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Ask & Find  ·  14 questions

Work and money

What you are building, and what it is for

Work takes up most of your waking hours, and most people never sit down and ask it a straight question.

These do. Not about the CV. About what you would do with a free Monday, what enough looks like, and who you want beside you for the next ten years.

01

What part of your work would you do for free? What part would you not do for double the pay?

Those two answers draw a map of where to go next.
02

What were you doing the last time you lost track of time at work?

Flow is a pointer. It tells you what you are built for.
03

What would you do for work if status did not exist?

A lot of career choices are made for an audience that is not really watching.
04

What problem do you keep noticing that nobody seems to be fixing?

The thing that annoys you is often the thing you are meant to work on.
05

What does enough money look like? As a number, and as a life.

Without a number, more is the only goal, and more never arrives.
06

What did you learn in the last year that you could not have looked up?

The knowledge that only comes from doing is the knowledge nobody can take.
07

Who would you like to work with for the next ten years? Why them?

Long games with good people beat short games with anyone.
08

What are you spending money on that is not making your life better?

The honest answer is usually a short list, and cutting it feels like a raise.
09

What one skill would change your options most if you got good at it?

One skill, pursued seriously for a year, moves more than ten pursued for a month.
10

What would you build if you knew it would take ten years and be worth it?

Most people only ask what they could build by Friday.
11

When has work felt like play? What was different about it?

The ingredients of play are usually repeatable.
12

What good work are you doing that nobody sees?

Some of the best work is invisible. Naming it helps you keep doing it.
13

If your work disappeared tomorrow, what would you miss, and what would you be relieved about?

The relief list is as useful as the missing list.
14

What would you tell someone starting your career today?

Advice for a beginner is usually advice for yourself.