I quit my job to scale my side hustle. I've earned over $800,000 in 5 years on Fiverr by raising prices and optimizing my profile.

Tech Insider : Business, Style, Travel
Harlan Rappaport
Harlan Rappaport.

Ed Fortunato

I'd become the kind of adult my younger self would have pitied. A weeklong Arctic retreat helped me find my way back.

Tech Insider : Travel, Business
Stephanie Pensa is taking a selfie in Norway.
Stephanie Pensa was feeling lost and went on a hiking retreat in the Arctic to help her reconnect with purpose.

Provided by Stephanie Pensa

I quit my 40-year marketing career and became an EMT at 61. This is a role AI will never take.

Tech Insider : Business, Environment
A man sitting on the edge of the back of an open ambulance, posing and smiling.
Stephen Condon left his marketing career to become an EMT at 61.

Courtesy of Stephen Condon

I flip homes in the Hamptons. I made $360,000 on Airbnb last year, and I use brand partnerships on Instagram to save money on renovations.

Tech Insider : Business, Style
Blythe Graham-Jones stands in front of ktichen sink
Blythe Graham-Jones found that her project management skills, acquired during a first career in advertising, helped her excel at buying, renting, and reselling homes.

Courtesy of Blythe Graham-Jones

I quit my teaching job and earn more money as a freelance writer. Here are the 5 keys to my success.

Tech Insider : Business
headshot of Steph Mickelson
I quit my teaching job to be a writer and I've never been happier.

Courtesy of Andrea Anderson

I left my teaching job to become a freelance writer. I doubled my income in just 4 months.

Tech Insider : Business, Politics
Ryan Crawley
Ryan Crawley, a former elementary school teacher who left his job to become a freelance writer.

Courtesy of Ryan Crawley

I left a career at Amazon and Microsoft to start a hedge fund. After raising almost $10M in my first year, I'm never going back to Big Tech.

Tech Insider : Business, Environment, Style
Stephen Wu's headshot with the NYC skyline blurred in the background.

Courtesy of Stephen Wu

I was a graphic designer for decades and went back to school at 60 to become a teacher. It pays less but is more rewarding.

Tech Insider
Stuart Fuller wearing glasses and a black shirt and smiling at the camera against a plain background, the image is black and white.
Stuart Fuller went back to school at 60 to pursue teaching.

Photo credit: Simon Puschmann

A self-employed Gen Zer shares why she isn't planning to go back to working for anyone else

Tech Insider : Economy, Economy
A photo of Rachel Wells
Rachel Wells made a career pivot to being fully self-employed.

Courtesty of Rachel Wells

I used to be a public school teacher. Now I work as a 'middleman' government contractor and can travel when I want to.

Tech Insider
Wes Fisher in Dubai
As a middleman, I can make good money managing government contracts and still have the freedom to travel and work on other projects.

Wes FIsher

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