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When my twin brother Nick and I sold our landscape business at the end of 2012, at the age of 52, we agreed to stay on for another three years. Looking back, that may have been one of the best retirement decisions I never consciously made.
Those three years gave me time to ease into retirement instead of falling into it. They also gave me time to think about something I believe is far more important than deciding when to retire. It’s what are you retiring to?
After enduring another cold Maryland winter, I knew exactly one thing, I wanted warmth. Not just for my aging body, but for a life that could be lived outdoors every month of the year. I’d bought a condominium in Florida a few years earlier, and because I could work remotely, I made the move south.
That became my first step into retirement.
A few years later, Joey and I traded condo living for a single-family home. For the first time in my life, I wasn’t landscaping someone else’s property. I was creating my own. After more than 35 years building landscapes for clients, there was something deeply satisfying about planting trees and flowers simply because they brought me joy.
Then, in 2015, the paychecks stopped.
So did the alarm clock.
For decades my mornings had begun with somewhere to be, someone to meet, or a problem to solve. Suddenly there was nowhere I had to be. I discovered the pleasure of a second cup of coffee that wasn’t making me late for anything.
Retirement also gave us something else that had always been in short supply. Time.
Without a business waiting for me on Monday morning, Joey and I began traveling. We explored towns up and down the East Coast, visited the United Kingdom, the Caribbean, Costa Rica and the Philippines. Every trip reminded me that the world is much bigger than my own experiences. Meeting people whose lives were so different from mine somehow made mine richer.
Travel also awakened something I never expected. I started writing poetry after visiting the Philippines. Those poems gradually turned into personal essays, and eventually into articles for HumbleDollar. Writing has become one of the great surprises of retirement. It has allowed me to reflect on my life, my family, grief, gratitude, and the people who shaped me. In many ways, I’ve found a new purpose just as my old one ended.
Of course, retirement also meant trusting that we had saved enough. That didn’t happen overnight. For years I found myself worrying about money, even though the numbers told me we were financially secure. Old habits are hard to break. After spending a lifetime making payroll, watching expenses and preparing for the unexpected, it took time to believe that we no longer had a mortgage, no debt and no one financially depending on us.
Eventually I stopped asking, “Do I have enough?” Instead I started asking, “Am I living well?” Those turned out to be two very different questions. When people talk about retirement, the conversation usually centers on finances. Those are certainly important. But I’ve come to believe they’re only the admission ticket. Retirement isn’t simply about leaving work. It’s about discovering the life that work never left enough room for. For me, that life has been found in slow mornings, travel, gardening, writing, friendships and the quiet satisfaction of choosing how to spend each day.
That is what I retired to.
I was truly blessed to have a profession, primary internal medicine that I loved and that my patients told me I was very good at. I joined Buffett in “ tap dancing into work”.
I never made more than even the average salary but my wife loved working so she had our health insurance.
We didn’t mind a cheap house or cheap,cars and vacations saving our money for our kids education.
The only thing wrong with this picture is my practice was all consuming and my style of medicine dis not allow it to be part time. So when i was forced to spend four hours a day i
putting data into a computer I had no alternative but to retire.
Retirement gives me free time to catch up on ll my medical journals and other reading, get more exercise volunteer. I would like to help friends with their medical issues, but without a practice or insurance, that is impossible. Some states like Wisconsin apparently let you practice medicine immune from suits if you only do charity work, but not mine.
Thank you for sharing your story. It sounds as though you truly found your calling in medicine, and there’s no greater compliment than hearing from patients that you made a difference in their lives. I was struck by your comment that it wasn’t the work itself that led you to retire, but everything around it that changed. Sadly, I suspect many professionals have reached that same conclusion. It also sounds as though you’ve carried your love of learning into retirement through your reading, volunteering and staying engaged. I only wish there were an easier way for experienced physicians like you to continue helping others in a volunteer capacity. There is still so much wisdom to share.
I realized that working for a jerk CFO at the age of 55 made me pull the retirement rip chord earlier than I expected. I spent many years working for smart and driven CFO, but never a jerk.I spent the next year figuring out how we were going to make it with our current assets and my wife’s part-time work. It honestly wasn’t that hard and I never went back to work. I’ve read many times how people should retire to something and that’s always been frustrating for me. I realize that retiring to something like that extra cup of coffee or just not knowing what the day was gonna bring is just as rewarding as actually having something planned.
Edwin, I agree. I simply wanted to eliminate the stress of my demanding job, so having a set of priorities (e.g., fitness, travel, music, volunteering, personal growth) and a desire to get the most out of the Go-Go years with my wife was enough for me to pull the trigger 18 months ago at age 60.
Thanks, Edwin. I think you’ve made an important point. We often hear that we need to “retire to something,” and for many people that’s true. But sometimes what we’re retiring to is simply the freedom to enjoy an unhurried morning, an extra cup of coffee or the luxury of letting the day unfold without a schedule. That’s a perfectly worthwhile destination too. And I agree, working for the wrong boss has probably nudged more than a few people into retirement a little earlier than planned!
Excellent article Andrew. I eased into retirement, less and less work hours from 55 on. Decided to keep my foot in the door until age 78, when I officially retired. My blessing was at age 48 my company decided to downsize me. Best thing that ever happened to me in work life. You just cannot plan everything.
And my investments increased nicely in the last 4 years, and it is difficult to spend more than what is coming in. I guess I am a slow learner, but very blessed.
Thanks, William. I think your story is a great reminder that what first appears to be a setback can turn out to be an unexpected opportunity. Being downsized at 48 clearly changed the course of your career for the better, and easing into retirement until 78 sounds like it suited you perfectly. I also smiled at your comment about finding it hard to spend more than your investments are earning. After decades of saving, changing our mindset isn’t always easy, but it’s certainly a nice problem to have. Thanks for sharing your journey.
There is a huge transfer of boomer businesses going on as boomers retire. Unfortunately, many of these businesses are just end and are not successfully sold. The three years you stayed on likely make your sale successful and more profitable to you. So a win/win.
Thank you Anthony. You make an excellent point. Looking back, the three-year transition was probably one of the smartest parts of the deal. It helped ensure a smooth handoff for customers and employees, while giving the new owners confidence. As you say, too many successful businesses simply disappear because there’s no succession plan or buyer. We were fortunate that ours had a different ending.
As some people here know, I have three volunteer jobs. I am the treasurer of the tax district, the president of the investment club, and the head of the crossword blog. Although retired, I still have things I have to do and meetings I have to attend.
I have been thinking maybe I should retire completely when I am 80.
I had to smile at “retiring from retirement” at age 80. With three volunteer jobs, it sounds as though you’ve simply traded paid work for work you genuinely enjoy. That’s one of the wonderful things about retirement, we get to choose how much structure we want in our lives. And somehow I have a feeling that, when you turn 80, someone will persuade you to stay on for just one more year!
Andrew, for me, the activities of daily retirement have come pretty easy. The harder part has been changing my mindset from increasing wealth to spending it down. I’m not worried about running out, I just have this thing about seeing our net worth continue to grow. Come October, I’m 74 years old, it’s okay if the net worth chart starts to look a little like the Cleveland Guardians descent from division leaders to god knows where. Well, maybe not that steep.
I am the same way, I too have this thing about seeing net worth decline no matter how illogical it is. These past few weeks have not helped has investments have tumbled and taken me from my happy place.
My son in law is a managing direct at a Wall Street firm and warned me about this summer, but it doesn’t make me feel any better.
Dan, I suspect you’re not alone. After years of measuring progress by watching our net worth grow, it’s hard to embrace the idea that it’s okay, even expected, for it to begin funding our retirement. After all, that’s what we saved it for. And thanks for the Guardians analogy, I hope your portfolio has a much better second half!
I wrote my own reflections on completing one full year of retirement at the beginning of July, but since then I’ve added a new experience that turned out to be surprisingly satisfying and challenging.
Our church has for many years offered a large summer day camp for kids, usually during the middle week of July. My own kids went to it long ago, but being past that stage of life now, I haven’t been involved in it.
This year, a friend asked me to be his assistant director for the drama team he’s been leading for five years. He is VERY talented at it—he writes a script for a five-act play, casts it, directs it, gathers the props and costumes, and organizes the teams that build sets and provide lighting, sound effects, and video. It’s an amazingly high-quality operation.
I wasn’t sure what I really could contribute to all that except as a writer with some limited experience with theater (did some acting as a kid, helped with my daughters’ shows). But I ended up helping with the script, being a second pair of eyes at rehearsals, being “on book” when the actors needed prompting, and even contributing a loud offstage scream(!).
It turned out to be fun and rewarding. My friend has already expressed the hope that we’ll manage our July travel schedule so that I can help again next year. I had a little anxiety that I wouldn’t have much to offer, but trying something new and a bit out of my comfort zone was energizing!
Dana, thanks for sharing this. It’s a great reminder that retirement can still stretch us in unexpected ways. Stepping outside our comfort zone can be a little daunting, but it often leads to some of the most rewarding experiences. It sounds like you found a role that was both meaningful and enjoyable, and I hope you get to reprise that offstage scream next summer!
Any modern retirement advice needs to focus on the “what do I retire to” question rather than the “retire from” or the money.
Any number of calculators and/or your own modelling can answer the money questions to a reasonable degree (and there is no precise answer to the money side because of unknown and unknowable future events both macro and personal).
Well said. Money determines whether retirement is feasible, but purpose determines whether it’s fulfilling. We can model portfolios and spending with reasonable confidence, but no calculator can tell us what will get us out of bed each morning. That’s the question every future retiree should spend time thinking about.
Thanks so much, Andrew. A close friend will be retiring soon, so I’m sharing this with him. I’ve already encouraged him to join the HD community. I recently attended the board meeting of our local daycare where I was co-chair for three years until January. After many very serious issues during that time, it was so gratifying to see that my volunteering has made a real difference in the lives of our staff and family and that jobs and daycare slots are secure. I hadn’t realized how great volunteering can be, and how flexible. When it’s time to take a trip or a break, a fellow volunteer usually steps up.
Thanks, Linda. I hope your friend finds as much value in the HD community as I have. And congratulations on the impact you’ve had through your volunteering. It’s a wonderful reminder that retirement doesn’t have to mean stepping away from making a difference, it often just means choosing where and how we do it.
Sixteen years in retirement and I can still relate to what yoù write. But I still have not been able to break the habit of waking up at 5:00-5:30 AM
We are well beyond the halfway point, traveling is over, but I did and still find enjoyment writing every day, returning to my art and playing golf. We have made new friends after moving to the next town.
No desire for warmer weather, other than sometime in Florida in the winter. Being near children and grandchildren is the top priority.
I don’t worry about money, but if it were not for my pension I’m not sure I could cope living off investments alone.
As I have said and learned in practice, once you retire, don’t delay anything you really want to do.
Thank you so much for reading the article and your comment. I especially like your last point because I think it’s one of retirements most important lessons: Don’t postpone the things that matter. None of us knows how many healthy years we have, and retirement has reminded me that time is every bit as valuable as money.
It’s also encouraging to hear that, sixteen years on, you’re still finding purpose through writing, art, golf and new friendships. That gives those of us earlier in the journey something to look forward to. And I agree, being close to children and grandchildren is a wonderful reason to choose one place over another.
Thanks for sharing your perspective. It’s a great reminder that while every retirement looks a little different, the freedom to spend our time on what matters most is the common thread.
Andrew, although I’m only 16 months into retirement, you’re hitting all my buttons. After selling my business, having personal time again is wonderful — that second, unhurried morning coffee (which I’m enjoying right now), working in the garden, and being able to travel without weeks of prepping the business for my absence. Having the resources to make this possible matters, but the true luxury is the freedom of unencumbered time.
I’ll admit I still don’t fully trust my numbers, so I kicked that can down the road by buying ten years of guaranteed income — a way to ease myself into the right mindset. As for your wish for heat, family and friends keep me anchored to a cooler climate, so I suppose I’ll just have to depend on global warming to work that angle for me!
Thanks, Mark. I had to smile reading this because it sounds like we’re discovering many of the same things. Time really does become the greatest luxury. It’s amazing how much pleasure can come from something as simple as an unhurried cup of coffee or spending an afternoon in the garden.
I also relate to not immediately trusting the numbers. After a lifetime of earning, saving and planning, it takes a while for your head to catch up with what the spreadsheets have been telling you all along.
As for the warmer climate, I have to admit Florida has been kind to me. But I suspect having family and friends close by is a pretty good trade off. Thanks for sharing your journey.
Thanks Andrew for another great article. Glad you discovered your talent for writing.
I’m currently 52 and recently sold our business. But after that, our stories diverge a little. The Australian superannuation system means that we can’t access our retirement savings until 60, so I’m working for at least another 8 years. But even if we could get our hands on retirement income, I still enjoy the routine and structure of work and would be happy to continue.
It will be interesting to see how I feel in 8 years. Maybe happy to keep working, or it might be time to head for the exit? Time will tell!
Really glad to hear that retirement worked so well for you.
Thanks Greg. One thing I’ve learned is that retirement isn’t something you have to rush into. If work continues to give you purpose, routine and enjoyment, there’s no reason to leave it behind just because you can.
The writing was a complete surprise to me. If someone had told me 15 years ago that I’d be spending my retirement writing articles and poetry, I’d have laughed. It’s been one of retirement’s greatest gifts.
I’ll be interested to hear your perspective in eight years’ time!