Retirement Story Interview Questions – Couple


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We don’t need to talk about all these. I mainly want to get some ideas out there and have you respond to the ones that most resonate with you, and that you think might be most inspiring and entertaining to others coming along in your footsteps.

Pre-retirement: I’m trying to get a sense of things that help transition to retirement

  • Was the timing of your retirement your own decision, or was it imposed on you? Did the two of you agree on the timing or were negotiations involved? Was the date set far ahead of time, or was it more of a short-term decision?
  • What were you most glad to leave behind?
  • What were you most looking forward to?
  • Did you have a special event to celebrate (party? trip?)
  • As you look back on the things you did to prepare for retirement are there any that were especially helpful? Any that were a waste of time?

Early retirement: how did the reality compare to what you had imagined?

  • Did you both have the same idea of what you wanted retirement to look like?
  • What was the biggest surprise to you?
  • Did you have a detailed plan for how you would transition from work to retirement, or did you more or less wing it? Do you think this is representative of your personality and overall approach to life?
  • What did you miss most about work? Least? Did you have any kind of identity crisis when you, and others, no longer looked at you in terms of your job title?
  • Is there anything that, had you known it ahead of time, might have made the early retirement experience a better one for you? Words of wisdom you can share with others coming along behind you?
  • Was there any particular time that you felt something “click” and you just sort of settled into your Beyond Enough Life? If yes, when was that, and what did it feel like? If no, do you expect this happen at some time?

Settled in Retirement:

  • How has the reality of your retirement compared to what you thought it would be? Are you content with your retirement life?
  • Is there something you thought you would enjoy doing once you no longer had to work for money that hasn’t worked out the way you expected it to? Have you added or dropped any hobbies or other leisure activities? How did these changes come about?
  • Is there anything bringing you joy, or causing you concern, that wasn’t even on your radar screen before you retired?
  • What retirement myths did you believe when you were working for money that have been busted?
  • If you are part of a couple, what is the balance between joint and solo activities for the two of you? Has this changed over time?
  • Is there an element of service to others in your life now? Is this any different than it was before?
  • What have you learned about yourself since retiring? What has been your greatest source of joy and satisfaction so far in your retirement life? Was this a surprise to you?
  • Do you think the experience of retirement for Baby Boomers is going to be different than it was for previous generations?
  • What aren’t I asking about your retirement experience that I should be?

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