A couple years ago I wrote about the myths & realities of long-term travel while running a business: How to (REALLY) Travel the World, Run Your Biz & Not Go Broke or Crazy.

In that epic post, I demonstrated that:

  • working on the beach sucks ass, and is a lie
  • executive function is your most precious resource
  • compartmentalization is your friend
  • you should travel like a snail
  • and pay out the nose to avoid internet cafes

But many questions remained, such as “What kind of work can you actually get done while you’re traveling the world?”

Now that Thomas and I are off on another month-long trip with many stops, it seems like a great time to start on Part 2.

Enjoy this dispatch from semi-sunny Rotorua, New Zealand!

Being Creative on a Long Trip is Nigh Impossible

Packing, unpacking, moving, finding your accommodation, hunting down the local cafes and grocery stores and figuring out the grill and getting out the maps and picking your fun to-do’s for each spot…that’s the stuff great vacations & great adventures are made of.

And it sucks for trying to work.

Long-term travel like that burns executive function like a…like a….I’m reaching for a metaphor here but (ironically) none are arriving in my brain. What burns a lot? Steam engine? Yeah. Let’s go with steam engine.

Long-term travel burns your executive function like a steam engine burns coal. There we go.

Executive function, aka willpower, is the stuff that creative work is made of. It’s what you need to sit down for a length of time, tune out distractions, and bring the full power of your attention to bear on a problem.

And unlike an actual steam driven train, you don’t have any burly sooties to keep your brain tootling along. (Or if you do, send them my way please!)


That’s why working on stuff that requires tons of creative discipline? Not so great for travel. Either you’ll get shit for work done…or you’ll get shit for enjoyment out of your trip. Pick one, you lose.

Luckily that’s a false dichotomy. There’s a third way to work, the smart way: Use what executive function you have in the most efficient way possible.

What kind of work can you really (truly, actually, for realz) get done?

My advice is to stick with projects & tasks that are:

  1. modular
  2. well-defined
  3. comfortable, routine
  4. creative, in a corralled & controlled way

That way you’ll be able to work in batches, finish things, and draw on the power of knowledge, habit & familiarity to power you through any executive function shortages.

Modular, well-defined, routine, corralled work looks like…

So for me, on this month-long trip, I’m working on three things in order of Executive Function drain:

Assessing Freckle’s workflow and working on incremental design improvements. Not a redesign, but a refinement. Focus Level: Medium. Why so low? Because, for the most part, I will be tackling one interaction (or at most one ‘screen’) at a time. I won’t need to do the huge mental marathon of synthesis & symphony for a full redesign.

Mentoring students in the 30x500 Exercise program, once a week live chat (2 hours) and periodically by email. Focus Level: Medium-Low. What? Am I not paying attention to my students? Au contraire, I very much pay attention. But 30x500 is something that gives me crazy flow; I’ve been doing it for 4 years now, I live and breathe it. I’m actually in 30x500 mode all the time. It is comfortable, familiar, routine, modular (once a week chats, email every other day or so).

Writing some new blog posts/ebook chapters. Focus level: Medium to Medium-Low. I love me some writing. Once I do a quick outline, I can bang it out quite comfortably. Comfortable, familiar, routine, and modular again… write a post, it’s done. Bam. And creative, in a controlled way, because writing for me is less about crazy genius and more about helping my reader achieve some small something.

None of these things are new to me…even though the work product itself, the deliverable, is new. I’m not designing a new app; I’m not starting a new project; I’m not running a new class. I’m keepin’ on keepin’ on.

And these things are also…

5. No Urgent Work, No Firm Deadlines

I’ve done work to hard, unmissable deadlines while traveling. It is the very definition of hell.

Fixed, firm deadlines mean there is no room for error. Need the internet? There will be no internet. Need to get somewhere? The weather will fight you. You’ll break your laptop; your cell phone; you’ll need to download a file and it’ll be corrupted and you’ll have to download it again; your rental car will break or the internet cafe will close for a leak. That’s just how the universe works.

(When you try to outfox the universe and plan in some extra space for error, the errors simply get bigger…and they outfox you.)

What will happen if I don’t finish the Freckle design work on this trip? We’ll ship the design updates later. No big deal.

What will happen if I miss a 30x500 chat? Unlikely, and unfortunate, but in the worst case scenario my partner in crime, Alex, is more than capable of holding down the fort by himself.

What will happen if I don’t post for a month on my blog? I might lose a few potential subscribers, but the loss of something you never actually had is minor indeed.

Preparation is the secret to survival…

…and beyond survival, enjoyment.

Preparation is the secret that’s hidden behind every item in this list:

  1. modular
  2. well-defined
  3. comfortable, routine
  4. creative, in a corralled & controlled way
  5. No Urgent Work, No Firm Deadlines (capitals for impact!)

You can take more wild, freeform, novel, or even urgent work and turn it into digestible bits for yourself.

I didn’t arrive in NZ thinking, “I’m going to redesign Freckle!” Nope.

Before we even left, I planned out what I would do. We made a list. I even did some sketchy wireframes & interactions in my notebook before we got into the real business of traveling. (Long plane rides are great for this because you can’t escape.)

coffee pens and notebook

I don’t have to open my laptop and ask myself, “What should I be working on?” It’s in my notebook. My present self can rely on my past self to save itself the mental work of choosing: Right now I’m working on the navigation layout. Next I’ll be working on the setup screen for our brand new goals feature. Then I’ll probably work on how to visualize goal progress.

For an hour or two I’ll need high focus, but because I’ve defined, modularized and contained the work, I can pick it up or put it down as I need to.

As for my blog posts…well, if I were better prepared, I would have queued up a bunch of finished posts and just scheduled ‘em to go out. (I did queue up a bunch of tweets.) But I didn’t get it together enough to finish those posts.

I did, however, put a bunch of partial drafts & outlines in my blog editor. I don’t have to come up with a new topic; I can just call up my list of drafts and finish one.

This one I had written 60% before we left and now I’m wrapping it up in Rotorua, NZ, on a day I’m feeling bored!

And that’s the secret.

That, and…

Don’t get high on your own supply

It’s tempting to think: I’m going to go on a retreat! And redesign all the things! And come up with a brand new way to do X! And revolutionize!

I think of this as energy overflow: You’re psyched up for a trip and you misinterpret that as a wellspring of creative energy. Your cup overfloweth! DO ALL THE THINGS! IT’S GONNA ROCK!

Ah, but that’s just your body gearing up for the stress of travel. You’re generating all this extra energy because you have to spend it on the day to day work of travel.

So, prep your work (prep prep prep!), keep it contained, corralled, familiar, routine, and flexible.

And enjoy your trip!

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PS — You probably figured this out by now, but these rules are the secret to actually getting shit done at home, too.