• jamesbriankerr

Ticking Off the Retirement ‘Challenge List’

Note: A version of this articlle appeared in HumbleDollar and in MarketWatch.



In two weeks, I will be turning sixty-two, that milestone age when so much of the magic—and the decision-making—of retirement begins to happen.


For the record, although I recently left the workforce early to pursue a long-simmering passion for writing, I will not be starting Social Security payments early. Unless something changes health-wise, nor do I intend to begin required minimal withdrawals of my IRA funds anytime soon. Before I go down those two routes, I plan to live off my taxable-account savings and minimal dividend income for as long as I can.


In the meantime, I’m busy pulling together my “challenge list” of things I want to experience and achieve in the years ahead. Note that I call this a challenge list, not a bucket list—a term I find horrid. I mean, do we really want to be counting down a list of to-do items before we kick the bucket?


Not me. I want to be stretched in the years ahead. I want to be learning new skills and plumbing unexplored parts of myself, as well as the world. I want to be doing things that will demonstrate to me, and maybe to society as well, that age is but a number and people shouldn’t limit what they try just because of the year they were born.


After all, we stretched ourselves in our working careers. Why should we stop now that we are no longer clocking in? Research has consistently shown that seniors who engage in stimulating activities–ones that challenge their bodies and their brains—tend to stay sharp and vital longer.


William Shatner flew to the moon at the age of ninety. My eighty-eight-year-old mother keeps herself mentally sharp by reading the paper every day and doing thousand-piece puzzles.


My own challenge list is a mix of experiences, activities and goals that will push me in new directions, physically and mentally. I’ve already started to tick some items off the list.


The first challenge I set myself was a big one: On the first day of my retirement (I call it “repassioning”), I hitched up my 30-foot trailer to the back of my F150, threw the dog in the back seat (she jumped in, actually), and set off on a month-long, cross-country adventure to Colorado.


It’s something I’ve wanted to do since my middle son moved out to Denver three-plus years ago to take a job after college. Since my girlfriend had to work and none of my friends wanted to do something so crazy, I did the trip solo. And it was incredible.

There’s nothing like spending the whole month of September in Colorado to kickstart a new, creative phase of your life. The big skies, the rugged mountains, the broad vistas burning with the gold and reds of fall foliage—it all gives you a sense of life’s possibilities and our limitless human potential.


Will I do a solo cross-country trip in the camper again? Probably not. Driving home alone for 31 hours over three-and-a-half days, with a three-ton travel trailer hooked to the back, is not easy.


But I did it. I met the challenge and can tell myself I achieved what I set out to do.


First item on the challenge list—check.


What else is on my challenge list?


  • I want to write books and get at least a few of them published. My first non-fiction book, The Long Walk Home, will be coming out next year from Blydyn Square Books.

  • I want to publish articles and blog posts like this one. And look here—I’m doing it!

  • I want to learn Canva or another design program so I can do my own graphics and visuals for my personal blog.

  • I want to do a road-hiking trip through the French countryside and hike in the Scottish Highlands.

  • I want to go fly fishing in Canada and Argentina.

  • I want to get into yoga.

  • I want to keep jogging and get as much mileage as I can out of my arthritic left hip of mine before I submit to getting a new one.


And on and on. My challenge list grows every week. I’ll never get to all of them, but that’s all right. The point is not so much accomplishing all these things as setting them out there and giving them a shot.


When it comes time for me to kick the bucket, I want to make sure it’s a big bucket I’m kicking. And that it has plenty of dents from all the places we’ve gone together.


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