One More Win Before Bed

Let’s win one and call it a night.

Around midnight, either I or a friend would always say it. By the time it comes up, we’ve already dropped at least a game. Strangely, winning is more fun after losing a few first. I can only sleep once we’ve won. And among wins, a comeback is the best sleep aid of all.

There are conditions that make a comeback fun. The opponent’s skill should be similar to mine—or just enough better. Ideally, both sides are in good form. It’s better to win by playing well than by capitalising on a silly mistake. And as long as a comeback isn’t impossible, the more behind we are, the better. Finally, my role has to be big in the turnaround. Victory matters most, but it’s more electric when we win because I played well.

Work isn’t so different.

A company is at its most fun when it’s the underdog. Early on, the other side should be just enough better. It helps when both sides are genuinely competitive; if rivals are too weak, it’s dull. There needs to be a goal that’s hard but attainable—neither too easy nor too hard. The sweet spot is a target that feels within reach but not quite. The team has to stay positive to the end, pushing even when it’s tough; everyone needs to care about winning. And in the thick of it, my role should be big. Lastly, unlike games, reality is messier, which makes it even more important to have clear win conditions—a win everyone can feel and be satisfied with.

I remember the streaks, but the wins I cherish most are the comebacks. For that energy and that joy, I keep playing—and I keep building startups.