I got laid off from Amazon 3 years ago, and it changed the entire trajectory of my life — I couldn't be happier

Tech Insider : Business, Travel
Ricci Armani doing standup comedy
Ricci Armani decided to go all in on comedy after Amazon laid him off.

Ricci Armani

I quit finance at 54 to go full-time with my matchmaking side hustle. I love having a career where being older is an asset.

Tech Insider : Business
Cassindy Chao headshot
Cassindy Chao now works as a full-time matchmaker.

Courtesy of Cassindy Chao

I quit my $390K tech job to start my own business. I still question my decision, but this is the first time in years I've woken up excited for life.

Tech Insider : Business, Travel
Shiyao Tang sitting on edge of couch
Shiyao Tang says she spent 5 months planning her exit from her $390K job.

Shiyao Tang

Meet a millennial who pivoted from a corporate marketing career to owning his own business. It came with a pay cut but offered more flexibility.

Tech Insider : Business
Lloyd Fisher is next to his vehicle, that says
Lloyd Fisher left his corporate marketing career to run his own business.

Courtesy of Lloyd Fisher

I made a drastic career pivot at 27 and regretted it. Here are 3 things I wish I had done differently.

Tech Insider : Business
headshot of a woman in front of a light brick wall
Justine Tello.

Courtesy of Justine Tello

I quit my job at JPMorgan to run a restaurant group with my dad. It's the best decision I've ever made.

Tech Insider : Business
Tom and Kassidy Angelo are cooking in their restaurant kitchen, seasoning a huge slab of meat.
Kassidy Angelo is pictured with her father, Tom Angelo. She said opening a restaurant with him was a once-in-a-lifetime opportunity.

Photo courtesy of The Louis Collection

I've made 5 career pivots across music, retail, and startups. I reset my goals every few years — but 1 thing never changes.

Tech Insider : Business, Environment, Technology
Ryan Edwards with a screen showing audoo's logo
Ryan Edwards, who was previously in a band, founded Audoo.

Courtesy of Ryan Edwards

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

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