Last year, after selling a chunk of his stock and bond portfolio to purchase a house in cash, Sam Dogen found himself with too little passive income to support his family's budget.

The 47-year-old millionaire founder of Financial Samurai had been retired since 2012, but now that both of his kids would soon be attending school full-time, he decided to head back to work.

One of Dogen's readers turned him on to a fintech startup in his local San Francisco. Everything seemed ideal. He'd be writing content about helping couples build wealth — right up his alley. He'd only have to work 20 hours a week in exchange for six-figure pay. They even let him maintain flexible hours. He started in November 2023.

He called it quits by March.

It turned out, this particular gig didn't align with his personal or financial priorities at this point in his life. Though he thought working for a seed-stage startup would be exciting, it turned out to be chaotic. And while he was excited to create content on the firm's behalf, he found the CEO's editing style overbearing. Plus, the meetings, it seemed, were constant.

"It's too bad, because it could have been a perfect fit," Dogen says.

But there is one bright side to the false start: "The good thing about this, is that I realized what I don't want."

Here's what he would have done differently.

The luxury of quitting

It's worth nothing that not everyone has ability to up and 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 situation financially.

By last year, his passive income portfolio, which includes stocks, bonds and real estate investments, among others, was bringing in about $380,000 a year. After selling income-producing investments to buy his dream home, Dogen estimates he had about a $100,000 hole in his budget to cover.

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

Chiefly, he found renters for his previous home (which he had been planning to sell) who pay roughly $9,000 a month in rent. "That shored up a huge hole in my passive income," Dogen says.

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He also finished writing and editing his second book, a feat that not only comes with an installment of his book deal money, but also the promise of passive income in the future.

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

What Dogen's looking for next

So why didn't things work out for Dogen? One of the major gripes was managerial style. "One problem was too many meetings. If you're a writer, when you're in meetings, you're not working," he says. "And it was really hard for me to adapt to too much management."

Dogen, who runs a successful financial blog, describes getting rounds and rounds of edits on everything he submitted. "It was totally demoralizing," he says.

Plus, he says, with his younger child slated to start full-time school in the fall, it was tougher than he expected being away from the kids.

"Because I've been a stay-at-home dad since they both 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 re-enter the workforce once both his kids are in school full time this fall. Here are three things he plans to do when searching for his next gig.

1. Set boundaries

While it's difficult to know how a manager operates before you start working at a company, you can negotiate some ground rules before accepting an offer, Dogen says.

"I've learned that I'm going to set clear boundaries and expectations up front before I take that offer, and just say like, 'Monday, Wednesday, Friday: these are my days, it's 20 hours,'" he says. "Maybe I'll do time limits for work, or I'll do it by project base."

2. Find the right company culture

In hindsight, Dogen realizes that returning to work at a seed-stage startup was likely biting off more than he was willing to chew. "It means total hectic chaos," he says.

Dogen says he may look for his next gig at a later-stage startup or even a mature company — even if the latter doesn't feel trendy among the San Francisco tech crowd.

"Everyone makes fun of people who work at [big-name tech companies], because they only work 20 or 30 hours and get paid tons of money," Dogen says. "I mean, that sounds pretty good to me."

3. Prioritize his kids

Still, locking down a high-paying tech job wouldn't solve the problem of being away from his kids. To that end, Dogen is considering whether money is the most important factor in his next gig.

"I think maybe a more fulfilling job role is completely out of startup, tech and AI, but instead, in education — specifically, an educational role where I'm working at my children's school," Dogen says. "That way I can be part of a community and get paid. And see my children during the day every once in a while."

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