Rise of the Ronin

Mike Drak

SAMURAI WERE EMPLOYED by feudal lords in Japan. They were skilled in the art of combat and highly trained—the best of the best.

A ronin—meaning a “drifter” or “wanderer”—was a samurai who’d left his clan, usually when his master died. Upon leaving, he was free to use his skills to seek similar employment elsewhere or even to choose a completely different profession. A ronin then relied entirely on himself and his skills to get by. Most ronin were self-reliant, self-disciplined and very good at whatever they chose to do.

My friend Simon is a modern-day ronin.

Simon used to be like the rest of us, living by the rules and doing what was expected of him: graduating from university, securing a well-paying corporate job, getting married, buying a home, starting a family. He was careful with money—something his parents taught him—living within his means, paying down debt and saving as much as possible, so he could retire comfortably one day.

Things changed for Simon when his older sister became ill and he almost lost her. That experience served to remind Simon about what’s important in his life—his family—and what isn’t, which was spending most of his time working. He realized he was caught in a trap, trading his quality of life for money, and he didn’t want to play that game anymore.

He ran the numbers and calculated that he’d saved up enough money so he could work less and enjoy life on his own terms. He knew that he’d need to keep working to some degree to fund the lifestyle he was accustomed to, but now he could do work he enjoyed without worrying about how to pay the bills.

Because of the retirement assets he’s accumulated and the passive income it generates, Simon doesn’t have to make a lot of money. He just needs enough to cover his entertainment expenses and maybe put a little in savings. Simon can make $40,000 a year and yet have a happier life, one with less stress than his former self suffered while working for a bank making $200,000 a year.

How sweet is that?

Spending more quality time with friends and family, and doing work he loved, became Simon’s big “why.” His “why” gave him the confidence and courage to leave his well-paid corporate job to become a ronin and fend for himself.

His wife was supportive. But when he told his parents and coworkers what he intended to do, they thought he’d lost his mind and was going through a midlife crisis. They said he was crazy to give up what he’d worked so hard for, and it wasn’t going to turn out well for him and his family. But Simon was undeterred by the criticism and used his “why” to push forward with his plan. Today, these same people are in awe of what Simon has accomplished and some are a little envious of how happy he is.

Simon gets to call his own shots. He’s free to pursue work that’s interesting and meaningful to him. He works at multiple jobs at the same time, providing him with financial security and stability. When one source of income dries up or he decides he doesn’t like working there, he just moves on to something better. Having more than one source of income allows Simon to be picky when looking for something new to do, and it gives him more control over how and when he works.

These days, Simon would never do work that he doesn’t like, no matter how much it pays. He chooses how long he’s going to work at a particular place. He chooses when to take time off. He chooses the people he works with and the location he works at. No more brutal commute for him. He won’t tolerate a bad boss or a toxic work environment. While at work, his focus is on the job and learning as much as possible.

The pandemic was a massive trigger event for many workers. Forced isolation gave them a lot of time to think about themselves and the work they do. They realized how precious and short life is, and that it was a mistake to wait till they were retired to do all the fun things they’d planned. They know anything can happen and, if they wait, they could end up being physically unable to do the things they love to do. What if they got sick or their spouse died?

Because of the pandemic, many people decided they no longer wanted to waste their precious life working a stressful job, putting in their time while waiting to retire one day, so they could then be happy. This change in thinking led to the Great Resignation we recently witnessed.

But it’s far from over. I believe after a period of rest and reflection, together with a dose of reality, many of these folks will re-enter the workforce as ronin. These people want to continue to learn and contribute. They want to work for an organization led by someone they admire and for a cause they believe in.

Ronin like Simon don’t want to retire, although they could. They want to keep working, doing what they’re passionate about at their own pace and in jobs where they can call the shots. Quality of life substantially improves for people like Simon, when they’re able to cover their financial needs with both passive income and a paycheck from work they love to do.

Becoming a ronin changed Simon’s life for the better. If he could do it, there’s no reason you couldn’t do it as well. For the record, I’m teaching my kids to become ronin.

If you’d like to learn more about Simon’s story, download the free book I co-authored, Longevity Lifestyle by Design.

Mike Drak is a 38-year veteran of the financial services industry. He’s the co-author of Longevity Lifestyle by Design, Retirement Heaven or Hell and Victory Lap Retirement. Mike works with his wife, an investment advisor, to help clients design a fulfilling retirement. For more on Mike, head to Check out his earlier articles.

Do you enjoy HumbleDollar? Please support our work with a donation. Want to receive daily email alerts about new articles? Click here. How about getting our twice-weekly newsletter? Sign up now.

Notify of
Oldest Most Voted
Inline Feedbacks
View all comments

Free Newsletter