💻 Business: Working Remotely From Anywhere — This Is What 19 Years of Proof Looks Like

Not a highlight reel. A photo archive. From Maui in 1998 to the Dominican Republic in 2022 — every place I've worked from, raised a child in, and built a business out of.

In 1998, I was 20 years old, standing in Maui, Hawaii with my 2-year-old son Tristan on my hip. I did not have a plan. I did not have a roadmap. I had a kid and the belief that life did not have to look the way everyone said it had to look.

Ten years later, I became self-employed.

And then I started going everywhere.

The formula was simple, even if executing it wasn't: self employment + traveling = bliss. That's it. That's the whole thesis. The photos below are the footnotes.

What follows is not a guide. It's evidence. Twenty-four years of evidence that working from wherever you want is not a fantasy reserved for a certain kind of person. It is a skill set, a decision, and in my case — a lifestyle I built one country, one casita, one beach at a time.

California — Where It All Started

White water rafting somewhere in the mountains. Sausalito. Marin City. Oakland. Placerville. Santa Barbara. San Francisco — the bay bridge, the view from the Golden Gate, the view of the city from across the water in Sausalito. Monterey. Los Angeles.

California was my base for a long time. It was where I grew up after my mother moved us from Puerto Rico, where I first learned that geography shapes you whether you ask it to or not.

Nevada & Arizona — The Desert Years

Las Vegas at its most theatrical. Valley of Fire, red and ancient and impossibly dramatic. Mt. Charleston, where you can drive an hour from the Strip and stand in snow. Hoover Dam. Lake Mead. Red Rock Canyon. The Grand Canyon in Arizona — we made exactly one stop.

The desert teaches you something the ocean doesn't: how to exist without green, without rain, without the comfort of familiar things. It's useful training for a nomad.

Florida — The Home We Kept Returning To

Melbourne. Orlando. Miami. Florida was our reset button — three times over the years. The place we kept coming back to even when we were trying to leave. Even from the road, it found ways to feel like home.

Panama — The First International Jump

The Panama Canal. Panama City. Isla Colon in Bocas del Toro — our boat drop-off to the jungle. Red Frog Beach, which is exactly as wild as it sounds. Boquete, up in the mountains, cooler and quieter than anything else in the country.

Panama was my first international trip, taken in 2013 with my sister, our brother who insisted two grown women with children needed to be supervised (we let him come), and zero experience doing anything like it. It cracked something open.

Costa Rica — Where Slow Travel Made Sense

Jaco in the early morning — "6am!! I could NEVER!!!" (I didn't write that caption. A photo from someone who was very much not a morning person.) Montezuma, our boat drop-off to catch a bus to Samara. Samara itself — the kids walking their pet pig down the road, which is a completely normal thing there and one of my favorite memories anywhere. San Jose. More of Jaco.

Costa Rica is where I understood what slow travel actually means: staying long enough to stop performing tourist and start living.

Mexico — Islands and Cities

Isla Mujeres: turquoise water, no cars, the best fish tacos I have ever eaten. Merida in the Yucatan, a colonial city that moves at its own pace and doesn't apologize for it. Sisal beach in Yucatan, quiet and local and utterly itself.

Belize — Ambergris Caye

Clear water. Barrier reef. The kind of place that makes you wonder why anyone lives landlocked.

Jamaica — Treasure Beach and YS Falls

Treasure Beach is where I understood that paradise doesn't have to be loud. YS Falls in Negril — water falling everywhere, green climbing everything.

Jamaica was, for me, the beginning of understanding what it means to be in a place that has its own rhythm and asking yourself to match it instead of the other way around.

Dominican Republic — Where This Blog Was Born

Las Palmas in Las Terrenas, steps from the beach. A casita on a loma built by a French family who arrived 23 years ago and never left. Playa Bonita.

The Dominican Republic is where I stopped traveling and started living. It is where I opened this blog and started writing things down.

That's where we are now.

And Where It All Started: Maui, 1998

Tristan is 2 years old. I am 20 years old in 1998. This was 10 years before I became self-employed and started purposefully traveling the world. It's just one of my favorite pictures of Tristan's (my 26-year-old) and my first vacation in Maui, Hawaii.

Everything in the photos above grew from that moment. One woman, one toddler, one island, one decade before the plan clicked into place.

If you're reading this thinking the life in these photos is not available to you — I want you to look at that last image again. I was 20. I had a 2-year-old. I had no money and no map.

You have more than you think.