Everybody’s got a plan until they get punched in the face.
Mike Tyson said that. And as someone who’s spent years on the Jiu-Jitsu mat, I can tell you — he’s right.
I’ve stepped onto the mat convinced I had my opponent figured out. I’d mentally rehearsed every move, every sequence. And then he’d throw something totally wild and unexpected — and suddenly I’m on the defensive, scrambling to survive, trying to reverse the situation from the worst possible position. I’ve had more close calls like that than I’d care to admit.
Ditto for planning at work. I used to be an obsessive planner. I’d work myself up when plans didn’t materialize, then turn my world upside down trying to make the plan work. Following a rigid plan has cost me far more unnecessary chaos than having a broad idea of what I want to achieve and letting things unfold. Because anything can happen — an unavoidable call that derails the whole day, an argument that kills the motivation to do anything at all. Who knows.
Smart people fall for this because formal planning feels deeply rewarding. Gathering data, producing spreadsheets, filling in templates — it feels like rigorous, decisive management. And leaders hate admitting they can’t accurately forecast the future because it requires surrendering their ego. There’s always someone else claiming they have this superpower — and if it all comes down to made-up confidence in made-up numbers, you might as well do epic BS.
I know because I’ve done exactly that. I once produced wildly erroneous financial projections because leadership wanted them — there was no data, no pipeline visibility, nothing. The inner economist in me (which is demented) couldn’t help but rely on bogus statistics that would certainly cement my place in hell. Naturally, it was a disaster. I wasn’t fired. The only thing those projections were actually good for was creating baseline data for next year’s planning, which would be marginally less terrible.
They say 90 percent of major infrastructure projects go over budget because managers rely on detailed internal plans while wearing blinders to external reality. Sometimes the plan simply doesn’t have a leg to stand on.
There’s no such thing as enough planning — ask anyone with OCD in your team if they’ve ever felt satisfied with a plan. They won’t be. The key is knowing when you have enough to move: a clear picture of the big picture, the key priorities, the top things that need your attention. That’s the moment to start. My own transition from obsessive, detailed planner to outline planner took fifteen years. It’s been worth it. Because three months of planning and not starting is always worse than an imperfect plan in motion.