Most people don't have a judgment problem. They have a speed problem.
I was sitting across from a founder in my portfolio a few weeks ago. He'd just let someone go. You could see it in his posture. Shoulders dropped. Breathing slower. The kind of relief that only shows up after you've been carrying something way too long.
I asked him how long he knew.
Three months.
Three months of watching projects slip. Three months of other team members quietly picking up the slack. Three months of his own credibility eroding in front of a team that could see it before he could admit it.
And look. I'm not going to sit here and pretend this is unusual. It's the single most consistent issue I see across every portfolio company we touch. Founders and operators hanging on to decisions they already know the answer to. Not because they lack judgment. Because the decision feels heavy in the moment, and tomorrow always seems like a better day to deal with it.
It never is.
This is a tough concept to learn and an even tougher one to implement. But the analogy is simple.
I held up my cold brew. If I told you to hold this straight out at arm's length, could you do it?
Obviously. Yeah.
Could you hold it for five minutes?
Sure.
What about six months?
He laughed. I told him I was serious. And honestly, if you know me, you know there's a cold brew in my hand more often than most things. So believe me when I say I've thought about this analogy a lot.
That's what delayed decisions feel like. You’ve heard the logic before…
The weight never changes. A cold brew weighs the same on day one as it does on day 180. But your arm starts shaking. Your posture breaks. Everything in your body starts compensating for that one small thing you refuse to put down.
The point I want to emphasize is the compensation - you hold onto a decision and put it off. Nothing burns. You assume it’s because it’s not a decision to make. When in reality most things around you just “compensated” for your lack of choice.
The worst part…
You're not holding one cold brew. You're holding six. Maybe ten. Every unresolved decision is another weight at arm's length. And it's not just that each one gets heavier over time. It's that the total load compounds. You wake up exhausted and you can't even name why. You feel behind on everything but can't point to what's actually wrong. That's the weight. That's all the open loops running in the background, draining you while you sleep.
Even when the decision is late, you still have to move. You still have to clean it up fast. The fact that it should've happened sooner doesn't give you permission to keep delaying. If anything, the lateness makes speed more urgent. The team already knows. They're waiting to see if you'll act.
Here's a filter I use now. After every hard decision, I write down how long I actually knew. Three months? Six? A year? Then I ask what that delay cost me. Not just money. Morale. Trust. My own energy. My own clarity.
If you made the right call three months late, you already have the judgment. Now train the speed.
Put the cold brew down.
