How to Stop Overthinking Your Decisions

You've got a decision you've been putting off. Maybe it's a career move. An investment. A difficult conversation you keep rehearsing in your head but never starting. You tell yourself you need more information. More data. More time to think. But you're not gathering information. You're hiding behind it. What looks like due diligence is actually overthinking in disguise. The certainty you're waiting for doesn't exist. It won't exist until after you decide and see what happens. I call this mindjacking: when something hijacks your ability to think for yourself. Sometimes it's external. Algorithms, experts, crowds thinking for you. But sometimes you're the one doing it. That endless research? It feels like diligence. It functions as delay. You're not being thorough. You're mindjacking yourself. Today, you'll learn a framework for knowing when you have enough information, even when it doesn't feel like enough. Because deciding before you're ready isn't recklessness. It's a skill. And for most people, that skill has completely atrophied. The Real Cost of Waiting At a California supermarket, researchers set up a tasting booth for gourmet jams. Some days, the display showed 24 varieties. Other days, just six. The bigger display attracted more attention. Sixty percent of people stopped to look. But only three percent actually bought jam. When shoppers saw just six options? Thirty percent purchased. Ten times the conversion rate. More options didn't help people choose. More options paralyzed them. The jam study has been replicated across dozens of categories since then. The pattern holds. More choices, more overthinking, fewer decisions. Think about your postponed decision. How many options are you juggling? How many articles have you read? Every expert you consult, every scenario you play out in your head... you're not getting closer to certainty. You're adding jams to the display. And while you're researching, the world keeps moving. Opportunities close. Competitors act. Your own situation shifts. The decision you're avoiding today won't even be the same decision six months from now. Waiting has a cost. Most people dramatically underestimate it. The Two-Door Framework So how do you know when you have enough information? Jeff Bezos uses a mental model that's useful here. Picture every decision as a door you're about to walk through. Some doors are one-way: once you're through, you can't come back. Selling your company. Getting married. Signing a ten-year lease. These deserve serious deliberation. Most decisions, though, are two-way doors. You walk through, look around, and if you don't like what you see, you walk back out. Starting a side project. Trying a new marketing strategy. Having that difficult conversation. The consequences are real, but they're not permanent. The mistake most people make is treating two-way doors like one-way doors. They apply the same level of analysis to choosing project management software as acquiring a company. They're not being thorough. They're overthinking reversible choices. That's how organizations grind to a halt. That's how careers stall. That's how opportunities evaporate while you're still "thinking about it." Before you gather more information, ask yourself: Can I reverse this? If yes, even if reversing would be annoying, you're probably overthinking it. The 40-70 Rule General Colin Powell used a decision framework he called the 40-70 rule. Military leaders and executives have adopted it for decades. The Floor: 40% Never decide with less than forty percent of the information you'd want. Below that threshold, you're not being decisive. You're gambling. The Ceiling: 70% Don't wait for more than seventy percent. By the time you've gathered that much data, the window has usually closed. Someone else acted. The situation changed. The decision got made for you, by default. The Sweet Spot That range between forty and seventy percent is where good decisions actually happen. It feels uncomfortable because you're not certain. That discomfort isn't a warning sign, though. It's the signal that you're doing it right. Most overthinking happens above seventy percent. You already have what you need. You're just not ready to commit. If deciding feels completely comfortable, you've probably waited too long. The Productive Discomfort Test "I genuinely need more information" and "I'm using research as a hiding place" feel identical from the inside. Both feel responsible. Both feel like due diligence. I once watched a friend spend eleven months researching a career change. She read books. Took assessments. Talked to people in the field. Built spreadsheets comparing options. She knew more about the industry than people working in it. And at month eleven, she was no closer to a decision than at month one. The research had become the activity. The feeling of progress without the risk of commitment. She wasn't preparing. She was hiding. And she couldn't tell the difference. So how do you tell ...