My Biggest Retirement Mistake: Retiring Early With No Plan

Paul Ollinger felt adrift until he realized a first love could be his second act

Reyna Gobel,

AARP

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Published May 30, 2025

Paul Ollinger on the rooftop deck of his apartment buiding in New York City. Despite financial freedom after a career in tech, he initially struggled in retirement because "I wasn’t up to anything, I wasn’t a part of anything."

Photograph by Peter Ross

When Paul Ollinger retired in 2011, he knew money wouldn’t be an issue. He’d been one of the first 250 employees at Facebook and left as a vice president of sales for the Western U.S. Selling his company stock meant that at age 42, he had the financial freedom to pursue his next act. He just hadn’t given much thought to what that would be.

Like many retirees, Ollinger initially focused on traveling and spending more time with his family. The realization arrived a few months in. “One day, after dropping my kids off at school, I came back to my [home] office, opened my laptop, and there were no messages there,” he recalls. “I realized I wasn’t up to anything, I wasn’t a part of anything, and I felt very adrift.”

Seeking to regain his sense of belonging and importance, Ollinger returned to the tech world, accepting an offer to become president of a small social media software company.

“The easiest way to have an identity is to get a job doing what you’ve always done,” says Ollinger, now 56. “It’s a perfectly acceptable, respectable way to spend your time — but it’s safe, and it’s not really what you want to do.” He quit a little over a year later.

But what, really, did he want to do? He remembered some posters he’d seen around the Facebook office that read, “What would you do if you weren’t afraid?” The answer, for Ollinger, was stand-up comedy.

Evenings at the Improv

Though he’d made his career in media and tech starting in the late 1990s, Ollinger’s heart had been in comedy ever since he was a kid in Atlanta in the late 1970s, discovering Steve Martin and George Carlin records. “It blew my mind,” he says. “When I heard Dennis Miller’s comedy in the late ’80s, early ’90s, I felt as if he was talking directly to me.”

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But ambitions of pursuing a comedy career ran up against fear that he wouldn’t be able to make a living or provide for a family. Growing up with parents shaped by the Depression, that fear loomed large. They were thrifty (Ollinger says that when he got his first filling at age 12, his dad told him to forgo the Novocain because it added $20 to the bill) and steeped in the ideal of stability: “You go to college, you get a job, you work for 40 years, then you retire, and you die.” Comedy wasn’t stable.

Still, Ollinger gave it a shot. In the mid-2000s, after leaving a job at Yahoo, he went to work as a host at the Improv in Irvine, California, part of the famed comedy club franchise. Along with introducing the headliners, he got to perform for 10 or 15 minutes a night.

“They gave me this great opportunity, and I hosted for Norm Macdonald, Kevin Nealon and other big names,” Ollinger says. But after two years, he was worried he’d never make it as a comic — not one who had “a steady paycheck that paid for at least half the food and mortgage.”

One night at the club, Ollinger says, the late stand-up comic Ralphie May gave him some advice: “ ‘You’ll start to get the hang of it in eight years.’ And here I was, coming from the digital media world, [where] I was making real money,” says Ollinger. “Years of that income is millions of dollars. So I went back to the corporate world.”

Getting to ‘Reasonably Happy’

In 2007, Ollinger quit the Improv, went to work at Facebook and married his girlfriend. Four years later, when the company was moving its staff to new headquarters in Menlo Park, California, he decided to leave.

“The stock options I got at Facebook were worth more money than I ever imagined happening,” he says. “I kind of was like, ‘I don’t think I want to move to Menlo Park. I think I want to go home [to Atlanta] and be a part of my family and figure out what to do next.’”

After his period of drift and the brief, unfulfilling return to tech, “I realized that if I have the financial flexibility to do what I want to do, doing anything other than my dream is a dereliction of opportunity,” he says. “I didn’t really know where to begin or where it was going to take me, so I just started going to open mics and writing every day.”

In the decade since, Ollinger has steadily built his comedy career, and he now does up to 200 performances a year. He’s also developed sidelines as a podcaster and speaker, both rooted in his realization that the money he made as a techie hadn’t brought fulfillment.

“I started to understand that by redefining what it means to be a provider, I could contribute not only through financial means but by inspiring those around me to pursue their passions, too,” he says.

paul ollinger on stage at a stand up comedy show

Ollinger performing in 2021 at the Coca Cola Roxy in Atlanta, the city where he grew up and became a comedy fan.

Jennifer Troche Walsh

Ollinger started the Reasonably Happy podcast in 2019 to talk through his feelings about “identity and success and happiness” and to help figure out what mattered to him. Subtitled “A Skeptic’s Guide to Achievable Contentment,” the show delves into creativity, family and financial freedom and how all can contribute to joy. His guests have included Dr. Drew, Deepak Chopra and Paul Shaffer.

Listeners inspired by what they’d heard started hiring Ollinger for speaking gigs, which accounted for more than half his income last year. He still doesn’t make what he did in tech, but he’s more than reasonably happy.

“I’ve just found that my need for self-expression continued to get louder as I came into middle age and have moved through it — that I really want to be myself,” he says. “I want my work to be an authentic expression of who I am, and I think that’s the opportunity that you have in retirement to use.”

paul ollinger sits on a couch with two dogs

Ollinger at home with his French bulldogs, Theo (left) and Colonel Tom Parker.

Peter Ross

What the pro says

Sofia Pertuz is an executive coach and founder of Mainstream Insights, a company that helps people navigate career and life transitions. She calls the type of second act Ollinger has fashioned a “portfolio career,” combining multiple skills into a satisfying whole. Ollinger hesitated to pursue his passion after retiring because he thought being a successful comedian just meant doing stand-up. He found success, on his terms, when he learned otherwise.

That’s par for the course in comedy, says Stephen Rosenfeld, founder of the American Comedy Institute, which helps budding comics develop performing and writing careers. “Almost no one makes their money exclusively as a stand-up,” Rosenfeld says. “Stand-ups aren’t just stand-ups. They’re writers. They’re producers. They’re actors. They’re toastmasters.”

Pertuz says it’s a lesson that travels.

“A coaching client recently came to me after taking a buyout from a corporate role she held for over 20 years,” she recalls. “She came to me with a mix of exhaustion, fear and excitement, saying, ‘I know what I’m walking away from. I don’t know what I’m walking toward.’ ”

After talking with the client about her values and what drove her, Pertuz and the client mapped out opportunities together. “She realized she wanted to pivot toward a portfolio career, which included consulting part-time, mentoring emerging professionals, and joining a nonprofit board focused on educational equity,” Pertuz says.

For people who find themselves voluntarily or involuntarily leaving a career without a clear idea of what to do next, Pertuz offers four key steps.

Give yourself time to exhale. “Leaving a long-held role is an identity shift as much as a career one,” she says. Rushing to fill it can lead to what Ollinger did: going back to his old work identity before taking time to explore other options.
Get curious before you get busy. Take classes, volunteer, read, or arrange to chat with people in different fields. “Exploration is productive,” says Pertuz.
Document your story. “Many retirees underestimate their transferable skills. Write down your accomplishments, what lit you up and what drained you,” she suggests. “This helps clarify future roles and value propositions.” For example, experience in teaching, communications and event organizing can translate across multiple industries and volunteer opportunities.
Find a support network. Reach out to people doing the work you want to do. When Ollinger restarted his comedy career, he found comedians at his level to plan shows with and compare notes on podcasting. “LinkedIn, professional associations and alumni groups are helpful for this,” Pertuz notes.

Having been through this wringer, Ollinger has some advice of his own: Be patient with yourself as you figure out what comes next. “The first step is kind of declaring your values,” he says. “What do you care about? What are you willing to do for free? What are you willing to spend 10 years getting good at?” And if you wake up in the morning feeling good about the path you're walking, stay on it.

“It doesn’t mean you’re taking an easy path," he says, "but it’s the right one.”

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Reyna Gobel is a personal finance and wellness writer and author whose work has been published by The Atlantic, Reuters, Harvard health, WeightWatchers.com and Today.com.