Desmond DixonVentures · Investing · Global Life Learn from Dez

The second home theory

Own the places I’ll return to. Rent for the life I’m living now.

Buy a small number of second homes in places I can visit for one or two months every year, for the rest of my life. The primary residence can stay a rental, giving me the freedom to change cities as life changes.

Own
Lifetime return destinations
Rent
The current primary residence
Return
One or two months in the places I own
Live
Three to five months in Brazil and Thailand

The rhythm

Select the months I would be away.

April and October away every year, for life.

01 · Theory

Flexibility at home. Permanence in the places that matter.

RHorizon · this season

Rent the primary residence.

A primary residence serves the life I have right now. Career, family, community, and daily routines can change, so renting keeps that decision flexible.

  • Career
  • Family
  • Community
  • Routine
OHorizon · decades

Own the second home.

A second home serves a longer horizon. Somewhere I want to know deeply, return to across decades, and build traditions around. It is not a property that simply looks attractive today.

  • Traditions
  • Seasons
  • Depth

02 · Shortlist

Two places worth studying slowly.

Both offer a distinct reason to return each year. The next step is familiarity across seasons, not urgency.
01

Japan

Country life with Tokyo within reach.

Outdoor sports, mountain and countryside seasons, and occasional escapes into Tokyo.

  • Outdoor movement
  • Seasonal reset
  • City contrast
Best months
JFMAMJJASOND
02

Italy

Slow living near the Mediterranean.

Long meals, homemade food, warm seasons, and a pace that makes returning feel restorative.

  • Mediterranean life
  • Food and ritual
  • Slower pace
Best months
JFMAMJJASOND

03 · Long stays

Two places I stay in long enough to live there.

Three to five months a year, not a visit. Long enough for ordinary days, routines, and people. Long enough to learn whether owning would ever make sense.
BRLong stay · three to five months

Brazil

Family, language, and the life I am already building toward. The longest stay of the year, and the one that needs no reason.

  • Family and language
  • Citizenship path
  • Ordinary days
Best windowDecember through March · four months
JFMAMJJASOND
Brazilian summer. Warm weather and the months family is around.
THLong stay · three to five months

Thailand

Warm months, a training routine, and a cost of living that makes a long stay easy to repeat every year.

  • Warm all year
  • Training and routine
  • Easy to repeat
Best windowJune through September · four months
JFMAMJJASOND
Gulf side dry season, and the half of the year Brazil is not calling.

04 · Home

Brazil is home. It is not a deadline.

Brazil will always be part of my life. My partner is Brazilian, and I am working toward citizenship. That permanence does not create pressure to buy a place before the right city, season of life, and reason are clear.

Priority · belongingNo purchase date

05 · Buying rules

A home has to earn permanence.

The filter stays intentionally strict. Select what a place clears.
2 of 5
Two of five. Still a holiday, not a base.