Change one thing at a time. Being a nomad brings chaos to your day to day. If this is the road you want to go down, other variables need to be on lock. Don’t try to transition between responsibilities whilst traveling between countries.

Don’t say “I’ll be my own boss” without knowing exactly what you’re a boss of. Traveling constantly exposes you to (good) distractions whilst also being in pursuit of reliable infrastructure. Your work is the one thing that shouldn’t shift dramatically as you change locations. You need to have a strong vision of where you’re going, even if ultimately you have no idea where it’ll take you.

In practical terms, you should have a granular and established way of generating income. As I’m constantly on the road, notepads have become impractical, so I use two Trello boards to collect all professional and personal tasks. Whilst it doesn’t have offline capability yet, they are working on it. Your routine should be strong enough to be able sit anywhere and get into it within minutes, you need to have a system for work as opposed to simply being reactive to email.