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My Five Lessons

Joe Kesler

FOR MOST OF MY LIFE, I didn’t plan to retire. Probably reflecting the influence of religion, I’ve long thought we were put here to spend our time working in the productive service of others.

This was reinforced by my experience as a manager early in my career. I often had to oversee folks in their 50s and 60s who were no longer engaged in their career and yearned to retire. I never wanted to become like them. Staying productive and continuing to work seemed like the wise move.

But my views on retirement began to change as I read about how baby boomers and the FIRE—financial independence-retire early—movement were changing the definition of retirement: It was no longer seen solely as the pursuit of leisure. I liked the redefinition, which included remaining fully engaged in life, including doing work that you love. My resistance to retirement was slowly softening.

Then it was accelerated by a really bad day.

It was a frigid Montana morning. My car said it was five below zero. I left early to drive more than three hours to one of the remote bank branches I oversaw as the bank’s CEO. I was going around 75 mph when I rounded a curve and hit some black ice. My Suburban, almost in slow motion, began to drift until I found myself going backward in the wrong lane. It was the first time I ever thought, “So, this is how it’s going to end.”

I was lucky. The car drifted into a ditch and crashed into the side of a mountain. The impact blew out all the passenger side windows and burst two tires. But I wasn’t hurt. My first thought was a prayer of thanks that I had more life to live.

After the battered Suburban was loaded onto a wrecker truck and we were on the road, the driver asked me what I did. As soon as I said I was the CEO of a bank, he exploded, “You SOB, why did you take my home from me without working with me?”

For the second time that day, it dawned on me this was the day I might die. Fortunately, I was able to talk him off the ledge, and he realized that he was confusing my bank with the credit union that had repossessed his house.

After two brushes with death within two hours, I decided it was time to explore this new world of retirement. After another year of work, I took early retirement at age 62. Six years later, what have I learned on my new journey? Here are five lessons.

First, my wife and I wanted to experience what it was like to live in a retirement community. We rented a place for six months in a Sun City development in Tucson. The benefits were real: more than 100 clubs to join, new friendships came easily, and the restaurants, fitness and other facilities offered were great.

Still, the almost college-like atmosphere couldn’t compete with our overwhelming longing to be a part of our grandchildren’s lives. We decided it was a great experiment, but we’ll do our future snow-birding on the East Coast, where the weather isn’t quite as nice as Arizona, but the family ties are strong.

Second, much of the literature on retirement is about staying curious and learning new skills. It sounds good in theory. I’d always loved music, but never played. My neighbor in Sun City told me about the ukulele club. Seemed like a great idea, but my ukulele now sits in my office accumulating dust. Perhaps someday I’ll pick it up again. Still, I’ve found it difficult to get excited about a new hobby unless I already had some history with it.

Pickleball, on the other hand, is a different story. Having played lots of tennis and ping pong during my life, it was a natural extension of my past into the present. I’m pretty good at it, and the sport offers a great opportunity to meet others and make new friends.

Third, I’ve never been a big fan of the worship of youth that’s so common in American culture. Indeed, throughout history, many cultures have revered not youth, but rather the elders in their community.

I think about this in terms of today’s work world. The stress of managing people and budgets is better suited for younger professionals. But there’s a role for those of us with decades of experience. I sit on the board of a couple of banks, as well as some nonprofits. A seasoned board can offer an organization wisdom and good governance—including the hard-earned lessons of our own mistakes.

Fourth, many of us prepared well financially for our retirement years. One joy I’ve learned over the past six years: the happiness to be had from giving generously with the retirement income we don’t need.

A few years ago, when I was elected to a bank’s board of directors, I called the outgoing director I was replacing. He gave me some good advice: “I don’t need the board fees, so I give all the money to the local food bank.”

Finally, I was a hypocrite for much of my life. I served as a church elder for many years, encouraging church members to slow down, and set a regular time each day for prayer and meditation. But I didn’t follow my own advice. I was too busy raising five kids, managing banks and working in nonprofits to have much time for quiet reflection.

Today, I’m happy to say that I’ve finally learned to slow down. I’ll enjoy a cup of coffee, while practicing the spiritual disciplines that I’ve long encouraged others to pursue.

I know it’s just a matter of time before I enter retirement’s slow-go and no-go years. When pickleball is no longer an option, I’m hoping I can fall back on the spiritual muscles I’m now developing, and they’ll help me to find meaning and contentment as I age.

Joe Kesler is the author of Smart Money with Purpose and the founder of a website with the same name, which is where a version of this article first appeared. He spent 40 years in community banking, assisting small businesses and consumers. Joe served as chief executive of banks in Illinois and Montana. He currently lives with his wife in Missoula, Montana, spending his time writing on personal finance, serving on two bank boards and hiking in the Rocky Mountains. Check out Joe’s previous articles.

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Kevin Lynch
6 months ago

Nice article Joe.

I retired in January, from a 3rd career. I am a bit older than you, at 73, but I like your renting in Sun City idea. I want to do it in The Villages, FL, for the activities and chances to make freinds, but my bride of 50 years (this June) is not keen on the idea. We are going to go down for a “Lifestyle Visit” in April for a week, to check it out. Han;t considered renting, but that might be an idea to consider.

My two kids haven’t had children, and I doubt they will. I know we would have been wonderful grandparents, but they made their choices and we living with it. That frees us up from the emotions of wanting to be near the grandkids anyway.

We thought about a 2nd home near our daughter, but as you mentioned, their careers could have them relocating in the future, so that’s a no go for me.

Like you, I never really thought about retiring, since my last career was in academics, and I truly enjoyed teaching the skills I had practiced for 40 years prior, in financial services and financial planning. But I decided that life was too short to spend my remaining years being subjected to woke ideology and agendas and having DEI crammed down my throat. My pronouns are American Patriot and I haven’t got much patience for the “America Last” crowd, which has a strong representation in academia.

Getting back to my religious foundation is also one of my goals, as challenging as it is these days. I was raised a Roman Catholic and I feel like I never left the church, rather it left me when it veered off into the land of marxism and “social justice,” but I m trying.

I am also looking forward to mastering Pickle Ball. Ha!

Again, thanks for a great article and the ideas it generated for my consideration.

Chris Roessler
7 months ago

Glad you made it to retirement and are enjoying it, Joe.
I’ve been interested in early retirement for many years. Thanks to this site, I’m getting a lot of input on how to do that. Super helpful. Target is 4 years away at 59.
Question for you – third shot drive or drop;?
Love pickleball and tennis, as well.

Joe Kesler
7 months ago
Reply to  Chris Roessler

Haha! Thanks Chris. I’m in transition trying to become more of a drop artist, but it’s such a rush to drive the ball that it’s taking some time. How about you?

Chris Roessler
7 months ago
Reply to  Joe Kesler

Understand, Joe. Driving is fun and very effective if they don’t handle it well. Drop is great though if it’s working and you can keep them from driving it back at you. I’m more of a finesse player so inclined to drop but I find mixing it up keeps other side off balance. Like throwing in an occasional topspin lob to their backhand, too. Guess it depends on the situation, what’s working, and who I’m playing.
Lived in Missoula for one winter in ’96-97. Had a great time teaching skiing at Snowbowl. Guess you have to play pball indoors this time of year.

Linda Grady
7 months ago

Wonderful article, Joe. I agree with everything you wrote. I’m eight years into retirement. It took me a few years to find the pace and activities that really suit me. Some folks still try to give me advice about how much I would enjoy pursuing their interests. Though I appreciate the advice and sometimes hear about something I want to try, other times I know it’s not for me, like chair yoga, crocheting or knitting. On the other hand, I’ve resumed dance-type exercise like Zumba and Jazzercise. Occasionally I sit down at my laptop to try and learn Mandarin (the first language of several of my grandchildren) with Rosetta Stone. Serving on the board of a local non-profit brings a lot of satisfaction, as does the available time for spiritual reading and reflection. I hope you continue to enjoy what you’re doing and keep writing for HD!😊

Joe Kesler
7 months ago
Reply to  Linda Grady

Thanks Linda! There are a lot of choices in retirement. Sounds like you have found a nice rhythm. I appreciate your note about others giving you advice on what you should do. All well intentioned, I’m sure, but we have to be the CEO of our retirement!

mark ahlenius
7 months ago

Thanks Joe for a good article. You bring up good stories how events in our lives can cause us to evaluate life and how we now spend it. I appreciate you sharing your experience with renting at Sun City and honestly realizing that for you the family relationships were more important (ie grands). We are retired, still in our original home, yet in the middle of a geographical triangle from our 3 kids. We are toying with the idea or purchasing an “investment property/townhome” near our 3 grands, where we could stay and visit. We really want to be a part of their lives. It’s a hard decision as nothing stays the same any any of our children could get up and move again.
thanks again for sharing this story.

Mike Wyant
7 months ago

One of the better pickleball players at our club is 84 years old! He’s got a mean spin and always knows where to place it. You’ve got alot of pickleball life left in you. Btw, he’s always the first one there in the morning to blow off the courts.

Joe Kesler
7 months ago
Reply to  Mike Wyant

Mike, I know some of those octogenarian pickleball players too! They are my inspiration for trying to stay healthy and become one someday.

R Quinn
7 months ago

You illustrate my philosophy. You don’t need to plan everything when it comes to retiring. You don’t have to keep busy or make friends unless that is your thing, there is no need to start an activity you never did before.

You will know when it’s time to retire, you don’t have to keep working or retire early, go with your gut.

Good move renting in Sun City and not going with the crowd and buying. Being near family is a blessing in retirement. We could move to our second home and save thousands each year, but it would be six hours away from family. That is a bad tradeoff.

By the way, FIRE is largely a farce. Few are retired in the true sense. They make money telling others how they led a frugal life to drop out at 45. Some sponge off the rest of us by receiving various subsidies and benefits intentionally keeping income low.

mytimetotravel
7 months ago
Reply to  R Quinn

Really? I retired from full-time work at 53, and completely at 56. I didn’t make money talking about it, and I don’t consider my pension sponging. Just because you didn’t retire early is no reason to diss those who did. Maybe you should stop hanging out on FIRE websites (which I have never done) if they annoy you so much.

Fund Daddy
7 months ago
Reply to  mytimetotravel

I’m glad it works for you but I never wanted to worry about what if. I retired after 23 years of investing (using 401K) while enjoying life, the safe way with a portfolio of 25+ times our annual expense, not including SS and no pensions. It is now doubled. I don’t want to get on “fire” when I don’t have enough and think about what is next.

Last edited 7 months ago by Fund Daddy
Kevin Rees
7 months ago
Reply to  mytimetotravel

Glad your retirement is working out well for you.

i retired at 62, but am still working part-time for “mad money” and mental stimulation.

however, when people talk FIRE nowadays they are not talking about either of us. I think 45 would be considered “old” for a true FIRE adherent. It is a totally different game than our boomer dreams of “early retirement”.

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