I retired at 34 and had to go back to work a decade later. I wish I'd stuck it out for 5 more years — here's why.

Tech Insider : Business, Environment, Politics
Smiling man in a light blazer with a blue shirt and pocket square, seated outdoors against a rock wall with greenery.
Sam Dogen wishes he had done a few things differently in early retirement.

Courtesy of Sam Dogen

I dropped out of college at 22 and started a business. Here's how I raised over $50 million and got Mark Cuban to invest in it.

Tech Insider : Business, Crypto, Technology
A man with his hands in the pockets of his black coat standing by a window overlooking a city.
Chen said the first few years after he left college were the most challenging of his life.

Courtesy of Injective Labs

I'm 90 and work at a convenience store. I make $14.90 an hour and money is tight, but I hope to retire.

Tech Insider : Economy, Business
Vince
Vince Scidone, 90, works at a convenience store chain in Oklahoma.

Katrina Ward for BI

I got a job at Google 2 years ago. Here's what's changed and my advice for new engineers entering Big Tech.

Tech Insider : Business, Environment
A man smiling and posing for a headshot in a black suit in front of a gray background.
Harsh Varshney has been a software engineer at Google for 2 years.

Courtesy of Harsh Varshney

I moved to the US for the American dream, then decided to leave it behind. It's too painful to stay.

Tech Insider : Politics, Business, Economy
Alice Lassman wears a Columbia graduation robe
Alice Lassman

Alice Lassman

I'm a former professional sailor-turned CEO living in Monaco. Here's a day in my life leading the Red Bull Italy SailGP Team.

Tech Insider : Business, Sports, Travel
Jimmy Spithill, the CEO of the Red Bull Italy SailGP Team
Jimmy Spithill.

Wendell Teodoro/Getty Images

This as-told-to essay is based on a conversation with Jimmy Spithill, the 45-year-old CEO of the Red Bull Italy SailGP Team, about his daily routine. It's been edited for length and clarity.

I used to spread out my PTO days to squeeze in weekend trips. Now I take a "Fellesferien" period every summer like they do in Norway, and I'm more well-rested.

Tech Insider : Travel, Business, Economy
Jessica Furseth embraces the concept of Fellesferien
" A little bit of Norwegian vacation spirit is something I'd recommend to anyone," writes Jessica Furseth, shown in Valencia, Spain in 2024.

Courtesy of Jessica Furseth

I'm providing my daughter with free childcare. How do I ask if I can move in?

Tech Insider : Business, Economy
Over the shoulder view of Grandmother's hands, braiding a little girl's brown hair in a domestic setting.
The reader (not pictured) wants to move in with her daughter's family, and wonders if she should ask.

Elva Etienne/Getty Images

I became a full-time content creator, but quit after I realized I was sacrificing my morals for a paycheck. It made me insecure and anxious.

Tech Insider : Business
Evelyn Ramli sitting in front of a window wearing a black dress with a drink on the table by her side.
Former influencer Evelyn Ramli took a pay cut when she quit content-creating and got a corporate job.

Photo courtesy Evelyn Ramli

I was earning $300,000 at Google and saving for early retirement — then I quit for a more flexible life. It changed how I view success.

Tech Insider : Business
A man standing in front of a light-up Google sign at one of Google's offices.
Tang initially thought he'd stay at Google for life.

Courtesy of Jim Tang

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