Working on the Road

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Working in Good Earth Market in Delaware

I decided to take a road trip for about six weeks, 38 days to be exact. There were a lot of things to consider and plan for a road trip this long. One of the biggest was how I would work from the road along the way. While I could have used PTO for most of the trip, I decided to balance time off with working from home. Well, wherever “home” was. There were definitely some bumps in the road, but it was mostly a successful adventure. Here is what went into the process:

Planning & Approval

The first step in the process was to get approval from my company to go out on this adventure. In order to do this, my plan had to be fully complete to present for approval. That meant putting together the schedule of where I would be and when. This was extremely important because that determined my PTO schedule and the days I would be working. Since I was going to be camping and in areas with limited or no cell reception, I needed to get the PTO approved along with the trip itself. With the schedule set, the discussion started on how it would all work out.

The logistics of working on the road had to be planned out. The top considerations were travel days, where I was staying, ensuring I had adequate work space, and that I would be available to my team. Not only did I have an awesome team to manage, but I also had a new team member join weeks before this trip. And of course there were client deliverables along the way. Everything had to go smoothly, so planning each location was key. I spent days planning out the perfect Airbnb rooms, making sure I had all the equipment and supplies, and scheduling meetings around my PTO & travel schedule. The plan was set and my company had given me the approval, so off I was!

My “Offices”

Planning this trip out was definitely interesting. If we were in a normal working environment, I would not be comfortable being away from my team/office for this long. But with us all working from home since March, and for the foreseeable future, I realized my “work from home” could be anywhere. I still needed to be able to work effectively though, so I made sure to pick rooms/houses with adequate space and a desk if possible. Operating on a budget meant I was not able to spend on private houses or hotel rooms. I actually had a lot of luck with the places I chose, but a few small hiccups too. I also brought with me a monitor, keyboard, mouse and plenty of supplies to make sure I could have as normal a workspace as possible.

Working from the Road in Portland, ME
Working from the Road in Burlington, VT
Working from the Road in Providence, RI

Most of the rooms I booked had a desk inside the room, including stops in CT, RI, MA, & VT. I created some makeshift workspaces in ME, VT, NY, & PA on a bed, couch, or dining room table. I learned a lot in my first stop of DE because I didn’t have a designated workspace. I wasn’t sure exactly how I was going to work, but the market had some booths and wasn’t busy during most of my workday. So I had claimed a spot, was well taken care of, and tipped the staff well for letting me take up space. For those following along the rest of the road trip blogs, I was not working in SC, NH, WV, or NC.

Doing the Work

The 38 days on the road included 9.5 PTO days, 1 holiday, and 12 weekend days, which meant only 15.5 days of working. There were many projects, client deliverables, team meetings, and team management needs along the way. I especially couldn’t let anything drop or allow issues to occur while I was out enjoying this road trip. Some days that meant working later and having to miss out on some activities or sites. The 5 months of working from home had me fully prepared to work through Zoom, Slack, and other forms of communication though. Bringing an extra monitor and other supplies definitely helped when I had to work on audits, reporting, and other projects requiring more space/screens. It wasn’t always perfect or easy, but the work got done and the team had what they needed too. The work days also went by fast and overall the trip did too from a work perspective.

The Good & The Bad

Most of the working times went pretty smooth. Meetings were all attended, all deadlines were met, the team was able to get their work done, and there was support during my PTO days. Choosing rooms with private office space was definitely important and my roommates in most locations were respectful and didn’t interfere. There were definitely hiccups along the way though. Working from another location than your normal office isn’t easy and it can take a little bit to get settled. It’s tough to get settled when you move offices every 3 days. I had never done traveling for work, so many people probably know all about this, but I didn’t. Luckily most of my rooms made it easy, but it wasn’t always that way.

In Delaware, the noise sometimes made it difficult to have meetings. After realizing this on the first day I tried to take calls outside, walking around a garden with butterflies, so it wasn’t exactly a horrible problem. Internet connections and phone service definitely gave me some problems too. They weren’t persistent, but it did affect a couple calls or slow me down a little on some projects. Those issues aren’t uncommon in a work from home environment though. Forgetting the right headphones also meant buying a new set, as well as a few extra supplies along the way. Overall no major issues occurred though.

Working from the garden in DE

Tips & Advice

I learned a lot planning and going on this long road trip. Overall the adventure was great, but I am glad I spent so much time planning or it could have been much more stressful and difficult. Here are some final tips and advice if you are planning yours out:

  • Booking your Stay: Do your research on potential places. Ask about WiFi and noise in the area. Understand the shared space situation and what is in the area for meals or printing/shipping needs. Don’t expect to be able to effectively work from coffee shops or restaurants the whole time.
  • Discussing with Company: Make sure you have your plan fully thought out before the discussion. Know what deliverables, meetings, or commitments you have during this time and ensure confidence. Choose dates for the trip and PTO that don’t interfere with large projects or deadlines.
  • Pack your Office: If you commonly use certain things during your work day, bring those with you. Bring a small monitor for when you need more than one screen to get your work done. Ensure all technical needs are packed, including mouse, keyboard, headphones, chargers, extra cords, etc. Don’t forget supplies like pens, notepads, and business cards for people you meet along the way.
  • Be Realistic: It isn’t always going to go perfectly. Understand that you are going to have some issues along the way, but prepare for them so your downtime is minimal. Make sure you aren’t trying to overdo it and put the priority on fulfilling your work duties before the fun.
  • Have Fun: It can be stressful at times balancing the work, travel, and seeing each city. You might get anxious or worried along the way. If you did the planning, everything should go pretty smoothly. Get your work done each day and enjoy your evenings and weekends in whatever city you find yourself in.

Good luck on your next “work from home” adventure!