Billy's Thoughts

Mechanics of Indecision

Posted on May 31, 2025 — 8 mins read

Inspired by these two Dr. K videos

Preamble: The impetus for this post was that early this year I was in the thick of indecision myself, deciding between if I should stay on sabbatical or apply to grad school (two very different routes!). This post is intended to be a sort of “technical reference manual” of the thoughts and learnings that eventually helped me resolve my own indecision. And then hopefully it’ll make writing my own personal account easier, which I plan to do next.


“What do I do? I need to make a choice, but I can’t decide. I don’t want to make the wrong decision…”

Being stuck here sucks. It’s like getting pulled in multiple directions by the choices in front of you, and yet despite all of that pulling you feel no closer to a clear answer. Like you’ve been jerked around yet you still find yourself in the exact same spot.

Why is this so painful? And is there a way to make this less painful? As always, I think the first step is to try to understand what’s actually going on in the mind.

“I don’t want to make the wrong decision…”

What does “making the wrong decision” mean? What is a “wrong decision”?

Is a decision only the “right decision” if it produces the desired outcome? Or is it “right” if you’re sufficiently content with your decision-making process, regardless of the outcome?

Is all of this even the right framing? (spoiler: I don’t think so)

Fear, conditioning, human nature

Often what’s at the heart of not wanting to make a wrong decision is fear. Specifically: fear of the unknown. Fear of feeling bad. Fear of regret. Fear of pain, of having to deal with a resulting sh*tty situation. Fear of feeling shame, for having landed yourself in that sh*tty situation. Fear of missing out on something good. Fear of extinguishing a possible amazing future (when having to choose between two equally compelling options).

“If I make the wrong decision, then things are going to turn out badly…”
(Or worse, it might mean that I am bad.)

It doesn’t help that this fear is reinforced early on in our lives, via school. Learning itself is not what’s rewarded; getting good grades on the test is what’s rewarded. Further, mistakes can stick and become black spots on your record, with long-term effects. “Pain is temporary, GPA is forever,” as they say.

(Even though, if your priority is truly to learn, then making mistakes is often how you learn quickest in real life! e.g. when picking up a new hobby.)

It’s better to graduate ASAP and get the best job you can right out of college in order to kickstart your career. If you graduate college at 23, there’s no way you’ll catch up to someone who graduated at 21. Hitting all the milestones and winning at 28 is better than winning at 40.

Speed to Competence >>> eventual Competence (is what the world tells you).

(I think this is just one of the components of a negative spiral that makes things difficult, particularly for younger people. Fear making mistakes → take less risks → resilience is underdeveloped. And then when you do take a risk and it doesn’t work out, you think, “the fear was right, I should’ve listened.” Add in the fact that the old promise of “just work hard and get a college degree and you’ll be set” is no longer true today, and you wonder why young people aren’t taking risks. “Why bother doing hard things if I’m going to eat sh*t regardless?”)

Hence wanting to “make the right decision”.

The Fantasy of the “Best Decision”

I think people also largely have this fantasy of the “best decision” – that there exists a “perfect” choice, where if you choose it then everything will work out perfectly and you’ll have all you’ve ever wanted. And they lived happily ever after, the end.

Should I move to SF or New York?
Should I continue on this pathless sabbatical path or should I go to grad school?

Between Option A or Option B, I want to pick the path that is going to give me the best life. But I don’t know which one will actually be better. So I’m gonna do a bunch of analysis and forecasting and hypothesizing in order to try to calculate an answer (and spare myself some potential pain).1

I think this is a framing trap.

This framing implies that the choice is what makes the outcome, that I need to choose the “right” option in order to get the best results. If I pick the “good” path, then I’ll be set. And if I pick a path and then something bad happens, it’s very tempting to blame the initial choice I made. “Moving to New York was a mistake. If only I hadn’t moved here, then I wouldn’t be so miserable.”

If you’ve noticed, there’s also something here around an abdication of agency and responsibility, and I think that’s a key element involved too.

Because actually you have the ability to continue to make decisions and adjustments if things go awry or don’t turn out like you’d thought they would.

What do decisive people do?

There are some people out there just being Decisive. They make decisions quickly, execute, and do that over and over again. Are these people just constantly making inefficient decisions, facing sh*tty consequences, or dealing with regret all the time?

Actually, no. It seems like they’re pretty chill, and they seem to be able to make things work every time. They don’t seem to be suffering like we indecisive people are!

How are decisive people able to be so decisive?

I think it’s that they hold some, or all, of the following:

Essentially: instead of trying to make the right decision, just make a decision that you feel decently good about, and “make the decision right”:

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Can you still end up screwed? 100%. Something is going to hit the fan one way or another, no matter which path you pick. This is a fact of life. But we can move forward in spite of this, and deal with whatever else happens.

What can you do?

Idk man. I personally think the decisive way is how I would like to live. And if you want to be like that, you kinda need to find the right framing/beliefs that speak to you, and nurture them and practice them so that you’re able to make bigger and bigger decisions with equanimity.

Some frames that I find compelling:

Alternatively: start small.

Intentionally make a choice that you think is the “the wrong decision”. The next time you go to your favourite restaurant, order something different than your favourite order. (And notice any discomfort you feel, and dig in to where that’s coming from.)

Try developing a “noticing practice” – of when you feel discomfort or fear, when you want to shy away from deciding, when you want to avoid pain, when you shut down ideas because you think they aren’t going to work. Keep a note on your phone tallying when you feel this way. Bonus points if you can use these opportunities to inspect what’s going on3. I’ve found this type of noticing practice can bring up new details and insights (e.g. in frequency, patterns), which can help with further unclenching.

I’ve also heard some people really benefit from “playing the tape through” and simulating bad outcomes in their head. Imagine you made your choice, and X bad thing happened as a result. What’s bad about it? And then how would you respond?3

This is all I’ve got for now. We’ll see if any of this remains useful the next time I have to make a big decision :)


  1. Even better if our analysis can tell us that one choice is clearly better than another! Then we don’t have to make any hard choices or face any excruciating trade-offs. The decision becomes obvious. “Just tell me what to do.” ↩︎

  2. This can be tricky. To believe that you can influence events after making a decision, you sort of have to believe in having agency already. It’s a chicken-and-egg problem. Versus: if you think the decision was the thing that determined the entirety of the outcome, you’ll spend a lot of your energy thinking about the decision, regretting it, wishing you’d chosen differently, fantasizing about the road not taken, etc. Which becomes its own negative feedback loop. ↩︎

  3. One way to inspect uncomfortable thoughts/feelings is the Vertical Arrow Technique. Essentially, you ask yourself: “if this were true, what is causing me to be upset?” about the feeling X and that gives you some output Y. Then you ask yourself the same question about Y to get Z, and you continue until you get something foundational. It’s like the Five Whys but applied to the emotional. ↩︎ ↩︎