My wife and I did things backwards. We married a year and a half ago, but still don’t have a home. Let me explain.

We travel for a living. Our business is online and we’re fortunate enough to be wherever we want, whenever we want.

And we’ve done just that. Bali, Thailand, Italy, France, Hong Kong, Malta, Las Vegas, Orange County, London and Barcelona are a few of the places we’ve called home over the last two years.

Everything we physically own we can carry in two suitcases and we never plan more than a few days, or one city ahead. That’s the rule.

Well, rules are meant to be broken. Tired of taking road trips with a Vitamix, we decided it might be time to find our nest. The problem is where?

How does one choose when they can be literally anywhere in the world? I started with the Economists guide to the “Best Places to Live”. That narrowed it down to three continents.

Half way there.

Talking to family, friends and anyone and everyone we met, we realized that nobody really had a system to which they chose their place to live.

95% were out of practicality. They had work or family there and simply didn’t have much choice. The few whom could chose inevitably lived close to home, thus in a way, opting not to exercise choice.

We suffered from yet another first world problem. What started as a blessing now seemed like a curse. We didn’t have the “luxury” of not choosing. The mere fact that my wife’s Italian and I Californian meant we would have to do some serious grinding, and put together a list of our top priorities.

Here they are:

Me                                                                                                    My Italian Wife
DEAL BREAKERS

• Price: Want a place where                                  Weather: Not too cold in winter. Hot summers.
  we can afford 1000 sq feet

• Safety: Would I think twice about                     Family: It’s gotta be close.
  my wife walking home alone at night?

EXTREMELY IMPORTANT

3. Opportunity: What about this city               Walkability: Can I live there for a week without having to drive?
   makes me want to be there?
4. Healthy: Food, air, fitness, lifestyle            Connection: What towns are nearby? How easy is it to get there?

MODERATELY IMPORTANT

5. Functionality: modern, walk score, ease of life        Ease of Travel:
   accessibility to daily life
6. Weather: Don’t care about temperature                     Nature:
   but I need sun!
7. English: Need to do business in my own language   Close to Water:
8. Taxes: I don’t want to get extorted                                Quiet: Even if in the city, need our own place to escape or detach

LESS IMPORTANT

9. Ease of Travel: Is it close to a major airport?          Safety: Not important… Batman will protect her
10. Long Term: Can I raise a family?                               Healthy: Good, organic food
11. Close to Parents: Sorry guys.                                     Healthcare
12. Healthcare                                                                      Long Term: Can I raise my kids?

It’s good that I married a woman whom doesn’t have the same priorities as me. Oops.

Then we each made an independent list of cities we thought would best fit the above.

Me                                                       My Italian Wife

MUST SEE

1. San Diego                            1. Milan
2. Boulder                                2. Bardolino
3. Antibes                                 3. Antibes
4. New York                             4. New York
5. San Francisco
6. Vancouver
7. San Luis Obispo
8. Milan
9. Beverly Hills
10. Portland 

    POSSIBILITIES

    1. Malta              1. Malta
    2. Monaco         2. Monaco
    3. Honolulu      3. Frankfurt
    4. Zurich            4. Prague
    5. London         5. London

Bad News: We didn’t have much in common for our top priorities.
Good News: We both agreed on several cities: Milan, Antibes, New York.

So we started our adventure. Given our proximity at the time of this writing, we decided our first stop would be Milan. It’s time to find a home!