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My Retirement Stories

We do not see things as they are.
We see things as we are.”

                                                         ― Anais Nin

What does a good retirement look like to you? A bad one? If you are part of a couple, how does your vision of nirvana compare with your partner’s?

Whether we’re aware of it or not, the stories we tell ourselves about what retirement is “supposed” to look like have a major influence on how contented we feel. We may think there are things we should or shouldn’t do, or can or can’t do. The goal of this worksheet is to help you dig into what your own stories are. Then you can decide whether to leave them as is, or to make some changes in what you believe.



  • What was the retirement experience of your parents?
  • Have any of your siblings or cousins retired? What has their experience been?
  • How about your grandparents?

Friends and Co-workers

  • Is there an ideal that gets bandied about as the perfect retirement? Age? Income? Activities? Place to live? Have your attitudes about any of these things changed with your life experiences?
  • Are there any people you know whose retirement lifestyle is something you absolutely don’t want?

Role Models

  • Whether you know them personally or not, is there anyone whose lifestyle inspires you? Are there pieces of others’ lifestyles that you’d like to include in your life? 
  • Are there any attitudes or activities you have seen in retirees that would disappoint or horrify you if you found yourself having or doing them??


After reflecting on your retirement stories, is there anything you might want to change about what you think a successful or failed retirement looks like?


Just to get you thinking, here are some things that have popped up for other clients. Remember, none of these are right or wrong, your goal is to be aware of your own biases.

  • Is it OK to take vacations in an RV? To sleep on the ground in a tent? To stay in a five-star hotel?
  • Is it OK to own more than one home?
  • How much time “should” a grandparent spend with grandchildren?
  • What is an ideal balance between spending time alone and with friends? In pursuit of my own interests vs. those of my partner?
  • How much “should” a parent leave as an inheritance (which may, of course, affect optional spending)?
  • Is a retiree “supposed” to volunteer?
  • “If I can’t take care of my own ‘farm’ [she was referring to her family home, but came from a long farming tradition] I shouldn’t live there any more” – it is not OK to hire help.


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