Learn to be okay with being wrong and reversing your decisions.
Before I joined a three-person startup, I thought I was a good decision-maker. I had strong opinions and always advocated for them. But when I joined The Sentience Company and immediately started owning every non-technical function, I had to make decisions fast—dozens or even hundreds a day.
At first, I deliberated extensively to find perfect solutions to small problems, wasting time and causing myself unnecessary stress. I didn’t feel comfortable committing unless I was sure I was making the right call. Then decisions started piling up, and I didn’t have the luxury of triple-checking anymore. As the weeks went on, I became comfortable pulling the trigger even when I wasn’t 100% sure.
The reason most people’s decision-making muscle is weak is that they’re not in an environment conducive to strengthening it. Many people spend years in a job and never make a single consequential decision. Worse, many larger, more corporate environments actively discourage speed and reward agonizing and double-checking. Investment banking analysts spend hours perfecting slide decks and spreadsheets, consultants spend weeks on analyses, product managers spend months on planning and roadmaps—all to hand the decision to a superior who often tells them to redo their work.
Think of it like learning to hit a golf ball: if you spend ten minutes making sure your form is perfect before every swing, you’ll never get enough reps in to improve. Form is important, but every minute you spend reconsidering a decision is a minute you’re not getting feedback, which is where the actual learning occurs.
Part of the reason making decisions was so difficult for me is that the solution space was often unbounded—in other words, I could have solved most problems in 100 different ways. This pattern shows up in other places in my life: every time I shop for groceries, I feel the need to traverse every aisle to see whether I’m missing out on anything I might want. As a result, my shopping trips take twice the time they should, and I buy twice the groceries I need. More potential choices often create more deliberation, more regret, and more paralysis—exhausting the search space rarely justifies the time and energy it takes.
Something Sam Kececi has drilled into me is that most decisions are two-way doors. You can always unship bad code, swap out a vendor, or delete a post you made. Our brains make it seem as if these decisions are permanent because it feels safer to check one more time than to be wrong. But when the cost of being wrong is low, the simpler decision chosen quickly almost always beats the “better” decision made slowly.
Not every decision is worth making quickly. When we were deciding which features to put front and center on the Sentience homepage, we took our time: the homepage was the core of our product, and our direction was going to influence countless decisions down the road. But decisions like this are rare, and making the less consequential ones fast and often clears mental space and time for the weightier ones.
Whether it’s a side project, a hackathon, a community you’re leading, or a job at a three-person startup, put yourself somewhere that requires you to make lots of decisions quickly. Train your decision-making muscle the same way you’d train any muscle—with volume. Err on the side of the simpler, quicker option and get comfortable reversing your decisions.
Many people who seem like natural-born decision-makers aren’t. They just got their reps in before you did.