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Sam Dogen retired early at 34, returned to work after a decade, and retired again after four months.
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Dogen sought extra income at a startup in San Francisco but faced micromanagement and stress.
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He plans to focus on family, side hustles, and a new book after leaving the startup job.
Sam Dogen, 47, retired from his corporate job in 2012 and achieved FIRE — financial independence, retire early — but over a decade later, he returned to the office. Little did he know, he would only stay for four months before retiring for a second time.
Dogen wanted to return to work for extra income as his children got older, and he felt he wanted to contribute more to the Silicon Valley startup scene. He got a job as head of content at a startup, where he wrote articles and newsletters.
However, within a few weeks, he already knew this job wasn’t working out. He said he was frustrated by management, he struggled to return to constant meetings and Slack messages, and he had a strained relationship with some employees. He decided to leave his position unceremoniously and go back to being a stay-at-home dad — essentially retiring early for a second time.
“Everyone who has retired has told me that it’s impossible to go back to work and take direction from someone else once you’ve retired, but I had to experience it for myself. And they were right,” Dogen said. “I doubt I’ll ever go back to work again now. At 47, going back to work sounds as appealing as eating a rotten apple.”
Retiring early, but still working side hustles
Dogen had always been frugal. During his first investment banking job, he split a studio apartment, worked late to get free cafeteria food at his office, and saved over half his paycheck. He rose the ranks at his job, moving to San Francisco and making over $250,000 a year.
He survived seven rounds of layoffs at his company, but at 34, he decided to retire with a net worth of almost $3 million, which he achieved through an 80% savings rate, smart investments, a strong real estate portfolio, and side income from his blog, Financial Samurai.
He negotiated a favorable severance package in 2012, and for the next 11 years, he didn’t return full-time to an office. His wife, who made about $120,000 a year, retired a few years later at 35.
Though neither held full-time jobs in the years after retiring, as both were stay-at-home parents, they had various income streams beyond their investments. Dogen worked side gigs such as Uber driving, consulting for startups, and tennis coaching, with passive income from his book and blog. His wife also taught piano lessons. It’s allowed the family of four to have a yearly budget of about $280,000, about a quarter of which is his mortgage and property taxes.
“I realized that having side hustles where I could make money autonomously without any boss was actually quite enjoyable,” Dogen said.
However, though he loved staying home with his kids and prioritizing his passions, he started to consider returning to work in April 2023 for some extra income, aiming to save up for his children’s future college costs. He and his wife also bought a new home in October 2023 after selling much of their stock and bond positions.
A short-lived new job
He took a part-time position at a fintech startup in San Francisco as head of content, hoping to stay for a year and then renegotiate a full-time position. The pay was solid, though he said it wasn’t enough to motivate him to go beyond expectations.
Dogen said he was surprised by how much of his day was devoted to meetings and how little time he had to actually focus on work.
“I can’t believe how inefficient meetings are — any meeting over 15 minutes seems way too long to me,” Dogen said. “Over 30 minutes seems like it’s a productivity killer.”
He also didn’t expect his tolerance for management and criticism to be so low. He said in his 20s and 30s, he craved criticism and guidance, but after publishing three articles a week on his blog for 15 years, he got used to being his own manager. He said he felt like a “caged bird” being told what to write about, and he felt “demoralized” after having his articles edited frequently with few compliments.
Because he lacked editorial control, he said he lost his voice and personality as an author. Even after many rounds of edits, he said his colleagues would rarely read his articles.
“I was overly managed, micromanaged, to the point where it was completely unenjoyable,” Dogen said. “Once you’re a consultant, you’re on someone else’s schedule. You need to be present for those meetings. You need to be a responsible person because you report to someone else.”
It also took him time to adjust to constant communication during the day on Slack and video conferencing apps, as he kept his phone on sleep mode for most of the day prior to starting the job. He said he got used to taking naps after lunch during his retirement years, but he said the expectation was he would be accessible during all hours he was logged on. He said the sheer number of chats he was in was also a “productivity killer.”
He said he was met with microaggressions at work, which he didn’t experience a decade ago. Shortly after he was brought on, he delivered a signed copy of his book to his office as a thank-you gesture, but the next week, he saw his book was being used as a monitor stand, which made him avoid the office and work remotely. He also got into an argument with a coworker over an etiquette decision at a restaurant, which he perceived as culturally insensitive.
Calling it quits
Dogen acknowledges working at a seed-stage startup wasn’t a great fit, as the work is “endless,” given the product hasn’t launched yet. The culture was more stressful than he experienced at his past jobs, and he said the unpredictability of his schedule ate into the time he could spend with his daughter at home. He said the company deserved a full-time employee in his place.
Ultimately, he decided to leave the company just four months in, an “unceremonious ending” to his short stint back in the corporate world. He said if he started working when his daughter was in school, he would have a much easier time staying, though he felt intense guilt for working so many hours while also being a stay-at-home dad.
He figured he would be more than fine financially to walk away, given he found tenants for his previous house and his stock portfolio was outperforming. Worst case, he said he would sell one of his four investment properties or other assets.
He said he hopes to spend the next two months with his daughter before she starts school and find peace again with being retired. He has a book coming out in the spring of 2025 about millionaire milestones, and he hopes to travel the country giving book talks. He also wants to once again enjoy the “RE” part of the FIRE acronym.
“I’ve realized that if I sit too still and do nothing for too long, there’s this kind of existential dread that fills my mind, and it could correspond with a midlife crisis where I start wondering, what am I? What is my purpose here?” Dogen said.
Are you part of the FIRE movement or living by some of its principles? Reach out to this reporter at nsheidlower@businessinsider.com.
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