When I arrive in a new city or country, I need to get my bearings before I sit down and plug into the matrix.

Once I can get into “work mode” I’d either be hiding alone in a cafe or struggling to concentrate while strangers from all over the world were laughing, meeting and making plans for their day.

My attention shifts from the conversations around me, back to the website copy I’m writing. Sometimes people will chat you up while you’re working, on your laptop but mostly I felt like I was operating in two different worlds:

An endlessly stimulating, adventure-filled, fully-present experience with people from around the world.

2. An endlessly complex, problem solving, nit-picking, internal dialogue, as you proof-read that email to make sure you are fully understanding and addressing the buzzwords your client in San Francisco just sent you.

Later that night I’d make an amazing connection with a stranger I meet.

“Oh my God this is my new best friend!!” I’d think to myself.

But when they ask if you want to fly to Cuba with them in two days (there’s not much wifi there) or join them on an off-the-grid island volcano hike, you remember, you’re not actually traveling and you won’t be spending anymore time together.

Peace!

It was only after I lost my laptop in Bali, that I realized how much of a travel experience I was truly missing.

Being fully immersed in the “travel experience” for three months was 10x more enjoyable than about six months of working while traveling.

4. Freelancing or ‘High-touch Consulting’ Is Tough Work

When people ask how my job allows me to travel I tell them “I work for myself” but have to quickly follow with, “but that’s a bullshit phrase because really I work for clients as a freelancer and consultant.”

Because I’m helping people articulate and grow their business in a way that both energizes them and resonates with the outside world, it can’t be completed overnight with a few emails.

I know some nomads have e-commerce stores or other “low-touch” businesses that don’t require customer calls, ongoing collaboration and project scoping as an ongoing endeavor, but that’s not how things go in my consulting work.

One of my friends often tells me I should “create a business where I don’t have to talk to anyone” but working with and helping people, especially new business owners, is the most satisfying part of my job.

I want a world filled with small businesses and new companies bringing value to the world, not just faceless/nameless transactions in a digital economy.

5. The Logistics War With Workspaces, Wifi, and Timezones

Tulum Art Club — The best cafe to work from in Tulum

As a freelancer working in the US, it can be tough to find a good work environment with solid internet, nice aesthetics, access to food/coffee and a decent social environment.

Working abroad those challenges are multiplied.

Co-working spaces are available in some cities, but they can also be sterile, isolating and overpriced.

I typically support local coffee shops and cafes, hoping that the money I spend on coffee and snacks will be exchanged for a decent wifi connection.

Unfortunately half the cafes I try the wifi doesn’t work and if it does work, sometimes it’s filled with other people who make wifi speeds crawl.

In Mexico City the other morning I had to go to four different cafes and spend almost an hour and a half dealing with terrible wifi, instead of getting anything done.

When I finally got settled, I was able to do the four hours of work I had promised my client, but then I was running late for my flight that afternoon.

I made it to the airport 45 minutes before my flight, only to be told I couldn’t get my boarding pass because I needed to be there 2 hours before a domestic flight.

The next available flight was at 6:00 am the next day so I spent my birthday, not on a beach like I planned, but alone in an airport.

I could go on and on with these first world problems in the developing world stories, but I won’t go into the details of food poisoning, theft, travel cancelations and bed bugs.

I remember one night being covered in sweat, hiding out in the upstairs corner of a sports bar in Vietnam at midnight.

It was the only place I could find with wifi after 10 pm, after I had been kicked out of a coffee shop and had to leave my Airbnb cause the wifi was crap.

My shirt is clinging to every inch of my back with sweat as I receive an email from the client,

“Sorry I can’t make the call today, can we reschedule for the same time tomorrow?”

“What the hell am I doing this for?” I thought to myself.

There are only so many meeting spots you can make with a 13 hour timezone difference so all I could really reply with was, “No problem, let’s do it the same time tomorrow.”

Then I started to think about what the generation before me was doing in Vietnam.

50 years ago nobody chose to go to Vietnam cause “they felt like becoming a digital nomad” and they weren’t complaining about their war with wifi. They were literally in the hell of war that most of us can’t imagine.

And so many other people in this world are living in their own version of hell, that I start to feel like a piece of shit again.

In Conclusion

It’s not that I regret giving this lifestyle a try or that I’m completely miserable, I just want people to know that this path is not all smiles and rainbows.

My freelance income is much smaller than my SF salary, but my life is overall more healthy and balanced than startup life in SF.

I’m extremely blessed to be in this situation, but I’m left pondering my own question that I ask many young person I meet.

“If you had all the money in the world and could do anything, what would you do?”

They often reply with some version of, “I want to see everything. Travel the world and visit every country.”

“And after you’ve seen every country and climbed every mountain, what then?”

They don’t know.

And sometimes it’s nice to be reminded you’re not alone.