You can do everything (but you probably shouldn’t) — I thought I’d learned everything I needed to know about launching a business from my first venture. But my second business had other ideas. This time it was different for two important reasons: I was entirely solo, whereas the first was a joint business with my wife, Charlie Brown. It…

Condensed into a 3-minute read — Nearly two and a half years ago I took my minimalist lifestyle to the next level. I sold my house, car, and pretty much everything else I owned and left the UK for a life of perpetual travel with only one suitcase (and a Charlie Brown) for company. My bag…

If you’re thinking of changing direction maybe you can relate — I feel like a hypocrite. A couple of months ago I hosted a workshop at a Digital Nomad conference to help people pivot their careers in a new direction. As I have already had 5 different careers, this is a subject that is well within my wheelhouse. I focused on…

And it’s not just about the money — Applying lifestyle deflation — continually pushing for an ever lower cost of living — is the most powerful way to forge a simpler, more meaningful life and achieve your financial freedom. But it takes guts. Society, friends, family, will judge you hard if you reject societal norms and start trading…

Avoid these behaviors and you can live a successful life on the road — The Digital Nomad lifestyle is about as different from a cubicle career as it is possible to get. Gone are the office politics, presenteeism, and all the other corporate BS. Becoming a Digital Nomad was one of the best decisions I’ve made in my life. But that doesn’t mean it’s…

But here’s a dose of harsh truth — Some people seem to have it all together. In their early 20s they’re already saving and investing, with the goal of retiring by the time they hit 30. I was not one of those people. I had terrible money habits. I blew a $20,000 paycheck in a day. I assumed…

I swept my answers under the rug and my business became a burden — How did I not see it at the time? I was so excited to be my own boss, that I glossed over a lot of the major problems I knew were there from the start. A few years later I suddenly realized that instead of setting myself free, I had…

Normalizing debt by calling it good is harmful and wrong — We have our ideas about good debt and bad debt all wrong. The argument goes that good debt is debt that makes you money. Buying a house using a mortgage would count as good debt because you are using debt to buy an asset which (should) appreciate in value and…

Would you? — “Sorry, sir, the card terminal is telling me I have to phone the security team immediately. This shouldn’t take too long.” At the register in a high-end audio store, I already know what the problem is. I’ve been on a spending spree around town, and my bank has blocked my…