A Young Snowbird’s Remote Experience

It had to be different this year; something had to change. Winter in Minnesota requires and demands both physical and mental resilience, even for people who’ve lived through it for many years. The cold and darkness takes a toll in so many different ways that even the hardiest of residents will complain about it at some point. February of 2014 for me was one of the lowest points I’ve experienced in my life and I wasn’t able to put a finger on exactly what pushed me there other than the brutal conditions. I haven’t really been able to enjoy or appreciate winter since I was a kid, especially the dark months of January and February, and I likely have seasonal affective disorder. With that in mind I decided to look into heading south for an extended period of time last winter and I was lucky enough to earn permission. While some WordPress agencies, and Automattic itself, are completely distributed, Westwerk is not. There are pros and cons to each approach and even though I’m not sure if I could handle remote work full-time, I felt like doing it for a month or two would be an interesting experiment and wanted to see if weather and temperature really were causing my problems that seemed to surface around the same time each year.

Last fall I started looking into Airbnb rentals and was initially looking into Austin, TX because I haven’t been and have heard many great things. After comparing average temperatures, prices,  and learning that a relative’s condo in Florida would be open for a discounted price around the time I was looking though, I easily decided that Florida made the most sense. Fort Myers isn’t exactly comparable on any level to hip and trendy Austin but Florida weather and temperatures were a much safer bet, not to mention the ocean and beaches. I also decided to drive since the area I was headed wasn’t walkable and I didn’t feel like I wanted to spend that much additional money on what was already looking like a pricey adventure. I hadn’t been to Florida since I was a kid and I had never been out of the Midwest for more than a couple of weeks.

In mid-January I said my farewells and began the long drive across the country. I decided to take the St. Louis route instead of going through Chicago because Google Maps indicated it was around twenty miles shorter, I didn’t want to run the risk of getting stuck in Chicago traffic and I had never been to the “Gateway City.” I was surprised that the snow seemed to end by the time I hit Missouri – I’ve always been amazed at how different temperatures can be after driving just a few hours south. These days I’d be tempted to call St. Louis the “Red Light Camera City.” Many drivers at night seemed to trigger the cameras and they had an awful strobing flash that was so distracting it seemed dangerous. I’m not going to detail all my stops, and didn’t really take the time to explore any place along the way since the drive was so long, but I did try to check out some highly rated restaurants along the way. I’ll just note that The Silly Goose, in Nashville, was well worth the stop despite delaying me on my way to Atlanta. I’d also recommend avoiding driving in or around Atlanta at all costs to anyone. Coming into that city at night on a busy twelve lane interstate where everyone seemed to be driving 75+ mph was extremely stressful. They most certainly drive faster in the South.

The condo in Fort Myers where I stayed was fantastic but definitely left me feeling like a bit of an outsider. Picture a young, single, bearded, hipstery guy who doesn’t golf in a gated golf and tennis community consisting primarily of retirees wearing lots of white and beige. I walked around the community every day (that it wasn’t raining) at lunch and often a second time after I was done working and was always concerned the community patrol vehicle was going to bring me to golf jail for trespassing or not complying with the dress code (yes, there was one in certain areas). In truth, they did ask me what I was doing once on my way to the clubhouse for a late night exercise session, which I suppose seemed odd since most of the community seemed to start counting their Zs around 9 – 9:30PM EST. I’m admittedly more of a night owl and I also stayed on CST to keep in synch with Westwerk back in Minneapolis. Staying in this community was a bit socially isolating but I was so active exploring new places and relaxing on the beaches on the weekends that it didn’t really matter much to me. I hiked, kayaked in the ocean, hit almost every beach in the area, tried some great restaurants, saw some wild alligators, checked out other nearby beach towns, and visited several tourist attractions.

I had initially planned on being in Florida for four weeks and I ended up taking a couple vacation days for my trip down, the trip back and to extend a few weekends. Due to unfortunate circumstances, the guests that were renting the condo directly after me had to cancel their trip at the last second, giving me the opportunity to extend my stay to a total of seven weeks (another plus for driving instead of flying), which I went ahead with as soon as I received approval. The biggest thing that I like to point out to people is that if I add up all the weekends during that time it adds up to two full weeks and I took some vacation days on top of it. Not only did I feel like it was a great way to really experience a new area, it was also a way to “vacation” on the weekends while keeping my actual spent employee vacation days to a minimum.

To ensure that I would be able to stay productive in Florida I replicated the exact computer setup of my work desk at Westwerk. In addition to my work MacBook Pro I brought along an additional 22” monitor, external keyboard and mouse, and purchased the same Griffin laptop stand. Internet initially wasn’t problem until I got a call from my relative about my bandwidth usage. Little did I know that I was running off a shared cell data plan. My usual Spotify and Netflix habits sucked up the plan’s limits in just a few days. My solution was to Amazon Prime an Alpha Networks long-range network adapter and use one of those evil Xfinity WiFi hotspots for the remainder of my time. I had to stay in a certain spot in the condo to keep it working but it prevented me from having to go to a coffee shop every day. So despite the fact that the Xfinity hotspots seem highly dubious, they’ve saved me from no internet more than once.

Considering it was my first time giving remote work a try for more than a couple of days, I should state that I didn’t find staying focused was a problem for me at all. It really seems to depend on the person but because I’ve never had an issue with it for short periods I didn’t expect that I would find it very difficult for longer periods – and I didn’t. As long as I had a stack of work on my plate that needed to be completed, I didn’t find it troublesome to stay on task. It was sometimes difficult to look out the condo at the beautiful day while sitting on my computer but I would compensate by walks at lunch and would also try to do things after work as much as possible. It also definitely helped to keep in touch and stay in the loop with the Westwerk HipChat channels. I’d say some kind of chat app would always be essential for remote working. The main drawback of being one of two remote employees at this time was that I was one of two remote employees at the time, and it seemed like I would occasionally be forgotten about or excluded from meetings, etc. Overall though, it was a very positive experience and it really helped me realize that my commuting back in Minneapolis, something that averaged around 25 minutes one-way but could increase exponentially during winter or an accident, was a big point of daily stress. I’ve since moved much closer to the Westwerk office to alleviate this.

In terms of my mood it was clear to me that escaping the depth of the Minnesota winter was hugely beneficial. I’ve found that I become the most frustrated when life falls into too much of a routine and because I usually avoid the outdoors in the coldest months, everything begins to feel much too repetitive and automated. The lack of sunlight and a coldness that seems to bite through to the bone makes it all much worse. Breaking out and doing something completely different in a more favorable climate where the sun stays out a bit longer in the winter worked wonders.

My trip was nothing compared to the epic journey that Westwerk Partner Travis Totz and his wife Jenna embarked on but it was still unusual compared to the typical everyday office job. As internet speeds increase and wireless data plans become less expensive and more accessible around the globe, I only see digital nomadism increasing. Escaping the winter for one or two weeks just isn’t adequate in my opinion. For me, getting out of the worst months of the Minnesota winter was worth its weight in gold. Not only did it allow me to truly experience a new area that I’d never been to, it also helped me to avoid the difficult symptoms I experience when the sun sets around 4:30PM and the thermometer usually doesn’t rise above 20℉ at best. If I have the funds available and permission to do it again next winter, there is no doubt in my mind that I’ll make another trip south.