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I had good reasons every time:

What I was actually doing was avoiding the one thing that terrified me more than failure:

Being wrong in a way I couldn't take back.

Optionality sounds like prudence. It sounds like the move a sophisticated person makes because they understand that the world is uncertain and rigid commitments are for people who have no other choice. The financial world even gave optionality a respectable name. Options have value and, so long as they’re valuable, keeping them open is rational.

Except when it isn't.

Optionality has a cost that doesn't show up on the balance sheet. Every option you keep open requires a small, ongoing payment of attention, energy, and identity. You're not just holding a position in a portfolio to hedge your main position. You're maintaining something separate which requires feeding it and defending it to yourself when someone asks why you haven't decided yet on something.

The longer you hold the option, the more expensive it gets because now you've invested so much in keeping the option alive that closing it feels like admitting you wasted the time or made a bad bet.

This is how smart people end up paralyzed. Not because they can't decide, but because they've turned indecision into a strategy and given it a sophisticated name.

The real name for this is called the sunk cost fallacy and it’s way harder to cut ties or exit these bad bets in the moment when you are ego attached or personally interested in keeping the options open.

The reason closing feels harder than it should has a name too: loss aversion.

Psychologists have known for decades that the pain of losing something feels about twice as powerful as the pleasure of gaining something equivalent. Your brain isn't weighing the open door against the closed one on equal terms. It's running a rigged calculation where every potential loss gets doubled and every potential gain gets discounted.

It's not some sort of character flaw, it’s your brain being stuck in an irrational state that most never take the time to call out.

But here's where it gets worse:

The longer you hold the option open, the more you've "invested" in it (time, mental energy, identity, money) and the more the sunk cost inflates what closing it would cost you. The door feels heavier every year you don't walk through it.

This is the same mechanism that keeps people pressing buttons at video slots. You’re smart enough to know the machine is rigged against you (at least I’m hoping my readers don’t play video slots), but you don’t realize you’ve been gambling with your life this whole time by not committing to something.

Every door you keep open is a loss disguised as a win. The fear of potentially losing something greater is why you won’t quit now when you’ll strike gold eventually. Just gotta keep looking for the right time, information, person, or place.

Your brain is running ancient survival software that was designed to protect you from immediate physical loss, applied to a problem it was never built to solve. Knowing that doesn't make the door easier to close, but it does mean you can stop blaming yourself for how hard it feels to close it.

I've watched guys do this with career pivots they knew they needed to make two years before they made them. I’ve seen this with the businesses they were "thinking about starting" for so long that the idea went stale or that lightning in a bottle timing was gone. The same with relationships, health, creative work, or anything else that required them to fully close one door to open another.

Modern life preys on this part of you with ruthless effectiveness and it has led the younger generations to be stuck in this perpetual state of waiting for the right moment.

The tells are always the same:

Said with the confidence of someone being prudent, when what they're actually being is scared to commit to doing the things that scare them but will lead to the growth and purpose they claim to want.

Here's the part that stings:

The option you're protecting is almost never as valuable as you think it is.

Most of the time, what you're really protecting is the story you get to tell about why you haven't started yet. The open option gives you permission to stay in the planning stage indefinitely. It lets you feel like you're working on something without having to test whether you're actually capable of it.

You allow your dopamine seeking brain to stay in the good consumer state. Keep scrolling, keep learning, keep watching, but for the love of God do not act and risk failure until you know for certain you know enough to get started.

Commitment is terrifying because commitment produces data. Once you close the other doors and go all in on one thing, you find out quickly whether you were right. You find out if you're good enough, if you actually wanted it, or if you just liked the idea of wanting it. Optionality protects you from all of that information.

And you still wonder why you feel stuck?

The men I've seen break out of this pattern didn't wait until they were sure. They got tired of paying the maintenance cost on options they were never actually going to exercise. They looked at the open doors they'd been protecting and asked an honest question:

Usually the answer was no and they knew for a while subconsciously. The open door was part of their mental clutter where it had became familiar enough that they'd stopped seeing it.

Closing the doors hurt. Not because of what you lose, but because of how long you’ve been pretending to actually step through them and risk being locked in instead of peering inside.

Here's the question I'd leave you with this week:

What option(s) are you keeping open that you already know you're not going to take?

Not the one you're genuinely undecided about that you actually need to deliberate on. I'm talking about the one that's been "still figuring out" for longer than you'd admit out loud. What is still on the table because closing it would mean acknowledging that the time you spent protecting it is gone, and now you have to decide what to do with what's left?

Don’t make your indecision be a permanent prison of your own making.

Make your choice of doors be the terminal to your next destination.

The planes are leaving when they’re scheduled to.

The question is whether you can walk through the gate.

Until next week,

Ian