I've worked remotely from 15 different countries. Here's what I've learned and what I'd never do again.

• Rhiannon Cook has visited 15 countries while working remotely in marketing over the last five years.
• Cook, who most recently worked from a tiny Italian town, likes programs catering to digital nomads.
• She talked to Insider about her adventures abroad, including what she's learned to do and not to do.

This as-told-to essay is based on a conversation with Rhiannon Cook, 34, about her experience working as a digital nomad abroad.

She most recently lived in the 2,600-person town of Santa Fiora, Italy, for a month via a digital-nomad program called Kino that aims to bring remote workers to towns "off the radar for most people." 

In addition to Italy, over the last five years, Cook has worked in Kenya, Thailand, and 12 other countries. She shared her preferred time zones, workspace necessities, and other lessons she's learned while living nomadically.

The conversation has been edited for length and clarity.

I have worked in marketing my whole career. In 2018, I was working for an advertising agency in Pittsburgh; my clients were in Atlanta. I would fly to Atlanta twice a month to meet them. Half the time, the client wouldn't show up because the traffic was so bad. So I would fly in and fly out the same day — and we'd still do the meeting virtually. 

I tried to convince my agency to let me go remote, but legal wouldn't let me do it. So I told them I was quitting.

At the time, startups were the only type of company I found that were open to fully remote work. Generally, startups aren't investing capital in offices anyways, so there is none to go into. When I told my first startup I wanted to work remotely from outside the US, they just wanted to know if it affected how taxes are paid and anything related to payroll. It didn't, so it was all good. 

I would ask startups whose jobs I was applying to, 'It says remote. Do you guys mean it? Cool, because I'm in Asia.'

I often choose digital-nomad programs over figuring out new cities on my own

I'm very comfortable going to other places by myself or with one other person and exploring that place on my own terms. But when you do that for six months, you get to a place where you would just love to have some people you can co-work with during the day and maybe grab dinner with at night.

When I started doing this in 2018, remote working like this wasn't as common as it is now. I knew no one else who had this life, so I started with a program to help take care of the logistics and take that off my plate.

Now, since more people have access to this life because of remote work, a number of companies have cropped up for this exact kind of thing. I've done a lot of different nomad programs both before and after the pandemic. 

I've worked remotely while in Croatia, Bosnia, Czech Republic, Portugal, Morocco, Vietnam, Malaysia, Singapore, Taiwan, Thailand, Laos, Japan, Chile, Peru, Colombia, Kenya, Rwanda, Mexico, Hungry, Ireland and Northern Ireland, Holland, Denmark, Germany, Spain, France, and Italy.

I don't think I missed any, but there is a good chance I might have.

I did Kenya, Mexico, Colombia, Peru, Chile, Vietnam, Thailand, Malaysia, Czech Republic, Portugal, and Italy with a program, the rest was either solo travel or group travel with friends.

These programs usually range between $2,000 and $3,800 a month now. When I was doing them more, they were about $1,850 including flights, so it made financial sense. The prices now mean that many people have US tech salaries and are coming from the big expensive cities.

I recently spent a month in Italy using one of these programs

I was in Santa Fiora for the entire month of October in 2022, via a program organized by a company called Kino. 

They had a real passion for these small communities in Italy. Those places are hard to access when you're just a nomad on the road or a traveler by yourself. It's hard to feel like you fit in. 

We had about 15 people there, which was really great, because some of the other nomadic programs had larger groups. That would completely overwhelm me. I got to know people well enough to figure out and sustain friendships.

For the entire month, it cost $850. That included some experiences and some other things, but mostly a space for co-working as well as my house. I had my own cabin in the woods — that was fantastic.

One of the activities included was hiring a driver to take us to Siena, which is one of the closest bigger towns. Then Kino's two founders gave us a tour. We had a whole day, and it was all included except for food.

Here's my advice for other digital nomads

Some of these programs I've tried — definitely not all of them — are designed to have maximum social-media appeal. 

I've seen that reflected in programs that set up their own workspaces and design them to look pretty — but no one who designed it has actually worked in the space. Think working spaces with chairs that don't have backs, bean bag chairs on the floor, or swings.

Those look very pretty, and I'm sure there are some people in their early 20s who can make it work. But I'm in my mid-30s and need lumbar support. People I travel with have laptop stands, external mouses and keyboards, and sometimes dual screens. If we show up and you have coffee tables with bean bag chairs, I'm asking for my money back.

Also, there are a lot of companies out there building long-term resorts where you only talk to other nomads. You don't really integrate with local communities. It doesn't really feel like travel. 

I would travel slower if I could do it over

When I started, I wasn't sure how long I would be able to do it. Now that I know remote work is always a possibility, I don't feel a rush to run through a place in four weeks like I did at first. 

Four weeks may sound like a lot, but remember you're working full-time, trying to keep healthy routines, and have life to deal with. Four weeks for me as a nomad is like five days for someone on vacation.

Personally, I would probably never do Asia again while working. I did that for five months. It was really hard because I'd have to wake up at 4 a.m. to take calls at the end of the West Coast day. Then I'd work until noon and try to have the rest of the day to myself. 

I do like that idea of being ahead. I do five to six hours of uninterrupted work while everybody else is sleeping. It's a wildly productive time because I can actually get stuff done instead of being bothered.

Why I chose a new home base in Mexico City

I stopped nomading last year — even though I did do six months of traveling. 

I've lived in Mexico City for two years as my home base. My apartment is here, I'm getting residency, my friends are here. 

But I still travel about three months out of the year.

I have furniture again. My wardrobe is not based on what I can fit in a suitcase. I don't really want to live that way anymore. 

I loved the ability to have lived that way for four years. It was an incredible gift. 

I got to go to a lot of places, but after a while I realized that my curiosity about other places was getting less interesting, and what I really was craving was consistent pillows and sheets that I could invest in.