An early retiree who earns $380,000 annually in passive income returned to work but quit after just 4 months.

Sam Dogen, who sold a portion of his stock and bond portfolio to buy a house in cash, discovered that he had insufficient passive income to cover his family's expenses.

Since both of his kids would soon be attending school full-time, the 47-year-old millionaire founder of Financial Samurai decided to head back to work.

Dogen's reader introduced him to a fintech startup in San Francisco, which seemed perfect. He would write content about helping couples build wealth, something he was passionate about. He would only need to work 20 hours a week and receive a six-figure salary. They also allowed him to have flexible hours. He began working in November 2023.

He called it quits by March.

It was discovered that the specific job he had taken on did not align with his personal or financial priorities at present. Although he believed working for a seed-stage startup would be thrilling, it turned out to be chaotic. Moreover, he was thrilled to produce content for the company but found the CEO's editing style to be overbearing. Additionally, the meetings appeared to be non-stop.

Dogen laments that it could have been a perfect fit, saying, "It's too bad."

The positive aspect of the false start is that I discovered what I don't desire.

Here's what he would have done differently.

The luxury of quitting

Not everyone has the ability to quit a job they don't like without something else lined up. Dogen would be the first to acknowledge that he's in a unique financial situation.

Dogen sold income-producing investments to buy his dream home, resulting in a $100,000 hole in his budget.

Dogen says, "I was feeling anxious about it, but a few things happened to alleviate the pressure."

Dogen found renters for his previous home, which he had planned to sell, who paid approximately $9,000 in monthly rent, thus filling a significant gap in his passive income.

Financial wellness leads to happiness, wealth, and financial security.

Additionally, he completed writing and revising his second book, which not only brings him a portion of his book deal money but also guarantees future passive income.

He received a six-figure cash distribution from one of his real estate investments, which gave him the cash cushion to paper over some short-term cracks in his finances. However, this won't produce passive income unless Dogen reinvests it.

What Dogen's looking for next

Dogen faced issues due to his managerial style. One of the main complaints was the excessive number of meetings, which interfered with his writing work. He found it challenging to adjust to the high level of management.

Dogen, a successful financial blogger, found the process of receiving numerous edits on his submissions to be demoralizing.

Being away from the kids was tougher than he expected, especially with his younger child starting full-time school in the fall.

"Since I've been a stay-at-home dad since they were born, I thought I would find it easier to break away and go to the office and not spend time with them, because I need that reprieve — something different to do," he says. "It was the exact opposite."

Dogen plans to search for his next job once both his kids are in school full time this fall. Here are three things he plans to do during his search.

1. Set boundaries

Before starting work at a company, it's challenging to determine how a manager operates, but you can establish some guidelines before accepting an offer, Dogen advises.

"He plans to establish clear boundaries and expectations before accepting the offer, stating, "Monday, Wednesday, Friday: these are my days, it's 20 hours," and possibly implementing time limits or project-based work."

2. Find the right company culture

Dogen now understands that going back to work at a seed-stage startup was probably too much for him to handle. "It was complete madness," he says.

Dogen may consider seeking his next job opportunity at a later-stage startup or a mature company, even if it is not popular among the San Francisco tech community.

"Dogen remarks that people who work at big-name tech companies are often mocked because they work fewer hours and earn substantial salaries. He adds, "That sounds great to me.""

3. Prioritize his kids

Dogen is contemplating whether securing a high-paying tech job would address his issue of being separated from his children.

"Dogen suggests that a more fulfilling job role may be outside of the startup, tech, and AI industries, and instead in education, specifically in an educational role at his children's school. This way, he can be part of a community, get paid, and see his children during the day occasionally."

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