Sailing Away

Alina Fisch

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: 

  • Evaluate what you already enjoy, and explore how to move from passive to active enjoyment. A foodie might take a culinary course, a sports fan could join a local league, an art lover can learn to paint, a pop-culture aficionado can join a trivia team and animal lovers might try volunteering at a shelter.
  • Revisit things you used to love when you were younger. Refresh your dance skills if that was your thing. Join a knitting club if you used to be into arts and crafts. Perhaps pick up your dusty tennis racket or your old guitar. 
  • Make a bucket list, and choose something that would require regular practice or comes with opportunities to meet others. That might mean joining a running club, foreign-language conversation group or photography club.

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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