Japan, side projects & being a Hobo CEO: Talk with Chris Kirkland

Chris Kirkland speaking at Pecha Kucha Tokyo

Hobo CEO Chris Kirkland speaking at Pecha Kucha Tokyo

Chris Kirkland is one Hobo CEO we can all learn from. He started moving around after an extended vacation in Goa in 2004, at a time when there was practically no information to be found about the nomadic lifestyle. It’s extraordinary to meet someone who started so early and managed to maintain this lifestyle for many years, while also staying interested in the philosophical aspects. And the amount of hype you see around being a nomad these days makes Chris’ advice even that much more valuable and unique.

Chris has been working remotely since 2004, using self-learnt IT skills and while also launching various side projects. Two of those, ArtWeb (a web hosting platform and a gallery for artists) and TokyoCheapo (a popular knowledge base for traveling Tokyo on a budget) have really taken off. Others side projects, like the HOBO CEO podcast, were left drifting at sea, keeping their listeners with no captain. And that’s exactly the way it should go: pick your winners and leave behind (or freeze) the projects you think will provide limited value.

Listen to the full interview here:

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A few insights from this interview:

Chris prefers the term Hobo CEO to digital nomad. For him, not taking yourself too seriously is critical as you embark on a nomadic journey. He prefers surprising people with what he can do and build, to creating hype and making declarations that might result in disappointment. As a side note, I feel just like him about this. Hype and declarations result in promises that can’t be fulfilled, or shouldn’t be fulfilled. A declaration is an attachment of sort, and attachments are not very nomadic.

Chris understood that skills are key to sustaining the nomadic lifestyle. His IT skills allowed him to take the first plunge into nomadism by working remotely, and he says life would have been much more difficult without developing a core skill. We will later discuss his transition from remote work for clients to building products and services that can scale. He aspired to own his time, rather than work by the hour. BecomeNomad recently discussed this important mindset change and evolution in our digital nomad careers episode.

How to find an idea that will make a successful business

At some point in this interview, Chris mentions that we are extremely lucky to live this lifestyle. Up until recently, the Hobo CEO life of constantly changing locations while generating income could only be done by the ultra-rich. He brings up a great point that we should be grateful for this opportunity.

Chris expands a little bit about Japan, a fascinating destination that seems to become a home base for many who visit it with no intention of staying. Japan is full of surprises, and not as expensive as you might assume. He saw this gap between people’s perception of Japan, which was the reason he launched both TokyoCheapo and JapanCheapo. Those gaps are what make a business successful. Find a need and deliver a solution that “doesn’t suck”.

Communities over location

We discuss a theory about forming tribes and communities while traveling. Chris reached a sort of equilibrium where his main consideration of where to move next is linked to the people that he will meet up with once there. For Chris, the people he shares time with are more important than the location itself. He made me think about the importance of keeping in touch with the people I connect. In the future, I may try to either pick locations where I can find the people I care about or try to schedule a meet up with them in a location that works for all of us.

Test the waters before venturing out to sea

Chris shared outstanding insights about his way of sustaining himself working on fun side projects, which can then become his main project, but only after trial and error. Anyone with interest in business can benefit from the mindset Chris adapted. He won’t decide what his main project will be, until sending a few small ships out to sea. This allows you to see which one doesn’t sink, and that one will be worth doubling down on time and resources. Test the water before you burn all your other ships.

We also spoke a little bit about the benefits of intermediate fasting. Chris has been experimenting with fasting way before it became trendy and shares his insights. He also shares his experience with some other ultra-experimental exercises with fasting and sleep, some of which he doesn’t recommend doing today. In any case, whatever you do, you should consult with your physician before you try it.

The interview ends with a discussion about the importance of discipline and tactics to achieving your goals by taking into account our psychologies. For more, check out Chris’ blog at www.MrKirkland.com

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