You’re not here to finish 2nd

Shaunae Miller dives for the finish line. Got this photo from Twitter.

Your game will improve dramatically the moment you decide you need to win. I know this sounds like random, useless success-speak, but there’s a truth here that too many people figure out too late.

This story is the kickoff of a new series called Saturday Morning Quarterback, where I dive into startup topics along more life-oriented angles, like sports and parenting, to name just a couple. Visit my author page for more serious startup stuff.

Obviously, there’s a sports-to-life metaphor in that line of thinking. I’ve played organized sports my whole life, and I’m of the generation that was just on the tail end of the era where not everyone got a medal for showing up. When we lost a game, we got an orange slice and a cold shoulder from the coach, if we were lucky.

Thus, I’ve been ultra-competitive in and around sports my whole life. I’ll be the first to admit that I hate losing, probably more than anyone I know, and I’m not good at it. To this day, if you put me on a golf course or in a first person shooter lobby or a poker room, I’m going to try to beat you, and I’m not going to hide it, and I’m going to be a jerk when you beat me.

But then I had kids.

I’ve been coaching my kids in various sports since they were toddlers. My deepest coaching run is with my son, now nearing the end of his Little League career. I changed gears for coaching, understanding that at the youngest ages, love of the game and a healthy dose of sportsmanship (sportspersonship? I’d be down with that) are more important than any trophy. This has worked, and all my kids are little competitive machines who are way more gracious in defeat than I ever was.

But we’re now reaching the point where love of the game has ceded to skills development and further ceded to performance. Just over this last year with my boy, practice and games have been about trying hard to win, and then pulling out all the stops, just short of naked aggression, to win.

“Have fun and do your best” has become “You’re not here to finish 2nd.”

I’ll say, “within reason,” because I don’t want to sound like that dad.

But they have to know where that line is, and they have to be comfortable approaching that line. More than that, they have to understand the transition from participation to competition, and with that comes lessons in focus, risk, patience, and work ethic.

You can’t teach that in a friendly, because life isn’t made up of friendlies.

The kicker is that these lessons apply to everything you do, especially when it involves your career. Believe me, there are plenty of people around you who aren’t playing the game for love of the game, especially in something like startup where the score is kept in dollars and customers, not titles and certificates of appreciation.

I realized this pretty early on in my career, watching people in various leadership roles fill their calendars with internal meetings, stare at spreadsheets that no one else ever saw, and do everything they could to maintain the status quo, keep their job steady and risk-free, and race to the end of the day looking busier and more important than everyone else.

They were always running late, always impossible to reach, always in crisis mode, but if you stripped everything away, you’d realize that they were there to survive. They were there to finish 2nd, maybe a respectable 3rd or 4th. Hey, not everyone can win, but at least they weren’t relegated to the minors.

Please don’t live your life like this.

Yeah, not everyone can win. Losing sucks. It hurts. It’s usually painful and embarrassing. And losing without trying can look a lot like charm if you play it off just right.

But losing is why former athletes are usually good at startup, not because of what we traditionally associate with sports culture — the bow to authority, the camaraderie of teamwork, the old boys network — it’s because they learn that at some point it stops being about the game and starts being about wins and losses. If you don’t have the drive and don’t play to win, eventually you’re relegated to the minors anyway, the sort of dustbin of career history, the rooftop of Hooli.

I’m still learning this. I like to play poker, it’s the only thing I do at the casino these days. And I spent way too long playing tournaments and trying to finish in the money. It was fun. But then it wasn’t, and I realized that there was no reason why I couldn’t win, other than I wasn’t trying to.

Then I started winning.

I don’t win every time, not even close. But I never walk away wondering what could have been, thinking I did OK against a bunch of pros and other miscreants. Once I started thinking “why not me, why not now” I started playing a different game, one where my focus was sharper, my moves were more purposeful, and one where I learned a whole new level of strategy.

And it’s still fun. Just in a different way.