How to Work While Traveling (When No One Else Is)

I’ve got a harsh reality for you:

Not everyone wants you to work on your business.

In fact, I’m willing to go out on a limb and say that in most cases your hustle will be an inconvenience to others.

As I write this I’m three weeks into an 8 week trip around the world with my wife.

Here’s my current view in Milan, Italy:

The trip has been great. We’ve walked all over NYC, drunk beer at Oktoberfest in Munich, hiked in the Dolomites, and went wine tasting in Tuscany — amongst many other memorable experiences.

And every single day I’ve tried valiantly to get half a day of work in.

And you know how successful I’ve been?

Not very.

You see, the people around me (to absolutely no fault of their own), don’t have online businesses.

My friend Ryan is a tour guide and is in his offseason. His girlfriend is a teacher and on her fall break. And my wife, Tate, is on a two month sabbatical from her job that she’s looked forward to for years.

These are just a few of the people we’ve traveled with, and nearly all of them have their own goals and agendas, which unfortunately for my productivity doesn’t include taking days off of sightseeing to work.

Here’s the thing I’ve come to realize after working online for nearly a decade:

This doesn’t change.

Whether you’re traveling, at home, with family, with friends — no matter where you are, most of the people in your life will actively try to keep you from doing your work (even if they don’t realize it).

And if you’re trying to build a lifestyle business, then, as you might know, things are already hard enough.

Despite books, blogs, and videos that have made this type of work seem much more attainable — the reality is, you’re still trying to go against the grain and against what society says you should do.

These days I have to fight for my right to work.

It sounds odd, but it’s true.

The last four weeks have been some of the most enjoyable and memorable that I’ve had in years — and I wouldn’t trade the experiences for anything.

One of the many tents at Oktoberfest in Munich.

At the same time, I have responsibilities to myself, my members and my readers to get things done despite being on the road — and for the first part of this trip, I hadn’t done a very good job.

You’d think after this long, I’d have all of the tips and tricks locked down.

Spoiler alert: I don’t.

Fortunately, there are some strategies I’ve had success with, even if there are productivity demons lurking around every corner.

Here are a few things you can implement to help you do the work even if those around you aren’t so keen on it.

1) Wake Up Earlier…No Matter What

Mornings are my favorite. Even though it can still be difficult for me to wake up early, once my coffee is made and I sit down at my computer, I find early mornings are by far the most productive time of the day both at home and on the road.

On this trip, my travel companions have been sleeping in until 9 or later. So if I get up at 7 I’m often able to get in 3 hours of work before they even realize what’s going on.

It’s not enough to get everything done that I’d like, but it allows me to stay on top of emails, participate in our Location Rebel forums, and get the occasional blog post written.

2) Schedule Work Days in Advance

Whether you’re traveling solo, with a just a couple friends, or a larger group, doing at least a little bit of planning is important.

I’m notoriously bad at planning. I’ll put off booking things til the last minute, not schedule out tours or treks, and try and leave as much of my trip up to serendipity as possible.

This becomes a problem when you have to work.

For instance, this trip to Sirmione on Lake Garda was completely unplanned…

Try and schedule your rough plan for at least a week out and identify two days where you can make work your #1 priority. This might mean missing out on something fun, or taking a night off drinking — but this is what you signed up for.

There’s a cheesy adage that states “work for 8 years when no one else will, and live the rest of your life like no one else can.”

While this definitely doesn’t explicitly apply to what we’re doing, there’s some truth in the concept.

I’ve been working for years, and continue to occasionally miss out on fun opportunities — but because of this, I’m able to take a two-month global trip without having to ask for permission or worry about the business falling apart.

3) Know Exactly What Needs to Get Done

This plagues me all too often. When you’re traveling and are the only one working, you’ll often have to rely on pockets of productivity.

45 minutes here, 20 minutes there — it could go on like that all day, so knowing exactly what you need to get done, and what order you need to do it in, is absolutely crucial.

When I’m at home I’ll often spend 20 minutes cruising news or social media before getting down to work.

On the road, those same habits will ensure nothing ever gets done.

I use Asana to manage all of my to do items, projects, and tasks.

So at least 4 times a week while I travel (daily if I’m at home), I review what has to be done, organize them based on importance, and make sure that as soon as I sit down for my next work session I know exactly what to do and can jump in right away.

The view overlooking Florence, Italy

4) Create Buckets of Tasks

While traveling, not all work time is created equal. You might be on a train without wifi, squished in the back of a van on the way to the airport, or have a full half day to spread out at a local coffee shop.

My buckets look like this:

Can Do on Phone

These tend to be more simple activities like posting to social media, responding to forum posts, or answering light emails. If I end up waiting for a bus or a train, these are the things I can easily tackle in short bursts of time.

Can Do Without Internet

I’ve been on a lot of trains on this trip. Unlike many of the Amtrak trains in the States, many of the European trains we’ve been on, don’t have wifi.

But that’s ok!

So much of the work I need to catch up on is writing.

Blog posts for Location Rebel or Breaking Eighty and updates to Location Rebel Academy or Hobby Hacking — are top priority right now. If I find myself without internet, I can still get these done.

We didn’t have much internet in the Dolomites. But we did have sweet Cairns.

Need Computer and Internet

If I need to do any research, or if I’m going to go on a big email binge — it’s best to have a computer and internet. There are ways to do email offline, but if I have a big backlog, it’s just easier to do it when I’m logged on.

Other examples of these tasks are:

  • Doing any kind of online research for writing
  • Doing SEO Work
  • Working on a website or landing page

Need Perfect Workspace

And then there’s the work that I feel like I need the best workspace possible and a significant chunk of time to make progress on. We’re talking a full table at a coffee shop, noise canceling headphones and at least a couple hours to dig in.

These tasks are usually things like writing sales pages, email copy, or anything marketing related.

Personally, I have to be a certain headspace to write effective copy, and I don’t even bother unless I get a nice workspace where I know I’ll be productive and not waste time.

My point in sharing this with you is that if you plan for these buckets and these pockets of time, you’ll be able to tackle different tasks at the times when it’s most prudent to do so.

Remember, It’s No One’s Responsibility But Your Own

As this trip has gone on, I’ve found myself getting frustrated at times with the people around me (aka, my wife) for not being quite as encouraging about my work time.

But that isn’t her responsibility. If I want to take an extended vacation, it’s my responsibility to get things done around her schedule, she shouldn’t have to plan out her sightseeing around mine.

This can mean early mornings, late nights, and some frustration in the process.

But as far as I’m concerned? It’s a small price to pay.

When you’re first starting out, learning how to deal with both working from the road, and being around people who don’t have the same needs or goals as you is a bit of a daunting task.

My mantra for years was I’d almost always choose play over work.

And while often that’s still the case, I’ve also come to realize that I’m very fortunate to do what I do. It’s a privilege, not a right.

And if I want to maintain freedom and flexibility in my lifestyle — then I have to be willing to sacrifice at times, and also put my foot down and do the work when it needs to be done.

While I’m certainly not as productive while traveling as I am at home, it does lend itself to new ideas, new insights, and if done properly, can still afford me the ability to grow my business while working from some more unconventional locations.

Other additional resources work checking out are Do the Work, Get Things Done and our Productivity Posts.

Originally published at on October 16, 2017.