My main adjustment was to (mentally) let go of all my inessential belongings. Pretty much all my important things now fit in a small, maximum-legal-carryon-size

My main adjustment was to (mentally) let go of all my inessential belongings. Pretty much all my important things now fit in a small, maximum-legal-carryon-sized suitcase, along with a small backpack and the stuff that I wear on my body. This lets me live and travel loosely, whether hopping between Airbnbs in Europe or lucking into enticing month-long sublets back home in SF. If I get tired of my surroundings, I can pick up my life and move somewhere else in the course of a day. It's extremely liberating, both physically and mentally. (Of course, this presupposes that you don't have an SO or dependents.) It took me a while to figure out my optimal "toolkit". Productivity-wise, my essentials are a Roost dock, Logitech wireless keyboard, and Logitech wireless gaming mouse. Working from cafés is really great now. (And my shoulder pain is gone!) Productive travel advice: don't do hostels. Airbnbs are awesome, but only pick ones with private rooms that have a nice desk and chair. It's way more convenient than spending extra money on a coworking space (unless that's your thing). If you're planning to actually get work done, stay in a given city for at least two weeks, and preferably more than a month. Traveling to a new city always takes some adjustment. I started with $100,000, but that's way more than you need. (I just didn't have very many expenses over the course of my SV career.) When I was Airbnb-traveling in Europe, I think I spent about $30,000-$35,000 a year when all was said and done. This was very comfortable living in Western Europe though, and I probably spent about half to two-thirds of my time eating out. You can definitely do $20,000 or less a year, especially if you visit cheaper countries, sublet places for at least a month, and cook for yourself more. If you have more than, say, $10k in savings, put some of it in FDIC-insured accounts with ~1% returns (e.g. Ally), and invest some of it index funds (Vanguard). It's basically free money unless you happen to invest right before a major recession.