Fifteen years of semi-retirement: A real-life look at what it’s like to live more and work less

Today’s “money story” is an article from Bob Clyatt, author of the outstanding Work Less, Live More, which is one of my favorite books about financial independence and early retirement. [My review.] It’s an update on what his life has been like since moving to sem-retirement fifteen years ago.

I had the good fortune to start a digital design firm in 1994. I sold it during the dot-com frenzy, leaving me with a bad case of burnout and full retirement accounts. It seemed like the right time to pull the plug, so in 2001 — at the age of 42 — I left full-time work.

I embarked on a self-funded post-career lifestyle that wasn’t quite retirement (at least not in the traditional sense). I chose to do part-time, work-like activity in order to stay challenged and engaged while also closing budget gaps. Five years later, I wrote Work Less, Live More, which popularized the notion of semi-retirement.

So, I guess the big question is: Does semi-retirement work? What has it been like for me and my family? What lessons have I learned since embarking upon this path?

The Way to Semi-Retirement

The quick answer is: Yes, semi-retirement can and does work. The investing approach outlined in Work Less, Live More has sustained our spending since the day my wife and I quit work in early 2001. Our savings have allowed us to have part-time, low-paid (but intrinsically fun and meaningful jobs) at a time when the normal people in those jobs can’t actually make ends meet — and can’t enjoy them as a result.

My wife works ten or twenty hours a week in a large specialty women’s clothing store. Her job allows her to stay connected to her interests in fashion while spending time with a younger generation of women: her co-workers and managers.

Meanwhile, I got to pursue my dream of becoming an artist. I went to art school, then built a sculpture studio. I now show and sell my work everywhere from Hong Kong to Paris, from trendy art fairs in Miami to galleries in Manhattan. [Check out Clyatt’s contemporary sculpture at his website.]

Bob Clyatt, sculpting

I’ve certainly had fifteen-hour days and eight-hour weeks in semi-retirement, but mostly I putter around in the morning before going to my studio after lunch. I spend an active afternoon sculpting. At night, I’m parked on the couch just like the rest of the country.

Like all artists, I sigh that I don’t have as many sales as I’d hoped after an art fair or gallery show. But then I pinch myself and remember that the art itself is getting better. I remind myself that creating the art is deeply meaningful and our financial needs are still covered by our savings.

Our Time in Eden

We have a close family.

Our two sons (now 21 and 25) were short-changed for Mom & Dad Time during the 1990s. Business trips and long hours at the office scarred me deeply and took me away from the kids. This was probably the driving force pushing me toward early retirement, actually.

But were able to spend a lot more time with the boys once we chose the path to semi-retirement. (They probably got too much time with us by the time high school and college rolled around!) We bought a boat and took plenty of family vacations, and there was always time to play catch or Frisbee while the kids were growing up.

Once I left the rat race, I got into yoga. I spent more time working out than the average executive could ever dream. Staying fit takes time and energy. I had plenty of both. We also took the time to to prepare healthful meals at home. As I get older and I’m unable to eat as much without packing on the pounds, preparing exciting, well-made food has been something of a compensation.

Now that our kids and in-laws have moved out, our house is more than we need. It requires plenty of work, but is a source of enduring pleasure for us. The gardens and grounds are Edenic. We entertain a lot at home, and the studio I built on the property a few years back has made me something of a homebody (gladly so!).

Work Less, Live More I have the time to think, to read, to putter — and still get my errands done and art created. Mornings inevitably involve a long read of the Wall Street Journal over a big cup of strong coffee, looking out on the gardens and digesting what’s happening out in the world.

Art has been a good avenue for opening up the world further. We’ve met lots of young, interesting people, and enjoyed at least ten trips a year to art-selling or exhibition locations where my work is being shown: art fairs in Miami or fine craft fairs around the Northeast, international symposia in Europe or Asia. We’ve found that it’s always more fun to travel with a purpose, and weaving together art and travel has been something my wife and I enjoy doing together.

Our marriage is no doubt stronger for having gone down the semi-retirement path. I’m convinced a lot of marriages founder out of need for more time and energy for each other. Finding that time and energy can be so difficult when juggling full-time work, commutes, and the inevitable life-maintenance that everyone has to attend to.

We often look at friends who work full-time, especially those at the lower rungs on the pay ladder, and wonder how people can possibly hold it all together given the stresses. So we’re grateful for the gift we’ve been able to give ourselves of time, and the extra bit of cash it sometimes takes to keep irritants at bay: a parking ticket doesn’t ruin our day or cause us to fight, but the irony is we have more time to drive around to find a parking spot in the first place so the issue just doesn’t come up.

Our social lives are active. We have rich friendships among people and couples of all age groups in our community. We participate in community groups and volunteer for causes we care about. We feel connected to our town and the people in it. We never had time for this when we worked full time. But now I pop up regularly in the local paper because of one project or another. (Usually I’m mentioned for helping to bring sculptor friends’ work to our town for temporary installations around our parks and public areas.)

The Downside to Downshifting

All that probably sounds idyllic — and it is. But there are things cropping up after fifteen years of semi-retirement that are less than perfect. I’m not complaining, but I feel like I should mention these in the interest of full disclosure.

My concerns aren’t financial. We’ve kept our lifestyle in check, so we have enough — and then some. While my aging friends have started to show up with flashier cars (Maseratis and Teslas are “in” with my male peers), and they’ve started buying second and third homes, this isn’t a problem for me. I’m not wired to envy them or to feel left out.

What is concerning, though, are questions of identity and accomplishment. When you leave life in the fast lane a decade or two before your peers, some of the folks you know will go on to become Big Dogs at a time when you’re feeling more like a Chihuahua!

Sidenote: It’s rare to be a Big Dog in the art world, especially for a late-bloomer like me. Most artists subsist on the joy of creating and the satisfaction of nudging a body of work into the public sphere to some admiring fans and a few sales.

I’ve always had the respect of my still-working friends. They like having a window into my aesthetic, alternative lifestyle. They admire the chutzpah it took to walk out on the System and chart my own course. Still, the fact is that on conventional metrics they have gone further and achieved more in their extra years, allowing them now, as they approach traditional retirement age, to play the next few decades at a level I hadn’t really foreseen. That world is now closed off to me.

For example, I have friends who are entering their sixties with large career accomplishments are becoming directors of significant public companies, an ideal semi-retirement role. Others who have done well financially are in a position to engage in philanthropy at a level I simply can’t.

In addition to the genuine good they’re doing through their gifts, they’re invited into advisory roles where they can help steer the vision and activities of their chose charities. This work is deeply meaningful for them. These roles also bring accolades that keep the older semi-retiree feeling appreciated, respected, and useful in a significant way, while remaining connected to other high-achievers.

Because I left the fast lane early, I don’t have as many post-work opportunities.

I’m certainly appreciated and respected in the circles I move in. But those circles sometimes feel rather quiet and small. When I chose semi-retirement fifteen years ago, I understood intellectually that this would happen. I made an intention choice to pursue a quieter, more introspective bath. Yet there’s a sense of loss — of missing out — that comes when you realize certain paths are closed off forever.

J.D.’s note: I’ve experienced this in my own life. When I chose to enter semi-retirement, I left near the top of my field. In the years since, others have produced bigger and better websites. Now that I’ve resumed writing about money, I feel like a young pup instead of a Big Dog. I’m glad for the success of my colleagues, but can’t help wondering what might have been if I’d elected not to cash in my chips.

Know Thyself

Of course many readers will have no interest in embarking on any kind of high-profile semi-retirement activity: “Let me have a quiet place to do what I want and leave the living large to others!”

But plenty of early retirees are able to save big precisely because they’re high-achieving, high-energy people. When they’re done working, they want it all: lots of relaxation while retaining the sense that they’re connected and needed. This simply might not be possible if you drift away from the limelight for an extended period.

Don’t get me wrong: I’m glad I made the change to the slow lane. But before you make the shift, think about your own needs to be useful and/or achieve recognition. Make sure your future is going to be a good fit for you in the long term.

To learn more about Bob Clyatt, check out his gallery of contemporary sculpture. You can buy Work Less, Live More on Amazon or visit the book’s website. Lastly, you might want to check out my review of the book.

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