Overnight Success

Most people overestimate what they can do in one year and underestimate what they can do in ten years. ― Bill Gates

For most of my life, I’ve wanted to be a writer. I have a weirdly specific memory from kindergarten which I ascribe to the first time I realized that I wanted to be a writer. We were sitting at those tiny little tables designed for people who aren’t quite four feet tall. (Side note: a point of pride is that David and I were the first people in our class to hit four feet and we both did it within days of each other in kindergarten.) While Allison drew what was to me the most magnificent apple I’d ever seen, I was drawing maps of a world that didn’t exist and thinking of stories to go along with them.

Unfortunately, in the subsequent years, I’ve allowed that dream to be snuffed out by fear of failure. That fear stopped me from practicing, from honing how to tell stories. For all intents and purposes, it stopped me from writing.

Sure, I’ve written on and off, but it’s almost always been non-fiction. As my friend Graham might say: when it came to telling stories with writing, I had crippling anxiety.

Still, the dream that one day I can write full time, even make a living at it, has stuck with me, dormant, waiting for a chance to stretch its legs. The amazing thing about dreams is that they can be just about anything you want them to be if you think big enough. They hold infinite potential. At some point, however, if you don’t put in the work, dreams will remain just that: dreams. Dreams never turn into reality simply by wishing them.

There’s a lot that’s going to have to happen for my dream to become a reality. For starters: I’m going to write. A lot. Way more than I have before and probably way more than I even think I’m capable of doing.

While I have doubts about my abilities, however, there’s something really inspiring about seeing (or hearing) about what others are doing. I was listening to some authors talk about their personal definitions of success recently and was heartened by the reminders. The reminder that the definition of success is personal. That what it looks like, what it means, is not a universal construct, but one that’s tailored to my personal situation and to the things I care about.

On the other side of the ledger, it’s useful to remember what I have accomplished.

Almost six years ago, I was working at a healthcare startup. By most accounts, I’d been quite successful. I’d parlayed a series of jobs into bigger and bigger ones until I was leading a few teams of engineers and building products that improved health outcomes and reduced hospitalizations.

But, something was missing and I was restless. In part, that was because I didn’t actually know how to build the products. I was hamstrung by a lack of knowledge. I could set a vision, lead a team, and produce something that made a difference, but I was frustrated that I was always at arm’s length.

So, I decided to do something about it. Instead of going to business school, which had been my plan for years, I enrolled in a coding boot camp to learn the rudiments of software engineering. With effort, persistence, the support of my cohort, and a lot of hours with my butt in a chair and my hands on the keyboard, I did just that.

For more than three months, I averaged somewhere around 10 or 12 hours a day, six days a week, in front of a computer practicing. That was enough to get my first job as an engineer. Barely.

The next four years I worked tirelessly to rise through the ranks of engineering from junior to mid to senior and so on. (Side note: titles in engineering are funny.)

I’m back in management these days, leading a team of engineers again, but I no longer feel handicapped. At least not as much. I’m able to engage with my engineers way more deeply, discuss the tradeoffs for various decisions, and challenge them to think of ways to improve designs.

Being an engineer was once just a dream. I thought it would be nice to be able to build things every day. For a while, I was afraid of this dream too and nearly didn’t pursue it. A series of fortuitous circumstances and well-timed conversations with friends and most critically, my mom, set the train in motion. Then the work started.

This is how I know there’s no such thing as overnight success. When I compare where I am today to where I was just five years ago, it feels like apples and oranges. Sure, I was a human then, too, but from an engineering perspective, I’m practically a new person. I’m a walking Ship of Theseus.

I’m also just getting started. There’s so much left to do.

I feel so lucky to have had this experience with engineering, particularly right now, as I dream of being a writer. I don’t want to dream of it. I want to do it. And I know I can, because I have. I’ve made this transition before and I know there is no overnight success.

Barring winning a jackpot or stumbling upon a pot of gold at the edge of a rainbow, there’s only one way to succeed¹: putting my butt in a chair and hands on a keyboard.

So, when it comes to being an overnight success, I’m playing the long game. I’m shooting for the moniker of the decade-long overnight success.