Asking questions about working life opens a chapter that usually gets left out of family conversations. We know what the person did, but rarely why they chose it, what they are proud of and what they gave up. That is exactly where the most human part of a career lies.
The first job
If the person wants to remember their early work, ask:
- What was your first job, and how did you get it?
- What did you do with the first money you earned?
- Did someone teach you something back then that you carried through life?
Choices, turning points and fresh starts
- Was there a moment when your working life changed direction? What happened?
- Did you ever have to start over from scratch? What was that like?
- Which hard decision did you make that you are grateful for today?
Pride and regrets
The questions that reveal the person behind the professional:
- What are you proudest of in your work?
- Is there anything you would do differently?
- What advice would you give someone starting out in your field?
Answers like these are the backbone of a life story and connect with our questions to ask yourself.
From account to life story
If the person agrees to be recorded, agree on the purpose, who will be able to listen and how they will review the account. Recordings can be the basis for chapters, but they need editorial selection and organization; they do not become a book on their own. Confirm names, dates and any shifts in meaning with the storyteller before sharing.
Work also has a place, a language and a community
Ask where the person worked, which language they used and what changed when they switched teams, provinces or countries. In a Canadian career path, paid work may sit alongside family caregiving, studies, volunteering and periods without a job. Avoid treating retirement as a mandatory crisis or as the end of life. Ask which activities still matter today and which stories the person wants to leave for those who come after.
Further reading: StoryCorps — great questions.