Digital Nomad 101: 6 Things I’ve Learned After 6 Months On The Road

The digital nomad lifestyle has been the holy grail of the internet business set for years now. To be truly location independent is, for many, the absolute epitome of entrepreneurial success.

On a level, I’ve been a digital nomad for years. I read The 4-Hour Workweek, fell in love with the lifestyle, and got my butt on that train as fast as I could. But my digital nomad adventures have only been true as far as they’ve been true. I’ve been cheating. I haven’t really done much working on the road. I worked at home… and then spend a bunch of time traveling.

Don’t get me wrong – that’s a lot of fun. I still do it as often as I can. But for the last ten years, while I’ve fancied myself a digital nomad, I haven’t really been able to identify with the reality of the lifestyle.

Six months ago, that all changed. For a variety of reasons, I gave up my Art Deco love-nest of an apartment, put my money where my mouth was, and got on the road. I packed up my clients, I packed up my unschooling, and went on walkabout. I’m still away and on many levels, I still don’t have a clue what I’m doing. But enough dust has settled that I’ve started to learn some lessons.

Here’s what I’ve learned so far:

Some people are more creative away from home. You may or may not be one of them.

Digital Nomad

I researched a lot of digital nomad perspectives when putting off work and calling it research getting ready to write this. “I’m so much more creative when I’m traveling” seems to be a common experience for people working on the road.

They pull up in Paris or Dubrovnik or St. John’s and are just so darn INSPIRED they can’t stop the words from flowing.

I would like to be those people. If you have any suggestions, I would be very open to hearing them.

I still find creativity very difficult while traveling. It seems I am more a creature of habit than I ever realized. I can write things that are highly structured – my ebooks and classes and such have been fine. But creative stuff? Stuff that I think up off the top of my head? Sometimes I don’t feel creative enough for tweeting, let alone starting a YouTube channel.

I have had to become much more disciplined since I’ve been on the road. At home (well, when I had a home) I could wait for the muse, the mood, or inspiration. Now I have to take my damn Instagram pictures whether I like it or not.

Digital nomad takeaway #1: If you can, you have to find the creativity. If you can’t, then you have to find a way to work without it. Creating a stockpile of creative work before you leave that you can draw on when you’re overwhelmed and disoriented and jetlagged would be a good idea, too. I wish I’d done that.

Other people’s priorities are not necessarily your priorities.

Digital Nomad

As I got involved in the idea of traveling, I started reading books and blogs. Most of the people who write about extended travel are either insanely rich or insanely broke. (Spoiler alert: Most are insanely broke.)

For every James Altucher, who lives in AirBNBs, there are 1000 broke kids who blog on free platforms because they can’t afford web hosting.

It got to me.

Eventually, all those thousands of broke kids started affecting my consciousness, and I started thinking I was a broke kid. I would haunt reviews on Trip Advisor to see if some hotel’s wifi was good enough for Skype video, forgetting that I hate Skype video, and I have a perfectly good phone.

Ten bucks a day gets me unlimited long distance from a hundred countries. I could call you from Moldova and talk for eight hours and it would cost less than a lemon drop martini. I could call you from Bangladesh! From Liechtenstein! From Bonaire!

(I don’t even know where Bonaire is, but I know I could go there, call you, talk for as long as we want, and IT WOULD COST ME TEN BUCKS!)

I’m not broke.

I spend all this time thinking about how to save money on things I do not need to save money on. I started thinking that I was living a digital nomad lifestyle because it was cheap.

Yes, it’s often cheap, and that’s pretty cool. But if I can go to a spa at home, I can go to a spa on the road. If I can buy a smoothie at the mall, I can buy a smoothie at an airport. If I can buy a new pair of socks at home, I can buy a new pair of socks in France.

I put myself through a lot of unnecessary hardship to avoid problems I won’t have because I seemed to forget that… newsflash! I am not a backpacking teenager!

Digital nomad takeaway #2: Know YOUR reasons and priorities. Don’t forget them, but also don’t let them creep slowly towards somebody else’s. Remember this especially when you’re reading other people’s experiences. That includes this article.

Upgraded equipment leads to an upgraded experience.

Digital Nomad
Before I left, I upgraded my computer to a fully functional, not-broken-in-ANY-way Macbook. It has revolutionized my work. I had no idea how much I was just putting up with because I was too wussy to spring for a computer manufactured in this decade. (Upper limit issues, anyone?)

Now I make an image in Canva and I can see it in the same colors as everyone else sees it.

I don’t have to charge my laptop after two hours of work.

I can reliably play and work at the same time and my computer doesn’t make that alien spaceship about to take off noise.

As I’ve traveled, I’ve upgraded more and more pieces of equipment, and with each change, I’ve been happier and happier. Turns out, a good speaker makes it a lot more pleasant to listen to music. It means I can play thunderstorm tracks on Spotify to cover street noise in a hotel without it sounding weird and tinny. Impressively, proper noise-cancelling headphones cancel noise.

It’s not just work equipment either.

I bought new luggage (Dauphine, from Delsey) and my carry-on weighs less than three pounds. My kid can carry it, fully loaded. My suitcase weighs less than five.

I bought an iPhone 6 Plus. It can do everything my iPad does and more, and it fits in my pocket.

I bought a fancy-pants classy trench coat. I am SHOCKED by how much I do not have to pack, hang, or clean because I finally have something good that I can wear in every conceivable life situation.

I haven’t bought more stuff, I’ve just bought better stuff, and I’ll tell you – it’s better.

Digital nomad takeaway #3: I tried really hard to find a nicer way to say this, but I got nothing. STOP SETTLING. You are a digital nomad. Your computer is your OFFICE and your suitcase is your HOUSE. Pay some money like a grown-up.

You don’t know the quality of a system until it’s tested.

Digital Nomad
Perhaps you are a very organized person who crosses off every item on your to-do list and has color-coded file folders you use for something other than coasters. If that’s you, your systems are probably awesome, and your systems on the road will probably be even awesomer than that.

(If that’s you, and you would like to be my personal assistant, please get in touch.)

My systems are not awesome. They seemed pretty good. But then I had a family emergency in Anaheim, and the power went out for three days in Quebec, and I got a mysterious infection in France, and Donald Trump became the President of the United States.

It turns out? My systems are absolute shit.


Because they’re all predicated on the word every.

Every day I will pin 10 times to Pinterest. (Yeah? Even when there’s no cell service?)

Every day I will log in to Twitter and engage with humans in a brand appropriate way. (Yeah? Even when all anyone wants to talk about is US politics?)

Every time I write a blog post… (Yeah? Even when the power’s out?)

Every morning…

Every new prospect…

Every night before bed…

Travel, and disorientation, and the sheer amount of time it took to adjust to new surroundings blew all my everys to smithereens.

I’m getting my head above water now. My systems are improving. Batching is helping a lot.

But travel made me realize that I was sliding by on the safety net of familiar surroundings, and I have a lot of work to do to turn my motley collection of habits into a functioning system.

Digital nomad takeaway #4: Be aware that your systems may be great, or they may be no more than a set of interlocking rituals. Bulletproof what you can before you get on a plane, but be aware the settling-in phase might be long. Have patience with yourself.

You may have to start working in smaller chunks.

Digital Nomad
One of the cool things about being in new and exciting locations is that they’re filled with new and exciting things. Places to see, things to do, people to visit – there’s always something cool going on.

You ever tried to work when there’s always something cool going on?

This has been like trying to work on my Masters’ thesis and having Hugh Jackman tap me on the shoulder every 12 minutes saying, “Wanna make out?” Why, yes! Yes, I do!

Since opportunities continue to present themselves, me waiting for “a good chunk of time” to get some work done is absurd. A good chunk of time is not coming. (Well, it is. But I’ll be using that time to make out with Hugh Jackman, thank you very much.)

My rusty old Getting Things Done skills are helping here. Breaking down tasks into next actions has been useful, because there’s always something small that can be done. But it requires the mental shift into believing small tasks matter, and that goes against my nature.

I don’t want to delete 10 old blog posts, I want to delete ALL the old blog posts. I don’t want to set up three Instagram posts, I want to set up FOREVER’S Instagram posts. I don’t want to outline this blog post – I want to outline it, write it, title it, image it, post it, email about it, and then post it to social media. I want it DONE!


Digital nomad takeaway #5: If you have any grandiose fantasies of huge swaths of productivity, now is the time to get over that. (Alternatively, the other option is putting boundaries in place. I’m told Betsy Talbot writes for a three-hour block every morning, no matter what crazed, psychotropic bender her husband is on with the locals. If you can do that, you’re better at this than I am.)

Replace “routines” with “objectives”.

Digital Nomad
When I had a home, I had a little routine. I would put the coffee on – I had a Tassimo, so it only took a minute – and while I did that, I would clear out the junk mail from my inbox. Then later, when I was ready to process email properly, there wouldn’t be very much to do. It would be a pretty clear space.

Once I started traveling, I didn’t have a Tassimo anymore. I would go to the hotel restaurant or bar to get a coffee, or I’d go make a pot in the AirBNB kitchen. The trigger for my routine – “I’ve got nothing to do for a minute” – didn’t exist anymore, so the routine went to hell.

Suddenly, when I went to clear out my inbox, it was a lot more overwhelming than it used to be. It took me about three months to figure out why. Because I didn’t have my usual trigger – the coffee – I didn’t clear out my inbox. Since I didn’t clear out my inbox, it felt overwhelming. Since it felt overwhelming, I put it off. Since I put it off, it was more overwhelming the next day.

Now, if this had only affected my junk mail, I wouldn’t have had too big of a problem. But it affected TONS of things. It affected strategic planning, homeschooling, studying, washing my clothes, washing my FACE, doing yoga. (Yoga! I remember yoga! It’s that awesome thing I haven’t done in six months, despite carrying a yoga mat through multiple countries, states, and provinces!)

My routines at home made a lot of things easy. When your routines disappear, easy things become hard.

The way I’ve started to solve this – started to, because it’s hardly beaten yet – is to replace my routines with objectives. I’ve had to start being crazy explicit with what I’m trying to do. I have to say to myself, “I think I need to clear the junk out of my inbox before I’ll feel ready to tackle it in earnest”. Amazingly, this is far more effective than, “Oh God, I STILL haven’t gotten to my email.”

I haven’t had to be that conscious with my language in the past, but now it’s necessary if I want to get anything done.

I have to think to myself, “Naomi, you have to find a time, space, and way to watch that documentary with Jack this week.” That’s the objective, and I have to separate it from the usual routine.

Digital nomad takeaway #6: Don’t wait for the universe to magically rearrange itself to create a space that looks like your old routine used to. Not happening, honey. It’s on your head now. When the routine disappears, replace it with an objective, and figure out how to meet that objective. It’s actually pretty easy once you make it a priority.

Becoming a digital nomad is totally possible, but it takes some getting used to.

If you take an active approach to making the lifestyle work, and you have patience with yourself, you really can have all that cute, weird stuff you want. But seriously – buy a decent suitcase, OK?

A few other things to do while you're here:

  • The Emergency Turnaround Clinic (100% FREE!) – A re-release of our “how to survive the recession” class from Back In The Day – no sign-up required
  • The Karma Store – 12 of our products are still on pay-what-you-want, so if you need anything in there, you can still get it.
  • Unlock the IttyBiz Freebie Vault (now featuring the Money Masterclass!)
  • Naomi’s new blog – it’s about how to take care of yourself and the people you care about
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