- Seven professionals shared how they knew it was time to switch careers.
- They left industries including finance, law, tech, and even space exploration.
- Personal fulfillment, work-life balance, and pursuing passions drove their career transitions.
Planning a career pivot raises some big questions: in which direction should you move, how do you make the shift, and, crucially, when is the right time to do it?
In 2025, Business Insider spoke to professionals who made mid-career pivots, including some who did so more than once.
Some left the corporate world to pursue their dreams, like a former Goldman Sachs banker-turned hiking guide. Others went the opposite way, such as the frontman of a deathcore band, who now works in AI at Microsoft. One even walked away from a career as an astronaut for something a little more desk-based.
Here's how seven of them knew it was the right time to make a change.
Shireen Eddleblute went from working in investments to becoming a children's book author in her 50s.
Courtesy of Shireen Eddleblute
A couple of years after losing her mom, Eddleblute was feeling lost. In her 50s, after a decadeslong and fulfilling career in investments, she knew it was time for a change.
Eddleblute wanted to build something that could outlive her, so in 2024 she decided to pursue her passion: writing kids' books on financial literacy.
When she started out as a children's author, she knew little about writing or publishing. But, she told Business Insider in August 2025, "It's one of the best decisions I've ever made."
Read more about Eddleblute's career pivot.
Joe Spector, 45, lived out his childhood dream of working for JPMorgan. Then, he found startups.
Joe Spector is the founder and CEO of Dutch.
Courtesy of Joe Spector
When Spector moved to the US from Soviet Uzbekistan as a child in the early 2000s, he wanted to live the American dream.
For him, back then, it meant working on Wall Street. He started his career at JPMorgan in 2002. While the pay was lucrative, he didn't love the "rinse-and-repeat" work or the "boiler room" atmosphere.
He left in 2004, did an MBA, and found the world of startups. First he co-founded Hims, and has since launched another successful company: Dutch.
Spector told Business Insider in October 2025 that startups "showed me how fulfilling it could be to create products that improve people's lives."
Read more about Spector's career pivot.
Matt Jones, 35, was the front man of a deathcore band before he pivoted to Big Tech.
Courtesy of Matt Jones
Jones dropped out of school to be the front man of the band Martyr Defiled and toured the world. While life on the road was fun, it was also hard work and not as lucrative as he would have liked.
The band split when he was 28, and it was time to find a new career. A friend's dad hired him to work in IT.
Fast forward several years, and multiple applications to Microsoft later, Jones now works in Big Tech as Microsoft's global cloud and AI leader for UBS.
"I think about how I ended up here all the time," Jones told Business Insider in September 2025. "My unconventional and nonlinear pathhas given me a perspective that's unique and valuable in the corporate world."
Read more about Jones's career pivot.
Aurora Bryant, 40, was a trial attorney. Now, she finds AI solutions for the legal data industry.
Aurora Bryant pivoted from working as a trial attorney to working in legal AI solutions.
Courtesy of Aurora Bryant
Bryant always wanted to be a lawyer. She spent 15 years in the profession, including a decade at the Department of Justice.
In her late 30s, she became frustrated by the DOJ's limited resources and motivated by a passion to find new ways to modernize legal work through AI and other technologies.
At 40, she took a role with Relativity, a company that uses AI to solve complex legal challenges.
Bryant's advice for those considering a pivot: "Before deciding what's next, you have to understand your goals, what you enjoy, and how you can best leverage your experience."
Read more about Bryant's career pivot.
Justin Pines, 42, pivoted three times — from attorney to rabbi to CEO.
Courtesy of Justin Pines
Pines became an attorney after attending Harvard Law School, which he saw as a "safe" career path, even though he dreamed of having a job that involved bringing Judaism to the world.
After working as an attorney for three years, he was looking for something more meaningful, so he decided to leave law and train as a rabbi. Then, a few years into working as an Jewish educator at a faith school, he pivoted again, to working at a think tank.
Not long after appearing as a guest on the Jewish Broadcasting Service, the CEO role was up for grabs. He got the job, and now hosts his own show on the network. "I feel blessed to love what I'm doing," he said.
Pines said that finding the right job for you involves finding balance between priorities like meaning, financial stability, and passion.
Ready more about Pines's career pivot.
Cliff Goldstein, 40, left behind careers in finance and tech to become a hiking guide.
Cliff Goldstein leads hiking adventures in the Catskills and Hudson Valley.
Courtesy of Hike with Cliff
Goldstein interned on Wall Street because his classmates were. He continued down that path, working at the now-defunct Credit Suisse and, later, Goldman Sachs.
While he enjoyed aspects of the finance world, the lack of work-life balance wasn't something he wanted in the long term. In 2013, at 27, he made his first pivot: into tech.
But Goldstein found working at tech startups intense, and he wanted to one day pursue his dream career: leading groups on trails around the Hudson Valley and the Catskills.
"I'd always thought that if I were ever in the financial position and had achieved enough in my corporate career, I could finally give myself permission to pivot," Goldstein told Business Insider in September 2025.
He became a full-time hiking guide in 2023, having reached his savings and investments goals. "I've never been happier," he said.
Read more about Goldstein's career pivot.
Tim Marshburn, 65, was an astronaut. He left NASA behind for a desk job.
Courtesy of Sierra Space
Marshburn had a career many kids dream of. As an astronaut, he completed five spacewalks and saw Earth from above.
After 18 years in NASA's Astronaut Corps, his time as part of the SpaceX Crew-3 mission made it clear to him, however, that it was time to explore something new.
"I was in my sixties," Marshburn told Business Insider in July 2025. "There were a lot of new, good people who needed to fly, and I didn't want to take their spots."
In 2022, Marshburn went into the private sector, taking a job as a VP with the commercial space company Sierra Space. The desk job is a little more "sedate" than life as an astronaut, but, he said, it was the right move at the right time.
Read more about Marshburn's career pivot.
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