Ask a 6 year old what they want to be when they grow up and chances are you’ll get an answer like astronaut, fireman or super hero.  No need to worry about feasibility or practicality when you’re 6.  Just pick something that sounds awesome or involves flying.

Ask an 18 year old the same question, however, and you’ll probably see a wave of anxiety wash over their face.  That’s because college is just around the corner and the “what do I want to be” question is starting to take on some urgency.

I’ve helped hundreds of people plan for retirement over the years and there’s a similar dynamic when you ask people about retirement.  Ask a 40 year old what they want to do when they retire and you’re likely to get the grown up version of “astronaut.”  Buy a sailboat.  Plant myself on the beach.  Climb Everest.  Retirement is decades away, so they usually just list off some things that sound fun and that don’t involve work.

Ask a 60 year old, however, and you’re likely to get a different reaction.  The decision has some urgency.  Sure, it will include some items from the Bucket List, but they’re not planning a vacation.  They’re planning what to do with the next 20 or 30 years.  That can be intimidating.  What will you do with all that time?  What will provide purpose and satisfaction?  What will be interesting and challenging?

If retirement is on the horizon and you’re feeling a bit of anxiety about how you’ll fill your days, I want to help.  Here are 10 questions that should help get you thinking about what to do during retirement.

1)      If you could relive your life, knowing everything that you know now, what would you do differently?

2)      What are your highest ideals and/or priorities?

3)      If you died tomorrow, what would be your top 5 regrets?

4)      If you were to design an improved version of yourself and your life, how would it be different?

5)      Who are the people that matter most to you and who do you matter to?

6)      Reflecting back on your life, when were you the happiest and why?

7)      What skills or talents do you have?

8)      What hobbies or activities do you enjoy?

9)      What are 5 things that you would STOP doing tomorrow if you could?

10)   What would you say if you were at a cocktail party and someone asked you, “Why do you want to retire?”

I hope a few of those questions were helpful to you.  For a much deeper dive on the topic, keep your eyes open for my Ideal Retirement Design Guide.

As always, thanks for reading and, for those of you here in the U.S., enjoy Thanksgiving tomorrow with your friends and family.

~ Joe

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How to design your ideal retirement