People Who Reinvented Themselves in Their 30s

Many people think their 30s are “too late” to start a new path.

I walked away from a good career at 32, and I’ve discovered many others who made big life transitions around their early to mid-30s. Here are some of my favorite examples.

Ram Dass

At 29, Richard Alpert was a serious tenure-track professor at Harvard, studying “achievement anxiety.” At 32, he was fired for exploring the study of psychedelics with Timothy Leary. He reinvented himself as a spiritual teacher, Ram Dass.

Gretchen Rubin

Gretchen Rubin went to Yale Law and ended up clerking for Sandra Day O’Connor on the Supreme Court. While clerking, she realized:

I’d rather fail as a writer than succeed as a lawyer.

She was at the start of a high-paying and promising law career. Yet she understood that if she kept going and never took a chance on becoming a writer, she would regret it.

Peter Thiel

Peter Thiel went to law school and then worked as a lawyer for less than a year before losing interest in the work. Then he went to Wall Street and lost interest there as well. In his late 20s, he ended up in California and shifted his attention to tech. You know the rest.

David Whyte

David Whyte was a successful naturalist. Growing up fascinated by Jacques Cousteau, this was his dream. Yet at around 30 he walked away and decided to become a poet. His book Crossing the Unknown Sea explores that journey, shifting from being a naturalist in the Galapagos to working in a non-profit to quitting without much of a plan to become a poet.

Michael Jordan

At 30, Michael Jordan decided to quit basketball and become a professional baseball player. He ultimately went back to the NBA, and there are many conspiracies about this move, but some think he was burned out from basketball.

Brian Koppelman

Brian Koppelman walked away from a “dream job” at 30 and wrote Rounders by 31.

Jeff Bezos

At 30, Jeff Bezos left Wall Street to start an internet company.

Albert Einstein

While Einstein was publishing research and giving lectures on the side, he didn’t move into academia until he was 30 and wasn’t a full professor until 32. Before that, he worked at the patent office, one of an endless list of people who went out of their way to protect the work that mattered to them.

Trung Phan

In his 30s, Trung Phan shifted careers to become a writer, blogger, and professional shitposter. When he came on my podcast, he described the moment it clicked:

the thing that really made me realize that I should just go fully solo was like building my own distribution… I should definitely try to go solo. and truly write about things that I care about and at the cadence I want

Michael Ashcroft

Two years after a burnout situation, Michael Ashcroft decided to leave his job in his early 30s to explore the creator economy and life outside of consulting. We recorded a podcast about the months before he quit. He told me:

as I progressed up the corporate ladder, I found myself kind of enjoying it less and less. I had a burnout experience around when I turned 30. 31.

I feel like it was a message from a part of me that knows or knew better than the rest of me knew at the time. Kind of, this is not the path.

Kyle Kowalski

In 2015, at 30, Kyle Kowalski was a marketing executive working 60- to 80-hour weeks when he hit what he calls an existential crisis. He spent the next two and a half years learning everything he could about life while still employed, then left his career in 2018 to start Sloww. We talked about it on my podcast, where he described those years:

I was at the peak of my career. I had my highest title. I was getting paid the most I had ever been paid.

Amanda Natividad

Amanda Natividad was a cook and worked in the corporate world in her twenties, then pivoted into digital marketing in her 30s. She went on to become VP of Marketing at SparkToro. She shared her story and some great advice on Twitter.

My own story starts here.