What Would You Do In My Position
Personal · 2026-10-23
The Problem With Asking "What Would You Do In My Position"
Someone asks you for advice, and the honest answer is you don't know, but you say something anyway. That's the whole racket, really. Advice-giving as performance, not information.
I've noticed this a lot lately, mostly because I keep catching myself doing it. Someone lays out a genuinely tangled situation, work thing, relationship thing, doesn't matter, and instead of sitting with the tangle for a second, I just... reach for a script. "Have you tried talking to them directly?" As if that hasn't occurred to a grown adult. As if directness is some secret technique I've unlocked and they haven't.
Anyway. The bit that actually interests me isn't that we give bad advice. Everyone knows advice is mostly useless, that's not news. What interests me is why we keep asking for it when we already know it won't help.
The Asking Isn't About The Answer
What nobody quite says out loud: when you ask someone what they'd do in your position, you're rarely after their actual plan. You're after permission. Or witness. Or just someone to say "yeah, that sounds hard," so you can stop turning the thing over in your own head for five minutes.
Which is fine! That's a real need. But it gets confused, constantly, with information-seeking, and the two want completely different responses.
If someone wants information, they want your honest read, even if it's blunt.
If someone wants witness, they want you to slow down and actually hear the situation before you say anything useful at all.
Most of us skip straight to solving. It's faster, it feels more helpful, and honestly it flatters the advice-giver a bit too. There's a small ego hit in being the one who "figured it out" for someone else. I don't think that's shameful exactly, it's just worth noticing, because it changes how you listen. You stop listening for the actual problem and start listening for the point where you get to jump in.
Why "In My Position" Is Doing More Work Than You Think
The phrase itself is a trap, a bit. "What would you do in my position" assumes the position is transferable, that if I imagined myself with your job, your history, your particular fear of confrontation, I'd land somewhere useful. But I wouldn't be in your position. I'd be me, wearing your situation like a coat that doesn't fit, and whatever I'd "do" is really just what I'd do with my own risk tolerance, my own blind spots, grafted onto your circumstances.
So the advice comes back distorted. Not wrong exactly, just... shaped by the wrong person's instincts.
Imagine a founder wrestling with whether to fire someone who's likeable but underperforming. Ask five people what they'd do "in that position" and you'll get five completely different answers, and every single one will be a projection of how that particular person handles conflict, not an actual read on the situation. One person avoids confrontation their whole life, so they'll say "give it more time." Another person values decisiveness above almost everything, so they'll say "cut it now, you already know." Neither answer came from the facts. Both came from the person answering.
That's not a knock on advice. It's just worth knowing what you're actually getting when you ask for it.
What Actually Helps (When Anything Does)
I think the useful version of advice-giving looks almost nothing like advice. It looks more like questions. Slower, more annoying, less satisfying in the moment, but it actually respects that the person asking probably already has more information than you do.
Things like: what are you actually afraid will happen if you do the obvious thing. Not "what should you do", but what's underneath the hesitation. Half the time the answer to that question makes the original question disappear entirely.
There's also just... sitting there. Not saying much. Letting someone finish a thought without redirecting it. This is much harder than it sounds, especially if you like being useful, because silence doesn't feel like help. It feels like nothing. But it's often the only bit that actually is help, because it gives someone room to hear themselves think, which, in my experience, is the actual scarce resource here. Not answers. Room.
Anyway, none of this means stop giving advice, obviously, that's not the point, and also I will absolutely keep doing it badly myself, probably starting later today. It's more that "what would you do in my position" is a slightly broken question dressed up as a reasonable one, and most of us answer it on autopilot without noticing what we're actually being asked for.
Which, funnily enough, is a decent thing to notice next time someone asks you.