Work & purpose

№ 01

“What's the thing you most enjoyed building, making, or growing in your life?”

№ 02

“What did you imagine yourself doing for work, when you were ten?”

№ 03

“Tell me about a job you loved, and a job you hated, in equal detail.”

№ 04

“What's the best boss you ever had like — at their best, on a good day?”

№ 05

“What's the worst boss you ever had like — at their worst?”

№ 06

“Tell me about a piece of work you're quietly proud of, even if no one made a fuss at the time.”

№ 07

“Was there a project that took everything you had — and then some?”

№ 08

“What kind of worker were you in your prime?”

№ 09

“Tell me about a moment your work made a real difference to a real person.”

№ 10

“Was there a piece of work you wish you'd been brave enough to do — and didn't?”

№ 11

“Tell me about the day you started your most important job.”

№ 12

“Tell me about the day you left a job that had defined you for years.”

№ 13

“Was there a teacher of your craft — formal or otherwise — who taught you how to be good at what you did?”

№ 14

“What did you find boring, repetitive, or unglamorous about your work — and how did you keep doing it well?”

№ 15

“Tell me about the longest you ever stayed in a single role — and why.”

№ 16

“Was there a year your work and your life felt like one continuous fight?”

№ 17

“What did money from work mean to you across your career — survival, freedom, identity, comparison?”

№ 18

“Tell me about a craft, hobby, or unpaid practice that became as important as your job.”

№ 19

“Was there a time you helped someone get into their own working life — a child, a niece, a junior colleague?”

№ 20

“What did retirement, semi-retirement, or stopping look like — when, why, and how did you handle the first year?”

№ 21

“Tell me about a time you were unemployed, between jobs, or seriously broke.”

№ 22

“Was there a piece of work — an idea, a process, a product, a way of doing things — that outlived you in the place you did it?”

№ 23

“What's a question someone newer to your line of work has asked you, that made you think harder than you expected to?”

№ 24

“If you could go back and choose a different career path with no penalties, would you?”