Working on the Road

From the beginning of our trip, I had a thought that it would be great if by the time we got to New Zealand, I had found some freelance programming work, partly as a way to start to get back in to the groove of working, but also to start earning some money to help alleviate the pain of spending so much over the past year. As luck would have it, I ended up having a lot more than a little bit of freelance work.

One of the co-founders of my previous employer, FlipKey, reached out to me in August, wondering where in the world we were and if I’d be interested in chatting about a new project he was working on. It turned out that Danielle and I were deep in the Shenandoah Valley in Virginia and heading back to Boston a week later. We got together for coffee and started chatting about his project – a new home management company, focused on taking the pain out of finding and hiring a contractor for maintenance and repair projects around the home. The vision for the company sounded great, but just as exciting was the opportunity to partner with Jeremy, someone who I had spent much of my six years at FlipKey collaborating with on projects. As I arrived in Croatia, we continued to work out the details, but pretty quickly I was up and running, improving the website and adding new features.

At a cafe in the Moscow Airport writing up tech suggestions.

At a cafe in the Moscow Airport writing up tech suggestions.

Over the next month and a half, I put in an hour or two here and there to improve the base functionality of the platform. With the base platform functioning well, we ratcheted things up around Thanksgiving and began building the v1 user dashboard and new landing pages. With lots of iterations, redesigns, and tweaking, we launched a fully functional user dashboard, several landing pages, and a robust platform to allow users to communicate their home repair needs to the customer service through texting. The most exciting part of all this was that I did it from Thailand, Cambodia, Vietnam, and New Zealand. In between visiting the golden temples and lying on golden beaches, after climbing steep mountains and viewing beautiful glaciers, before Danielle woke up and after she’d gone to bed, and most often from a cafe with good internet and better coffee, I helped create a website and a company.

It sounds pretty awesome and it was. But it was also exhausting and stressful at times. Each week in December, I put in over 20 hours of work. This doesn’t seem like a lot, but when you’re a full time traveler, it’s sort of like adding a part time job to your full time job. Ok, not really – it’s way better than that – but in terms of the time commitment, it is. Trying to take full advantage of places we were in and knowing that this was quite literally a once-in-a-lifetime visit to most places, while still trying to complete projects and get features out the door, was a true lesson in finding balance. When we took a three-day trip to Ha Long Bay in Vietnam, it felt like a real vacation. I left the computer at our hotel and left the work behind. It felt so refreshing to focus on spending time with Danielle and seeing some amazing sights and not be thinking about how I can solve whatever current problem I was working on. As we traveled through New Zealand, the work was steady, but more often five to ten hours a week. It was exciting to continue to contribute at a manageable pace and to look forward to arriving back in Boston with a project to work on.

We’re still figuring out where it will go and, as with any startup, if it will even succeed. I’m thankful for the opportunity to put my skills to use during our travels and to Danielle for supporting me and taking on the bulk of planning and blogging, while I spent much of my free time working.

The current Breezeway home page.

The current Breezeway home page.

If you’re in the Boston area and are a home owner, I’d encourage you to checkout our company, Breezeway. We have just launched our first product – a spring maintenance package, aimed at focusing on some of those things you don’t think about – either because you don’t know they are important or because you just don’t want to even think about them (refrigerator coils, here’s looking at you), as well as a home check to help determine what you should be focusing on for maintenance in the future. Having moved back into our condo two weeks ago, I’m excited to take advantage of this to kick start getting our home ready for the summer and some fun home projects we have coming up. If you own a home or condo, I’d highly recommend you check it out (with a special price just for our friends and family) – we’re small and new, but I’m excited to see how we can start helping homeowners have a better experience with home maintenance and repairs.

Breezeway Spring Maintenance

Spring Maintenance from Breezeway

Sorry for the pitch, but this post wouldn’t be complete without me promoting the thing I’ve been working on for the past six months. For anyone thinking about working while traveling (either as a freelancer during long-term travel or just taking work with you on a vacation), here’s a few things I took away while working on the road:

Find a good coffee shop to work at
If you’re on vacation or traveling, there are a hundred things you could be doing other than working that would probably be more fun. Find a way to treat yourself, so you don’t feel so bad about working instead of swimming in the ocean or climbing a mountain.

Cong Caphe was one of my favorite places for coffee and for work in Hanoi.

Cong Caphe was one of my favorite places for coffee and for work in Hanoi.

Carve out a chunk of time for work
I often tried to fit work in the free minutes we had. Often this was just frustrating, because I couldn’t get in a good groove. When I was trying to figure out a problem, I often needed an hour or two to really dig into it and research solutions. Trying to make incremental gains in 10 minutes usually was just wasted time and I would have been better off simply waiting until I had the time to really spend solving the problem.

Go for a hike
Standford did a fancy study, but I have lots of anecdotes. Often when we went out for a hike, I would be working over how to fix a problem or design a certain feature. Out on the trail, away from my computer, I often came up with a creative solution to the current project. It was always rewarding to experience the beauty of nature and to make progress on a project I had waiting at home.

Hiking was good for our souls and bodies, but also for our minds.

Hiking was good for our souls and bodies, but also for our minds.

Appreciate those traveling with you
While you’re working, they’re probably planning your next adventure. This may not always be true, especially if you’re on a short-term vacation, but if you’re traveling like we were, there was always lots of planing to do. Danielle was amazing to take this all on and throughout much of New Zealand, I just went where she told me to. She never failed to plan an amazing adventure and give me plenty of time to finish my work.

Taking a break from work to enjoy some food together at one of our favorite cafes in Hanoi.

Taking a break from work to enjoy Christmas Eve dinner together at one of our favorite cafes in Hanoi.

Working on the road can be great and it can be hard. Hopefully, one way or another, it’s helping you earn some extra income or save vacation days. Take a little bit of that and go splurge. It was great to take some fancy dates to celebrate a long day of work.

Don’t do it on a family vacation
I loved being able to work during our travel and I would do it again in a heart beat, but after seeing how much time it took and how hard it was to just enjoy all the amazing things around us, I’m not sure it’s a great idea on a family vacation. Actually, I’m pretty sure it’s a terrible idea. Vacation is a time to get away from work and celebrate family – make it about that, not about work.

After a year on the road, trying to both travel and work, it’s been pretty refreshing to have a relatively normal schedule and an office to work out of, but the past year was an amazing experience. The ability to work during part our journey is a big piece of our story. If you have the ability or the chance to combine some work with your long-term travels, I’d say try it out – especially if it means you can travel for longer or cheaper. The main thing to remember if you try this: hold fast to your boundaries between work and play. When you’re working, work. When you’re out and about, be fully present in the place you are. Keeping this in mind will allow (and your travel partners) to fully enjoy wherever your travels may lead you.

One thought on “Working on the Road

  1. Hi –
    Thanks for this post. Uncle Russell forwarded it to us here in Seattle. We often work while we travel and can closely relate to your experience.
    Good luck!

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