The biggest mistake digital nomads make is treating trip planning like a vacation itinerary.

You need a system that accounts for visa runs, tax residency, banking requirements, and flight logistics. I learned this while acquiring Portuguese residency, running LTD in the UK, while hopping around Asia.

Now I map routes around bureaucratic deadlines, not just bucket lists.

The key? Track your days in each country, book accommodations with flexible cancellation, and always have a backup plan.