# Questions people are afraid to ask themselves

> Sixty questions about career, money, focus, courage, work, creativity, leadership and discipline. Pick one and put it to a table of the greatest.

Sixty questions we would rather not answer alone. Pick one — the table is already set for it.

Every question opens a table of three advisors chosen for it. You can change the table before you ask.

## Career

Questions about the path you chose before you knew yourself.

- I'm building the career I chose at twenty. Is it still mine?
- I've been offered a promotion that leaves me cold. Should I take it?
- Ten years in my field and I'm still waiting to be found out.
- Start my own thing, or stay where the money is steady?
- I'm valued for the work I find dull. What do I do with that?
- I'm the youngest in the room and nobody listens. How do I change that?
- I'm forty and thinking of starting over. Is that courage or escape?
- Who do I want to be to people who don't know me?

## Money

The arithmetic people do alone and never say out loud.

- I earn more than ever and somehow there's never money.
- How much money would actually be enough to stop the fear?
- Should I borrow for a venture only I believe in?
- I'm afraid to ask for more and take the first number offered. Why?
- Save for ten years, or put it all on one risky shot?
- My business is growing and the bank balance is shrinking. Where did I go wrong?
- Should I sell the thing I spent seven years building?
- I live as if I had more money than I do. Who am I performing for?

## Focus

About what you'll have to give up for anything to happen.

- Twenty things started, not one finished.
- I'm busy every day and going nowhere. What am I doing wrong?
- How do I choose what to drop when everything feels worth keeping?
- I can't finish anything until it's perfect. So I don't finish.
- My attention falls apart in a minute. Is that fixable?
- If I could keep only one thing in my work, what should it be?
- I promise more than I can deliver. How do I stop?
- If I could keep only three meetings a week, which three?

## Courage

Questions you already know the answer to and haven't acted on.

- I know what to do and haven't done it for a year. What am I waiting for?
- What would I do if I stopped fearing how foolish I'd look?
- I'm scared to show my work. Ship it raw or wait?
- I failed in public and everyone saw. How do I come back?
- Tell my boss the truth and risk the job, or stay quiet?
- I'm waiting for permission nobody will give. Whose permission is it?
- What will I have to lose to get the thing I keep talking about?

## Work and you

Where the job ends and you begin.

- I'm burned out and can't stop. Rest feels like defeat.
- Work has become my whole life. When did that happen?
- I've hated Mondays for twelve years straight. Is that normal?
- My co-founder and I are pulling in different directions. Do we split?
- I got promoted and stopped doing what I loved. Should I go back?
- I work with people I don't respect. How long can that last?
- How do I tell tiredness from the work genuinely not being mine?

## Creativity

About work you'd want your name on.

- My work is done well and nobody remembers it.
- I'm afraid I've run out of ideas. What now?
- How do I know an idea is good when only I like it?
- I imitate the people I admire. When does that stop being a copy?
- I have no time for creative work. Is that true or an excuse?
- They tell me it's too strange. Do I listen or keep going?
- How do I make work I won't be ashamed of in twenty years?

## Leadership

What only your seat lets you see.

- My team agrees with me on everything. Why does that scare me?
- I can't fire anyone, so I keep the people dragging us down.
- How do I lead people through a year with no wins in it?
- Do they fear me or respect me? And how would I tell?
- I do everything myself because nobody does it better. Is that a dead end?
- How do I decide when every option hurts someone?
- My people are being poached. Do I hold them with money or something else?

## Discipline

About what gets decided on Thursday, not Monday.

- I start every Monday and quit by Thursday.
- How do I keep going when there's been no result for six months?
- Do I need motivation, or do I need a routine?
- I compare myself to the people ahead and give up.
- How many repetitions until this stops taking willpower?
- I postpone what matters and do what's urgent. How do I break out?
- What am I doing daily that will show a year from now?
- I don't know how to rest. Is that pride or fear?

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