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Questions to ask · Advice and life lessons

Questions to ask for advice and life lessons

A long life teaches things that cannot be looked up. Your parents and grandparents have made big decisions, changed their minds, weathered hard seasons and worked out what mattered in the end. Most of them will happily share what they learned, if someone asks in the right way.

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The right way is usually indirect. Ask a modest person for their wisdom and they will say they have none. Ask for the best advice someone else gave them, or what they would tell themselves at twenty, and the answer arrives with a story attached. That story is what makes the advice stay with you.

These questions suit the turning points in your own life: a graduation, a first job, an engagement, a new baby, a move. Ask when you really want to know, and say so. The questions below are a small sample. The linked ones open a full guide with tips on how to ask, different wordings, follow-ups and an example answer. Write the answers down in their exact words. The phrasing is part of what you are keeping.

Advice questions to try

Ask who gave them the advice and when. The moment it was given is usually the best part of the answer.

The rest of the questions are in the journals

Every Tell Me Your Story journal includes a chapter on what life has taught them and closes with pages written to the next generation. In their own handwriting, the advice is there to reread whenever you need it.

Free printable

The 25 questions you’ll wish you had asked

For your Mom, Dad, Grandma or Grandpa: the stories families most often lose, on one page to print or keep on your phone. Free when you join the porch list.