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.

Sat, Aug 30, 2025, 1:11 PM 5 min read

• Sam Dogen said the purchase of his current home brought him out of early retirement.

• Dogen suggests working longer during bull markets could have increased financial security.

• He advises testing living on a reduced income before retiring to plan for a smooth transition.

This as-told-to essay is based on a conversation with Sam Dogen, a 48-year-old early retiree, author, and stay-at-home dad based in San Francisco. It's been edited for length and clarity.

I retired at 34 in 2012, and my wife retired a few years later at 35 in 2015. We've been mainly living off our passive income and investments since.

In 2023, I bought an expensive home I didn't need, becoming house-rich and cash-poor. Buying this house affected our desired lifestyle in San Francisco. As a family of four with two children, we had less liquid or passive income, which made me feel quite uneasy.

In retrospect, retiring early was not the optimal career path. I'm 48 now, and if I were to talk to my 34-year-old self, I'd say stick it out for another five years and try to find a different work environment. Before anyone considers retiring early, I would suggest they speak to someone who has already done it and ask them what they would've done differently.

Real estate and stocks were in a total bull market from 2012 to 2017. If I had worked longer, I probably would've been able to save and invest an extra $1 million. That decision could've generated $40,000 more in passive income at a 4% return rate, and I would maybe be more financially secure now.

Instead of retiring early, maybe I could've gone to a different office within the firm, like London or Hong Kong. Changing offices could've reset my experience, colleagues, restaurants, clients, and travel.

That would've probably enabled me to enjoy work more, and I would never have to wonder what it would've been like to work in Asia or Europe during my finance career.

I sold stock and treasury bonds to buy my new house. My passive income went from about $380,000 to $230,000, and I kept thinking about how I could regain that liquidity and passive income to feel more secure.

The fear was intense. It's psychological, like a loss of identity or purpose. One of the biggest risks as an early retiree is that you can never get a job again. I kept that fear in check when I found a FinTech startup to join part-time at the end of 2023.