← All public decisions

three years in, why do i keep picturing what it would be like to leave

Stop asking whether leaving is right and start deciding what you actually want from your next three years.

You're using 'should I leave?' to avoid making choices, so neither staying nor leaving feels like yours. The guilt of wanting out is louder than any actual desire, and certainty is just another excuse not to decide. Name what you want concretely, then see if this place makes it more or less likely.

  1. What specifically are you carrying that makes staying feel unbearable?

    That I chose this and now I'm stuck with the choice.

  2. If leaving weren't so complicated, would you have done it already? What's the real barrier?

    I don't know if I'd be right or wrong about this. That's what keeps me here.

  3. What are you actually scared of in that freedom?

    Being alone with my own choices.

Anonymous10 RoundsWork

The whole Grilling

three years in, why do i keep picturing what it would be like to leave

  1. Round 1

    Three years in and still picturing leaving. You didn't ask how to leave — you asked why you keep seeing it. That's the part worth pressing.

    When you picture leaving, what specifically are you picturing? The act of walking out, the life after, or just the relief of not being here anymore?

    • The relief of not being here anymoretheir answer
    • A specific different life waiting on the other side
    • The moment I finally do it and they react
    • Honestly, all three depending on the day

  2. Round 2

    Relief, not a destination. That tells me something — but let's make sure we're not dressing up avoidance as clarity.

    If I took away the relief — if leaving meant no escape from whatever you're escaping, just being somewhere else with the same weight — would you still want to leave?

    • No, then it's pointlesstheir answer
    • Yes, but it'd feel different
    • I don't know, never thought about it that way

  3. Round 3

    So it's not about leaving. It's about the relief. Which means the question isn't really about going anywhere — it's about what you're carrying right now that makes staying feel like drowning.

    What specifically are you carrying that makes staying feel unbearable? Name the thing, not the feeling.

    • The work itself
    • How I'm treated here
    • That I can't see an end to it
    • That I chose this and now I'm stuck with the choicetheir answer

  4. Round 4

    Three years ago you made a choice. Now that choice feels like a cage. But here's the thing — if it were truly unbearable, you'd have left by now. You haven't. So what's actually keeping you?

    If leaving weren't so complicated, would you have done it already? What's the real barrier between you and walking out?

    • Money / practical stuff
    • Fear of being wrong about this
    • I'd rather not face what comes next
    • Honestly, part of me doesn't want to leave

    In their own words
    I don't know if I'd be right or wrong about this. That's the thing that keeps me here.

  5. Round 5

    So it's not that you're stuck. It's that you don't trust your own judgment on this. You made a choice three years ago and now you can't tell if it was right or wrong — so you're just... waiting? For what, exactly?

    What would make you feel confident enough to decide? What information or clarity are you missing that would tell you this was the right choice or the wrong one?

    • Knowing if I'll be happier later
    • A sign from somewhere that this is meant to be
    • Comparing myself to someone else who left
    • I don't know — maybe I just need to stop thinking about ittheir answer

  6. Round 6

    You can't stop thinking about it. That's why you're here asking. So let's try something different — what if you stopped trying to figure out whether the choice was right or wrong, and just asked yourself what you'd do if you knew for sure either way?

    If you woke up tomorrow knowing with absolute certainty that staying was the right choice, how would you feel? And if you knew leaving was right?

    • Staying: relieved. Leaving: terrified.
    • Staying: trapped. Leaving: free but scared.their answer
    • Both would feel equally wrong somehow

  7. Round 7

    There it is. You know what would feel right — freedom. But you're scared of it. Which means your question was never really "why do I keep picturing leaving?" It's "why am I so afraid of the freedom I want?"

    What are you actually scared of in that freedom? Not the practical stuff — the deeper fear underneath.

    • Being alone with my own choicestheir answer
    • That I'll make another wrong decision
    • That I won't recognize myself without this anchor
    • That I'm not brave enough to actually do it

  8. Round 8

    You're not afraid of leaving. You're afraid of being responsible for whatever comes next. That's a much bigger fear than any job or relationship — it's the fear that without this structure, you'll have to actually decide who you are and what you want. And that terrifies you because right now, at least, you can blame everything on this choice you made three years ago.

    If you left and it went badly — if the freedom turned out to be exactly as scary as you think — would you rather have tried and failed, or stayed and never known?

    • Tried and failed, at least I'd know
    • Stayed and never known, safer that way
    • I don't know, both sound awfultheir answer

  9. Round 9

    Both sound awful because they both require you to actually live with a decision. But here's what you're missing — you're already living with a decision. You chose to stay three years ago, and you've been choosing it every day since. The only difference between staying and leaving is that one choice is visible and the other is invisible.

    What would it look like if you stopped asking whether this was the right choice and just started making choices about what you want your next three years to be?

    • I'd have to actually decide things, which is terrifyingtheir answer
    • That sounds like what I should do but I can't
    • Maybe that's the point — stop waiting for certainty

  10. Round 10

    Terrifying, yes. But you're already doing it — every day you stay, you're deciding. You just don't like that you have no control over the outcome. The truth is, there's no version of this where you get certainty before choosing. You choose, then you deal with whatever happens. That's not a flaw in your thinking — that's just how being alive works.

    So what's actually keeping you from making the choice you want to make? Is it the fear of being wrong, or is it something else you haven't admitted yet?

    • I'm afraid I'll regret it no matter what
    • I don't trust myself to handle the consequences
    • Part of me thinks I should be grateful for thistheir answer
    • I genuinely don't know what I want anymore

Shared Understanding

Stop asking whether leaving is right and start deciding what you actually want from your next three years, because the answer to that question will tell you more than any amount of certainty about being right or wrong ever could. You've been using "should I leave?" as a way to avoid making choices, and now you're stuck in limbo where neither staying nor leaving feels like it belongs to you.

The Question

Three years into something, why do you keep picturing what it would be like to leave?

What you actually want

You want permission to stop feeling guilty about wanting out, and clarity on whether that desire means you've made a mistake or just need to change course.

What you decided

  • The relief of leaving is what draws you in, not any specific better life waiting on the other side (defaulted)
  • You're carrying the weight of having chosen this path and feeling trapped by that choice
  • Leaving without escape would be pointless — you're running from something specific here
  • You don't trust yourself to handle the consequences of choosing wrong
  • Part of you thinks you should be grateful for what you have, which is complicating your ability to decide

What you're assuming

  • That there's a "right" choice that would bring certainty and relief
  • That if you could just know you'd be happier later, you'd feel confident enough to act
  • That gratitude and wanting to leave are incompatible feelings
  • That being alone with your own choices is inherently terrifying rather than just unfamiliar

What you're avoiding

  • Naming what specifically makes staying unbearable beyond the abstract "I chose this"
  • Admitting that part of you might not want to leave, or that leaving might be less about escape and more about wanting something different
  • Facing what it would mean to actually make decisions about your next three years instead of waiting for certainty

Next step

Write down three things you want from the next three years — concrete, specific, not "be happier" or "feel free" — and then ask yourself whether staying here makes those more or less likely. Don't try to answer whether leaving is right yet; just see what your actual desires look like when you stop filtering them through guilt.

All Work decisions