Big decision.

What’s the real question underneath the one I keep asking?

The harder question hiding behind the one you keep asking, and what gave it away.

2 versions

Which fear has been making my decisions for me?

One fear, the choices it has quietly shaped, and a low-risk way to test whether it’s right.

2 versions

Show me how I actually decide, not how I think I do.

Your decision habits drawn from three real choices, your typical mistake, and one rule.

Which two things do I want that I can’t have at once?

The tug-of-war behind your stuck decisions, named, with three honest ways to settle it.

2 versions

What’s the strongest argument against what I’m about to do?

The best honest argument against your plan, before reality makes it for you.

It’s a year from now and my plan failed. What went wrong?

The most believable story of how your plan fails, its first warning sign, and one fix to make now.

Which of my assumptions is really just a hope?

Every assumption under your plan sorted into fact, guess or hope, with a test for the shakiest.

Say I get exactly what I want. Then what?

The knock-on effects of a choice traced three steps out, with the one you’d miss marked.

Can I undo this if I turn out to be wrong?

Your decision split into parts you can undo and parts you can’t, so you know where to slow down.

I keep going back and forth. What does this choice come down to?

The one trade-off underneath a two-way choice, in a sentence you can say out loud.

Both options feel wrong. What’s the third one?

Your either-or decision restated as a wider question, plus four options you hadn’t put on the table.

I can’t have everything on my list. What do I give up first?

Your real priorities for a choice, weighted by the trade-offs you made, not by what you said.

I’ve never done this before. What don’t I know to ask?

Five questions a first-timer misses, each with who can answer it and what answer should worry you.

I don’t want advice. I want better questions.

Five questions that keep the decision yours, then a playback of what your answers said.

What would I tell a friend who was in my exact position?

Your own situation handed back as a friend’s, so you can hear the advice you’d give them.

On paper it’s a yes. So why does my gut say no?

A name for what your gut is reacting to, and whether it’s information or just nerves.

If I take this on, what gets less of me?

The real price of a yes: what it costs in plain units, and what it quietly pushes out.

How do plans like mine usually turn out?

The outside view on your plan: what typically happens, how long it takes, and who beats the odds.

Needs web search

Ten years from now, which choice will I wish I had made?

A look back from the future at each option: what you’d regret, and which regrets you could repair.

Could I try this for a weekend before I bet a year on it?

Three small tests of a big move, each cheap, short and clear about what it would tell you.

The deadline is Friday. What’s worth finding out, and what can I skip?

A plan for the time you have: what to find out, what to ignore, and a rule for the deadline.

We want different things. How do we decide this together?

A fair agenda for one conversation: both positions, where you really differ, and how you’ll decide.

I got the job offer. What do I ask for before I say yes?

What’s open to discussion in a job offer, the two things worth asking for, and a reply you can send.

What needs to be in place before I quit to go freelance?

Five checkable conditions for going freelance, which ones you already meet, and a date to decide.

What am I really buying when I buy this?

The real reason behind a big purchase, cheaper ways to get it, and a fair test before you pay.

How many times would I have to use this to make it worth it?

The honest cost per use of something you want, at the rate you’d really use it.

Someone close to me asked to borrow money. Do I say yes?

Three honest options beyond yes or no, what each could cost you, and kind words for each one.

Is renting really throwing my money away?

The conditions under which renting or buying wins for you, plus the numbers and questions to take to an adviser.

Should I tell my friend what I really think?

A straight answer on whether to speak up, and the kindest honest wording if you should.

I’ve had two tabs open for a week. Which one do I buy?

A side-by-side on the few differences that matter for your use, and a pick with reasons.

Before I sign this, what should I be asking a lawyer?

A plain-language map of your contract and the questions to bring to a lawyer or adviser.

What do people who move abroad wish they had asked first?

A checklist of questions for a move abroad, each matched to who can answer it.

Stop agreeing with me. Tell me where I’m wrong.

Honest pushback on your ideas for the rest of the chat, without the fake toughness.

Now read your answer like someone who wants to prove it wrong.

The weakest claim in the last answer, the best objection to it, and a clear keep or change.

Where did you get that? Show me sources I can open.

Each key claim in the last answer matched to a source you can open, or marked as unsourced.

Needs web search

Another assistant told me this. What would you have said?

An independent read of another assistant’s answer: where it holds, where it slips, what to check.