How Traveling With My Dog Changed What Remote Work Actually Feels Like

The first year, I moved between two cities without him. Mexico City, then Medellín.

The work was fine. The wifi was fine. The cafés were fine.

At night was when it got harder.

I was waking up at 4AM convinced I was late for a meeting that hadn't existed for over a year. Monday mornings hit with the same adrenaline, the same low-grade dread, nowhere to put it. I'd left fourteen Slack channels, returned my badge, deleted the work email from my phone. Done, right. Except my body hadn't gotten the memo. The decompression, the phantom schedule, the dreams where I was still sitting across from my manager trying to find the words — I wrote about all of that here.

What I didn't write about was the quieter thing underneath it.

I missed Mochi. Just a low, steady absence. I knew he was home with my mother, fed and walked, sleeping somewhere he wasn't supposed to. He was fine.

But the apartment was just an apartment in a way it had never been when he was in it. Two cities, eight months, and not once did any of those places feel like I'd actually arrived somewhere.

By the end of year one, I'd made the decision. Flying a dog is complicated — carrier dimensions, health certificates, timing the paperwork to the departure date. I knew all of this going in. I started anyway.

Why Bringing Him Was the Harder and More Necessary Decision

The full preparation is documented here — what to file, when to file it, what the airport actually looks like when you show up with a toy poodle in a soft carrier. That guide covers the logistics.

What the guide doesn't cover is the six weeks of paperwork convincing you this is too much trouble, followed by the moment you remember what month eight in Medellín felt like at 11PM on a Tuesday.

That's the actual reason.

Mochi arrives somewhere and he's already home. First hour in a new apartment — he finds a corner, circles twice, lies down. The place has been decided. I'm still checking Google Maps for coffee shops two weeks in.

How I Chose Lisbon

City selection the second year had a different filter. Wifi speed and cost of living stayed on the list. They got company: does this city have a functioning pet rental market, or will finding an apartment take two weeks of explaining that a toy poodle is not a situation. Are the streets quiet enough that Mochi isn't on edge for every walk. Is there outdoor café seating where a dog is part of the arrangement.

Lisbon cleared everything. Príncipe Real specifically — hilly enough to keep the streets quiet, walkable enough that the vet, the café, the grocery store are all within fifteen minutes.

The airport confirmed it before we left the terminal. Lisbon Humberto Delgado has a dedicated dog bathroom — wc canino — water points, waste bags, disposal container. We used it within twenty minutes of landing.

Good start, Lisbon.

The Gear System That Makes Traveling With a Dog Actually Work

This took the most iteration to get right, and it matters more than most travel-with-pets content admits.

The problem is simple: the logistics double without the bag space doubling. One person, one dog, one airport situation — everything has to fit into a system that doesn't require unpacking to find anything in the first hour of a new city.

The 8807 backpack is the main carry. It's a backpack with enough structure to stay organized across a fourteen-hour travel day — laptop, cables, documents, and the full dog kit in the same bag without either side getting buried. The dog kit lives in its own section and doesn't move between trips: collapsible water bowl, waste bag dispenser clipped to the exterior loop, treat pouch in the front pocket, the stuffed toy Mochi has had since he was eight weeks old. Same position, every city, every trip.

The collapsible water bowl gets used more than anything else in the kit. Príncipe Real has bowls outside several cafés — but the bowl is for everywhere else. Long layovers, new neighborhoods before the dog-friendly spots have been figured out, afternoon walks when the heat arrives and nothing is close. It folds flat, weighs almost nothing, has been on every trip since month one.

The waste bag dispenser clips to the exterior loop. Reaching into a bag at the bottom of a carrier while managing a leash in an unfamiliar street is a specific frustration that a clip on the outside solves completely. It gets restocked before every departure.

The treat pouch stays in the front pocket, separate from everything else. Treat timing when traveling is specific — going into the carrier, clearing security, boarding. The pouch stays accessible and dedicated so none of that timing gets lost.

The stuffed toy goes in last, on top. On longer flights it goes into the carrier before Mochi does. By the time he's zipped in, it's already there.

A small carry-on handles everything else — clothes, toiletries, the items that don't need to be immediately accessible. The backpack is the operating system for the first few hours of any arrival. The carry-on is storage that can wait.

One backpack. One carry-on. One soft carrier. Light enough to manage alone through an airport with a dog, structured enough that nothing needs to be solved on arrival.

What the Third Month Felt Like

Mochi settled into the Príncipe Real apartment within an hour. Corner near the window, circled twice, done.

I was still figuring out the wifi password.

Within two weeks the coffee shop two blocks away knew his name. The man near the garden square stopped every morning — in Portuguese, which Mochi found acceptable. The woman at the small market asked where he was on the one day I came in without him.

None of it happened to me directly. It happened through him, and I followed.

By week three I had a regular café, a regular walking route, a regular morning. Things that took four months to establish alone in Medellín. The apartment stopped being an apartment around day ten.

The first year taught me what this life costs. The second year, with Mochi in the corner by the window, taught me what it can actually feel like.

Flying with a dog requires advance preparation. Airline cabin pet policies, country entry requirements, and health certificate regulations vary and change. Verify all requirements directly with your airline and official government sources before booking.