Working on the Road: A 22 Day Experiment

Spending 22 days working on the road proved to have unexpected challenges, but also great benefits. It’s time to weigh in on the results of the 22 day experiment in location independence.

The Dream

For years I dreamed of a time when I could travel anywhere and do anything whenever I wanted. But the dream always seemed like just that, a dream.

Years ago I incorrectly believed, like so many others, that the only way to live a life of a millionaire was to in fact be a millionaire. This couldn’t be further from the truth.

The dream isn’t to have a wad of money in the bank. Being a millionaire would be nothing if you weren’t living like you’d imagined a millionaire to live. If being a millionaire requires that you work 80 hours a week doing something you hate then you sure aren’t gonna be a happy millionaire.

The key is that it doesn’t take a million dollars to live like a millionaire, it simply takes the freedom.

I’ve thrown the term location independence around a few times on the blog already. Being able to live and work anywhere may sound difficult or even impossible to you right now, but with the reach of the Internet it’s actually easier than you may think.

Granted your current employer may not be one who offers any sort of opportunity for location independence, my previous one sure didn’t, but if you want it bad enough maybe it’s time to sever those ties and start fresh.

My Story

Some people have been curious about how I was able to swing 22 days in Europe. Recently a buddy of mine even asked if I had exhausted all of my vacation time for this one trip.

In my current situation I don’t have a single vacation day, a single day of sick time, or any paid holidays. But what I do have is the freedom to get my proper rest, eat fresh home cooked meals 3 times a day, exercise, and then get work done when I am most productive, which is usually at night.

This is possible because I’ve broken free of the corporate machine and work with a group of like minded individuals. Instead of spending our time on corporate time wasters (meetings, office hours, etc) we focus on turning out results that have our clients shouting praise.

We’re spread across The US and Canada, all working from the comfort of our homes, or wherever we call our home at that moment, and collaborating on the web.

You see the freedom to be anywhere and do anything doesn’t come down to money in the bank, it comes down to the degree of ties that you have to your location. If your source of income requires that you be in person at a physical location then, in my opinion, you’ll never be free.

Working on the Road

I’ve been part of the Men with Pens team for some time now but this latest trip was my first experiment in semi long term travel while working from the road. I say semi long term because although I consider 22 days to be a long trip, I know to some people anything short of 3 months is nothing.

Now That’s an Office

The most amazing experience for me working on the road came in Paris. It was a Tuesday afternoon, clear skies, about 70 degrees F, and I was busy working. It would be just like any other summer day in Chicago, however this was infinitely better. I was sitting on the lawn in front of, and looking directly at, the Eiffel Tower. I couldn’t help but think about the fact that I use to spend 8 hours a day sitting behind a desk in a poorly lit room without a single window to the outside world.

My new “office” was heaven. The same wave of amazement swept over me on the train from Venice to Milan. It was nowhere near the same experience, but it was simply the realization that I was living the dream and it wasn’t a pie in the sky, win the lotto or be bought out by Google dream. By all accounts it was simply a result of shifting what work means for me.

First Thing’s First

My number one rule of travel is to try my best to actually take in the entire experience. I love snapping photos and just finally started to get into doing videos, but I do my best to also step back and take everything in through my own eyes, not just the lens of my camera.

This also means that although I was setup to work on the road, I didn’t want it to take me away from the trip itself. Doing so would be completely counterproductive and I’d just as well stay home and work.

So the first step to working on the road was to streamline my workflow and remove as many dependencies as possible.

Supply List

I’m a web developer so first and foremost I needed my laptop. Although working from an iPad would be more convenient packing wise, there’s apps on my laptop that are vital to my work, specifically Photoshop and Coda. These are the 2 apps that I cannot do work without. Photoshop for slicing up designs (before I start coding), Coda for the actual coding and uploading via FTP.

One dependency that I typically had, however was an Internet connection. The typical plan of attack for developing a new website involves my working either on our development server, or directly on the client’s site. This of course was the weak point in my workflow because I needed to connect to the servers through the Internet.

Not knowing if and when I would have a solid Internet connection meant that I had to remove that dependency. So what I did was install XAMPP, an extremely easy to setup webserver that can run locally on my laptop.

This was the key that allowed me to develop websites without an Internet connection and was the perfect solution for my needs.

The Benefits of Being Disconnected

One of the most efficient work environments that I had while on the road were the train rides between cities. Our train rides ranged from just an hour to over thirteen hours on the overnight train so they always provided ample time to get work done.

The benefit of not having an Internet connection though was quickly apparent when I was able to do the first part of my work, slicing images out of Photoshop, in what felt like record time.

Usually I’ll be connected to AIM/gTalk, my email, and of course the Internet itself. Although it’s obvious that these little distractions can slow down productivity, it wasn’t truly apparent as to how much more efficient I am when I can (or have to be) completely cut off from the net until I actually was.

Without the possibility of distraction I was able to maximize my efficiency and get things done much quicker; definitely a benefit of this new working environment.

Even the actual development time was nicely reduced. This was partly due to the lack of distraction but even more so due to running the web server from my computer. Normally I would be connected to the web, connected to our development server and working on files directly on there. It’s funny but every 0.5 to 1 second file save or image upload adds up to take more time than it seems. Without having to wait for files to upload via FTP saved very little time short term, but was actually noticeable when looking at the big picture of an entire project.

The Downside

Although being disconnected from the net was a plus when it came to developing new sites, many other tasks, including making said sites live on the web, require a stable Internet connection and therefore became more of a challenge.

Early on, in London, we stayed at a budget hostel (by budget I mean 24 people per room, and 8 or so rooms…yep it was cheap) that offered wifi. The only problem was that the router seemed to have a very low threshold for number of allowed users. This meant that other than early in the morning before breakfast time, there was very little opportunity to get access to the net. And even if I was able to connect it was extremely slow.

Luckily though we had Marla’s cell phone with an unlimited data sim from Orange. This gave me the option of tethering my laptop to the phone and accessing the net that way.

The speeds through the phone weren’t great but they were much better than the wifi in the hostel and were, for the most part, reliable.

The sim worked in London and technically worked in Paris but no one could give us a definitive answer as to whether or not we would be charged roaming fees so we opted avoid using it.

When we arrived in Venice we stopped at the first cell store we could find and got another unlimited data sim, this time from the Italy cell provider Wind. This did the trick until Marla’s phone died a few days later.

Aside from wifi access being sketchy, I never thought about the connection being locked down. There was a least one occasion where the hotel’s wifi did not allow FTP traffic. This was an enormous inconvenience as everything I do requires FTP, but at least this only happened once. It’s one of those things though that I simply took for granted before it happened, but it’s definitely something to look out for.

It’s Electric

One thing that outperformed it’s cost was my All-in-One Travel Power Plug Adapter. I made sure to check all of my gear ahead of time and everything was able to properly handle both US and European voltages. This meant I was able to stick with just the budget adapter converter instead of an actual voltage converter, keeping the cost and the weight both low.

If you find yourself in Europe just make sure to check that your electronics accept both 110V and 220V. As long as you’re covered there you can safely stick with an extremely affordable all-in-one adapter and stay charged on the road.

Up in the Air

My 13″ Macbook Pro has proven it’s worth to me time and time again. But while it’s much more mobile than my daily workhorse (17″ Macbook Pro) it still is a substantial amount of weight to add to 22 days of luggage.

On our next big trip I will definitely pare down the amount that I bring in my single carry on once again, but now there’s a new option for the ultra mobile, location independent worker.

Previously way overpriced, but now quite affordable, the Macbook Air provides and new ultra mobile experience. While I have no plans on picking up an Air, due to it not being a necessity and my lack of confidence in how it will stack up next to the performance of my 13″, I still can’t help but think that it’s finally the answer for an ultra mobile solution.

All in all 22 days working on the road in Europe proved to me that not only is location independence for me, but it’s also quite doable without much hassle.

Now it’s your turn. What experiences have you had while working on the road? Tell us about the good, the bad and the ugly in the comments.

10 responses to “Working on the Road: A 22 Day Experiment”

  1. Chrissy Avatar

    I can go anywhere they need vet med, and they need it everywhere… think you can unstick mike from the world?

    1. Jeff Sarris Avatar

      I don’t even know that he needs “unsticking” I think he just has 2 criteria that need to be met. First, be able to pay the bills and second, not be bored. Set it up so he’s sure that both of those needs will be met and I think he’d be open to it 🙂

  2. James Chartrand - Men with Pens Avatar

    Yeah, when you freelance, you can work from almost anywhere in the world – all you need is an internet connection and a bit better time organization than usual. When I took off on my 3-week road trip last year (and subsequent trips to TO, etc), I just made sure every hotel had ‘net and that everyone understood my work hours would be 6am to 9am and 7pm to 9pm.

    (Which reminds me – next time you go on a trip, let’s work out work hour scheduling, mmkay? :P)

  3. Kristy R. Langstraat-Bolte Avatar

    I would love nothing more than to have a job where I can work from home or anywhere else. It is so depressing being stuck behind a desk, or in a building, with no windows, and missing out as the world flies by without you. However, I’m stuck as to what I could do, seeing as I am in no way a web developer or anything like that. As far as computers go, I am an amazingly fast and accurate typist, I can do 85-95 words per minute!

    1. Jeff Sarris Avatar

      Sure web development and writing lend themselves to making a living on the web, but you may be surprised how far you can take your skill set with just a little bit of creativity.

      Take my friend Adam for example. He’s a woodworker who designs and builds beautiful furniture. Typically you wouldn’t expect a woodworker, which is seemingly very location dependent, to build a successful business on the web. While building furniture does require access to his shop and tools he’s also started The Woodworker’s Journey where he helps other woodworkers build their own profitable business. By doing this he’s following his passion, helping others and also opening up the opportunity for location independence. While he doesn’t have or want total location independence since he loves what he does, I think it helps to show that by creatively looking at your skill set you can do a lot more than you may expect and a typical day job isn’t necessarily the only solution.

      Is making a change and figuring out exactly what you can do to help people a simple task? No. Can someone else plan it out for you? No. Is there a “secret” that you can buy to magically have it happen? No. Is it worth the effort involved to get to that point? Absolutely 🙂

  4. Kristy R. Langstraat-Bolte Avatar

    Thanks for the encouraging words Jeff, definitely something to think about! What I’d really love to do, is own a travelling booth that sells fair food, and travel to all the fairs, and in the winter go south to their fairs, unfortunately the husband doesn’t agree with me, hehe!

    1. Jeff Sarris Avatar

      Well that’s cool. Maybe if you start small and work with an existing seller you can test if it’d be cost effective and then use that to convince him 🙂

      My Dad’s friend’s son Aaron did just that. He worked with a guy that would go fair to fair with a funnel cakes trailer. They only worked IL so they’d work just 3-4 months out of the year, but then after a couple years the original owner decided to sell so Aaron bought him out and did it on his own. It meant working long hours all summer long, but he did surprisingly well so it’s definitely a viable option.

  5. Kristy R. Langstraat-Bolte Avatar

    Wow, cool, definitely something to think about! I suppose if I still don’t have a ‘real’ job by next summer I could probably find something like that and just work IL during the summer and make sure I reallly like it!

  6. kolonko Avatar

    Way cool to read about someone who is actually doing what I’m trying to figure out how to do as a freelance medical writer. I’m encouraged and inspired. Thanks!

    1. Jeff Sarris Avatar

      I’m glad to hear that, thanks for reading and good luck on your journey! 🙂