Author: Keem A

  • The Six Months I Spent Winning the Wrong Game

    There’s a specific high that comes from shipping fast: the backlog gets shorter, the feedback loop gets tighter, and you start to feel like you’re good at your job in a way that’s easy to point to. For six months I chased that high everywhere at once — career, health, sleep, relationships — throwing things at the wall in every direction and calling the motion progress.

    The problem is that a shorter backlog isn’t the same thing as a better one. I was optimizing execution on a list of priorities I’d stopped questioning. Every week I won the game in front of me without checking whether it was the game I actually wanted to be playing.

    Career, health, sleep, relationships. Gym five days a week. Up early, down early. More hours on work outside of work, trying different tactics to stay on top of things. Friendships maintained because they were friendships — no test beyond that.

    Every one of those was defensible on its own. Together, they collided. The extra hours on work came directly out of the sleep I was supposedly protecting, and I ran that trade for months without once naming it as a trade. Nothing on the list was wrong. There was just nothing above the list deciding what beat what.

    The tell, in hindsight, was how rarely I zoomed out. Tactics reward speed, and speed punishes the pause it takes to ask a bigger question. So I stopped asking it, and got very good at answering the small ones instead.

    It took writing it all down in one place to see it — that’s next week’s story. What the notebook showed me was simple enough: I was a chicken with no head. A generalist is supposed to move across categories. But a generalist without a strategy is just someone good at multitasking — a lot of motion in a lot of directions, none of it pointed anywhere.

    What changed wasn’t the tactics — it was where I was pointing them. The skills were fine. Waking up early is a good skill. Putting in effort is a good skill. But if you’re using a hammer to drive a screw, you haven’t got a tool problem.

    What I’d actually lost was the long view. Every decision was getting made against the next week, so trying harder was always the answer — and trying harder was the thing making it worse. The fix wasn’t more effort. It was standing back far enough to see all the pieces at once and asking which habits get me where I want to end up, instead of which ones get me through the month.

    This series is the record of trying to fix that: fewer sprints, more standing back, and telling the difference between winning and winning the wrong game.