7 people who switched careers in their 30s, 40s, 50s, and 60s share how they knew it was time to pivot

Tech Insider : Business
Cliff Goldstein and Tim Marshburn
Cliff Goldstein, left, became a hiking guide. Tim Marshburn, right, was a NASA astronaut.

Courtesy of Cliff Goldstein and Tim Marshburn

I asked 4 people how to break into AI, from a Microsoft PM to a Meta senior director. They shared the same, simple piece of advice.

Tech Insider : Business, Technology
From left to right: Mostofa Shakib, Patrick Leung, Sophia Sun
In 2025, I interviewed four tech industry professionals about how to break into AI.

Courtesy of Mostofa Shakib; Patrick Leung; Sophia Sun

I left my dream job as a trial attorney and pivoted into AI at age 40. It showed me the power of leaving my comfort zone.

Tech Insider : Business, Technology
Aurora Bryant
Aurora Bryant pivoted from working as a trial attorney to working in legal AI solutions.

Courtesy of Aurora Bryant

I quit my career at 40 when a diagnosis stopped me in my tracks. Prioritizing my health was scary, but it helped me redefine success.

Tech Insider : Business, Sports
Woman sitting on a wooden railing in a forest, smiling at the camera, wearing a sports top, shorts, and slip-on shoes.
Melissa Hoeppner quit her job last October to reevaluate her priorities and take care of her health.

Courtesy of Melissa Hoeppner

I pivoted into AI at Google in the 2010s. Here's my top tip for breaking into the field, now it's easier than ever.

Tech Insider : Business, Environment
Patrick Leung standing in front of a Google sign
Leung shared his top tip for breaking into AI with Business Insider.

Courtesy of Patrick Leung

I've worked in Big Four consulting and Big Tech. Both were stressful, but I know which I'd pick if I restarted my career.

Tech Insider : Business, Technology, Travel
Mandy Liu in front of a stone wall.
Mandy Liu worked at EY for two years and at Meta for three years.

Courtesy of Mandy Liu

I quit investment banking at Citi and professional tennis after burning out. I learned about when to walk away from a job.

Tech Insider : Business, Sports, Style
Vitoria Okuyama playing tennis, left, and the NYSE, right.
Vitoria Okuyama played tennis professionally before going into investment banking.

Courtesy of Vitoria Okuyama

I quit investment banking to work in Big Tech. My work life balance is better but it's harder to make friends.

Tech Insider : Business, Environment
Dana Schoolsky
After two years of working in investment banking this former analyst left for a job at TikTok.

Dana Schoolsky

4 steps to change careers after 40 if you're feeling completely stuck, according to a career coach.

Tech Insider : Business
Ashley Jablow
Ashley Jablow uses four steps to help her clients overcome feelings of " stuckness" in life and their careers.

Ashley Jablow

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