Last week some folks from my wife’s company threw a going-away party for a coworker who is leaving for a higher-paying job.
He spent a good chunk of the evening talking about the money. The new role, the pay bump, all of it. He was proud, and honestly, he’d earned the right to be. He’d worked for it.
Then someone else, quietly, said one sentence that I think a lot of people missed.
“That’s great. As long as you’re willing and comfortable doing everything that comes with that pay bump.”
Nobody argued. Nobody piled on. The conversation moved on. But I sat with it for the rest of the night.
The person didn’t question his decision. They questioned his question.
He’d been answering “can I get more money?” That’s a real question with a real answer, and he found it. He did the work, made the case, got the offer. By every measure of the question he asked, he won.
But underneath it exists a question he may not have asked yet: am I willing to do everything that comes with the thing I just said yes to? The travel. The meetings. The version of himself he’ll have to be on a Thursday in month nine. A pay bump comes with a life attached, and he was only pricing the paycheck.
That’s my projection, to be fair. I don’t know what his internal dialogue sounded like or what conversations he and his wife had before he accepted. I base it on one thing: his demeanor changed when the travel came up.
I hope this turns out to be a great move for him and his family. I have no reason to think it won’t.
But I couldn’t shake the pattern, because I’ve lived it. You can get very good at answering a question and never once check whether it’s the right one. The effort feels like progress. The answers keep coming. And the whole time, you’re getting better at the wrong thing.
Every stuck season I’ve ever had turned out to have a question underneath it, and usually it was a question somebody else wrote. A parent. A boss. An old version of me. The fix was never to think harder. It was to check whether the question was even mine before pouring another year into answering it.
The problem is that most of us don’t catch that in real time. We catch it in the post-mortem. The meeting that circled and went nowhere. The decision reversed within a week. The strategy everyone quietly stopped believing in. The friction was there the whole time. It just looked like effort.
So the skill isn’t asking better questions in general. It’s noticing the wrong-shaped question in the moment, while there’s still time to swap it out.
Three tells that a question needs upgrading
The answers aren’t changing your plan. Three answers deep and your next move looks identical to before you asked. You weren’t gathering information. You were gathering comfort.
You’re repeating yourself to be understood. That’s usually not the other person’s fault. It’s the question being the wrong shape. A better question reframes the tension so the answer gets easier, not louder.
You’re asking “should I” instead of “what would have to be true.” Should I take this job? produces opinions. What would have to be true for this to be worth it? produces conditions you can actually check.
If you spot one of those, you’re not stuck on an answer. You’re stuck on a question with nowhere to land. Your mind will happily keep circling it, because circling feels like work and comes with a little hit of endorphins. That isn’t thinking. That’s a loop.
Here’s what I run instead.
The Question Upgrade
1. Name the decision the question actually feeds. “What should I do about my career?” isn’t a question. It’s a fog. Find the decision underneath it: am I willing to trade this many hours of my one life for this much money and this much identity? Now you have something to work with. If there’s no decision underneath, you’re not planning. You’re worrying with extra steps.
2. Run the Either Way test. If yes and no would produce the same Monday, the answer doesn’t matter and you’re stalling. If they’d produce different Mondays, you just found the real question. This kills more fake questions than anything else I know. It’s brutal and it’s fast.
3. Ask what would have to be true. “What should I do?” pulls opinions from people who aren’t living your life. “What would have to be true for staying another year to be worth it?” produces conditions. Conditions can be checked. Conditions can be falsified. Conditions put you back in the driver’s seat instead of waiting for the room to agree.
4. Name what would change your mind. This step is easy to skip, and it’s the one that matters most in my opinion and experience. If you can’t name a single piece of evidence that would flip you, you’re not deciding. You’re waiting to be right. That’s the difference between a question and a defense of a conclusion you already reached.
Run that four times on real decisions and something shifts. You start hearing the wrong-shaped question as it comes out of your own mouth. You stop needing the post-mortem, because you caught it live.
Someone at that party had that reflex. One sentence, no lecture, no advice. They held up the bigger question and let him decide what to do with it. That’s what it looks like in the wild. Not a smarter answer. A better question, offered at the right moment.
So the next time you catch yourself circling, don’t push harder on the answer. Stop and ask the smaller, sharper thing:
Is this even the right question?
Because the past doesn’t get a vote, and neither does someone else’s scoreboard. The game you’re winning might not be yours. Noticing that is the first decision that actually is.
Until next week,
