Why Working and Traveling the World Can Kinda Suck

Have you ever had an idea you were fixated on?

An idea so powerful, so enticing, you just know you’d be the happiest person in the world if only you could have X, Y, or Z.

If I only had that car, I could get this girl’s attention..

If I only had this computer, I’d be so much more productive..

If I only had this body type/masters degree/amount of money/new salad spinner.. my life would be complete.

Our economy is largely built on this fantasy. We will be happy.. once we get this next thing.

And typically it’s a marketer’s job to play up this fantasy.

In the past few years there’s no shortage of people living and traveling abroad playing up the digital nomad fantasy.

Just imagine. You’re in Bali surrounded by palm trees, rice fields and ocean breezes. You ride your scooter to your favorite organic cafe, open up your laptop and begin to engage your mind with work you love and all the coconut water you can drink.

If you asked me two years ago what would make me the happiest person in the world, I’d probably have said something like my description above.

And everyday I meet travelers on their one week, one month, or one year journey that say,

“Oh my God, you can work and travel? That’s my dream!”

I’m quick to follow with, “That’s what I used to think as well.”

First off, running your own business is fucking tough.

Second, doing it while “traveling” is like fighting two simultaneous, unpredictable battles, which are constantly in flux as you move to new places or tackle different projects each week.

To be clear, I still absolutely 110% support people quitting their jobs, traveling to places they’ve never been and starting a new business or side hustle.

But doing all of these, at the same time?

I don’t fully recommend it.

Here are the downsides from my 2 years of backpacking, van-lifing, digital nomadic experience.

1. Instagram Life Porn isn’t Real Life 

When you hear the world “traveling” or when you see an image of someone on the beach in their van, it will automatically fill your mind with fond emotions and memories of your fun-filled week long vacations or carefree weekend.

However the everyday experience of working and traveling abroad is not the same as your week of vacation.

In reality, traveling abroad or van life is just another backdrop in the never ending human process of trying to get your needs met.

“I’m hungry, I’m thirsty, I need to go to the bathroom, I need to do the dishes, do I have any clean clothes, where are we sleeping tonight?”

The difficulty of meeting these needs in an unknown place, often with unknown people, languages and landscapes can be a real challenge.

After 3-6 months (for me at least) the novelty of this new lifestyle wears off and traveling to your next destination feels like the same as if you’re back in the office doing TPS reports.

Okay it’s not that bad, but hear me out.

Before you know it, the incredible sunset over a volcano or the view on the remote tropical island looks awfully similar to the incredible sites you saw the day before.. and the week before.. and the previous month.

I found myself experiencing these incredible sights and “following my dreams” but it no longer shot the same amount of dopamine in my brain. I found myself wondering, “Why aren’t I fucking ecstatic right now?”

And I already feel guilty being privileged enough to go on this journey, but then I really start to feel like a piece of shit cause I’m not even thrilled about it.

And like a drug user, I need more dopamine for my nomadic fix so I share some photos on social media.

This inevitably makes me feel a tad better as I get to share a snippet of the experience with people I love from back home (and also random strangers on the internet) but it also perpetuates the cycle of never-ending travel lust.

But it’s never the same experience that someone projects on to your pictures.

Except that one time when my close friends from SF and I rode our vans down the Oregon Coast. That seriously felt like a dream state, but here’s the reality.

If you’re traveling, 99% of the time you’re not going to be with those close friends.

Which brings me to point 2.

2. Loneliness is Real and Relationships Are Fleeting

I’ve met so many incredible, loving, talented and inspiring individuals from all over the world while traveling.

This is truly a blessing.

These conversations and relationships can dive deep as you share and exchange ideas with people from different cultures and at different stages of life. Sometimes it makes you question your entire worldview and other times it helps you reaffirm your beliefs and gain perspective on things you’ve taken for granted.

The interaction may last 2 minutes, 2 days or 2 weeks, but 99% of the time.. it won’t last.

After a few months of traveling you realize meeting all these amazing people isn’t that amazing if you never see them again.

Sure you can ogle at their Facebook and Instagram posts from afar, but then you’re back exchanging real life and human connection for a digital hallucination.

I’m the type of person that loves to meet new people, but I wonder if it’s healthy to have my relationships consist of dozens of new people every week, that I never see again.

Something about that has become quite unfulfilling.

From an evolutionary perspective I wonder when in our 200,000 year evolution did we have this pattern of human relationships?

Meanwhile your friends back home are busy with their daily life. They don’t think to reach out to you, “cause you’re traveling” and if you get an international phone or SIM (strongly recommend it), then you no longer have your US #.

If you’re traveling alone sometimes meeting other people can be difficult, especially in major cities and while traveling in the US. Outside the US, the best way to meet people is by staying at a hostel, but a lot of the travelers you’ll meet there are in vacation mode, aka party mode.

Which leads us to point 3.

3. Your Environment Affects Your Energy

One of the biggest things I learned is that it can extremely difficult for me to compartmentalize my work and separate it from my immediate environment.

Doesn’t exactly make you want to put in a 12 hour workday, does it?

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:

  1. 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.


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

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.

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