the same thing happens in careers.

In my experience, the universe throws us a lucky break and we usually don’t realize it was a lucky break until it never happens again. In my case, there were a few big breaks: I got signed by a big agent who’d reached out to me and then sold my first book to my top choice publisher within a few weeks. I wrote one essay for an anthology and the New York Times snapped it up as a “Modern Love” without me having to even submit it. I co-wrote a story for Playboy that went the then-equivalent of viral before being optioned and made into a reality show pilot. I spent years being wooed by TV shows to come on and give sex and relationship advice and landed a job as a columnist for my favorite magazine.

At the time, I thought: “Well, sure. I always knew I was better than those people who peaked in high school. Why not?”

But then: I never again had a magazine story I wrote optioned, let alone made into a TV pilot. Magazines evaporated and there were thus no more columnist positions. Writing for the New York Times? Can’t imagine it. And if I can get on a big TV show today—which I did a few years ago—it’s a small miracle.³

Honestly, it sucked when I realized the big, shiny events were Good Things That Happened to Me and not The Way My Life Was Going to Be. It took a long time to get over it. But I truly am grateful for it because eventually I was able to start a business and thus create a life where I wasn’t so dependent on gatekeepers and lucky breaks for success.

Other people I know had lucky breaks that launched them into superstardom. I’ve definitely been accused of sharing this too much so forgive me if you’ve heard me say this before but Matt Damon was my college boyfriend. And the only wedding I’ve ever been a bridesmaid in was when my childhood friend Mackenzie married her coworker, a guy named Jeff Bezos, years before they moved to Seattle to start an online bookstore. If you’d told me back in the early 90s when I was hanging out with Matt and Mackenzie in New York that he’d go on to be the biggest movie star of our generation and she’d go on to become the richest woman in the world, I definitely wouldn’t have believed you.

Someone on Instagram accused me of sharing this photo of us in college too much but I would venture to say I haven’t shared it nearly enough

Anyway, I’d be lying if I said I was still in touch with Matt or Mackenzie today and thus have any idea how they feel about the way their lives have unfolded. But I have been around to witness the comparatively smaller successes of some other writers I know.

One had insane, meteoric success on his first book. We’re talking #1 New York Times bestseller, insta-fame, hit movie based on the book, the whole nine. After that run of a few years, he was spit out into…well, what-the-f-do-I-do-now land. Decades later, he’s still trying to figure that out. And he’s one of the nicest and coolest people I’ve ever known so it kills me to see it.

Another writer I know had even greater success. Became a household name. Made pots of money. Assumed—and this was a direct quote I heard him say this myself—that he was “the best writer in the world.”⁴ Today, he has a regular old job-job and while it’s a cool job-job, if anyone looked like they’d be set for life as a writer a decade ago, it was him.

Another writer I know has a story that isn’t as dramatic as the other two because her first book didn’t make her famous or dramatically alter her financial situation. But it was a beloved bestseller. Decades later, she continues to write books and make what I would assume is a solid living as a writer. It’s just that none of her other books are ever going to be as perfect as that first one.

So…what’s it like to live knowing that your greatest success is behind you? I’m happy to say that I don’t know the answer to that. All of my successes, except for those early lucky breaks, have been hard-won. I’ve pushed and persevered my way into them. As a result, I appreciate them in a way I never would have had they come to me easily.

And I have every reason to believe that even greater success lies in front of me. As should you. Because…why not?

1. Somewhere between writer fame and real fame

2. Something else my school didn’t have.

3. I’m lucky enough to have a regular gig reviewing books on a Portland TV show and I love it but the days of going on Today and The Talk are surely behind me.

4. To put it mildly, he is NOT the best writer in the world.