What prevents remote workers from nomading? People are naturally attracted to travel, it's in our genes to move, to be attracted to what's different. However, we face two obstacles preventing us from taking action on those inner desires: fears and high expectations.
Fear is what prevents you from going on a journey. Expectations prevent you from enjoying the journey, from learning to adapt.
Fear is usually overcome by having travel buddies or some sort of mentor figure. My parents told me the basics of living on the road, for example.
Expectations are harder to deal with. It's about your mindset, and overcoming the disappointment from unmet expectations is an introspective work.
When the founder of the Pléiade Joachim du Bellay traveled to Italy, the epicenter of Renaissance Humanism, he hoped to find transcendence. The mix of his a priori, ambition and preconceived ideas about Italy resulted in severe disappointment, which later led to the creation of his collection of poems The Regrets.
Travel comes with disillusions. Nomading is not fundamentally better than sedentism, it's an entirely different way of life with its own issues. Have an open mind. Be willing to adapt to make the most of the experience, no matter what.