Redirecting.work
Rebekah Jackson
Redefining Retirement - at 50
The Moment of Change
Rebekah Jackson never had a rigid life plan. Her career had unfolded organically, with opportunities arising, doors opening, and decisions made along the way. But one thing she and her husband had always been clear on: she would retire at 50.
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With a husband nearly two decades older, they knew their time for shared experiences—travel, adventures, even everyday moments—would be shorter than most couples’. If they wanted to enjoy those years together while he was still active, her career arc would have to be different.
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And so, at 50, she stepped away from a successful career in tech. Not to start a consulting business, not to take on a passion project that would morph into a second act, but to embrace true retirement.
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“I’m not working. I’m not trying to work. I’m not seeking anything that I would classify as work,” she says. “I’m just focused on me and the people in my life.”
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A Practical Yet Unplanned Journey
While Rebekah’s career had never followed a structured plan, her early retirement wasn’t something she stumbled into. She and her husband had made key choices—sometimes instinctively, sometimes strategically—that laid the groundwork for financial stability.
They lived below their means. They relocated to lower-cost areas, ultimately settling in Meridian, Idaho. When an acquisition threatened job security, they preemptively moved out of the Bay Area to avoid being tied to an expensive mortgage.
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Her husband had already left the workforce at 50, becoming the primary caregiver for their children as she took increasingly demanding roles. Her husband’s shift from career to home life was pivotal, helping lay the foundation for Rebekah’s future retirement.
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She hadn’t mapped out every detail, but she had built flexibility into her choices. And when the time came, she was ready.
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The Joy of Unstructured Time
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The first thing she did in retirement? Nothing.
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She turned off the alarm clock. She let go of schedules. She spent two weeks resisting the urge to fill her calendar, allowing herself to simply be.
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For someone accustomed to a fast-paced, goal-driven career, this was a radical shift. “I’m the kind of person who literally would have a color-coded schedule,” she admits. “Vacuuming Wednesdays at 10 a.m.—that kind of person.”
But slowly, she adjusted.
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She and her husband planned driving trips, with Costa Rica on the horizon. She spent time with her father, who lived nearby. She even took pleasure in cleaning—decluttering, making space, creating a home that felt lighter and freer.
This wasn’t about escaping work. It was about detoxing from a lifetime of doing and learning how to simply live.
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Writing as an Unexpected Path
One thing she hadn’t anticipated? How much writing would become a central part of her life.
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During COVID, she wrote a novel—a young adult story about a 16-year-old girl struggling to define her own superpower. The premise was personal. The protagonist could instantly recognize others’ strengths but struggled to see her own. Writing became a bridge - connecting her to her daughter, an avid reader.
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The story took on new meaning when Rebekah retired. She had spent years guiding others, helping teams succeed, and navigating corporate challenges. But stepping away from work made her reassess her strengths. Writing became her creative outlet, a way to stretch her intellectual muscles and explore a different side of herself.
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She immersed herself in the craft, joining critique groups and learning the industry. She’s now seeking a literary agent while drafting her second novel. More than just a personal project, writing is an exploration—giving her a way to share meaningful insights in a format that resonates.
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She had wrestled with the question every writer faces: Why my voice?
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Her answer? “Each of us brings a unique perspective,” she says. “Young adulthood is such a formative time, and stories can have a profound impact, helping young people see themselves in new ways.”
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Rethinking Success and Achievement
Retirement forced Rebekah to reconsider what success actually meant to her.
For decades, success had been measured in promotions, projects completed, problems solved. The corporate world rewards more: more responsibility, more recognition, more upward mobility.
But what if success wasn’t about climbing higher? What if it was about defining life on your own terms?
For her, success became about being present. Being fully engaged in conversations with her husband. Being available for her children. Being creative without pressure.
Society often defines achievement in external terms—titles, salaries, accolades. But she realized success could be something simpler, yet far more meaningful: living intentionally.
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Advice for Those Considering a Similar Path
Rebekah doesn’t believe her path is the right one for everyone. But for those considering early retirement—or simply reassessing their priorities—she offers this advice:
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Clarify what truly matters to you. Priorities shift over time. Understanding them helps guide your choices.
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Redefine success. Don’t let societal expectations dictate what achievement should look like.
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Live below your means—and be willing to move. Sometimes financial freedom requires trade-offs.
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Consider part-time work as a transition. It can help bridge the mental shift from work to retirement.
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Make a list of things you want to do. When you finally have free time, you may struggle to fill it—having ideas ahead of time helps.
A Life Well-Lived, on Her Own Terms
Rebekah’s story isn’t about reinvention. It’s about embracing the space to fully be herself.
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She’s not looking for the next big thing. She’s not chasing a new identity or trying to replicate her past career in a different form. Instead, she’s spending time with loved ones, traveling, writing, and being present.
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Her pivot wasn’t about what’s next. It was about what’s now. And that, she says, is more than enough.