by | Jul 28, 2023 | Personal Finance | 0 comments

It dawned on me the other day that I have worked with hundreds of retirees now.  I have been honored to witness and learn from many successful and unsuccessful retirement transitions.  And naturally I look for patterns in what contributes to the success or failure of this very special type of transition.  What common factors can make the difference in whether this experience is joyful or frightening?  There are many, but here I will summarize the top three. 

  1. Activities
    Yes, I am a financial planner, and yes, I am telling you that meaningful activity, not anything finance-related, is the Number One Thing that will make or break a retirement plan.  Not money. 

If you don’t have meaningful activity to fill your days, retirement can feel depressing, empty, dissatisfying, even downright scary.  On the other hand, if you have meaningful activity to fill your days, retirement can feel joyful, fulfilling, and like life’s next chapter.

What do I mean by meaningful activity?  Here are some real-life examples from clients who I have watched retire successfully. 

  • Volunteering at a local food pantry. 
  • Baby sitting grandchildren and great-grandchildren. 
  • Teaching English as a second language or tutoring. 
  • Helping out with a learn-to-read program or a summer books program at the library. 
  • Creating beautiful intricate quilts and donating them to nonprofit organizations. 
  • Crocheting the baby clothes and donating them to local families in need. 
  • Growing a garden including vegetables to use in cooking. 
  • Becoming a pickleball fanatic. 
  • Refurbishing vintage cars. Entering them into competitions and winning prizes. 
  • Writing and self-publishing books. 
  • Training Horses. 
  • Fostering cats or dogs. 
  • Working with hospice. 
  • Volunteering as a docent at a local historical site. 
  • Serving as a nature guide at a local Audubon society. 

While these activities are quite varied, they all have one thing in common. They all involve being part of something larger than yourself.  They involve being engaged with the world and being part of a community – even if it’s a different community from the one(s) you were part of during your working years.  

You could say that is a key to human happiness (and I believe there are studies that show it is), but the point I am making here is that it is also the key to a happy and successful retirement. 

 You certainly don’t have to know what you will do with every hour of your day after you retire (and if you do you probably are fooling yourself, anyway).  What you do need to have some sense of what you will do next, even if it’s just “get up and do my workout” or “explore what to do next.”  

If you have no idea or get stuck, it’s normal!  And it’s OK to reach out.  Talk to your friends, neighbors, pastor, mentor, or a professional.  Did you know there are professionals who specialize in financial transitions? I am one, and part of a great community that is trained to help people think about the bigger picture and get unstuck. 

  1. Assets

Here is where the money comes in.  Yes, of course, once your paycheck is no longer coming to you, you need another source of income (or multiple sources).  So you need to know: where’s the money going to come from, for you?  Social security, a pension, your 401(k)/IRA?  Other investments?  Rental property or royalties?  A combination of a lot of things? 

Unless you have only one, super-simple and straightforward source of retirement income, my suggestion is you may not want to do this part alone. Having a professional to help you map this out is essential so that you get it right and don’t have any nasty surprises.  

Taxes and inflation need to be considered, as well as planning for life’s emergencies and arrangements for after you are gone. 

It is easy to get overwhelmed by all of these questions on your own.  You have only done this once.  A financial professional does this every day.  A trusted guide who frequently answers these questions can be a steadying resource. 

  1. Health

It has been said that “true health is true wealth.”  If you are in constant pain or constant worry about your physical health, it’s difficult to enjoy the other aspects of life around you.  Your physical health is an important factor to think about in preparing for retirement.   

You certainly don’t have to be able to run a marathon, but you should consider these questions: 

  • How would you describe your current level of activity and your overall wellness? 
  • What level of energy will you need to pursue your interests in retirement? 
  • Do you want/hope/need to make any changes to your personal habits, to become healthier in retirement? 
  • Do you know what your health insurance coverage will look like after you leave the workforce? 
  • Do you know when and how to sign up for Medicare, and have you explored supplemental insurance options? 

The answers to these questions are at the root of other decisions you will make in retirement and beyond, such as decisions around housing and living arrangements.  These decisions, in turn, affect how to arrange your financial resources for the best possible outcome.   

The Result 

Over the years, I have observed that people who take the time to think about these three important aspects before they retire tend to have a better retirement experience than those who jump in unprepared or underinformed.  Don’t look at retirement as “finally, I get to leave!”  In the words of Mr. Rogers:      

“Often when you think you’re at the end of something, you’re at the beginning of something else.”   

So prepare for retirement as you would prepare for a new beginning.  Pack well for your next journey, and you will be better able to enjoy the trip.  

I’d love to hear from you!  Please email me if I can help answer your retirement questions at: