I’m about four years away from leaving the U.S. and building the next chapter of my life in Europe, most likely Italy. So what does planning actually look like this far out?

In this episode, I walk through what I’m actively working on now, what I’m deliberately not doing yet, and why timing matters so much when you’re planning a move abroad.

We’ll talk about the financial runway before retirement, tax planning, Roth conversions, language learning, location research, scouting trips, healthcare, residency, and the difference between understanding the process now and collecting documents too early.

I’ll also get into the personal side of the decision: why I’m leaving, what I want life to look like after the move, and why this is less about “escaping” America and more about designing the next phase intentionally.

If you’re a few years away from your own move to Italy or elsewhere in Europe, this episode is about using that time wisely.

Resources:
CaesarTheDay® — https://caesartheday.com
Escape Map 7% — https://italy7percent.caesartheday.com
Visto Facile — https://vistofacile.caesartheday.com
Books — https://caesartheday.com/books

CaesarTheDay® — Retire Abroad. Live Better.

If you’re three, four, or five years away from moving to Italy, the move has probably already started — whether you realize it or not.

In this first episode, Caesar explains why the visa should not be the starting point, and why the bigger decisions often begin years earlier. From taxes, retirement timing, Roth conversions, and healthcare to language, location, housing, and the emotional side of leaving the life you already know, there are multiple clocks running at once.

You’ll also hear why choosing a town as a resident is very different from choosing one as a tourist, why learning Italian needs to start earlier than most people think, and why collecting documents too soon can be just as unhelpful as starting too late.

If Italy is part of your next chapter, this episode is about getting the order right.

Learn more at CaesarTheDay.com

CaesarTheDay® — Retire Abroad. Live Better.