How to Have Your Dream Job in Retirement


If you look up the definition of “retire,” you’ll find synonyms like withdraw, retreat and recede.

Um, no thanks.

With Americans living longer than ever, retirement nowadays can easily stretch on for nearly 20 years. And who wants to withdraw for 20 years?

In fact, the AARP has an entire section on their website dedicated to helping readers stay professionally active post retirement. There’s even a word for it: recareering, or switching to an entirely new job path. And retirement is a great time to do it because, let’s be honest, there are only so many great American novels you can read.

Since so many people are choosing to recareer instead of retire, we decided to take a closer look at the trend to see who’s doing it, how it works—and whether you should consider giving the idea a spin for yourself.

The Rise of Recareering

In the next 20 years, 77 million Baby Boomers will retire. These are the same folks who have shelves lined with self-help books, and who tell their kids to “find your passion,” while talking on their cell phones on the way to a business meeting. While Generation Y may be identified with timidity and financial insecurity—along with an ironic sense of entitlement—it could be argued that their Boomer parents are the ones who made them that way.

In other words, they aren’t going to “retreat.”

Instead, many would-be retirees are seeking out part-time work, full-time projects or new careers altogether (teaching, writing, consulting and serving on corporate and nonprofit boards are popular choices). And a new service has risen up to meet this need: retirement coaching.

It’s estimated that there are 48,000 retirement coaches currently in business across the world, but since it’s still a somewhat nascent industry, there’s no hard data on exactly how many people they serve. At New Directions in Boston, one of the most well-established career and retirement coaching services, they work with about 100 new clients each year.

“The people who come to us tend to be highly charged and Type A. They have poured most of their activities and energy into their careers, and they haven’t really had time to think about what else is out there,” explains Samuel Pease, vice president and senior consultant at New Directions. “Frankly, a lot of them are stunned by having all of this free time.”

So How Do You Launch a Recareer?

When you sign on for retirement coaching with a company like New Directions, you’re assigned to a consultant who works with you for as long as the process takes—usually a year to 18 months.

You’ll also spend a few hours with a staff psychologist and take a series of personality tests, such as the Myers-Briggs, to figure out what’s most important to you in a job—but also in your life overall. Family members and friends also play a part: Your coach will speak with a select group of your nearest and dearest to get a true sense of your aptitudes, interests and even hidden talents.

Roberta Taylor, a retirement coach and trained psychotherapist based in Massachusetts, has found that many people are drawn to new careers that echo childhood interests that they abandoned to get “real jobs.”

Take 60-year-old Jim Dawson. After 40 years spent in the banking industry, he came to New Directions in late 2012 after discovering that he would be laid off due to restructuring. “They put my mind at ease about the separation,” he says of his first sessions. “All kinds of scary things come to mind: What will I do with my time? Will I have enough money to retire?”

Dawson, who now runs his family’s chain of hardware stores where he worked as a teenager, appreciates the perspective that the coaching gave him. “It’s not just about finding the next job,” he says. “It’s more about looking at yourself as a whole person to figure out what you can do to enjoy life more.”

Should You Consider a New Career?

According to Pease, there are two common hurdles that people who are looking to launch a new career in retirement face: the intimidating scale of the options available to them, and the need to pick up new professional skills and connections that are necessary to branch out into an entirely new field.

“One of the biggest mistakes I see is that people are playing by the old rules,” says Laurie Lawson, a New York City-based life and retirement coach. “They’re sending out resumes and waiting for responses, but what they really need to be doing is taking their experience and better accentuating the positives.” To get them in the right mindset, Lawson asks clients to jot down ten stories of personal career success that they’ve had—and then figure out common threads.

“Most of the time, they’ll say that they hated their jobs,” Lawson says, “but when we start reviewing and pulling out the good parts, they’re surprised to find that much of what they want to do has been supplemented and enhanced by what they’ve already done. For example, a person in finance may have hated accounting, but they loved watching money grow.” Lawson also points out that a person’s second career is typically related to the skills that the individual refined and enhanced in a first career.

There is one other consideration for would-be recareerists: finances. At New Directions, you’ll pay between $15,000 and $75,000 for the program; if you hire a private coach like Lawson or Taylor, you’ll be charged up to $150 per hour. But aside from whether or not you can afford the services of a retirement coach, post-retirement careers also depend somewhat on the right pre-retirement preparation.

Beginning a new career out of love is very different from pursuing a job out of financial necessity—ideally, you’ll want the luxury of choosing your post-retirement career based on a passion, not pay. “In retirement, you’re free to do whatever you want to do, and be your own boss,” Lawson says. “You’re the director of your life, so what is it that you really want to do? Because if not now, when?”

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