#21 Michael Henman from Nova Scotia, Canada

1. How and why did you choose to go nomadic?

I quit my corporate job in Tokyo last September and moved to Chiang Mai to focus on my online business. It was scary, but exciting at the same time. Even though my side hustle (flipping websites) was making some money, I had all these thoughts like, “What if I can’t make this work, and I end up just wasting a year?” or “What if I lose all my money and have to move back in with my parents at 35?”

I had some money saved up (and cashflow coming in from the websites I owned), but I think even if I didn’t, I was just done with the corporate thing and I had to try to make it work on my own.

I guess I’m more of a ‘stationary nomad.’ I have the freedom to travel when I want, but I choose to spend 10 months of the year in Chiang Mai because it checks most of the boxes: high-speed internet, low cost of living, a good business community, great food… The only thing I’m not thrilled about is the 200% tax on imported wine…

2. What was it like leaving your home country?

I’ve spent maybe six of the last ten years in Japan and three in Southeast Asia, so living overseas wasn’t new. But it was new to not have a job and be 100% working for myself.

It was tough leaving Japan, because I really loved living there, but it was way too expensive to bootstrap a business. I miss my friends, the food, the way the trains run exactly on time… But Chiang Mai is pretty great, so no complaints (except finding a decent bottle of Malbec).

3. What are your biggest struggles? Fears?

Since 90% of my business relies on search traffic from Google, I definitely have a lot of SEO anxiety. Like that overnight my websites will suddenly get de-indexed or lose rankings, and I’ll lose half my income…

But actually I’d say that my biggest fear is that I’m not growing my business fast enough. I’m reasonably happy with the growth that I’ve made in this past year, but honestly I expected to be much further along by now. I feel like since I’m older (I’m 34) and just starting out as an entrepreneur, I’ve got a lot of catching up to do!

4. How are you funding your lifestyle and what projects are you working on?

I make my living through buying and optimizing websites. My strategy has been to buy already-monetized websites that have a lot of high-quality content, and increase the earnings by improving search traffic, optimizing advertising, adding affiliate offers, building an email list, and repackaging the content to sell as ebooks or e-courses. When I reach the limit of how far I can grow a given website, I sell it for a profit.

Right now I’m mostly working on two websites in the leadership/team building niche, and I have a few other sites that are pretty passive. I have a business blog, ReturnOnConversion, where I (very sporadically) write updates about my business, and there’s also a guide on how to “flip” websites.

In May, I made the big decision to hire my first full-time staff by offering a 6-month internship. I hired Liza, who has been an amazing help. She’s a fantastic writer, has a great eye for design, and has contributed great business ideas that have helped grow my business. Her 6-month internship is coming to an end, but I’m hoping she might decide to stick around! (I know you’re reading this, Liza…)

5. What is the estimated monthly cost of living for one of your favorite locations? What lifestyle does that afford?

My monthly living costs (not including business costs) are usually around $1000 USD per month. When I first moved to Chiang Mai, I was spending a lot more, but I’ve downsized to a much smaller apartment that’s $250 per month. It has a kitchen, a really nice pool, and a decent gym.

Aside from business costs (Liza’s salary, coworking, web hosting, etc), my biggest cost is food and drink. A bottle of decent wine is at least $25 in Thailand, and I like to have a glass or two after dinner. I eat out for every meal except breakfast, and spend maybe 80 to 100 baht for a Thai meal and 200 to 400 baht for a good western meal.

I also bought a 125cc scooter a few months ago for $1,000, which lets me explore the area a little more. I spend around 150 baht a week on gas.

At this point, everything that I don’t spend goes right back into the business towards development and buying the next website.

6. What is your top tip for someone who aspires to earn money online and travel?

Get a job or apprentice with someone who’s successfully doing what you want to do. Take a pay cut if necessary, and go in with the mindset to learn and absorb as much as you can. If you want to do Kindle Books, offer to apprentice or do free work for someone who is already crushing it. I wish I’d done this myself, and I think I could have shaved a lot of time off my learning curve.

I’d also echo what a lot of other online entrepreneurs have said: take freelance gigs (copywriting, design, or whatever skill set you want to build) to cover your living costs while you work on the side to build up more passive income streams.

Any final thoughts?

If you’re just getting started, it’s so important to learn by doing. I meet a lot of people who want to start something, but they don’t know what. They end up overthinking it, and waste time when they could be getting experience.

It’s been just over a year since I quit my full-time job and flew to Chiang Mai to work on my business full-time. When I started, I had very different ideas of what I would be focusing on, and it took actually doing it to learn what would work. I’ve changed my business strategy quite a bit in just that short time, in ways that I didn’t expect (scrapping plans for a physical product, hiring Liza as an apprentice, building website brands). If I had waited until I had the perfect business plan, I would still be working at my old job.

I think the biggest thing is just to find something you’re interested in, and jump in. You’ll learn 100 times more than just reading, and you can always pivot later.