Build a Post-Career Plan With a Retirement Coach

A coach can help you home in on what you want to do in your second act.

Mature businesswoman in office, portrait, close-up
(Image credit: (c) Getty Images)

I don't know when I'm going to retire. At my age (63), it could be in a few years or maybe further out. What I do know is that I won't embark on the next phase of life -- which could be longer than my childhood, longer than the time it took to raise my family, and longer than my 21-year freelance career -- without a game plan.

That's why I had the idea of signing up for a few sessions with a retirement coach. Retirement coaches, who may have a background in psychotherapy, executive training or financial planning, help clients identify their interests and priorities, align their finances with their retirement goals, and give shape to the vast expanse of time that represents life after a career.

After researching coaches in my area, I set up a series of four sessions with Dee Cascio, a certified retirement coach and licensed therapist in Sterling, Va. The cost: $120 for each session, with an optional fifth session thrown in free. Like many coaches, Cascio sees couples as well as individuals and counsels them in person or by phone. I chose phone sessions for convenience.

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Assessing readiness. Before our first phone session, Cascio had me fill out the Retirement Success Profile, an online questionnaire that gauges retirement readiness. If anyone could flunk (which the instructions assured me is not possible), I certainly did. How so? The analysis revealed that working is essential to my well-being. Not only does it deliver a paycheck, it also gives me satisfaction, a sense of worth, the opportunity to socialize and built-in time management. Plus, I hate change, my attitude toward leisure is "anemic" (read: I don't have a lot of hobbies) and I'm leery of life transitions. People like me "have anxiety regarding their retirement," the report concludes. "They usually prefer their present situation to the unknown future."

You'd think the solution to all this angst would be to stay on the job as long as possible, or at least continue to write during retirement. Having spent my entire career working with words, however, I'm looking to try something new. To get a sense of what that might be, I'm tasked by Cascio with outlining my values (maintaining relationships with family and friends tops the list); my interests (cooking, travel and mastering new subjects); and challenges (having enough savings for retirement). She also asks me to imagine a typical day in retirement. I find it surprisingly difficult to populate even one day.

Filling a social gap. One reason my hypothetical day seems so empty, I soon realize, is that it lacks a key ingredient: people. I hope to maintain work friendships once I retire and to spend more time with family, but replacing the day-to-day camaraderie of the office is a worry. That's a typical concern, says Cascio. "It's the first thing people say -- 'I'll be leaving my friends.' " Further, because I'm single, I can't count on having a built-in companion in my future. (On the bright side, I won't have a stir-crazy spouse underfoot, either.)

Cascio's solution covers both sides of the equation: Set up a routine for seeing friends in retirement -- say, by scheduling a weekly lunch, a regular movie night, a daily walk or a weekend expedition to the farmer's market. "You have to think about how to build relationships and expand connections," she says. In my case, she also suggests that I join a group of freelance writers, despite my intention to try something new. "That's something that keeps you in the game," she says.

Exploring the possibilities. Cascio has addressed one worry, but I'm still concerned about having enough activities to fill the day; after all, my interests have been deemed "anemic." In the next session, we discuss options based on the list I provided earlier. Travel? I'd like to, but can't afford regular major trips. She suggests writing about travel or lecturing on a cruise ship about retirement planning to defray costs. I mention going to cooking school. Her response: How about using that as a basis for writing a food blog or getting freelance gigs for a food magazine?

Me: I could take classes at a nearby community college.

Cascio: Why not also teach writing or tutor students?

Sheesh. I thought I was retiring to a life of leisure, but Cascio keeps returning to the idea of working or volunteering or otherwise using my skills. What gives? "We think about work as what we do. Earning money, raising kids, that's work," she says. "Leisure is the break you take from what you're doing, to refresh you." Spending 25 or 30 years of retirement strictly on leisure, be it playing golf or creating pastry swans, isn't satisfying for most people, she says. Better to find a meaningful focus for your days and then build in time to play and relax.

Making a plan. After that pep talk, I consider the skills I could bring to this new form of career. One of them is expertise in college financing, a topic I once covered. Helping prospective college students identify affordable schools and apply for financial aid would be as rewarding for me as it would be useful to them. I also remember that I have two book manuscripts in a drawer, one a children's novel I wrote decades ago and the other a book of cooking advice I wrote for my kids a few years back. I've always meant to revise the manuscripts with the aim of getting them published or publishing them myself. In retirement, I'll have the time.

That's what coaching is all about, says Cascio, "digging around, eliciting your purpose, and appealing to your heart and intellect. At the end of the process, you want to say, 'This is my vision going forward.' "

What I learned from my coaching experience is that the job I have now offers the ideal opportunity to meet people, learn new things, travel to new places and add to savings -- the very goals I have for retirement. Rather than walk away completely, I'll keep my hand in, one way or another.

Find the right match

Retirement coaches can also be life coaches, financial planners, corporate trainers or psychotherapists. If you're mainly looking for financial planning, go with a certified financial planner who has carved out a niche in retirement coaching. If your goal is to retrain for a new career, look for a coach with expertise as a corporate trainer. Therapists can elicit your hopes and concerns and help formulate strategies, but coaching and therapy are not the same, says Cascio, who is certified to do both. "Coaching is more forward-looking than therapy," she says. "It helps you focus."

Coaching sessions range from $75 to $300 or more; figure you'll need at least four to six sessions to get the most out of the process. To search for a coach, go to Retirement Options, which provides certification specific to retirement, or the International Coach Federation, where you can plug in your criteria for a list of candidates who fit the bill. Ask what training their credentials represent, and find out how long they've been practicing in this niche, says Kim Mills, at Retirement Options. "How comfortable would you be working with someone who'd been a retirement coach for only a year?"

Ideally, you should start the coaching process three to five years ahead of retirement, says Cascio, the better to have a plan in place when you leave the workforce. But if you find yourself disappointed or at loose ends in retirement, it's not too late to benefit from a coach's help.

Jane Bennett Clark
Senior Editor, Kiplinger's Personal Finance
The late Jane Bennett Clark, who passed away in March 2017, covered all facets of retirement and wrote a bimonthly column that took a fresh, sometimes provocative look at ways to approach life after a career. She also oversaw the annual Kiplinger rankings for best values in public and private colleges and universities and spearheaded the annual "Best Cities" feature. Clark graduated from Northwestern University.