Challenging Myself

James Kerr

I JUST TURNED 62. That’s the 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 won’t be starting Social Security payments early. Nor—unless something changes health-wise—do I intend to begin distributions from my IRAs any time 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. 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 demonstrate to me, and maybe to society as well, that age is but a number. 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’re 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 just flew into space at age 90. My mother keeps herself mentally sharp at 89 by reading the paper every day and doing 1,000-piece jigsaw 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 retirement, I hitched my 30-foot trailer to the back of my F-150, threw the dog in the backseat (she jumped in, actually), and set off on a month-long, cross-country adventure to Colorado.

It’s something I’d wanted to do since my middle son moved to Denver three-plus years ago to take a job after college. Since my girlfriend had to work, and none of my retired friends wanted to do something so crazy, I took 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 cross-country RV trip solo 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, isn’t easy.

Our Free Newsletter

But I did it. I met the challenge and came back charged up and feeling good about myself. I call it repassioning. First item on the challenge list—check. What else is on my list?

  • I want to write books, and hope to get a few of them published. My first nonfiction book, The Long Walk Home, will be published early next year by Blydyn Square Books.
  • I want to publish articles and blog posts like this one. And look here—I’m doing it.
  • I want to sharpen my photography skills.
  • 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-biking 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 on this 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.

James Kerr led global communications, public relations and social media for a number of Fortune 500 technology firms before leaving the corporate world to pursue his passion for writing and storytelling. His book, “The Long Walk Home: How I Lost My Job as a Corporate Remora Fish and Rediscovered My Life’s Purpose,” is forthcoming in early 2022 from Blydyn Square Books. Check out his blog at His previous article was Reclaiming My Life.

Do you enjoy HumbleDollar? Please support our work with a donation. Want to receive daily email alerts about new articles? Click here. How about getting our newsletter? Sign up now.

Browse Articles

Notify of
Inline Feedbacks
View all comments
Ronald Wayne
Ronald Wayne
1 year ago

You’re right. I don’t want to think of my retirement goals as a bucket list! Congrats to you for pursuing your writing dreams. I feel fortunate to have spent 26 years in a very satisfying, rewarding and important career as a newspaper journalist, even though I never made lots of money and worked long hours. I then left newspapers for 10 years in media relations for one of the nation’s largest universities, during which time I earned my master’s degree and taught an editing lab as an adjunct. Although none of those accomplishments left me with a plush retirement, I’m still proud and happy.

Rick Connor
Rick Connor
1 year ago

Congratulations James. Great article. Best of luck in your list. I look forward to reading your book.

1 year ago

If you have a good job and a decent income, it is important to save in more than just a retirement account. If you push yourself a little to invest money in a taxable account, you will have a considerable fortune after 35 years of work. This will give you a lot more flexibility if you need to retire early.

R Quinn
R Quinn
1 year ago

Good plan, right attitude and good fortune. Go all out as long as you can because try as you may, you will slow down.

I’ve been retired nearly 12 years. My wife and have traveled to 45 countries, taken cruises, and driven across the US twice in that time.

We have been active in many ways and to some extent we still are. I want to do more traveling, I want to see Iceland, go back to Ireland for the fourth time and my wife wants to go back to Italy for the fifth time.

But now I’m 78 and my wife is 82 with a bad back and a limited ability to climb stairs or walk distances. Our abilities aren’t keeping up with our desires. Yesterday I heard my wife tell a friend our traveling days are over. I didn’t want to hear that, I’m not ready to give up, but sadly she may be right.

I don’t intend to sit around and vegetate, but things change so grab as much as you can while you can.

I play golf usually twice a week, I can still pick up the ball off the green, but getting it out of the cup four inches below the surface is not so easy, that’s what time does. That and how many tries it takes to get the darn thing in the hole.

Mik Cajon
Mik Cajon
1 year ago
Reply to  R Quinn

Long live the Richard…common sense extraordinaire.

Free Newsletter