5 Questions to Help You Make Better Choices in Retirement

One of the most common concerns I hear from clients is, “how do I avoid choosing the wrong things to occupy my time?”  You may be keenly aware of colleagues, friends, or family members who opted for pursuits that left them feeling aimless and dissatisfied, forcing them to go back to the drawing board, re-retiring as it were.

Given that your next chapter may span decades and considering that there are so many activities and avocations to choose from, it’s easy to feel that there’s a lot riding on your decisions about how to spend your time.  Here are 5 questions to help you make satisfying choices in retirement:

1.    How are you determining your options to begin with?  

If you don’t cast a wide enough net, or if you opt for what seems obvious, you run the risk of overlooking activities that could be a great fit.  For example, I know of folks who always enjoyed playing golf, so they assumed that two or three rounds per week would ensure retirement bliss.  For most of them, that wasn’t rewarding enough long term.  In other cases, I’ve seen clients dismiss ideas too quickly.  They have a spark of interest in something but reject it out of hand without investigating it at all.  Make no mistake, this process requires a good deal of thought and an open mind.

2.    What was satisfying about work?

What if you feel stuck because there are too many choices, or conversely, what if you can’t think of anything to pursue?  One exercise I do with clients involves listing key satisfactions they derive from work and then identifying alternative endeavors that are likely to provide similar benefits.  Satisfactions can be things like a sense of routine, relationships with colleagues, or the chance to solve problems. These satisfactions will be missed once you retire, so it makes sense to seek substitute sources. 

3.    What do you know to be true about your core preferences? 

Do you like to be busy or are you at your best when unhurried?  Are you comfortable taking direction or would you rather give it?  Is novelty appealing or do you prefer the familiar?  By the time you retire you probably have a good sense of your work style and how your personality contributes to it.  That said, be sure to take stock of your inclinations outside of work, too.  By being honest with yourself about yourself, you’re better positioned to choose activities and settings that are a good fit.

4.   What have you learned from past choices?

Think about previous inflection points in your life when you had to make important choices. Did you rely on your gut or your head?  Did you choose hastily or with excess deliberation?  Did you listen to others too much or too little?  Historically, what has led you to make good choices versus ones that you regretted?  Use this data to inform your decision-making process moving forward.    

5.    What would you like to accomplish during your retirement? 

A client once told me, “I’m a foodie, so I thought I’d take cooking classes when I retire.”  It’s not a bad idea to focus on your interests, but in my experience it’s not enough.  Although any given activity might keep you from feeling bored, most of my clients report greater satisfaction when engaged in something tied to a purpose or goal.  If you’re clear about what you want to accomplish in retirement, you will likely make even better choices about how to spend your time.  

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