-
Sam Dogen took early retirement at age 34, returned to work after ten years, and retired again after four months.
-
Dogen sought additional income at a startup in San Francisco, but was met with micromanagement and stress.
-
He plans to focus on his family, a part-time job and a new book after he quits his job at the startup.
Sam Dogen, 47, retired from his corporate job in 2012, achieving FIRE — financial independence, retire early — but more than a decade later he returned to the office. Little did he know he would stay for just four months before retiring for the second time.
Dogen wanted to get back to work to generate some 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, writing articles and newsletters.
But within a few weeks, he knew the job wasn’t working. He said he was frustrated with management, struggled to return to constant meetings and Slack messages, and had strained relationships with some employees. He decided to quit his job without further ado and return to life as a stay-at-home dad — essentially retiring early for the second time.
“Everyone who’s retired has told me that it’s impossible to go back to work and take charge of someone else once you retire, but I had to experience it myself. And they were right,” Dogen said. “I doubt I’ll ever go back to work. At 47, going back to work sounds about as appealing as eating a bad apple.”
Early retirement, but still a part-time job
Dogen had always been frugal. At his first job at an investment banking firm, he shared a studio apartment, worked late to get free food in the office cafeteria, and saved more than half his salary. He climbed the ranks, moved to San Francisco, and earned more than $250,000 a year.
He survived seven rounds of layoffs at his company, but at age 34, he decided to retire with a net worth of nearly $3 million, achieved through an 80% savings rate, smart investments, a strong real estate portfolio, and additional income from his blog, Financial Samurai.
He negotiated a favorable severance package in 2012 and did not return to the office full-time for the next 11 years. His wife, who earned about $120,000 a year, retired a few years later at age 35.
While neither of them held full-time jobs in the years following their retirement, as they were both stay-at-home parents, they did have multiple streams of income outside of their investments. Dogen had side jobs like driving an Uber, consulting for startups and coaching tennis, with passive income from his book and blog. His wife also gave piano lessons. It’s allowed the family of four to budget about $280,000 a year, about a quarter of which is their mortgage and property taxes.
“I realized that it was actually really fun to have a side job where I could make money independently, without having a boss,” Dogen said.
Although he enjoyed staying home with his children and prioritizing his passions, he began considering returning to work for additional income in April 2023, with the goal of saving for his children’s future college expenses. He and his wife also purchased a new home in October 2023 after selling much of their stock and bond holdings.
A short-term new job
He took a part-time job at a San Francisco fintech startup as head of content, hoping to stay for a year and then renegotiate for a full-time position. The pay was solid, though he said it wasn’t enough to motivate him to exceed expectations.
Dogen said he was surprised at how much time he spent in meetings each day and how little time he had to actually focus on his work.
“I can’t believe how inefficient meetings are — any meeting over 15 minutes seems way too long,” Dogen said. “Anything over 30 minutes seems like a productivity killer.”
He also didn’t expect his tolerance for management and criticism to be so low. He said he craved criticism and guidance in his 20s and 30s, 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 his articles were often edited with little praise.
Because he had no editorial control, he said he lost his voice and personality as an author. Even after many rounds of edits, he said his colleagues rarely read his articles.
“I was over-managed, micromanaged, to the point where it was completely uncomfortable,” Dogen said. “Once you’re a consultant, you’re on someone else’s schedule. You have to be in those meetings. You have to be a responsible person because you report to someone else.”
It also took him time to get used to the constant communication during the day via Slack and videoconferencing apps, since he had his phone on sleep mode for most of the day before starting his job. He said he had gotten used to taking naps after lunch during his retirement years, but he said the expectation was that he would be reachable during all hours he was logged in. He said the sheer volume of chats he was participating in was also a “productivity killer.”
He said he’s faced microaggressions at work that he didn’t experience a decade ago. Shortly after he was hired, he brought a signed copy of his book to his office as a thank-you, but the following week he noticed his book being used as a monitor stand, causing him to avoid the office and work remotely. He also got into an argument with a coworker over an etiquette decision at a restaurant that he saw as culturally insensitive.
Quit
Dogen acknowledged that working at an early-stage startup wasn’t a great fit because the work is “endless” since the product isn’t yet launched. The culture was more stressful than he’d experienced at his previous jobs, and he said the unpredictability of his schedule was cutting into his time at home with his daughter. He said the company deserved a full-time employee in his place.
He ultimately decided to leave the company after just four months, an “unceremonial end” to his brief stint back in the corporate world. He said that if he had started working while his daughter was in school, he would have had a much easier time staying, although he felt intense guilt about working so many hours while also being a stay-at-home dad.
He thought he would be more than financially fit to walk away, since he had found tenants for his previous home and his stock portfolio was outperforming. In the 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 goes to school and find peace with retirement again. He has a book coming out in the spring of 2025 about millionaire milestones, and he hopes to travel the country doing book reviews. He also wants to get back to enjoying the “RE” part of the FIRE acronym.
“I’ve found that if I sit still for too long and do nothing, there’s a kind of existential dread that comes into my head, and that might correspond to a midlife crisis where I start asking myself, What am I? What is my purpose here?” Dogen said.
Are you part of the FIRE movement or do you live by some of its principles? Contact this reporter via nsheidlower@businessinsider.com.
Read the original article on Business Insider