New Zealand tropical trees

If you follow me on Twitter, then you know where I am right now: New Zealand. For a month.

(Yep, that’s me, obnoxiously tweeting pictures of the creamy white sand and dreamy turquoise ocean. And the regrettable novelty taxidermy.)

It all sounds pretty exotic (and it is). But for me & my partner in crime (and biz), it’s a kind of normal. We travel a lot.

There have been years where we literally spent half the year abroad. At this point, it’s old hat.

This isn’t even our longest trip – no, that honor goes to a 2.5-month around-the-world “workcation,” a genuine circumnavigation of the globe including one 36-hour travel day with two back-to-back 12-hour flights, over 12 domestic and 4 international flights, 6 weeks of road tripping, 5 major cities on 2 continents, 2 conferences we worked (1 training/presenting, 1 running an exhibit), 1 major new project from scratch, and 3 seasons.

(Ahh, the trip that nearly killed us!)

So I think it’s safe to say that I’ve learned just about everything there is to know about traveling while running a business. The hard way, of course.

And it’s not what you think.

The Heartbreaking Myth of the Workcation

I do so love a good portmanteau and “workcation” is a great one. It means a “working vacation” — also known as the juicy dream of enjoying the beach while working on it, Piña Colada in hand, complete with umbrella.

laptop by the beach

Also known as “rarer than unicorn tears and twice as hard to come by.”

The problem is this: working requires great attention. So does being present on that beautiful beach.

If you’re any good at what you do — and you are, right?? — then you know what it’s like to really get shit done. You sit at the computer, and it sucks you in. You may nominally exist in your physical body, but your brain and your senses are somewhere else… in The Land Inside the Screen. Workland.

And when you’re in Workland, you can’t truly be in Beachland. You can work in Workland and commute to Beachland at night, but you can’t bi-locate. Physical impossibility and all that. Sorry.

The good news, such as it is? Working on the beach actually sucks. Even before you consider the sand-in-the-keys-underwear-and-nostrils factor.

The net result is this:

  • when you’re focused on working, you might as well be in a room with no view, and
  • when you’re not working (and you are enjoying that beach), there’s that little nagging thought in the back of your head that you should be working

It’s actually a subtle form of torture. Whatever joy you might have extracted from working on the beach was always, and would ever be, a fantasy.

Thomas tired at cafe working

But you don’t have to take my word for it. Try it yourself, and you’ll find that that:

You’ll return from your trip feeling like you never were really, 100% there.

Or you’ll have achieved just barely a fraction of what you planned to, with all the guilt & self-recrimination that comes with.

Take your pick. Which will it be?

Take the Green Pill: the Hidden Option C

Or choose the hidden option C: dump Fantasy by the roadside for being incorporeal and utterly unreasonable… and beg Reality to come home and bitchslap you with her wisdom, the harsh but steady mistress she is.

Without further ado, here’s how to best long-term travel instead of allowing it to best you:

1 Travel Like a Snail: Stay Put for Several Days

Stay in a location least 3 days if you want to get solid work done. Yes, really. Three days minimum.

Constant moving around is a huge drain on your mental & physical resources. It’s also the dread enemy of routine (and routine is necessary for flow).

beach view New Zealand

“But I’ve gone on vacation and slept in a different bed every night and that didn’t tire me out!” I hear you cry.

Yes, of course you did. So had I. Long, around-the-world trips aren’t just short trips plus extra days… they’re different. Long-term travel has a lot of emergent properties, and the exhaustion of constant motion is one of them.

Travel for 3+ weeks while trying to get shit done, and you’ll soon find out for yourself. You need that time to catch your breath, adjust, to create what little routine and ritual you can.

So give up whirlwind tours and adopt a more stately pace.

When you stay in a place for a while, you also get the benefit of enjoying it when you’re not trying to work. You don’t end up feeling like you missed out because you had to do some email. (And you get to develop a deeper understanding & enjoyment of it, which is the stuff long-term travel is made of.)

2 Segregate Work / Fun Times with an Iron Fist

You probably love your work. That’s why you started your own business in the first place, right? Me, I love my work. I love thinking about it, reading about it, doing things with it.

But even so, I love a good vacation. And so do you.

Amy on the beach in New Zealand

There’s a very special frisson you get from saying “fuck it, I’m on the beach!” Deactivate global roaming, forget what’s on Twitter, leave your inbox to handle itself for a few days, and get gone. “Fuck it!” is the alluring bumpersticker of freedom.

This is the irresistible urge you have to conquer if you want to have a successful work-around-the-world experience.

It’s great to let loose and take a break for a few days. But if you plan to work, and you say “fuck it, I’m on the beach!” – where will your business be?

Then again, if you never get to say “fuck it, I’m on the beach!” – what’s the point of going on a trip in the first place?

The trick is to give yourself both experiences:

Plan to work every 2nd, 3rd or 4th day. Then work all day. You know as well as I that when you work for just an hour or two, you can’t even escape the gravitational pull of Shit That Piled Up, much less Do New Stuff.

The solution is to work all day. But not every day. Otherwise, where’s the fun?

On the days you don’t plan to work… don’t work. Don’t check your email just for 5 minutes. Don’t do any “fun” internet stuff that resembles or leads to work coughTwittercough.

You may think there are alternatives. I ask you: are you, in fact, superhuman? No? Then there really aren’t alternatives.

Here are two strategies which I’ve tried, and which I’ve seen others try. They always fail:

crystal clear new zealand ocean

Myth: I’ll just do a little work in the morning and then we’ll enjoy the rest of the day!

Reality: It’s 1pm and you’re still doing email.

Myth: I ought to get that done… but it’s sunny out and the beach / markets / mountains / 4x4 adventure is calling. I’ll do it when we get back. Before/after dinner.

Reality: You have fun. You end up going to a bar or restaurant with your friends/loved ones/new acquaintances you picked up on the side of the road. You tell yourself, “I WILL get that work done later.” But when you get back to your hotel/motel/yurt, you don’t want your yay-I’m-on-vacation feelings to end. You want to bask. Or you’re exhausted in that very special, luxuriating-in-a-day’s-adventure way. Either way, shit does not get done. Then you feel guilty. Which sucks the enjoyment out of, well, your enjoyment.

You could, of course, maintain regular working hours and only “vacate” in the evenings. Like you had a job. But where’s the fun in that? You’re the boss. With great power comes a great ability to say “fuck it!” (Sorry, Peter Parker.)

Much better to keep your work/fun totally separate – since they can’t really be together, anyway – and to devote a full day to each, to wring the last drop of enjoyment, or last drop of focus, out of each and every day.

3 Hoard Executive Function As If Your Life Depended On It

Because it does.

Every little decision you make drains your Executive Function, that part of your brain that helps you make good choices and exert self-control. Research shows that simply walking down a city street with lots of visual stimuli cuts your self-control to pieces.

tropical foliage new zealand

Executive Function is the thing you rely on to help you crack open your laptop when you’d much rather be dirt-biking or learning all the different ways to say “I’m drunk” in the local language. And the thing that prevents you from telling an irritating customer “fuck it, I’m on the beach!”

In short: You need spare Executive Function. Badly. And traveling is the equivalent of pouring your Executive Function out onto the street and lighting it on fire.

How many decisions to you have to make when you travel? Let’s see…

thomas with a huge burger

Where do we go next? When do we have to leave to get there in time? Should we trust the GPS or break out the map? Should we take the cheaper room in the nicer motel, or the less fancy more expensive room with the jacuzzi tub? Should we take the scenic route or the direct route? Which suitcase should I put this in? Where should we eat for dinner? Should I have the burger with the egg, beet root, onion rings, hash brown, and pickles, or without the pickles? Is this taxi safe? How much do I tip? What do I enter as the code in the motel room safe? Should we buy tickets just for the Liliputbahn, or the combo ticket with the beer garden museum? How many Mai Tais can I drink before walking back becomes a hazard? And where exactly are we staying, again?

Shit, just writing that paragraph made me unable to resist the urge to eat a donut. Luckily there aren’t any in arm’s reach.

Since Executive Function is so critical, and long-term travel seems designed to piss it away, you have to take action.

Save Executive Function by streamlining, simplifying, and deciding in advance.

canned reduced cream

Eat & live simply. Give up the idea that you have to eat at a different restaurant every time you go out. Rent rooms with kitchenettes, shop at the grocery store, and cook and eat at “home.” (This also saves gobs of money and is infinitely healthier.) (Plus you get to experience things ‘like a local’ which is always fun and illuminating.)

Stay in the one place for a while. (Gee, that sounds familiar.)

Book attractions and places to stay in advance – or if you prefer to live fast & loose, settle on a max 2 or 3 possibilities in most places you will visit. Front-load your Rough Guide-reading, Tripadvisor-surfing and motel-benefit-weighing to save yourself hours of thinking and sheer buckets of Executive Function on the day of.

Drive a car instead of taking trains and buses everywhere. Again with the saving buckets of Executive Function by avoiding all the repacking, shuffling, stations, tickets, time tables.

canned reduced cream

Develop a system for rolling in & out: Always pack things in the same bag, in the same place. Have separate zipper or velcro bags for things like “all electronics cables” and “all bathroom products” and “all receipts/paperwork”. Have a checklist for things you can’t stand to lose. For things you are likely to lose because they blend into the room (e.g. a pillow), choose a bright color or otherwise make them stand out. When you travel with a companion, divvy up responsibilities so there’s no “Did I pack it? I thought YOU packed it” fiascos.

Plan your next bit of work in advance, so you’re always ready to dive in. This will save you “set up and break down” time when it comes to starting work, and will help you make the most of surprise grey, nasty days when you don’t particularly want to be outside.

Pay out the nose, if necessary, for a prepaid wireless cellular modem instead of always hunting around for a cafe, restaurant, or motel with decent wifi. In some countries, this time-consuming hunt can waste days of your trip in total.

Always arrive in the city the day before your flight/train/bus/llama caravan. Even if your departure is late in the evening. This will guard you against so much last-minute panic.

4 Finally: Enjoy the Hell Out of Your Trip

Yes, that’s a step!

I know that right about now, the romantic in you is screaming, “But… where’s the magic?!” A lot of these fixes, habits, and tips are, well… not romantic or magical at all.

Staying in one place? Working all day? Eating at home? Cutting your decisions? Driving a car?

new zealand wine with wine glass

Are these the ingredients for a rip roaring good time??

In a very real way, yes.

I’m not giving you this advice because I’m a boring old dried up travel-hater who loves to stab dreams in the eye til they bleed rainbows and glitter. (I love travel! And hate being bled on by dreams. Glitter is so hard to wash out.)

No, I’m simply telling you what I wish someone had told me before I thoroughly botched several very expensive, could-have-been-lifechangingly-awesome trips. And futzed up my business while doing so.

The ideal case is to not work at all on a long trip. That’s more achievable than you might think, but not always possible. (And that’s another essay in the works.)

But if you have to work, my advice will help you get good work done and enjoy your trip.

Follow my prescription, and you won’t find yourself home once more, saddled with that pitiful feeling that “you were never really there.” Nor will your business fall apart while you’re gone because you can’t seem to get anything done.

And… that’s it for now. Travel well!

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