I was successful but depressed at 41. I found a fulfilling side hustle in therapy, and negotiated a 4-day week to pursue it.

Tech Insider : Business, Environment, Style
A headshot of Ben Tye.
Ben Tye is the CEO of Gate One

BECKY MURSELL/Becky Mursell Photography

I drive for Uber and Lyft in Hawaii. I earn less than I did driving a cab, but this benefit keeps me coming back.

Tech Insider : Economy, Business
Richard Detty, a ride-hailing driver in Honolulu, wears sunglasses, a dark grey Hawaiian shirt, and a kukui nut lei while smiling and giving shaka signs with both hands.
Richard Detty drives for Uber and Lyft part-time in addition to his business as an Amazon seller.

Richard Detty

I quit my job at 54 to start a party boat business because I stopped feeling alive

Tech Insider : Business
A man with a beard and wearing a baseball hat smiles.

Courtesy of Jim Kukral; BI

I broke out in hives after severely burning out at my job — so I quit. I'm not willing to die for an early retirement.

Tech Insider : Business, Environment
headshot of a woman folding her arms in a black top
Audrey Wang

Courtesy of Audrey Wang

We're a married couple that runs an AI startup. We have no work-life balance, and that's OK.

Tech Insider : Business, Style
Jake Stauch and Tatiana Birgisson are pictured.
Jake Stauch and Tatiana Birgisson co-lead the AI startup Serval.

Serval

We're retired lawyers who started a podcast to figure out where to live. 5 years in, we've got a new idea.

Tech Insider : Travel, Business
A selfie of a couple with headsets and a mic.
Gilen Chan and Gene Preudhomme started a podcast to interview retirees about where they chose to settle.

Gilen Chan and Gene Preudhomme.

5 people explain how they broke into AI training and how much they make in their side hustle

Tech Insider : Business, Politics, Technology
A design featuring five individuals who landed AI jobs

Peter Intile, Jessica Hamilton, Fred Nau, Ryan Adams, Elizabeth Boyd; Getty Images; Tyler Le/BI

My wife and I met at a clown convention. Our retirement plan is to be Santa and Mrs. Claus.

Tech Insider : Business
Clowns on stage performing
Eric Zander-Hussey and his wife, Kolinda, have worked as clowns since 2011.

Courtesy of Eric Zander-Hussey

I left Florida for Spain. It's cheaper, but I miss being able to order from Amazon.

Tech Insider : Business, Politics
A woman takes a selfie on a Spanish rooftop holding a glass of wine.
Jennifer Cody Kemp is living the good life in Alicante, Spain.

Courtesy of Jennifer Cody Kemp

I was a senior director of GenAI at Meta. I have 4 tips for breaking into AI — including whether you need a Ph.D.

Tech Insider : Business
Devi Parikh smiling
Parikh quit her job as a senior director of GenAI at Meta in 2024.

Courtesy of Yutori

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