In December 2022, Peter O'Keefe was
A year and a half later, O'Keefe said he'll do no such thing.
"That would be a chance of never," he said. "Why would I stop doing what I love to do?"
O'Keefe listed many reasons for his decision. His business is growing rapidly, he loves the relationships he has with his clients — and, above all, his work gives him a sense of purpose.
"This is the gift God has given me," he said. "It would be foolish of me to walk away from a very exciting growth phase of the business."
O'Keefe makes a strong case for staying on the job, but he also exemplifies a common problem in wealth management. For all their expertise on retirement, many financial advisors have an ironic shortcoming: They don't know how to retire.
Tiffany Lee is an associate exit planner at
"Advisors are not the best at retiring, and they know it," Lee said. "Usually when we go into a prospect call, they're like, 'I know I'm going to be bad at this, so please help me!'"
Unlike their clients, Lee said, advisors typically have no trouble building a nest egg or planning out an income to last through their golden years. The hard part is the psychology.
"A lot of them are pretty confident in where they are with their retirement planning — some of them are overprepared," Lee said. "It's really the mental and emotional side of retirement."
READ MORE:
That emotional barrier could become a major problem for the industry. The average age of an American financial advisor is 56, according to a 2023
That's a lot of wealth managers who will soon be leaving the workforce. So it's worth examining the psychological obstacles that stand in their way. According to Lee, it comes down to three challenges: letting go of the business, making sure clients are in good hands and answering the biggest question of all: What comes next?
"It's really thinking through, 'How can I exit the business in a way that brings excitement to me for my next chapter — and are my clients going to be well taken care of?'" Lee said.
Mission complete
In a way, many financial advisors are the victims of their own success. They derive so much meaning and fulfillment from their work that it becomes very difficult to quit.
"I think it's the nature of the work that advisors do," Lee said. "They're very passionate about their clients. They're very passionate about the work that they do. It's where they find a sense of impact and how to make the world a better place."
How can advisors step away from this mission without feeling an enormous sense of loss? Lee's answer: They can't. The reality of retirement, she said, is that it usually does involve some sadness as well as excitement — and it's important to acknowledge that.
"There is a normal and healthy amount of grief that happens with this type of transition," Lee said. "Any transition, even a good one, is stressful."
READ MORE:
Advisors who head into retirement without expecting this grief, Lee said, often struggle with the changes. That's why a big part of her work is to tell clients something they don't often hear: This is going to be tough, and it may take a year or two to find your footing.
But she doesn't want to do all the talking — what's even better is if the client can talk to someone who's been through it before.
"One of the first questions we ask is, 'Do you know an advisor who is retired that you look up to, or who has successfully done it and is happy?'" Lee said. "Talk to them!"
The pass-down
To leave their business in good hands, any retiring advisor will need to find and cultivate a successor. But that practical challenge is also a psychological one.
"A lot of our clients are business owners," Lee said. "So the idea of handing off your baby to someone else, whether that's internally or externally, is very anxiety-inducing."
Lee's biggest tip for this process is simple: Slow down. The smoothest transitions, she said, are usually ones that happen in stages, sometimes over the course of several years.
"We encourage a phased retirement," she said. "What roles and responsibilities are you handing off, and at what point?"
To avoid conflicts, Lee said, it helps to work with a coach or an exit planner — and above all, put the plan in writing. The retiring advisor and successor should work together to write up a timeline for the transition, including projects where the junior advisor can "step into that role without the advisor looking over their shoulder."
READ MORE:
One success story is
"I'm really an odd duck, because I never had any hobbies," Gertsema said. "All I did was work. My hobby was work."
Just as Lee recommends, Gertsema oversaw a slow, step-by-step succession. Back in 2020, he and his son set a date for his retirement: February 15, 2024 — a day of family significance.
"He said, 'Dad, when are you going to retire?' and I said, 'On your mom's 65th birthday,'" Gertsema recalled. "So we had a hard date that we set, and then we just worked toward it."
After the date was set, Gertsema Wealth Advisors underwent a transformation — from the one-man firm started by Mike to the multiple-advisor boutique envisioned by Nick. The father transferred many of his leadership duties to the son, becoming more of a senior advisor than a CEO. But, importantly, he remained heavily involved in filling out the new team.
"The big thing for me was I was able to train the new advisors coming in, to really acclimate them to what we do," Gertsema recalled. "Once I knew that our clients were in good hands, it made retirement a lot easier."
Now and then, the two men stepped on each other's toes — Mike would overstep, or Nick would make a mistake leading the firm. But they communicated about these missteps, and little by little they got used to their new roles.
"The last year, when Nick was CEO, I just yielded," Gertsema said. "People would come to me because I was the owner, and I'd say, 'Listen, you run after Nick because I have an opinion, but it's Nick's decision.'"
When February 15 arrived, Gertsema felt comfortable enough to disappear.
"Nick always laughs about it, because it was an Irish farewell," he said. "I just said, 'Hey, listen, I think you guys can handle it now.' And I just left."
A new life
Then comes the most difficult — and, potentially, exciting — piece of the puzzle: What comes next? To summon the courage to start a new phase of life, it's crucial to have some idea of what that phase will look like. In fact, the lack of that vision was a big part of what held O'Keefe back from retiring.
"If I find something that gives me a higher sense of purpose, I'll go for that," O'Keefe said. "I don't know what that is today."
One thing it can't be, Lee said, is "perpetual vacation." Though this comes as a surprise to some, a retirement that consists of doing nothing is a recipe for unhappiness.
"Vacation is not meant to be a lifestyle," Lee said. "A vacation is a vacation. People need routine, people need community, people need ways to feel like they are impacting for the good."
What can fill the void left by professional work? That's up to each individual, Lee said. But she offers an important tip: Whatever they want to do in retirement, they should start doing it now.
READ MORE:
"Retire with something — not just from something, not just to something," Lee said. "Have some things integrated already into your schedule, into your calendar, into your network, so that you can build on it once you do retire."
At her practice, Lee has seen a wide range of post-career adventures. One client, an amateur pilot, is planning to spend more time flying. A husband and wife, both financial advisors, are buying an RV so they can travel the country. Another couple, already retired, is roaming through Europe, living in each country for a few months at a time.
For Gertsema, the ideal retirement is something simpler.
"I'm not a traveler," he said. "My wife and I, we just love to spoil our kids and our grandkids."
With three grown children and eight grandchildren, Gertsema has plenty to keep him busy. And the spoiling takes different forms: For the grandkids, he's building school desks and other furniture. For his daughter, a nun in Connecticut, he pitches in at the convent's investment committee and helps produce marketing videos.
"There's all these things that I'm finding that I enjoy and I never took the time for when I was working, because all I thought about was the practice and the family," Gertsema said. "I'm a different person now, because I don't have that stress."
But what about his former business? Gertsema said it was difficult handing the reins to someone else, but he has no regrets.
"You've got to let go of your ego," he said. "It's not about me. It's about the customer."
Like many retirees, Gertsema still does plenty of work — but there are differences. Instead of building portfolios, he builds Adirondack chairs. And instead of working nine-to-five, he has no schedule at all.
"I don't have to be any place at any time," he said. "I have freedom now. I've never had it in my life, and it feels pretty darn good."
