My Biggest Retirement Mistake: Letting Self-Doubt Keep Me at Work

“Instead of celebrating my wins and my success, I had been fixated on what I didn't accomplish or what I didn’t do,” she says. “When I look back, I’ve done some amazing things.”

A first-generation college graduate, Johnson went on to earn a master’s degree in organizational leadership and work for a Fortune 500 company. But the impressive résumé couldn’t silence the critical voice in her head.

“That pesky little voice said, ‘Yeah, but you didn’t make it to the executive level or this dollar amount of gross income or this number in retirement savings,’ ” she says. “This fear is real. All these messages. I was just convincing myself that I’ve got to do more, more, more and that I don’t have enough.”

Her perspective began to shift when she received notice in late 2024 that her position was being eliminated. Her last day was Jan. 10.

Rather than plunging into a job search, she saw the layoff as an opportunity — a sign that it was time to embrace the retirement life she and her husband had planned years ago. “When I got the message about this job ending, I said, ‘You know what, God? I am going to fully let go and trust you.’ ”

Annette Johnson enjoys the screened-in porch at her townhouse in Ocean Pines, Maryland. Now fully retired, she says she regrets not stepping away from her corporate job sooner.

Matt Roth

‘I should be at the beach right now’

The past three years had been particularly challenging as Johnson found herself increasingly disenchanted with her work. “It’s the same corporate crap and the same superficial lens and effort,” she says of her last role. “It’s been exhausting, and I’ve felt the weight of it all.”

That realization helped her see the need for change. “There are plenty of ways for me to feed my soul without it being attached to soul-sucking work,” she says. “It just drains the life out of you.”

Looking back, Johnson wishes she had recognized earlier how her negative self-talk and distorted perspective about her accomplishments were holding her back from enjoying the life she and Rufus envisioned.

“I felt like I was working and not enjoying life. At work, I was like, ‘I should be at the beach right now,’ ” she says.

She’s also coming to terms with what she has achieved and realizing that “there’s nothing left to prove.” That’s brought her newfound peace and appreciation for what she and her husband have built.

“We sit on our screened-in porch with a glass of wine, and we just take it all in,” she says. “We envisioned this house down to the T. I pray and I meditate out there. We listen to music, talk and laugh with company.”

Her advice to others approaching retirement is straightforward: “I do believe it’s important to have a plan. But trust the plan and work the plan. And celebrate what you have put into the plan and your wins. Don’t let fear ruin your plan and your vision.”

What the pro says

Johnson’s experience highlights a common challenge many professionals face when transitioning to retirement — letting go of a work identity that has defined them for decades.

“What we often see with high-achieving professionals is that their sense of self-worth becomes deeply intertwined with their career accomplishments,” says Jacqueline Schadeck, a certified financial planner and founder of Golden Wealth Strategies in Bethesda, Maryland. “Even when they’ve met or exceeded their financial goals for retirement, the psychological hurdle of stepping away from that identity can be enormous.”

Schadeck says financial confidence is the foundation that helps enable that mindset shift. “In retirement, people need to see their portfolio as a source of income — providing a steady paycheck, just like their job did for years.”

She also recommends that people approaching retirement spend time visualizing and even practicing aspects of their post-career life well before they officially retire.

“Start building parts of your retirement identity while you’re still working,” she advises. “Develop interests, relationships and routines outside of work that will carry over after retirement. This helps create a bridge between your professional identity and your retirement self.”

For those who feel stuck, like Johnson — financially ready but emotionally unable to retire — Schadeck suggests working with a certified financial planner, a financial therapist or a retirement coach who specializes in helping people navigate this transition.

“The decision to retire isn’t just financial — it’s very personal,” she says. “Acknowledging that fact is the first step toward making peace with your new chapter.”