The 1st 100 Days Trying to Work Around the World: My 4 Major Challenges & (Hopeful) Solutions

A metaphor for productivity on the road

The 1st 100 Days Trying to Work Around the World: My 4 Major Challenges & (Hopeful) Solutions

 “Everyone has a plan ’till they get punched in the mouth.” 

– Mike Tyson

Disclaimer: I realize I run the risk of sounding like an ungrateful ass for even bringing up today’s topic, but I assure you this is not me complaining. It’s me sharing a personal challenge that most “location independent” entrepreneurs don’t seem to fully disclose. I’d be doing you a big disservice if I didn’t bring it up. Thanks in advance for going into it with an open mind. I hope it helps.


100 Days Working with No Office (250 to go)…

I’m writing from the Transylvania Sunrise Express – my name for the 6:29 am 12-hour train from Romania to Bulgaria. We could have saved a few hours by bus, but I love trains (well, most of them). Plus, I could use some time to process the past few months.

100 days ago Chelsea and I finally did what we’d been talking about since we started dating a decade ago. We got rid of our (massively overpriced but lovely) 1-bedroom San Francisco apartment, sold our car and most our stuff, packed the remaining essentials into two 45-liter, 28-pound carry-ons (here’s what we packed), and hopped on a one-way flight to Buenos Aires to kick off a year around the world – and test out this digital nomad/location independent life the Internet seems to boast so much about.

We’ve always had a simple personal purpose for the trip… to do something deeply important to us that we knew we’d regret not doing later. To learn, explore and see the world before life tried to convince us it couldn’t be done. And hopefully inspire others to do some of the same.

Then, over the last few years, as Live Your Legend turned into the business and global community it has, with monthly meetup groups all over the world, a very cool new level of purpose sprouted – to run the business from the road and host LYL events and hang out with as many of you as reasonably possible along the way.

Since then we’ve met hundreds of you in dozens of cities in 11 countries, and have changed plans more than either of us can count. And I think I can add up on one hand the number of times we’ve successfully used a washing machine (don’t worry, we’ve hand-washed plenty!).

Here’s where we’ve been…

The map of where we've been April 29

We’ve done a lot of travel in the past (experiences have always filled the majority of our budget), but mostly for a month or less at a time, so we’re now in very new territory. Even the year-and-a-half I spent living in Sevilla, Spain has nothing on the (mostly) calculated chaos of the past few months.

While most people, societies and businesses seem to be hardwired to create as much comfort and certainty as possible, this year we’ve turned that on its head.

Our only certainty is uncertainty. Up until 3 days ago, we didn’t even know which country we’d be in next.

When it comes to running a business, this presents some (intense) challenges, and I certainly haven’t been immune to them. So today I want to talk about the reality of attempting to be “productive” (whatever that really means) and run a business while on the road.

Since so many people seem to aspire to the world travel/location independent/digital nomad lifestyle, I figured you all deserve an honest take on it.

(Then hopefully next week I’ll cover a bunch more of the fun and more personal travel lessons.)

But for now…

The Myth of The Productive Digital Nomad: My Challenges, Frustrations & (Hopeful) Solutions from Attempting to “Work from Anywhere”

1. The idea of a “productive digital nomad” feels like a bunch of s*#% right about now. 

And I say that with a huge “I told you so” smile on my face. 🙂 I’ve wanted to get this off my chest for a while, and no, this is not me complaining – I’m massively grateful the LYL business allows us the freedom to go on the kind of adventure I used to only think existed in books.

This is just me shedding a little much-needed honesty on something that gets massively over-glamorized on the Internet.

Building and running a business is hard enough while at home with a normal routine and a familiar, rather predictable environment. So is working productively towards anything meaningful. Throw in the awesome distractions of endless new places to explore and everything else that comes with a trip like this, and making progress on what Stephen Covey calls the Not Urgent/Important stuff starts to feel all but impossible – those things hardest to measure day to day, but usually most important in building a long-term impact.

I’ve barely even been able to get the weekly Urgent/Important things done (like working with the LYL team, writing this article and other necessary business maintenance) – hence my need for these long uninterrupted train trips!

Now, there’s nothing wrong with this. In fact, there’s no getting around it. If you’re going to go all-out in one area of your life, something else has eventually got to give. If it doesn’t, then you won’t enjoy either, and get subpar results from both – a waste on all fronts.

Yes, I realize I signed up for this and I wouldn’t change a thing (other than my expectations, which we’ll get to in a minute). I fully expected this to be my biggest challenge this year and had tried to anticipate it by planning to do fewer big projects – as if this trip and visiting our communities all over the world wasn’t big enough! But it was impossible to know what it would feel like until I was in it. Now I am, and this is me learning and adjusting.

Trust me, the Instagram pictures don’t ever tell the full story…

A view with jackhammers

One of my favorite offices yet, but you would have laughed at the irony of the jackhammers pounding the cobblestone from 7am-5pm all week, right below our balcony in Brasov, Transylvania.

But here’s the ultimate realization…

While most longer-term LYL projects are taking a back burner this year, this trip is one of the most Not Urgent/Very Important things my wife and I could be doing for ourselves, our relationship and our lives – something that many people talk about, but sadly never feel enough urgency to make happen. Getting to live that is priceless.

And on the business front, we’re getting to connect in person with so many of you, which is a Not Urgent/Important LYL “project” that would be impossible to achieve in my normal life in California. On top of that, I’m being forced to become a hell of a lot more efficient, which is also getting me to train the team to do things I probably should have a long time ago.

So, I’m not saying the uber-productive digital nomad life can’t be done (although I’m definitely not there yet, and I have some serious doubts about how smooth many make it sound).

I’m just calling a spade a spade, and giving fair warning to anyone who thinks they are going to set out to travel the world and start or build a business, that you’re welcoming an entirely different level of challenges in accomplishing what’s already incredibly difficult. 

There’s no way I could have pulled this trip off in the past few years while keeping LYL thriving (and not going totally insane), before we had a team and systems in place to make it possible. That took years of focused effort. And thanks to that, I believe LYL and our community will be stronger, tighter and more powerful at the end of this adventure, just in different, harder-to-measure (but arguably much more important) terms than first thought.

But that realization is coming with a massive mental adjustment, which I’m just barely starting to get my head around.

2. And while inspiration comes easy, creativity can be brutal. 

Usually inspiration and creativity (doing something with that inspiration) have come hand in hand, both on shorter trips and at home. This year has been surprisingly different.

While I’ve been inspired by someone or something at least daily this year (my favorite part about travel!), finding and creating the space to infuse that inspiration into my work has not been easy. It’s harder to sit inside and create if you could be outside swimming with a penguin (or whatever the once-in-a-lifetime cool distraction of the day might be) – who would have thought?? 🙂 And while I try to incorporate as much of it into my work today as possible, I know there’s so much more I can do with what I’m experiencing.

And that’s the exciting part. There’s this intangible “experience asset” that’s being built this year that I know I’ll be able to incorporate into future LYL (and other) projects for the rest of my life. I wonder what that’s worth?

Which is where #3 comes in…

3. Success is SO different, and expectations are a joke. Redefine (or totally remove) them.

The only realistic solution I’ve found is a massive reframe.

At home I had all kinds of numbers, charts and spreadsheets to objectively measure success in my personal and work projects (yes, my Achiever/Maximer strengths make me a little crazy). If I tried to keep to those same metrics and baselines this year, this trip would feel like a total failure and I’d return home probably wishing I never left.

There is no consistency on a trip like this. And everything takes waaaay longer. Wireless Internet often means a router plugged into an analog phone, causing an 11-minute video to take four days to upload; you budget 20 minutes to check finances but find fraud charges that consume four hours; a three-hour train arrives three hours late; you lose your driver’s license in Uruguay on day three of a 365-day trip; the vegetarian special is filled with pork knuckles; notarizing a document takes two cities over two weeks; 10 ATMs in three cities over three days don’t work (like in Argentina, causing us to convert a stray five Euro bill into Pesos to buy a couple empanadas), and so on…

So, after processing my newfound limitations, here’s how I’m redefining success…

This year personal success is…

Getting to see cool new places, meet interesting new people and have fun exploring the world with my wife (and urgently taking a writing break to look in awe as our train flies by the biggest endless rolling fields of little Bulgarian yellow flowers I’ve ever seen).

Priceless train views

This year Live Your Legend success is…

Getting to meet the passionate, interesting people that the numbers in my spreadsheets and Google Analytics so poorly attempt to represent. To actually hear and feel your challenges, fears, excitement, projects and incredible stories as we share a conversation, tea, beer, workout or elaborate local home-cooked dinner together, in the real world, all over the world.

Like during our traditional asado in the Argentine countryside with Matías, our Salta LYL Local host, and his family at his grandmother’s summer house (that lasted from 4pm to 3am). Or the traditional Filipino meal we had at another LYLer Lana’s house in the suburbs of Amsterdam a few weeks ago.

Matias the master of the mate

Matías teaching me how to drink maté, and sharing what it’s like to build a business in Argentina.

Before we left home, I had no idea how these experiences would make me feel. Now they’ve become the lifeblood of our adventure.

These things cannot be quantified. The only way to measure them is by feel. By smiles, laughs and (mostly) pleasant surprises. By me attempting to do an LYL event fully in Spanish (not pretty) or the look on my face when I saw the “Live Your Legend Ass-Kicker of the Month” pins that Laura and Krisztina, our Budapest LYL Local hosts, had thought up and created as prizes for their local group.

LYL ass kicker of the month in Budapest

Or the flooded apartment floor after the 6th failed encounter with a washing machine. Or perhaps the priceless look on Chelsea’s face when a man woke her up by pounding on our night train window at midnight yelling “Passport Control!!” somewhere along the Romanian/Hungarian border. And then when he did it again at 1:00am.

From this new perspective, so far both fronts have been a tremendous success.

4. Finding routine in no routine & removing rules.

I lived and died by my routine at home. Despite being an entrepreneur with nearly complete control of my schedule, I kept it very regimented. The first few hours of my day were totally scripted. That doesn’t exactly transfer over here.

Even though we’re usually renting Airbnb apartments a week at a time (which has helped tremendously, although that still makes for a lot of moving), the best days to explore, host events and catch up on calls, work or sleep are constantly changing.

So, like I heard a father of sextuplets describe as his key to success (and happiness)…

“The only real rule is to have very few rules.”

I know what I want to be sure I do nearly every day (explore with Chelsea, eat good local food, work out, write and meditate). Sometimes they all happen, sometimes they don’t. The fewer rules, the better.

Here’s the Real Lesson

As I write it all down, it starts to become so damn obvious (writing tends to do that).

I’m living and working differently this year, which means I’ll get different results. Results that require a totally different form of measurement, or perhaps the ability to stop trying to measure at all – and just be. To be curious of what comes of a new approach to a new year, instead of judging it by comparing today’s apples to last year’s oranges.

I’m realizing that this is the year of learning to appreciate and embrace the immeasurables, and being happy with that as an outcome in and of itself, which is something I’ve never been that great at.

So, that’s what I’m leaning into this year.

It’s taking adjusting, but it’s medicine I’ve needed for a long time. And you can’t beat a classroom like this. 🙂

So, at the risk of you thinking I’m an ungrateful ass for even talking about the struggles of balancing work on a dream trip like this, I’ve always been honest with you, and I would be doing you a big disservice if I kept it to myself. Every step has (often unexpected) challenges, and I share what I do with the intention of it helping you through whatever you might be struggling with right now. Today’s topic is no different.  

And if there’s a location independent digital nomad out there on the road who honestly believes they’ve figured it out, I’m all ears. Seriously, let me know your secret.

Until then, I’m done trying to quantify.

Now, I gotta go check out that medieval Bulgarian fortress on the hill over there.


P.S. You can learn more about the LYL World Tour and follow the adventure here.

And if you’ve  got any advice on how to handle the above challenges? Let me know in the comments.