How Indecision Destroys Startups: Stop Saying Maybe

Jan de Vries · 2026-03-20

It feels good to keep your options open, doesn't it? That's why we often hesitate to fully commit. We hire someone who's just okay, thinking maybe it'll work out. We take on an investor, hoping maybe they'll be the one to launch us. We pour money into a consulting agency, believing maybe they'll help us find our magic. Maybe, maybe, maybe. For a while, that indecision seems to buy us time. It gives us breathing room when things feel shaky. But that mediocre hire? They'll drain your limited resources—time and money spent on training and salary. You might even get comfortable and stop looking for someone better. That investor whose vision doesn't align with yours? You'll waste energy constantly steering your company back on course. That consulting agency? They might make you feel organized temporarily, until you compare results to the checks you're writing and realize you've wasted precious capital. ### The Hidden Cost of "Maybe" This isn't just about hiring or spending. It's a mindset. That "safe harbor" of indecision is an illusion. When it shatters, the consequences are real and painful. Every "maybe" becomes a temporary "yes" that can grow into a monster capable of wiping your startup off the map. I'm not being dramatic. History shows us the price. ### When "Maybe Later" Becomes "Never" Take Friendster. Users begged for months for a faster, more reliable site, warning they'd join this new thing called MySpace. The board focused on shiny new features instead of fixing core problems. Does anyone remember Friendster today? Exactly. Then there's Imercive. The founder got "caught mid-pivot" after burning through most of a $500,000 seed round. The new strategy needed capital and traction they no longer had. His biggest regret? Not pivoting sooner. Tract admitted they "took too long to reach the pivot point." Better competitor analysis would've revealed market issues before writing thousands of lines of useless code. These stories aren't rare. ### Why We Choose Maybe Founders aren't foolish. There's always a "why" behind the maybe. We don't have a crystal ball telling us which choice brings fortune. We set sail while still tied to the dock, hoping for safety. But being tethered doesn't prevent the ship from sinking. This indecision comes from our human need for security. But let's be real—you left safety behind when you quit that stable job. You chose the startup life. Now you have to own that choice. ### How to Escape the Maybe Trap So how do you break free? Count to ten? Play eeny, meeny, miny, moe? Roll dice? It's simpler. Borrowing from Mark Manson: it's either a "hell yes" or a "hell no." Make the decision. Time will tell if it's right. If it's wrong, make another decision to correct course. Here's a little secret: we don't have a decision quota. Stop treating choices like rare gems. Commit. I'm not saying rush in blindly. Do your homework. Set a time limit for research. Then, whatever conclusion you reach, commit to it fully. "But what if I'm wrong?" you ask. You probably will be sometimes. That's the point. That's how you build experience. Nobody is born knowing everything. Every situation is unique. - **Set decision deadlines:** Give yourself 48 hours for major choices. - **Define clear criteria:** Know what "hell yes" looks like before you start. - **Embrace reversible decisions:** Most choices aren't permanent. You can adjust. Indecision isn't neutral. It's a slow leak draining your startup's vitality. The safe middle ground is where dreams go to fade. Your company deserves decisive leadership—starting with you. So next time you feel that "maybe" forming, pause. Ask yourself: is this a hell yes? If not, it's a no. Your future self will thank you for the clarity.