22 Things I’ve Learned as a Digital Nomad


Digital Nomad: individuals that leverage digital technologies to perform their work duties and more generally conduct their lifestyle in a nomadic manner….

Over 2 years have passed since I quit my job.

Despite the image of me sipping Mai-tais on the beach somewhere (which can happen), there’s a big discrepancy between what my friends think I’m doing and what I’m actually doing. I write this overlooking the stunning crystal-blue water of the bay in Kuta, Lombok, but there’s a difference between me and every other traveler here:

I’ve been working on my laptop for 5 straight hours.

Luckily, I’ve known for a long time that the vision of life outside the real world wasn’t ‘hanging out’ on a tropical island. The vision was to build the structure that would guarantee freedom to define and execute my own goals.

Michael Covel: “Your dream is what? To go sit on the beach…and have no knowledge no wisdom or anything and just smoke pot and sit there and chase girls…? Is that what you want to do? Is that really what you want to do? Or is that the idiotic version that has been sold by media for the last 20-30 years?
Dan: “It’s the fantasy of someone who hates their life…”
From: TMBA#45 How to Get Rich

Leaving the “real” world was not an escape from life but an escape from the inefficient or (in my view) flawed systems that would never produce the results I was looking for. As Tim said in the 4-Hour Workweek, “if the recipe sucks it doesn’t matter how good a cook you are.” I was tired of cooking in someone else’s kitchen.

From some shaky beginnings I’ve seen that success at this is not just possible, it’s inevitable–assuming you have the right amount of focus and continuously applied effort. My initial goal was simple: by the end of 2012 make enough money to break even, and to do that from anywhere on earth.

Exactly one year after quitting my job I hit this milestone. I started making more than I was spending, regardless of whether I was in California or Timbuktu.

In the following year it became clear that my life would never be the same.  Once you’ve tasted complete control of your time and trajectory, it’s impossible to imagine giving that freedom away for any amount of money.

“And believe me, when once your tastes have conformed to the tranquility of such travel, you will suffer real pain in returning to the turmoil of civilization.” – Sir Richard Burton, in Burton: A Biography…

But the only way to guarantee success in the long-run is to build a system that creates consistent income. This is what being a lifestyle-business-designer is all about, something I’ve aspired to be for a long time.

What follows are some of the most important lessons I’ve learned from this journey:

1. The hardest part is getting out the door.

getting out the door

[Photo: Packing for the latest trip]

Quitting your job, getting rid of most of what you own, and leaving home–this is scary stuff.

Even now, when I embark on a new trip I always have a day of “WTF was I thinking?”. Much of this has to do how the brain is wired: we hate losing things more than we like gaining something else  (loss-aversion). But action conquers fear, and you just have to go for it to get started.

After quitting my job and traveling for 6 months, sitting down to start making income on the internet was about as fun as a trip to the dentist. But after a day or two of digging trenches I was waking up at 6am with an excitement I hadn’t felt in years.

Sometimes it doesn’t matter what you do to get started—it’s best to do anything to get going. The only way to find the path you want to be on is to start moving in the general direction.

On checking out of the real world, my advice is this: make a plan, but don’t wait for all your ducks to be in a row. You probably won’t be making 100% of your salary from side projects when you step out the door, but guess what, you won’t need to (it’s cheaper out here) and there’s no greater motivation than necessity.

Don’t kid yourself that you’ll build a side-business quickly while still in your current job. Think you’re going to work for an additional hour or two each night after work, the gym, and any other responsibilities you have? Yeah right. Get the hell out of there.

2. Everything in life is a trade-off, but you can get it all in.

“Don’t you get sick of moving around all the time?” my friends ask.

Well, of course. But don’t you get sick of being stuck in one place?

Everything is at least a temporary trade-off. I am deeply aware that every minute I spend here is a minute I’m not building community or some kind of “life” back “home”. These are the trade-offs that I’m willing to accept to have this lifestyle.

There is no question as to whether or not it’s worth it.

How do I know this? Because I know exactly what my goals are and I’m marching toward them at an astonishing rate.

The big misconception is that the digital-nomad lifestyle is a temporary aberration and eventually I’ll have to stop doing this and “settle” down. I may choose to do that, but I might not either.

The major logical fallacy here is thinking in either/or propositions. For instance, you couldn’t travel and  build a business, or you can’t travel and have a home base. I might decide to start spending 6 months in one place to build stronger ties while I spend the other 6 months traveling. You can do both. You can have your cake and eat it too. You just can’t always do everything at the same time.

3. Owning your time is an exceptionally large advantage.

'Office' in La Ventana, Baja Mexico

[Photo: ‘Office’ in La Ventana, Baja Mexico]

Besides the obvious perks it turns out that the time and focus available to someone with no 9-5 is incredible.

Guess what: most people are locked into a job that swallows most of their day, and the rest of it is used up by exercise, social events, and/or family obligations.

Additionally, most businesses these people work for can’t innovate for a number of reasons. They may not have the bandwith, they may be beholden to investors, or their employees may only be motivated to work hard enough to ‘do a good job.’

This gives those with no 9-5 a distinct edge:

  • You’ll have more time than anyone else to learn, research, experiment, and hustle.
  • Since you’re creating your own assets you will work much, much harder to make it work.

Of course, there’s a caveat to everything:  you have to be exceptionally driven to utilize this advantage.

4. All the how-to information is already out there, you just have to find (and learn) it.


[Photo: Kindle/Bintang study time in Bingin, Bali]

If  I could only provide one piece of advice it would be this: become an extreme autodidact. Become an expert in learning: figure out how to inhale information, process it, and immediately change how you do things.

Almost everything I know about building an online businesses I read in a book or found on the internet. Sure, mentors played a role, and I learned a lot from individuals I worked with, but most of it has been sitting down to read, test, repeat.

Over the last few weeks I’ve been reading a book a week. Experience has made it clear to me that this alone is the key to ongoing success.

We have access to more information on our iPhones than any other humans have had in history, and that rate of information-sharing synthesis is only accelerating, in every field. Let me underscore this point: the same amount of information is available to everyone. It’s all out there in a how-to blog post or book somewhere. All you have to do is dedicate the time and energy to find and learn it.

Ready to make something happen? Here’s the exact series of posts on building niche websites that I used to get started (Thanks Pat!).

5. It will take much longer than you think.

It seems to take about a year from idea to real revenue, unless you know what you’re doing.

All those tidy examples in the 4-Hour Workweek where Bob or Sally have a product idea and have it up and tested on Google Adwords in a day don’t pan out if a) you can’t figure out Google Adwords to save your life and b) nobody clicks on your ad anyway (or Google cleans out your bank account in 3 hours).

And there are always major distractions, especially if you’re traveling (that’s one of the major perks right?).

Trying to build a business on the road can be difficult unless you carefully manage your environment. In certain situations it can make sense to get some of the building phase out of the way before you leave home, which is another reason that some people opt to start their first project from the safety and predictability of a job they’ll be leaving.

As I said before, you won’t work as hard if you do this, so you have to start much further out. Get things going a year before you leave and you’ll be in good shape.

6. Building a lifestyle business and maintaining it are wholly different.

As with anything, maintenance is easy, building is not. I can check website stats in 5 minutes and not work more than that if I want to if everything is on track. But in order to get there I put in 2 years of effort in building websites, engineering systems, generating traffic, monetizing, tweaking, iterating, etc.

If you read the 4-Hour Workweek, the importance of getting the building stage out of the way was glossed over in roughly one sentence: ‘…at first you have to spend a few months throwing everything at the wall to see what sticks…’.

Right… It only takes 4 hours per week to maintain, but it will take 80 hours a week to set up the system in the first place.

I’d recommend blocking off something like 1-3 months for building projects. Be somewhere with few distractions, a quiet room with a workstation, and preferably terrible weather. This part is no 4-hour workweek—it’s more like working for a new startup. I easily spend 10 hours per day working under these conditions, usually in 3-4 hour chunks.

I can do this for two reasons: I’m building assets that I own, and because I know this phase won’t last forever (which is the difference between working for a real startup and building your own lifestyle company).

If you build things correctly, and by that I mean a process-based fully automated online business, then the rest is easy.

7. Lifestyle-design is a skill – Being 100% accountable for your life isn’t all fun and games.

Working in Canggu, Bali

[Photo: Working in Canggu, Bali]

If you aren’t having fun now guess who’s responsible?

Work or play? Stay put or travel? How many hours should you work, anyway? And what the hell do you do if all your monetary needs are actually satisfied by four hours a week?

Welcome inside the brain of a semi-neurotic lifestyle-designer.

Working for yourself and taking full responsibility for your life is no joke, and finding the right balance between working for the sake of work and blowing everything off is an ongoing process.

As it turns out, the “real world” is incredibly structured, and until you leave it’s hard to realize just how little free will you actually have when it comes to scheduling. It’s hard to imagine now, but in the US there may be virtually 2-3 weeks a year where you get to decide where you’ll be and when you’ll be there. The rest of the time it’s already set: this is where you have to be, and this is when you have to be there. End of story.

But upon reclaiming your time it’s interesting to realize how difficult basic decisions can be. If you’re working for yourself, having a hang-over can be a great excuse to take the day off. It takes an iron will or some incredible motivation to grit your teeth and be accountable to yourself.

Fortunately, like anything else, this kind of design-work is a skill. The payoff for learning the skill is massive, and once you start down this road it’s hard to imagine not having total control of your life. Having someone else define when and where you have to be is like being in kindergarten again.

It will take some work to figure out how to build your own reality, but there are more and more examples of alternative lifestyles as more people get involved in location-independent business and non-deferred life-plans. There’s a lot more information available than there used to be.

As it turns out, one of the hardest parts is to have a guilt-free way to stop working. Here are a few important points:

  • Everything is easy when you have goals in place. Start With the Why and Build out your Dreamlines. If you don’t know where you’re going how do you know where to stop?
  • If you don’t have a general routine (I try to work 5 hours a day in the morning), clearly defined goals (make over $1,000 a month in passive income by the end of 2012), and an month by month action plan (build website, get to X traffic level by doing Y), you’ll be hit by a vague sense of guilt whenever you stop working ‘early.’
  • When things are going well, I might work less. When they aren’t, I hunker down and shut out the world until something changes. Knowing that you’re on track for excellence makes it easy to pull the plug when you don’t really need to work.

8. The key to freedom is simplicity.


[Photo: El Hombre. Chicama, Peru]

I’ve written an entire essay on this, but basically, the less you spend the less you’re going to have to make from lifestyle business efforts to be a digital nomad and do whatever you want.

If you can figure out how to live on $500 a month (which can be done), I almost guarantee that that you’re going to figure out how to break even.

Do I want to live that way forever? No. But it’s a skill and an asset, and as long as I’m comfortable dropping to that threshold as needed I have infinitely more lifestyle flexibility and I can take bigger risks.

For a treatise on the topic, see:  The key to Freedom isn’t Making More, it’s Spending Less

9. Baselining in less-developed countries can be rough.

Oh yeah, living on $500 a month isn’t always that much fun. It’s important to understand that being productive requires at least a modicum of predictability, routine, and comfort. You can definitely work on the road and get things done, but it’s easy to get frustrated by slow internet, power outages, bad coffee, and the inability to sleep enough.

I’ve written an entire post on this too:  The Less Romantic Side of Geo-arbitrage

While there’s an inherent risk in working in a country where nothing works like home, that’s a big part of the adventure too. Success requires the right mindset and the right approach. I still live cheaply these days, but I will spend the extra money to get my own room and set up a predictable environment where I can get things done. I also travel much more slowly these days, posting up for a minimum of a few weeks so I can establish a routine.

The other major risk though is working too hard to enjoy where you are. If you always have your face pressed against your laptop’s screen you still get the cost advantages of the location, but you lose a lot of the experience of travel unless you make an effort (“Oh yeah, I’m in LOMBOK!”). That’s why restricting work inside strict parameters, having a routine, and cycling priorities is so important.

10. Hire virtual assistants/employees as soon as possible.

I read the 4-Hour Workweek in 2007 and I’ve had a virtual assistant ever since. His name is Paul, he lives in the Philippines, and he does great work for $4/hour. I also recently hired a part-time admin to handle higher-level tasks.

When you’re trying to maintain a small (hopefully automated) business while on the road, saving even 10 minutes a day can make a huge difference (especially if you’re only working for a few hours).

Besides saving time, handing work off to someone else will teach you how to create processes. It will force you to figure out what you’re actually doing by writing it down, creating a recipe for the task that is both an asset and a modular piece of your business.

Anything that you do more than once can probably be outsourced. Most people don’t believe this, but most people haven’t tried it. Some things I’ve outsourced in the last 5 years:

  • Website development
  • SEO
  • Social media
  • Reporting
  • Blog writing/posting/editing
  • Basic research
  • My email
  • Flight arrangements

The bare-minimum personal time requirement for one of my largest businesses now requires exactly 57 minutes per month for me to run. I work more than this because I love building systems, but I don’t have to.

I found Paul on Elance through a simple posting about a one-off task, but there are almost unlimited postings for VA’s and other contractors out there. Hiring is another skill-set, which means you have to work at it to get good at it, and I realize developing this skill is the entire future of my online work.

Task that needs to be done? => Delegate or Hire

Make sure you give people small test projects before you hire them for anything bigger.

11. You must continuously build yourself out of a job.

God help you if you do this in the real world, but you should always be building systems that can scale, be optimized, and be automated. I never want to have to do the same job forever, and neither should you.

If that sounds like I’m speaking in code, let me explain: everything I do more than once now I write down, to the nth detail (I mean, like “Open Chrome, navigate to X website, click THIS button”!). Do this a few times and you have a set of instructions for a given set of tasks. Once you have this you can then take a long hard look at the process to eliminate unnecessary steps as well as hire someone else to do them.

Once someone else is doing them you can focus on the next piece of the puzzle. The best part? A lot of these executable scripts will apply to just about any online work you do in the future. They’re assets, secret sauce, and the engine that drives a hyper-automated online business.

When people ask me what I do now, I want to say systems engineer. I usually say “online marketing” instead, so their eyes don’t glaze over (which happens anyway).

For more on this  Read Work the System or listen to the LBP #134: If it makes you money you shouldn’t be doing it.

12. Establishing a work routine is key to getting sh*t done.

“The acquisition of skill requires a regular environment, an adequate opportunity to practice, and rapid and unequivocal feedback about the correctness of thoughts and actions.” – From Thinking, Fast and Slow

Generally, I like to do things when I feel like doing them, but relying on your passion isn’t always a reliable way to make things happen. Sometimes you just have to grit your teeth and roll your sleeves up.

Often, this has meant locking myself in a room with no distractions for a few weeks and working feverishly until I have something to show for it. But on the road, unless you’ve stopped somewhere and have a living space, it can be nearly impossible to stick to any kind of routine or make anything happen. That’s why I now travel slowly, rent apartments, and pre-define when I’m going to work for a few weeks.

Although I’ve spent the last 2 years playing around with each of the different daily elements of when, how long, and how hard to work, play, sleep, and it’s still a work in progress. There is no one-size fits all routine.

  • You’re going to have to experiment to figure out what works best for you
  • What works best for a particular project or goal.
  • And, what works in your current location.

Sometimes I get up and exercise first. Other times I start working at the crack of dawn and finish early (like working 6:30-11:30). Often the tide or the wind determines my daily schedule for me.

Some of the most important things I’ve learned are:

  • Have a focus and a pre-defined schedule for set period of time, like 3-week work sprint followed by a few weeks of traveling.
  • Have a defined end-point for work each day.
  • Do the most important thing first.
  • Focus on only one thing at a time.
  • Organize your work around some kind of exercise.

13. Cycling priorities produces maximum results.

Stand-up desk on the N. Shore of Oahu

[Photo: Stand-up desk on the N. Shore of Oahu]

I’ve finally come to understand just how important cycling is. Variety really is the spice of life. As I learned in Thinking, Fast and Slow: everything depends on the ‘reference point,’ or put another way: things are only interesting in relation to the last thing you did.

A few rules of thumb I use for my own optimal results:

  • The optimal amount of time to travel is 3 months.
  • The optimal amount of time for an activity-specific trip is 6 weeks.
  • I work best in 3-6 weeks sprints followed by at least a week off.

Cycling makes things more fun, more productive, and more interesting. There is nothing you want to do forever, which is one of the big reasons that life after college sucks for most people: it’s a never-ending slog with no breaks. Humans are cyclical creatures, our bodies are tuned to circadian rhythms–nothing is static–and it makes sense to try to design our lives that way.

Right now I’m experimenting with a 3+1 schedule: 3 weeks of working hard with a transition/cleanup week on either end, then the same period of time for something else (traveling, surfing, learning a new skill).

Ultimately I think Tim may have nailed it with the mini-retirement schedule: 1-3 months of work paired with 1-3 months of mini-retirement language + activity focus. I have yet to successfully try this.

14. Organization is everything.


[Photo: My apartment in Budapest]

Win the first hour and you win the day. This is the most important habit I’ve developed this year. Sit down and spend the first hour looking at your goals and planning what you are going to do. Make sure that everything moves you closer to higher-level goals and don’t do anything that doesn’t.

In terms of how/where to organize: It doesn’t matter if you keep this information in an Excel spreadsheet or with an online project management tool. The important part is that you a) have it written down, b) look at it every day, and c) apply consistent effort toward the one thing that will make a project successful, and d) that each thing you do has a metric attached to it. Read the dreamline post for more on this.

I’m a big fan of the free project management tool Trello. I now create a new project board for a 3-week work sprint and then create a new to-do list for each week in advance. I don’t work on anything that is not on that list, and I recently started using the Getting Things Done system to deal with additional stuff that comes up.

There are a lot of project management tools out there:

  • BasecampUsed to be the best option but now charges for all accounts ($20 / month). I can’t justify paying for this when there are other free options.
  • Excel: I’ve got spreadsheets for my spreadsheets. One of the most important ones is a numbered list of general priorities (for life, work, fitness, etc) and the top 100 things I want to do before I die.
  • ToDoist: What I used until I needed to collaborate with others. ToDoIst is a glorified Google Tasks. If you don’t need complicated project management, start here. It’s free.
  • TrelloI’m a visual guy, so the card-based system works well for keeping track of simple stuff. I was skeptical at first but I’ve grown to love this tool. Makes picking up where you left off a snap.
  • AsanaFor more complicated stuff involving groups of people, I’d give this a shot.

The key here is that good project management tools allow you to a) stay focused and (most importantly) b) pick up where you left off. There can be a lot of interruptions on the road and you don’t want to have a huge startup cost (figuring out what you were working on) every time you come back to work.

One last thing: a project management tool is not enough. You need a system to make it work. Check out Getting Things Done for a good one.

15. Learning how to cultivate motivation/momentum is paramount.

Finding the motivation to get started is so critically important to owning your life that I can’t overstate it’s importance. And it’s something that only you can figure out how to generate.

If you’ve read this far down the page I’ll assume that you have a fair amount of motivation already, and most people have it for the first 6 months after quitting their jobs. But it’s a lot more difficult in month 8 when you’re out on your own with no guaranteed income and some loosely defined ideas about where things are going.

Some ways to develop motivation:

  • Start with why: Why the hell are you doing any of this?
  • Visualize the end-game: What do you get if you win?
  • Brain-storm how to get there.
  • Connect the dots with a plan.
  • Start knocking it out.

Keep in mind that action can create emotion. Hold a pencil in your teeth for long enough and the physical act of smiling makes you happy. In the same vein, I think the best way to generate motivation is to define the above and start a work routine. The hardest part is getting the ball rolling, but once it is moving, amazing things start to happen. My motivation comes from the development of that routine and the positive feedback that comes from seeing progress. It also comes from knowing that I’m building systems that move my goals forward.

And that’s where momentum, or inertia of progress, comes from: the snowball effect of this applied effort over time, and the positive feedback loop created when things go well and pick up speed.

Similarly, squandering momentum can be a deal breaker.

Momentum is like an avalanche you started. It’s a productivity multiplier. Not only do you get a lot more done but you have twice as much fun doing it–it’s where the real miles are knocked out. See how Sean Ogle’s struggled with this and ultimately cancelled a trip to Thailand in order to keep his business moving.

It’s also easy to blow things up if handled incorrectly. When things are moving, I leap out of bed in the morning, and when they’re not it’s hard to get more than a nod in the direction of any projects I’m working on. A lot has been written on the topic, but ultimately you’re going to have to experiment. As Dan put it: ‘when the winds of passion blow, put up your sails.’ The ephemeral nature of motivation/momentum means you need to make hay while the sun shines.

If you’re fired up and getting things done, don’t change anything. As time goes on, it gets easier to re-start momentum in any direction, but it’s so much easier to maintain than to re-start it that now I keep it going at all costs.

What to do when motivation wanes? Generally, I find it best to close the laptop and do something else. It usually comes back relatively quickly if I’m doing something I want to be doing.

16. Dedicated office space multiplies work efforts.

The office in Santa Cruz, California

[Photo: The office in Santa Cruz, California]

Working in coffee shops or hostel lounges doesn’t compare to what I can do in a quiet room with two screens and no distractions. When I’m really trying to get things done I like to roll out of bed and start working, which means I can get 4 hours of work done before I’d even make it to the coffee shop.

If you’re planning to nail it for a period of time, figure out how to get a room to yourself. You will probably have to pay extra, but it’s totally worth it. See my guide to finding cheap accommodation anywhere.

A few places around the world where I’ve worked:

  • In rented apartments either through locals or AirBnb.
  • In the homes of friends who work (means you have their house to yourself for the entire day).
  • Community college libraries in the US (dark, silent desks and fast internet). Public libraries usually aren’t as good.
  • In the back of quiet internet cafes (where I’ve paid for hours in bulk).
  • In the restaurant of my local homestay (currently).

Earlier this year I tested out free office space from Regus.com that I learned about through HackTheSystem. I won’t steal Maneesh’s thunder here so check out how to get free office space on HackTheSystem for more.

17. Don’t let work expand outside strict parameters.

Parkinson’s Law: Work expands to fill the time available.

If you find yourself working just for the sake of it without a clearly defined mission, close your laptop and get the hell out of there. There is nothing more soul-crushing than sitting in front of a computer screen in self-inflicted torment because of some vague notion makes you feel like you “should.”

Even if you come back and work more later in the day it’s worth taking a break and re-defining what your specific goals are.

The other most effective thing you can do to combat working for the sake of work is a) spend the first hour planning, and only work on the list you make from that, and b) to actively constrain available work time. When I create a firm deadline that I’m only working for 4 hours in a given day, all critical tasks somehow get done. Sure, I don’t answer my email or check stats 50 times or read any blog posts or Twitter updates or Facebook. Nothing is worse for productivity than endless office hours.

Time is also a poor measure of output. Only results matter. Re-reading the 4-Hour Workweek recently this quote jumped out: ‘lifestyle-design depends on massive output’.  With absurdly short deadlines you become a heat-seeking productivity missile. If you lose your focus, walk away and come back when you have it again.

Time constraints also add value to other activities.

I had this driven home in a big way last year when I went to Indonesia for an indefinite period of time. For the first few weeks I was listless and couldn’t seem to get motivated to do anything. Then, citing ‘not enjoying myself’ as the reason, I bought a ticket home.

Overnight my whole outlook changed. With a constrained time budget I now had to get my ass out of bed or I wasn’t going to see all the sights or accomplish anything while I was there. The sunrise was brighter, the scenery more brilliant, and the whole experience much sweeter.

Basically, it turns out that nothing unlimited is fun.

18. Only focus on one thing at a time.

Others might disagree with me on this one, but my general travel philosophy (“always say yes”) does not apply to work opportunities. I’d suggest “always saying no” to any distractions from the core mission.

It’s easy to get lost in the mundane details, but in my experience there are only a few important things that actually need to get done at any given time. If you do the one thing right that actually creates revenue, everything else falls into place.

More generally (in life), it makes sense to only focus on one major thing at a time, sometimes with a supplementary activity. For example, working and a language, sport, or travel. Pairings tend to work particularly well, a la Tim Ferris and the mini-retirement plan.

19. When in doubt, get some exercise.


[Photo: Los Lobitos, Peru]

This is one of the most important things I’ve ever learned early in life.

Most problems can be put back into perspective by getting your blood flowing. This goes for a general lack of motivation as well as being overwhelmed with existential angst (“what the hell am I doing with my life?”).

Every time I’ve been in a slump on the road I’ve been able to at least mitigate the damage by getting out the door. This isn’t always easy, especially where frequent hangovers are common (ie, living in hostels) or exercise is logistically difficult (smoggy cities), but like anything else the key is developing a routine. Running, renting a bike, Crossfit, doing pushups, surfing, hiking, whatever you can make happen where you are. If I can’t workout outside (due to smog, danger, or just unpleasantness) I’ll find a gym or do it in my room.

It’s generally more effective to exercise early in the day, but as long as you do it, it works. If you don’t know where to start, do this first.

For more on this topic, see my post on How I broke my body and then fixed it.

20. Figure out how to do as much as possible offline.

The hardest part about traveling in really less-developed countries, or just moving a lot in general, is finding reliable internet access and an associated workspace. I’ve spent time in places where it’s not just a wifi problem: power goes out for hours daily. Or the internet goes down for the entire region.

I’ve also been to a lot of places where you don’t have wifi where you’re staying, meaning that ‘commuting’ to a work location can be a major hassle and logistically limits the workday to a single session.

If you’re spending a lot of time moving, either on buses, planes, or trains, you’re going to have a lot of time wishing you could get things done.

Some tools I use to work on the road:

  • Iphone 5 with a local SIM card – This has been a game-changer, but I’ve been turning my phone into a wifi hotspot and working on perfectly functional internet from rural Indonesia lately. Total cost for 5GB a month data plan on Telkomcel is less than $10.
  • MarsEdit (Mac) or Windows Live Writer  – Let’s me write as much as I want and get basic formatting done for blog posts. While a basic notepad also works, these tools sync with your blog and give you the ‘feeling’ of what you’re working on. An intangible but important benefit for me. Download Windows Live Writer here (free) or the trial version of MarsEdit.
  • Gmail Offline –  Lets me answer emails on the road assuming I want to do that and don’t have wifi/internet. Gmail offline is still a little funky in that if you happen to close your browser window before you get reconnected you lose everything, and you also have to make sure it’s open before you go offline. Not perfect, but usable. Set up Gmail Offline here.
  • Kindle I’ve read more books in the last 2 years than ever. Besides fiction this thing is always loaded it up with at least 15 business-related books I want to read.
  • Podcasts – I make sure I’ve got an iPhone full of good podcasts at all times. I must have listened to the Lifestyle Business Podcast for 10 hours on the train from Budapest to Zagreb (and it’s probably the only thing that kept me sane).
  • A Business Notebook – Keeping a small business notebook with me at all times. At the very least I can start sketching out new ideas or outline projects or blog posts.
  • A laptop with good battery life – My new Macbook Air (see my rtw trip pack list) does extremely well, although not as good as the original Acer Aspire one (see entry-level gear for digital nomads).
  • Dropbox for storage – Don’t become dependent on Google Spreadsheets because you won’t have access to them on the road (I’ve never gotten offline functionality for this to work properly). Google Drive is also a poor substitute for Dropbox.

21. Celebrate your Victories.


[Photo: Somewhere in Baja, Mexico]

I’m terrible at this, hence the shortness of this section, but I’m working on it. As soon as something good happens I seem to expect this as the new baseline.

Make sure you take some time to celebrate the milestones you cross. Work hard, but take a lot of breaks. And when you do something great, enjoy it, because you’ll never get another chance.

22. Surround yourself with amazing people who are doing what you want to be doing.

I’ve only recently come to fully understand the maxim that you are the average of the 5 people you associate with the most.

It can be lonely out there in the ‘barren Sahara wasteland of entrepreneurship’, add to the fact that as a digital-nomad you often lock yourself in a room and avoid social situations.

A big part of writing your own success script is surrounding yourself with people you aspire to be like. Stop hanging out with people that don’t get or care about what you’re doing.

You’ll likely have to leave the real world to do this. Check out some of the big digital-nomad hotspots like Chaing Mai, Saigon, or Berlin, or the incredible online community the guys at TropicalMBA started (some of my original inspiration, and folks I’ll be meeting in two weeks!). There are a lot of great people out there who are working on similar things. Once you join this community you’ll wonder why you didn’t sooner.

Oh yeah, and don’t hesitate to reach out and get in touch!

You might also like: 365 Days: 20 things I learned from traveling around the world.

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