This essay reflects a conversation with Sam Dogen, a 48-year-old early retiree living in San Francisco, the author, and her stay-at-home father. Edited for brevity and clarity.
I stepped into retirement in 2012 at the age of 34, and my wife joined me a few years later in 2015, retiring at 35. Since then, we’ve mostly been relying on passive income and our investments.
Fast forward to 2023, and I found myself purchasing pricey homes—homes I didn’t really need—and it left me feeling stretched financially. This decision affected our lifestyle in San Francisco. As a family of four with two kids, our cash flow was tight, and it created quite a bit of tension for me.
Looking back, I sometimes think that early retirement may not have been the best choice. If I could speak to my 34-year-old self, I’d probably advise sticking it out for another five years and seeking a different work atmosphere. Honestly, before taking the plunge into early retirement, it’s important to chat with those who’ve been there and learn what they might have done differently.
Working for another 3-5 years would have made more economic sense.
During the bull market from 2012 to 2017, real estate and stocks flourished. If I had worked longer, I might have saved an additional million dollars—think about the possibilities! That could have added $40,000 a year to my passive income if I got a 4% return, giving me a much more secure financial situation now.
Instead of opting for early retirement, I could’ve potentially relocated within my company to places like London or Hong Kong. A change of scenery could have revitalized my work experience, colleagues, and social life. Looking back, I wonder if that might have made work more enjoyable and lessens those urges to explore different work cultures—like Asian or European environments—during my financial career.
The fear of not being able to properly take care of my family during early retirement was pretty intense.
I ended up selling stocks and Treasury bonds to finance a new home. My passive income dropped from about $380,000 to $230,000, and I couldn’t shake the thought of needing that liquidity and security to feel safe.
The fear was very real. It felt almost psychological—like losing my identity or purpose. One major risk of retiring early is the daunting thought that you might not be able to return to the workforce. When I landed a part-time position with a fintech startup toward the end of 2023, it alleviated some of that anxiety.
About 12 years later, back to earning and being part of a community? That was a huge relief. But after just four months, I chose not to pursue another job.
We definitely avoided the stress of endless meetings, micromanagement, and office politics. Interestingly, I managed to save around $10,000 a month, which helped make up for my lost income pretty effectively.
After retiring early, having children later in life changed the dynamics.
In a way, I might actually be financially worse off now. The upside? We got to have children. Trying to do that while working 60-hour weeks in a high-stress environment felt nearly impossible.
I genuinely wanted to embrace my role as a full-time dad during those crucial first years.
People really need to carefully consider their plans for children and how that aligns with early retirement goals if financial independence is the goal. Balancing those two can be quite a challenge.
If you can’t live on 50% of your salary for a year, you should probably keep working and saving.
During my early retirement phase, I relied heavily on investments and passive income to sustain my lifestyle. I often advise those contemplating early retirement to figure out how they could manage on 50% or even 80% of their income for a stretch of six months to a year.
Maintaining retirement benefits and health coverage plays a critical role in determining whether early retirement is viable. If you can’t sustain your desired lifestyle, it might be necessary to save more, invest, and possibly continue working.
There’s a wealth of resources out there—from early retirement websites to podcasts and books—aimed at helping those who wish to navigate this path.
Prepare yourself for a significant transition.
Not only should you provide at least a two-week notice, but it’s also vital to manage your finances wisely and secure a solid retirement package. If you can accomplish both, you’ll have a financial buffer during your transition to early retirement, which can prevent you from rushing back into the job market too quickly.
I’ve talked to many who jumped into early retirement, only to panic and find a job a few months later. The transition can be filled with uncertainty and self-doubt about the choices made; it’s a whole new life compared to what many have known.
I’ve shared my experiences on my blog, “Financial Samurai,” and I’m diving into these themes in a book I’m writing.
