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Key Facts

  • Seven professionals shared their career change stories, spanning ages 30s to 60s
  • Industries left included finance, law, tech, and space exploration
  • Primary motivations were personal fulfillment, work-life balance, and pursuing passions
  • Career changes occurred in 2023-2024, with interviews conducted in 2025

Quick Summary

Seven professionals shared how they knew it was time to switch careers, leaving industries including finance, law, tech, and even space exploration. Driven by personal fulfillment, work-life balance, and pursuing passions, these individuals made significant pivots in their 30s, 40s, 50s, and 60s.

The group includes Shireen Eddleblute, who moved from investments to children's book authoring at 50; Joe Spector, who left JPMorgan for startups; and Matt Jones, who transitioned from a deathcore band frontman to Microsoft's global cloud and AI leader. Others include Aurora Bryant, who pivoted from trial attorney to legal AI solutions; Justin Pines, who moved from attorney to rabbi to CEO; Cliff Goldstein, who left finance and tech to become a hiking guide; and Tim Marshburn, who left NASA for a commercial space role.

These stories highlight that career changes can happen at any age when driven by purpose and passion. Each professional faced the critical questions of direction, timing, and execution, ultimately finding fulfillment in their new paths.

🚀 From Corporate Ladders to Personal Passions

Several professionals made the leap from high-pressure corporate careers to pursue personal passions that offered greater fulfillment. Cliff Goldstein, 40, left behind careers in finance and tech to become a hiking guide. He interned on Wall Street because his classmates were doing it, later working at Credit Suisse and Goldman Sachs. While he enjoyed aspects of finance, the lack of work-life balance wasn't sustainable.

In 2013, at 27, Goldstein pivoted into tech, but found startup life intense. He had always dreamed of leading hiking groups in the Catskills and Hudson Valley. "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 said. He became a full-time hiking guide in 2023 after reaching his savings goals.

Shireen Eddleblute, 50, transitioned from a decadeslong career in investments to becoming a children's book author. After losing her mother, she felt lost and wanted to build something that could outlive her. In 2024, she pursued her passion for writing children's books on financial literacy. Despite knowing little about writing or publishing initially, she called it "one of the best decisions I've ever made."

"It's one of the best decisions I've ever made."

— Shireen Eddleblute, former investment professional

🎸 Unconventional Paths to Tech and Business

Some professionals took winding routes to reach their current success. Matt Jones, 35, was the frontman of the deathcore band Martyr Defiled before pivoting to Big Tech. He dropped out of school to tour the world, but the band split when he was 28. A friend's father hired him to work in IT, and after multiple applications to Microsoft, he now serves as the company's global cloud and AI leader for UBS.

"My unconventional and nonlinear path has given me a perspective that's unique and valuable in the corporate world," Jones said. His experience in the music industry provided him with a different viewpoint that he brings to his tech role.

Joe Spector, 45, took a different approach. He moved to the US from Soviet Uzbekistan as a child and dreamed of working on Wall Street. He started at JPMorgan in 2002 but left in 2004, frustrated by the "rinse-and-repeat" work and "boiler room" atmosphere. After earning an MBA, he co-founded Hims and later launched Dutch. "Startups showed me how fulfilling it could be to create products that improve people's lives," he explained.

⚖️ Legal Professionals Finding New Directions

Legal professionals also found new calling outside traditional practice. Aurora Bryant, 40, spent 15 years as a trial attorney, 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 modernize legal work through technology. At 40, she joined Relativity, a company using 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."

Justin Pines, 42, pivoted three times—from attorney to rabbi to CEO. After Harvard Law School, he worked as an attorney for three years but sought something more meaningful. He trained as a rabbi, then worked as a Jewish educator before moving to a think tank. After appearing as a guest on the Jewish Broadcasting Service, he secured the CEO role and now hosts his own show.

"I feel blessed to love what I'm doing," Pines said. He emphasizes finding balance between meaning, financial stability, and passion.

🪐 Leaving Space for New Adventures

Perhaps the most extraordinary pivot came from Tim Marshburn, 65, who left a career as a NASA astronaut for a desk job. As an astronaut, he completed five spacewalks and saw Earth from above. After 18 years in NASA's Astronaut Corps, his time on the SpaceX Crew-3 mission made it clear he was ready for something new.

"I was in my sixties," Marshburn said. "There were a lot of new, good people who needed to fly, and I didn't want to take their spots." In 2022, he joined Sierra Space as a VP. The desk job is more "sedate" than life as an astronaut, but he says it was the right move at the right time.

These seven stories demonstrate that career pivots can happen at any stage of life. Whether driven by personal loss, desire for work-life balance, or pursuit of passion, each professional found that understanding their goals and leveraging their experience led to more fulfilling work.

"Startups showed me how fulfilling it could be to create products that improve people's lives."

— Joe Spector, CEO of Dutch

"My unconventional and nonlinear path has given me a perspective that's unique and valuable in the corporate world."

— Matt Jones, Microsoft global cloud and AI leader

"Before deciding what's next, you have to understand your goals, what you enjoy, and how you can best leverage your experience."

— Aurora Bryant, legal AI solutions professional

"I feel blessed to love what I'm doing."

— Justin Pines, CEO

"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."

— Cliff Goldstein, hiking guide

"I've never been happier."

— Cliff Goldstein, hiking guide

"I was in my sixties. There were a lot of new, good people who needed to fly, and I didn't want to take their spots."

— Tim Marshburn, former NASA astronaut