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Sam Dogen retired 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 status — an acronym for 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 to contribute more to the Silicon Valley startup scene. He got a job as the head of content at a startup, where he wrote articles and newsletters.
But within a few weeks, he already knew the job wasn’t working out. He said he was frustrated by management, struggled to return to constant meetings and Slack messages, and had a strained relationship with some employees. He decided to leave his position 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 has 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 and moved to San Francisco, where he made 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 the Dogens chose to be stay-at-home parents in the years after retiring, they had various income streams beyond their investments. Dogen worked side gigs as an Uber driver, a startup consultant, and a tennis coach, with passive income coming in from his book and blog. His wife also taught piano lessons. Their side hustles have allowed the family of four to have a yearly budget of about $280,000, about a quarter of which goes toward their 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.
Though he loved staying home with his kids and prioritizing his passions, Dogen 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 after selling much of their stock and bond positions.
A short-lived new job
Dogen took a part-time position as the head of content at a fintech startup in San Francisco, hoping to stay for a year before renegotiating a full-time position. The pay was solid, though he said it wasn’t enough to motivate him to go beyond expectations.
He 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 he craved feedback 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 having his articles edited frequently with few compliments.
Because he lacked editorial control, Dogen felt he lost his voice and personality as a writer. 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 videoconferencing 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 that he’d 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 also said he was met with microaggressions at work, which he didn’t experience a decade ago. Shortly after he started, he said 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 at a restaurant over an etiquette decision, which he perceived as culturally insensitive.
Calling it quits
Dogen acknowledges that working at a seed-stage startup wasn’t a great fit, as the work is “endless,” given the product hasn’t launched yet. He said the culture was more stressful than he experienced at his past jobs and that 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.
He ultimately decided to leave the company just four months in, which he described as an “unceremonious ending” to his brief return to the corporate world. He said if he started working when his daughter was in school, he would’ve had a much easier time staying, but 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 since he’d found tenants for his previous house and his stock portfolio was outperforming. In a worst-case scenario, he figured he could sell one of his four investment properties or other assets.
Dogen said he hopes to spend time with his daughter before she starts school and find peace with retirement again. He has a book about millionaire milestones coming out in spring 2025, 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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Source: finance.yahoo.com