Would You Have the Courage
To face the discomfort of deciding and acting.
Startups can fail for so many reasons. But the most painful failure is when everything is there and the founder still doesn’t act, because they’ve stopped respecting their own judgment.
I’ve seen this happen over and over. Even with warnings, conversations, and proof, founders hesitate or act weakly, afraid of discomfort, afraid of judgment, whether they admit it or not.
You already know the hire doesn’t work. You already know this advisor or investor is misleading you but confronting them would create friction. You already know this decision is necessary. None of this is ambiguous. The only question is whether you’re willing to deal with the consequences of acting on what matters.
As a founder, you face a real choice. You can fully embrace the journey, the life path, the doubts, the existential tension that comes with it or you can let others take over. People inside or outside the company for whom this business carries no existential weight. You already gave up equity. Sometimes governance. The real question is whether you’re also willing to give up the implicit part of the role, the part where you are truly in charge, and where that responsibility deserves respect.
Sometimes, you tell yourself it’s about timing, or context, or being thoughtful. You rationalize. But what you’re really doing is negotiating with yourself. While you wait, something subtle changes: you stop being the place where decisions come from. You start explaining choices instead of making them. You justify instead of choosing. You’re slowly giving up authority over your own judgment.
And without noticing, you stop respecting yourself.
You stop treating your own intuition as something that deserves action. You start asking for validation where none is needed. You explain decisions before making them. You apologize for choosing. And the more you do that, the more space you create for other people to take control against your inner will.
Employees fill it. Advisors fill it. Investors sometimes fill it. Everyone believes they’re helping. And maybe they are, in their own way. But what they’re really responding to is the fact that the center is no longer firm.
This is the part nobody likes to say out loud: control in a startup is almost never taken from a founder. It’s handed over, piece by piece, in moments of self-doubt disguised as collaboration.
You don’t lose control because you were wrong. You lose it because you didn’t back yourself when you were right but uncomfortable.
And the longer you wait, the worse it gets. Decisions made late are always harsher than decisions made early. Conversations avoided turn into explosions. Clean separations turn into messy exits.
Too little too late.
I’ve seen founders burn out not because the job was too hard, but because they spent months negotiating with themselves instead of leading. Because they knew exactly what needed to happen and kept choosing temporary peace over courage and clarity.
At some point, the job of the founder becomes very simple, and very lonely: you have to decide whether you respect yourself enough to act.
Respecting yourself doesn’t mean being stubborn. It doesn’t mean being right all the time. It means accepting that your role is to choose, not to please.
A startup doesn’t die from one bad move… Or even several. It dies from the small things you chose not to confront, from a series of renunciations left unexamined, from everything you kept telling yourself you’d deal with later.
That’s how not to build a startup.
And that’s how you wake up if it’s not already too late.

This cuts right to the core of founder psychology. The hesitation you describe isn't about capability—it's about the courage to honor your own judgment when the stakes are high. Acting despite discomfort, not waiting for comfort, separates founders who build from those who deliberate. Respecting that judgment enough to move forward is the real work.
Wise words as usual. Every next level in life will require a new you. ✊