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I HAVE A FRIEND—we’ll call him Dave—who retired from Wall Street perhaps eight years ago, when he was in his early 50s. Soon after, he designed a sailboat and had it built, and he’s been sailing around the world ever since. In fact, judging from his Instagram updates, Dave is now on his second or third self-designed boat. Or is it a yacht? I don’t know anything about sailing.
At this point, you may be sighing with envy. But ask yourself: Would you actually want that life for yourself?
If your answer is, “I just want to be rich enough to do whatever I want,” I get it. But just for kicks, let’s examine this question a little more closely.
Dave is obsessed with boats. When he designs them, he doesn’t just make a pretty drawing and throw some money around. He’s deep in the weeds on every detail, from technical specifications to the brand of winches to the colors of the rig lines. He mostly either lives on the boat or visits his friends’ boats. He has other interests, like bike racing, marathons and military history, which keep him busy even when he’s alone in a new state or country.
Here’s the thing: When Dave retired, he knew he wasn’t simply walking away from a career that was core to his identity. Rather, he was walking toward something new and exciting that he’d been pondering in detail for some time.
Along these lines, Morningstar recently published a study about setting financial goals. When participants were asked an open-ended question about their long-term goals, their top three answers were owning a home, retirement and travel, followed by “being able to afford small luxuries,” which came in a distant fourth. Pretty predictable, right?
Then it got interesting. When participants were presented with a new version of the question, in which they were nudged with a pre-set list of 17 goals they could choose from, including the ones above, almost 75% changed their answers. The new top three were living a healthy lifestyle, donating to charity and having meaningful hobbies, with “having fulfilling work” sitting a distant fourth. It seems we’re less clear on what we want than we imagine.
Coincidentally, I read a beautiful, compassionate essay this week by Carrie Ditzel, a geropsychologist—a psychologist who specializes in older people—titled How to Feel Less Lonely as You Get Older. She cites the well-documented issue of loneliness among older adults, but suggests that loneliness isn’t inevitable if you have the right mindset.
Unsurprisingly, much of her advice aligns with what we already know about the importance of social connections to our mental health—that we should nurture relationships, cultivate hobbies, participate in our community, establish a daily routine, give back by volunteering and donating, and exercise, even if our mobility has declined.
Perhaps at this point you’re rolling your eyes and thinking, “Yeah, sure, like I have time for hobbies.” Or maybe you’re saying, “Excuse me, I’m still in my prime, why should I be thinking about this?” Again, I get it. But planning ahead is helpful, even if your kids are still little or even if your career is still thriving.
Saying “someday I won’t have to work, and I’ll have money to do whatever I want” is pretty vague. Moving to the South of France sounds great, but unless that idea is accompanied by specific things you’d do there—learn French, open an American bar, write your memoirs—and by strategies for making friends, you’d probably end up bored and sad, even if you have loads of money.
In addition, having an idea of how much your future life will cost, and whether you’ll potentially still be earning some money, helps clarify how much money to save and how long you’ll need to keep working. It can also help you identify the skillsets and connections you might want to start developing.
It’s common to look up from our insane to-do lists and suddenly realize we haven’t managed to cultivate outside interests. Here are three ideas for how to identify possible hobbies that could turn into regular social activities once you have more time on your hands:
Last week, I exchanged messages with Dave. He told me he misses work and the camaraderie of the trading floor, and that he now basically works full-time to find other things to fill his life. Luckily, he considers fitness and sailing to be rewarding both mentally and physically, so that’s what he focuses on, treating them as full-time occupations.
It’s probably no accident that both of these “hobbies” are quite social and have given him a global community of new friends that share the same interests. To be clear: Financial security has given Dave the freedom to live a life he enjoys. But it took more than money to get there.
Alina Fisch is the founder of Contessa Capital Advisors, an independent fee-only investment advisor. She’s worked in financial services for more than 25 years. Her focus today is on helping single and divorced women with their finances, a topic she also loves to write about. In her free time, Alina is an avid reader, animal lover, hiker, traveler and vegetable farmer.
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I think this may be one of the best Humble Dollar columns ever written. Several authors have written on this very topic, but somehow the writer’s approach in this particular entry really struck a deep chord in me. The data on 75% of the people changing their top three goals (based on how the question was presented) was very striking. We really don’t know ourselves as well as we might think we do.
One comment I would add along this line about really knowing ourselves is that it could have gone either way for her friend Dave. It is one thing to like designing and building wooden boats, and another to relish living fulltime on the water in essentially a small camper that rocks back and forth all the time. Similarly, it is one thing to visit a destination (such as France or Hawaii or wherever it might be ) occasionally as a tourist, and it is another thing to live there full-time as a resident. The author’s point to begin trying things well before retirement arrives is sage advise.
Work sets a lot of the agenda and keeps you busy, then you retire and life asks you to make a decision or two. Do I want to keep busy because I don’t know how to sit still, or do I want to learn to be comfortable being still. I chose the second and now when I want to be active it’s not because I feel guilty about or am bored with taking my rest. Socially I’m lucky, I still go to AA meetings after 43 years, sponsor several guys and have friends. I go to the gym 3 times a week and talk with millennials (when they aren’t looking at their phones and have their earbuds out). I hike with friends in the mountains in which I live, and make a concerted effort not to eat out in restaurants, most of which use more salt on one meal than I would eat in a week. My wife and I eat vegetarian and are both fit at 77. None of this has one iota to do with money.
I was born the middle of five children and the others had their closer siblings to be playmates with. I was master of my own time.
I find it’s not a huge issue for me to be alone. But, I do enjoy being with friends at times and just being free.
Color me cynical, but I don’t find the different responses surprising. Give people a choice of presenting themselves as self-interested vs interested in helping others and most will choose the latter. Also, all this concern for social connection overlooks the difference between extroverts and introverts. While the majority of Americans are extroverts, I’m an introvert. I spent about three years home alone during Covid, with lots of library books and my computers, seeing just a few people on the phone or Zoom, and even fewer in person. I was fine.
Loved the article and the points it raised. I’ve been retired for 9 years and I can’t say life is that different except I have a lot of free time. Something I started doing recently is helping at an animal shelter in Koropi, Greece. It has 50 dogs rescued from horrible situations and are available for adoption. I would adopt any one of them but I already have a dog that came from the streets of Athens 10 years ago and she doesn’t like to share me with other dogs. The point is to do something that fulfills you.
I was concerned when my wife retired a few years ago. She had been working long days and the abruptness of her stopping concerned me. To my amazement, she had no problems at all. But she had no “plan.” Turns out that wasn’t a problem either.
Personally, my days are filled with so much activity I never have time for everything. But I have a hard time recapping for anyone what I did during the day. Too many disparate activities.
My idol is Warren Buffett who still goes to the office every day. At 92 he’s slowing down a bit, but he still has full days doing what he loves. His retirement goal is not to retire. I can’t help wondering how many boats he could have built if he was into that sort of thing.
The ideal* is to find whatever it is that you truly want to do, and then find a way to do it. “Idol” is an excellent word for Warren Buffett, who excels at giving Capitalism a good name. May we each find whatever it is that we most want to do with our lives. The earlier we find it, the better.
(($; -)}™
Gozo
Alina, nice article.I’ve also observed that the social part of retirement is very important. Relocation in retirement can raise challenges for retirees. Dave must be a unique person.
Thanks for this article. I’ve recently been thinking about the social aspects of retirement. It varies by personality, but it is a genuine hole that needs to be filled.
Alina, thank you for a wonderful article. While reading your South of France question, I thought of the students who salivate over the thought of summer break, then wind up bored because they haven’t thought of what to do during their hiatus. Happiness takes effort.
What do you have growing?