When Early Retirement Turns Into A Total Bore

illustration of a man building a desk out of sand on an island

A workplace advice column at the New York Times recently ran an exchange with a reader who sold his business in his mid-50s and no longer needed to work. But in his early retirement he admitted to feeling totally adrift: “I’m finding that I am bored out of my mind. I miss the activity and satisfaction that came from building and running a company.” He wondered whether he should get back into the work force. And if so, how would he do so as a 55-year-old who felt too old to go back into the work force, which seems so focused on millennials.”

Another snag was that he didn’t feel he could talk to his friends about the issue since they were hard at work and couldn’t really identify with his boredom (let alone total financial freedom). Finally, he’d enjoyed 25-plus years of calling his own shots, and wasn’t sure what it would be like to start reporting to someone else (especially a millennial)!

Bob Walker, also known as the New York Times “workologist,” responded as follows:

“Congratulations on submitting the most enviable ‘workplace dilemma’ that I can recall. And as if the rest of us weren’t jealous enough already, you likely have better options than you realize. No need to head back to some mailroom to be bossed around by twenty-somethings 40 hours a week. You can dabble—consulting, taking on short-term gigs, freelancing.

“We’re seeing a massive number of people who, after retirement, come back to the work force by freelancing,” according to Stephane Kasriel, chief executive of Upwork, a site that freelancers use to connect with clients in a range of fields. Upwork and the Freelancers Union commission an annual study on this segment of the work force and found that in the United States 16 million people age 55 and up did freelance work in 2017.

To be sure, plenty are doing so because they need to: Maybe they were thrown out of work against their will, or discovered retirement is more expensive than anticipated. But some, Mr. Kasriel observes, simply found full-time leisure unsatisfying.

There are a couple of paths you might follow. You could look for freelance gigs that leverage your specific skills (related to whatever field you worked in), but on a temporary or project basis. Or, Mr. Kasriel says, you could hire yourself out as more of a coach, offering “the wisdom acquired” from building a business. “People that have been 20 or 30 years in the work force have a lot of transferable experience,” he adds.

You might also be able to find something suitable through a firm such as Patina Solutions, which offers “executive on demand” services to corporate clients large and small. “We were built for a guy like this,” says Mike Harris, the company’s chief executive. Patina’s network includes thousands of experienced executive-level baby boomers who are available for project-specific or limited-time gigs, or mentoring arrangements.

It’s true, Mr. Harris concedes, that you’ll have to “get used to advising and supporting and recommending, as opposed to bossing and telling and directing.” But plenty of companies are looking for experience and know-how without a full-time commitment.

You can experiment. Sound out your own social network; consider charitable or volunteer options. Mr. Kasriel, the Upwork C.E.O., mentions a user of the site who retired from investment banking, and now writes children’s stories. “It keeps him busy,” he says. “And apparently he’s pretty good at it.”

In the immediate term, Mr. Kasriel notes, a tight labor market makes experienced talent more valuable. In the longer term, structural shifts in that market are for better or worse tilting toward more demand for freelancers.

And Mr. Harris suggests that you are part of a broader phenomenon. Since founding Patina Solutions nine years ago, well before the “gig economy” notion took hold, he wrote a book called “Career 180s.” It is about experienced workers living longer, getting bored—and starting whole new professional lives. “We hear a lot of these stories,” he says.

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