Self-Employed Expat Life in Japan
Choosing self-employment in Japan comes with a different set of challenges than working for a company. Beyond building a business, you're also learning how to navigate a different language, a different culture, and a different way of doing business.
In this episode, I was joined by guest co-host Keito Suzuki to compare our experiences running our own businesses in Japan, from building professional relationships to adapting during the pandemic and finding opportunities along the way.
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Building Trust in Japan
One of the biggest lessons I've learned is that introductions matter.
Trying to establish new business relationships on your own can be difficult, but being introduced by someone who already has the trust of the other person often changes the entire conversation. It's one of those cultural differences that isn't always obvious when you first move to Japan, but it becomes increasingly important the longer you live here.
Different Paths to Self-Employment
Although both of us became self-employed, our journeys looked very different.
We talked about what led us to leave traditional employment, why we chose to work for ourselves, and the trade-offs that come with having more freedom. Self-employment offers flexibility, but it also requires accepting uncertainty and taking responsibility for every part of the business.
Adapting to Change
Like many people running small businesses, we both had to adapt when circumstances changed.
The pandemic affected each of our businesses in different ways, forcing us to rethink how we worked and where new opportunities might exist. We also discussed how technology—including AI tools—has gradually become part of our daily workflow, helping with tasks that would have taken much longer only a few years ago.
Creating a Long-Term Career
One idea that came up throughout the conversation was the importance of continually building new experiences.
Whether you're creating online content, teaching, or running another business, each project becomes part of a larger story. Skills developed in one area often become useful somewhere else later, even when you don't expect them to.
Living in Japan has reinforced that idea for both of us. Long-term success rarely comes from one big opportunity. More often, it's the result of consistently learning, adapting, and continuing to build on previous experiences.
If you're self-employed in Japan—or thinking about making that transition—I’d love to hear about your experience. What has been the biggest challenge or the biggest reward for you?