Trusting your gut is risky, and over-analyzing isn’t practical. Field notes on what actually works for most decisions.

It’s been over a decade, but one of my biggest unforced errors still lives rent-free in my head. Eager to ‘elevate myself,’ I hired a Director of Operations who attempted a coup and in a few short weeks managed to set the company back over a year.
I’d hired her by trusting my gut. And it turns out, we do this a lot, and our co-conspirator friends encourage it, too.
“Should I spend {large sum of money} on this?”
“Trust your gut”
“Is she the one? Should I propose?”
“Trust your gut”
Unless it’s a no-stakes decision, this is terrible advice whether business or personal.
In the book Extraordinary Tennis for the Ordinary Player, Simon Ramo saw something that’s more than just for that sport. Simon wasn’t a tennis pro, he was an engineer and businessman. He found that approximately 80% of the wins in amateur tennis weren’t due to superior skill, they were due to fewer unforced errors. Amateurs seldom beat their opponents. They just reduced mistakes that would have made them beat themselves.
Business and life aren’t tennis, but I think the same principle holds. Going with your gut is just risking unforced errors. You don’t know why you’re choosing, and when something goes wrong (you hire someone who tries to hijack your company, for example) you have nothing to help you make a better decision next time. Repeat.
The Spectrum of Important Decisions
Some decisions just don’t matter. They’re inconsequential (“I bought the wrong size garbage bags”) or reversible (“I’ll return the shirt that doesn’t fit”). Going with your gut here doesn’t matter, because the outcome is low stakes.
Some decisions matter a whole lot. They’re impossible or hard to reverse, and can have profound impacts on us (sell the company, marry that girl). Here we know better than to go with our gut, we’re hiring investment bankers and lawyers, or moving in before tying the knot.
But most decisions are in the messy middle, and the problem is that we default to gut, because that’s what we’re used to for a thousand small decisions every day and there isn’t a good way to make them quickly.
Rules of Thumb That Actually Work
This is why heuristics are useful. Rules of thumb. Little mantras you can say that can help ask the right question, or make the right choice.
I’ve got a few that I’ve made for myself and have stood the test of time. A sampling, with some “reason why” annotation so it’s less cryptic:
- “if everyone thinks something, it’s probably wrong” – outsider thinking is more valuable than consensus. Oh and yes, most people are wrong
- “default to saying no” – everyone has goals, and saying yes recruits me into their goals at the expense of spending time on mine
- “the calendar is the source of truth” – tasks, checklists, and projects are only aspirational unless there’s time allocated for it
I’ve got dozens more, but listing them isn’t the point. These are mine, for my temperament, my goals, my situation.
I probably pull one from my grab bag two or three times a day. At this point, it’s reflexive. And because I’ve made them for me, the weight of decisionmaking in the messy middle has gotten a lot easier.
Of course, there’s a dark side to this. A heuristic helps us make decisions, but sometimes they become unforced error factories. We think we have a good rule, but it’s foiling us – when we use it we don’t usually get what we want.
Fortunately, unlike with trusting our gut we notice because the rule is articulated, not vibes.
From There to Here
I probably started naming these things two decades ago. Over that time, I’ve worked backwards from my “target business” and “target self” to write my heuristics.
I’ve refined them and shamelessly stolen them from people smarter and more successful than me.
I started this bare-knuckled as a way to get to the outcomes I wanted. It’s made getting there more reliable, and cut down agonizing over decisions and simplified things.
But the most interesting thing is what happens after they’re refined, they work, and using them becomes reflexive. I’ve found that it’s easier to let go of the outcome that I thought I wanted decades ago. Still zig-zagging there, but the hold on the steering wheel is lighter.






