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28 questions

Work & Vocation

The jobs they held, the colleagues they remember, and what a lifetime of work taught them.

A lifetime of work holds more than a job title — it holds the first day, the mentor who shaped them, the proudest accomplishment, and the lessons only experience can teach. These questions about work and vocation draw out a side of a parent or grandparent their family may never have fully heard.

They're especially powerful around a retirement, or any time someone is closing a chapter of working life. Ask one at a time and listen for the story behind each answer. With Storykept the whole working life is captured in their own voice, not summarised into a sentence.

  1. Tell me about your very first job. What do you remember about the first day?

  2. Tell me about the first money you ever earned. What did you spend it on?

  3. How did you end up in the line of work you spent most of your life doing?

  4. Tell me about someone who taught you how to do your work. What do you remember about them?

  5. Describe the first boss or supervisor you ever had. What were they like to work for?

  6. Tell me about a skill or craft you became really good at. How did your hands learn it?

  7. Tell me about a project or piece of work you were truly proud of finishing.

  8. Describe the place where you worked. What did you see and hear around you each day?

  9. Tell me about a tool or piece of equipment you used so often it felt like part of you.

  10. Tell me about one of the hardest days you ever had at work and how you got through it.

  11. Tell me about a mistake you made at work and what it taught you.

  12. Tell me about a workmate who became a real friend. How did you meet?

  13. Tell me about a time something funny happened at work that you still laugh about.

  14. Tell me about any work or chores you did to earn a little money when you were young.

  15. When you were a child, what did you want to be when you grew up? Tell me about that.

  16. Tell me about a time you changed jobs or started over in something new.

  17. Tell me about a big risk you took in your working life.

  18. Tell me about a time you were recognized or thanked for your work. How did it feel?

  19. Tell me about a time money was tight and how you managed.

  20. Tell me about the first big thing you saved up for and finally bought.

  21. Tell me about something you made or built with your own hands that's still standing.

  22. Tell me about a customer, client, or person you helped that you've never forgotten.

  23. What was a normal working day like for you, from morning to evening?

  24. Tell me about a time you taught someone else how to do what you do.

  25. Tell me about your last day of work, if you've reached it. What was that day like?

  26. Tell me about how things changed for you when you stopped working.

  27. Looking back on your working life, what did your work come to mean to you?

  28. Looking back, what part of your work are you most proud to have left behind you?

Want these answered in their own voice — and kept forever?

Storykept guides your family through these questions by voice. No writing, no pressure. Free to start.

Work & Vocation — Questions to Ask | Storykept