How to Work from Anywhere (While Not Falling Behind)

By Sean Ogle •  Updated: 08/30/12 •  7 min read

How to Work from Anywhere (While Not Falling Behind)I still have a very vivid memory from my last trip to Thailand sitting in the back of a van from Surat Thani to Phuket.

There were about 13 of us crammed into 10 seats, and I was desperately needing to get some emails written after 3 days kicking it on Railay Beach.

I had my knees scrunched up to my head, my laptop awkwardly perched on top of them, and I was responding to my backlog of emails using Gmail offline.

Even if you’ve built a business online that you can theoretically run from anywhere, in practice it’s easier said than done.

It doesn’t matter if you’re heading to a conference for a couple of days, taking a two week trip out of the country, or going completely nomadic and traveling around indefinitely – you’ll undoubtedly run into productivity issues.

A Balanced Rebellion

If you’re relatively new to working on the road, the hardest part will be the internal dilemma of whether or not you should be working.  When I first moved to Thailand in 2010, I’d never been to Asia before.  I spent the first month traveling around throughout the country, and while I knew this was make-it-or-break-it time for my life as an entrepreneur, I couldn’t help but be drawn to, well, everything.

When you’re in a new place, especially a place you may only be for a few days before moving on, you want to experience it all.  You want to meet people, see the sights, eat the food, and if you’re still putting in 8-10 hours a day that doesn’t leave a whole lot of room for being an actual traveler.

In time I figured out that while on the road (or anywhwere) it’s not about working longer hours, its about doing more with the time you do have.

Luckily, this is easier to do when there’s massive incentive.

Step #1: Create a Schedule and Stick to It

While you may not always know how a day is going to unfold (that’s part of the adventure) you should know how your work day is going to evolve.

Pretty much any time I’m living abroad my work days usually look very similar.  I wake up go to a coffee shop and work for 4-5 hours.  I’ll then head out for the afternoon, and if necessary do 1-2 hours of work at night before calling it quits.

This totally varies by day and activities, but that’s the general schedule.

This works great while you’re traveling due to the extra incentive.  If I know I’m going to a waterpark at noon and that I only have 4 hours to get all my work done for the day, I’ll get it done.

Parkinson’s Law is now your friend.  When you aren’t on the road you’ll extend whatever work you have into a full day.  Now you have incentive for getting it done, if you only have three hours, you’ll make it happen.

Step #2: Don’t Rely on Yourself

If you’re traveling for awhile, one of the most dangerous things you can do is rely on yourself all the time to get stuff done.  Let’s face it you are nothing but a lazy procrastinator.  Am I right? Yeah I am.

However all you need to be successful on the road is another lazy procrastinator.

Wait, what?

Yep.  If you pair yourself with someone else who is normally a slacker as well, more often than not you’ll both get more work done than you would have on your own.  No one wants to admit to being the lazy one.  So if you have a friend or someone you can work with on a regular basis, you’ll work harder because of it. Bonus points if you find someone who’s not a lazy procrastinator.

This is even more effective if you put a timeline on it.  Agree that you are going to work from the cafe for two hours before heading out and doing something else.  This adds multiple layers of accountability, which helps you get more done.

When I used to work with a group of people at Third Place in Bangkok, we would all sit around a giant table and work.  I couldn’t slack off if I wanted to.  And I didn’t want to be the one with nothing to show for it when we went out for beers afterwards.

Step #3: Have the Right Tools

You need to prepare for everything when you’re on the road.  You should never have an excuse for why you can’t get work done in whatever down time you have.  Here are a few of the tools I find extremely valuable when on the road:

Here’s a list of other tools I use while I’m traveling.

Step #4: Create Clear Outcomes

I’m notorious for bouncing around from one project or task to the next.  It’s awful, there are days that I’ll make 20% progress on 10 different tasks – and while I got stuff done, when you work that way you feel as though you’re just spinning your wheels.

Now, if you focus on your three most important tasks for the day, and get those to 100% you not only feel more accomplished but because you haven’t left any loose ends lying out there you can go out and explore without having a bunch of partially done tasks hanging over your head.

Step #5: Don’t Overwork

Something that happened to me at times in the early days of traveling was that I’d work too much. I’d spend 14 hours a day in front of my computer, and I wouldn’t get a chance to actually experience all of the cool stuff that was around me.  Considering I was in Thailand for 7 months I didn’t see nearly enough of the city of Bangkok or some of the surrounding countries.

This in and of itself led to feeling guilty about not taking the opportunity to see more.  Balance is absolutely essential.  You can achieve that by being serious about applying each of the steps we mentioned today.

Enjoying the Process

While it takes a specific type of person to be able to successfully build a business on the road, I wouldn’t have it any other way.  Even on my vacation to Vegas last week, I’d spend a little bit of time each day checking in and making sure nothing had blown up.

It’s this type of business that for me, adds value to vacations.  I never have to feel guilty about being gone or wondering what I’m missing.  I’m always in the loop, and I can make the choice of whether or not I want to work or not on any given day.

So have you worked while on the road? What’s your best tip for remaining productive?

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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23 comments on "How to Work from Anywhere (While Not Falling Behind)"

  1. Kenneth Holland says:

    Excellent post Sean.

    This comes in handy for me as I prepare to travel in an RV while working starting next year.



  2. Jo says:

    I haven’t really worked on the road but I’ve pretty much been living out of a suitcase, across various cities and countries for the last few years.

    Dropbox has been a god send. And now I’ve installed Wunderlist on my phone, I don’t even have to worry about not losing my to-do list anymore.

    I think the best way to be productive is to sit down and make a list of what you want to achieve in that session. If you don’t, you’ll probably find yourself on Facebook or discovering a whole load of super interesting but ever so slightly irrelevant blogs and websites!

    Off to find out more about living in Thailand now…!

    1. Sean says:

      Really good advice Jo, couldn’t agree more!

      Also, what do you want to know about Thailand? 🙂 Shoot me an email, happy to answer any questions I can!

  3. Sabine says:

    Funnily enough I came to similar conclusions during a trip to the States earlier this month. I also realized that working anywhere was quite different from working on the go. My life saver was my netbook with over 7 hours of battery, Google Drive that I installed on my usual laptop to be able to access my notes and files from my netbook and the working schedule, that I usually have when working from my home office.

    1. Sean says:

      Yeah Google Drive can be huge when working on the road, I should have included that one. Thanks for the tip!

  4. Thanks for the tip about MarsEdit, Sean – will check it out! The best tip I can offer in return is one we learned when traveling to different locations during an extended period (road trip, whatever): Slow.Down. Spend at least a few days in a destination. This allows for better integration of ongoing work. Don’t spend all the time you’ve budgeted getting from one place to another. Schedule a work day in the midst of a stop. We’ll be slowing further down on our next extended period and spending more time in individual places. Thanks.

    1. Sean says:

      I learned VERY early on that I can’t do the “backpacker” thing for sustained periods of time. 2-3 days per place just doesn’t allow me the time to get into enough of a routine to be productive. I’d much prefer a couple weeks or ideally a home base for a couple months and then take shorter trips out from there.

  5. SEOCharles says:

    Awareness of performance versus time is key for me. I use Time Tracker which is a simple (and free) software to time all my tasks and challenge myself to do more with less time. It also helps me getting tasks/outcome clear in my head before starting. There’s something about knowing the timer is running that just make me more productive 🙂

    1. Sean says:

      It turns it into a game, which I’m a HUGE fan of. Steve Kamb just had a post about “gamifying” your life with some really good ideas in it.

      I’d never heard of that tool though, checking it out now.

      1. SEOCharles says:

        Thanks for the additional ressource, good stuff! Here’s the direct link to Time Tracker:

  6. I had no idea about Gmail offline—the clouds are parting and the sun is shining! I like the Marsedit idea for writing guest posts.

  7. MF says:

    The vans from Surat to Phuket are death-traps! I gave up all van and bus riding in Thailand in 2006 after, while on a trip up to Hua Hin from Surat. Five bus drivers – all driving kids, were racing up the highway, passing when it was dangerous… pure nuts. I’ve not taken a bus or van since – too scary!

    For a place to get stuff done – Surat works. Ao Nang doesn’t work for me, too much to see and do. Phuket would definitely not work. We based ourselves in Surat for just over a year and it’s great because you can work as much as you want, then bail out and go see amazing things that are close by when you’re ready to relax. I have tried to work on the road while in Phuket, Ao Nang, Samui, Hua Hin, Vientianne, Phnom Penh, Luang Prabang, Kuala Lumpur, it just doesn’t seem to go so well.

    I moved to Thailand with the idea that I could relax a little and get a LOT done. That is exactly what happened. Living outside the USA, it is amazing how little there is to distract one from work once you get settled into a place. I know a dozen or so expats that are enjoying their time in Thailand while working online. I know another half dozen that aren’t really enjoying it at all. To each his own. I think everyone should head over to southeast Asia and give it a whirl though. See if it’s for you. Best decision I ever made…

    Cheers Sean,


  8. IAN says:

    Hey Sean, great stuff in your website… you’ve had your share of experiences in Asia, but I haven’t seen anything about the Philippines….

  9. Myself and my business partner David went on a 6 week road trip throughout the USA. We had an amazing time; let it be known I fully understand the difficulties in getting work done and being productive. But as a duo, like you mentioned above, we were able to work out a great system.

    Tip 1: Wireless device (when funds are available).
    We were able to get our hands on a Verizon wireless device which was literally attached to us. It mean for a mere $140 we had internet for the full 6 weeks, no matter where we were – barr a few times in the mountains!

    Tip 2: Work on the road
    Again, as a duo we had the flexibility of one driver, one worker (or playlist maker hehe). We’d always have one of us driving, in which time the other could complete e-mails and any other necessary tasks to keep the wheels in motion. Then when finished, we could switch, or simply sit back and enjoy the road!

    Tip 3: Sleeping Arrangements
    Within just a few days of our trip, we’d already figured we could wake up, spend an hour or less doing the morning basics before heading out for a full-days intense exploring. Afterwards we’d retreat to our place of comfort, do another hour or so’s work before freshening up to head out and have a beer!

    These together gave us MORE than enough time to complete tasks and still have the trip of a lifetime. In fact, I think i’ll write a blog post about it myself… thanks Sean – inspirational as always!

  10. Darlene says:

    I use Rescue Time to track my time. I haven’t tried the free mac on though, thanks for that link.

    Two years ago my husband and I took at 6 month RV trip across the US. Internet was sporadic at best in some RV parks, some not at all. We didn’t buy an internet stick because we don’t have US phones (Canadian) and they wanted $400 deposit and a one year contract for it. We did find we got more done in the places we stayed for 4-6 weeks than one week. So I agree with you Sean, plan on more time per place.

    If I were to do it over again I’d plan ONE:ONE meaning one day of traveling or fun stuff exploring the place, then one full day working. I’ve tried the morning/evening work thing and play afternoon and it doesn’t work for me. Once we get out I wanna “play” all day and as a photographer the light is better at the beginning and end of the day so I’d rather be out shooting at those times. Also in my places our RV park was an hour subway or train ride away from the main city so it made it tougher to just split the day in half. If you’re staying right in the mix that would be different.

    Or change it up two work, one play or vice versa two play one work. I could also do emails and stuff offline while my husband drove. I am still behind on processing my photos from then though, 2 years later I vow to catch up!

  11. Darlene says:

    Downloading Mars Edit now! Thanks for that Sean!

    1. Darlene says:

      OR you could hire someone to slap you when you go on Facebook like Maneesh Sethi did! LOL

  12. Ashwin says:

    Great post Sean.

    For one, I always check to make sure the hostel/hotel I am about to stay in has a decent Wi-Fi. No Wi-Fi, no stay.

    I get up way too early in the morning, at about 4-5 AM, and start working ( either from the bed, at the lounge, or a nearby coffee shop ( just like you do). By the time breakfast happens, I am almost done with my work. 1-3 hours of work mostly follows at the end of the day. That’s the usual plan. Sometimes, all of this bounces off the windows of normalcy and I am left with a full-day of catching up to do.

    I see that I rarely go anywhere remote ( determined by Internet availability — now, that’s a bummer when I travel since I miss some Islands, etc).

    I thought Gmail discontinued its Gmail offline thingy. Gosh, I got to check on it again. Keep these posts coming, Sean. Loving it.

  13. Jamey says:

    Thanks for the Mars Edit recommendation. Was looking for something like this for a LONG time and had never come across anything good.

  14. Nico says:

    Great post, Sean!

    Indeed, it is easier to get things done in a couple of hours when you know you have a beach waiting for you afterwards. You feel productive without the sensation that everyone’s having fun but you.

    Thanks for Mars Edit advice, I’m gonna check it out too!

  15. Love these tips Sean! I’m not exactly aspiring to do any hardcore location independence like you, but I DO want to have the same lifestyle more locally and these same tips definitely apply.

    I love tips 3, 4, and 5 the most – especially the tip about not overworking. I tend to burn myself out, then have trouble getting started back up. I need to just pace myself so I can keep a consistent burn going.

  16. Sean,

    Really appreciate the info about Mars Edit under Step #3: Have the Right Tools. I have been looking for a good option to “think outside the browser” and blog while offline.

    Many thanks!

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