When Is the Right Time for a Career Pivot? Lessons From Seven Unconventional Paths
Planning a career pivot raises fundamental questions: Where should you go next? How do you make the transition? And perhaps most importantly, when is the right time to do it?
In 2025, Business Insider spoke with professionals who made significant mid-career pivots—many of them unconventional, and some more than once. Their stories span finance, law, music, technology, entrepreneurship, faith, and even space travel. Together, they offer valuable insight into what prompts people to leave familiar paths and how they know when it is time to move on.
Finding Purpose Later in Life
After decades in investments, Shireen Eddleblute found herself searching for meaning following the loss of her mother. In her 50s, she made a dramatic shift, pursuing a long-held passion for writing. In 2024, she became a children’s author focused on financial literacy—despite having no prior experience in publishing. Looking back, she calls it one of the best decisions she has ever made.
Leaving the “Dream Job”
Joe Spector once believed the American dream meant working on Wall Street. After immigrating to the U.S. as a child, he joined JPMorgan in 2002. While the compensation was strong, the repetitive work and culture left him unfulfilled. After leaving in 2004 and completing an MBA, Spector discovered startups. He went on to co-found Hims and later launch Dutch, finding purpose in building products that improve people’s lives.
From the Stage to Big Tech
Matt Jones spent his early career touring the world as the frontman of a deathcore band. When the band dissolved, financial instability pushed him to consider a new direction. Starting in IT, Jones gradually built a corporate career and now works at Microsoft as a global cloud and AI leader. He credits his unconventional background with giving him a unique and valuable perspective in the corporate world.
Reinventing the Legal Career
Aurora Bryant spent 15 years practicing law, including a decade at the Department of Justice. In her late 30s, she grew frustrated by limited resources and outdated systems. Motivated by the potential of technology to modernize legal work, she pivoted at 40 into a role focused on AI solutions for the legal data industry. Her advice: understand your goals, what you enjoy, and how your experience can transfer.
Multiple Pivots, One Throughline
Justin Pines’ career path included three major pivots—from attorney to rabbi to CEO. Though law provided financial security, he longed for more meaning. Training as a rabbi brought him closer to that goal, and later opportunities led him to a leadership role at the Jewish Broadcasting Service. For Pines, the right role balances meaning, financial stability, and passion.
Trading Corporate Life for the Outdoors
Cliff Goldstein followed a traditional path into finance and later tech, working at firms such as Credit Suisse, Goldman Sachs, and multiple startups. Over time, the intensity and lack of balance pushed him to reconsider his priorities. After reaching specific financial goals, he gave himself permission to pursue his dream: becoming a full-time hiking guide in the Catskills and Hudson Valley. He describes the move as life-changing.
Knowing When to Step Aside
Tim Marshburn spent 18 years as a NASA astronaut, completing five spacewalks and multiple missions. In his 60s, he realized it was time to make room for the next generation. In 2022, he transitioned to a private-sector role as a vice president at a commercial space company. While less dramatic than spaceflight, the move felt right—both personally and professionally.
A Common Thread
Despite their vastly different paths, these professionals share a common insight: career pivots are rarely impulsive. They are often driven by a growing misalignment between values, lifestyle, and work—and by the clarity that comes from experience. Whether the shift happens at 28 or 65, the right time is often when staying put no longer feels sustainable.
For many, the biggest risk was not changing careers—but ignoring the pull to do so.