Journey by House‑Sitting: A New Way to See the World

A San Francisco tech‑savvy professional, after almost a decade in a typical office job, owned a car, lived in his own house, had emergency cash and no debt—yet something felt missing. In 2022 he quit the job, bought a one‑way ticket to Italy, and decided to travel full time. What began as a short break turned into more than two years of roaming new countries, all funded by his savings.

The House‑Sitting Solution

To keep his money going and stay on the road longer, he discovered house‑sitting. The idea is simple: when a homeowner travels, the sitter takes care of the house—and sometimes pets—in exchange for free accommodation. Occasionally the host pays a fee, especially if animals are involved. This arrangement saved him from paying for hotels or rentals and stretched his budget.

Building a Global Network

His network grew while traveling. He found that the demand for house‑sitters is high not only in the United States but worldwide. He has now watched over homes and animals in more than fifteen cities, both domestic and international:

• Honolulu – Ocean views to wake up to
• Santa Fe, New Mexico – Sampling the culinary scene
• Chicago’s Gold Coast – Cycling along scenic routes
• Brooklyn (Greenpoint & Fort Greene) – Discovering hidden cafés

The freedom of this lifestyle is a major attraction. Rent, the biggest expense for many people, no longer worries him. By lining up his sits, he often avoids extra accommodation costs altogether. The experience has reshaped how he lives: staying in a house for longer periods lets him explore cities like locals instead of tourists passing through.

Trust and Connection

Relationships with homeowners are central to his journey. He values the trust placed in him and treats each home and pet as if it were his own. The generosity of hosts—who often go beyond the call of duty to make him feel welcome—is a highlight. The connections he builds are as rewarding as the places he visits.

Challenges on the Road

Living on a suitcase is not always easy. The next destination can be months away or decided within hours. Uncertainty and last‑minute cancellations add stress, but the flexibility he enjoys outweighs these challenges. He works remotely while juggling paid and free sits to keep traveling, unsure of when or if he will settle down.

The Road Ahead

For now, this itinerant life satisfies his desire to explore, meet people and discover new places. He still has a list of cities he wants to visit—whether through house‑sitting or other means. He does not see himself slowing down anytime soon.