Decide.

What decision am I avoiding?

The one decision you keep not making, what the delay costs, and a smaller version to make now.

2 versions

Am I still deciding, or am I just looking for permission?

An honest read on whether your mind is still open, and what would actually change it.

2 versions

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.

Stop giving me pros and cons. Which one would you pick?

One pick from your shortlist, the reasons behind it, and the fact that would flip the answer.

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.

How will I know when it’s time to stop?

Three clear conditions and a date, written now, that tell you later when to walk away.

I’ve put so much into this. Is that a reason to keep going?

A fresh look at whether to keep going, with what you’ve already spent set to one side.

Was that a bad decision, or did it just turn out badly?

A fair review of a choice that went wrong, separating what you could have known from plain luck.