Written by Stephen Ondich
We live in Southern California and run our own hardwood lumber business. However, we love Maine. As a result, we often take the entire family to New England and do the digital nomad thing. Despite being in rural Down East Maine, business goes on. In this article, I explain how we do business remotely from Maine. Also, based on my own personal experience, I give you 13 tips for your own successful Maine work-cation.
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How I Work Remotely in Maine
Our hardwood lumber company is located in Fontana, California. Accordingly, our business involves the production and distribution of wood products.Â
The reason I bring this up is to let you know our work involves products, not services. I am not a consultant, life coach, or lifestyle blogger.  Therefore, much of the daily remote work I do is time sensitive.
Additionally, digital nomad jobs are increasingly common in 2019.
Digital Nomad or Remote Worker?
However, I am not a digital nomad in the strict sense of the term. According to Wikipedia, digital nomads do not really have a home base. Thus, I am not really part of the digital nomad community on reddit or otherwise.
My work environment changes occasionally but it’s more predictable than a true digital nomad.
Since I’ve done working Maine vacations (work-cations) a few times, I have a set routine. Here is how I do it.
Planning My Working Trips to Maine
First, I decide where, when and how long I want to work remotely. I take into consideration the scope of work that needs to get done in my physical absence.
Next, I decide where to go in Maine.
Most of the time, my destination is our cottage in Milbridge. However, we may opt to stay at another location if we visit another part of the state. Maine is huge, after all.
Before I consider traveling to a new area in Maine, I check Internet availability and cell phone coverage. I use sites like Dead Cell Zones and Broadband Now to get information online. However, it’s often best to call ahead to the place you’re staying at to get feedback from people. Internet access is vague. If you need high speed for streaming and the Internet speed only supports email you want to know that ahead of time.
Then, I make a list of all the potential travel dates and look for competitive airfares. Once I find a good rate, I book quickly.Â
Southwest Airlines Rapid Rewards
I am loyal Southwest Rapid Rewards member. In addition to competitive rates from Los Angeles, CA to Portland, ME Southwest offers two incredible work travel benefits.
- No cancellation charges. Thus, if you book a Southwest flight and need to cancel or reschedule at the last minute, you receive 100% of your money back.Â
- Rapid Rewards Companion Pass. Regular travel and/or credit card purchases can qualify you for a Southwest Companion Pass. This perk allows you to bring someone along on your flight free of charge for a full year. Additionally, you can switch companions a few times within the year. This is a great way to bring family or friends along on work vacations.
Next, I print a hard copy of a travel packing list. I keep the list on my iPhone. However, I like to review and modify the list on paper. I’m old school that way!Â
My travel list includes all the items I bring. For example, laptop, laptop cord, iPhone, Phone cord, camera bag, toiletry kit, cell, portable charger, etc. The list is comprehensive and many items are obvious. However, there is a lot to remember and keeping a list that can be checked off helps ensure everything gets on the plane.
Then, I check the weather forecast and pack appropriate clothes.Â
Maine receives snow as late as May. Checking weather conditions is a worthwhile 30 second smartphone endeavor.Â
Prior to departure, I update all of my iPhone apps and make sure all of my cords are in good working order. Â
Next, I alert all of my work contacts that I will be away. Typically, I say that I’m out of the office but working and reachable. Also, I record a voicemail greeting message that conveys the same thing.
Finally, the last step is to back up my company files to a USB flash drive. I prefer a flash drive backup rather than a cloud-based backup.
In the event that I cannot access the Internet I still need access to my business data. This is a concern when travelling to rural Maine.
14 Tips For Planning Your Maine Working Vacation
Although, my work-cations mostly take place in Maine, these tips also apply to other work travel destinations.Â
- Â Forward Your Mail. Find a place to forward your mail before you leave if you are working for an extended period of time. Don’t rely on family and friend to collect your mail. Have it forwarded.
- Sign up for the US Postal Service’s Informed Delivery program. This is handy to have if you’re working remotely for a limited time and don’t need your mail but still want to monitor the mail you receive.
- Set up as many online bill pay options as you can. This saves time and hassle. Admit it, you’ve been meaning to do this anyway. Â
- Pick a fun location. For me, working from a cool/unusual/alternative location is empowering. What is the point of going to a unique location if you do the chain hotel thing? If you have the option of picking your venue, pick somewhere memorable.
- Be prepared with more than your smartphone. Maine has many remote areas. Relying on your smartphone’s Internet access could put you in a bad situation. You may end of off-grid and not realize it. Take a few old school maps and some printed directions. It’s a good idea to take phone screen shots of important info on your phone if there’s a concern that you may lose connectivity at some point on your trip.
- Amazon Prime. This is a life-saver for me. Where we’re at in Maine, there are local stores nearby but it’s about an hour drive to the nearest Walmart. An hour doesn’t sound that long. However, it’s 1 hour to drive to Walmart plus 1 hour to drive back back. Also, factor in shopping time and the cost of gasoline. Instead, let Amazon deliver packaged goods directly to your cabin or cottage. The delivery times may be longer than the 1-2 days in metropolitan areas. However, it’s still a great shopping option if you plan ahead.Â
- Research your area ahead of time. Don’t assume that you’ll have access to the same kinds of stores, restaurants and amenities commonly found in suburban areas. For example, our town has a supermarket. No big deal, right? I’ve since found out that all of our surrounding towns have no such grocery store. Most of them drive to our store to shop. You want to know what is available in your vicinity before you make the trip.
- Bring or pre-ship your favorite foods. Again, don’t rely on the local supply, especially if you are particular about brands.Â
- Check Maine weather conditions. Have a plan if you experience severe weather. Everyone knows about Maine winters. However, even in Fall wind storms can knock out power for extended periods of time. No power means no Internet, no charging your electronics, no electric heat, etc. Emera of Maine has a web page devoted to power outages here.
- If traveling with others, select a location where your guests can explore while you work. If you provide the only means of transportation and there’s nothing to do close by, it will not be a relaxing trip for anyone.
- Internet Cafes. If you need really strong fast Internet for work, look for Internet cafes close by. Many hotels, rental houses and AirBnb’s offer wireless Internet but there’s often no distinction between intermittently functional and stellar connectivity. However, an Internet cafe’s main purpose is to provide reliable bandwidth. Make sure you know where one is.
- Check cell coverage. You may have the best coverage where you live but things change region to region. Check out a site like Dead Cell Zones to find out how your cell phone is likely to function at your destination. FYI, US Cellular is commonly used throughout the state of Maine. Â
- Designate a work space separate from your living area. This is especially important when traveling with companions. It helps keep the stress level down for you and your guests.
Jill
19 May 2019I’m staying in Maine for a month and will be leaving soon. It will be the first time that I’ll be working remotely; good tips and advice.
Stephen
20 May 2019Very Cool, Jill! What part of Maine are you headed to?
Heidi
21 May 2019Great tips, thanks! I never thought to use amazon prime in that way! I’ll be stealing that idea for sure.
Stephen
21 May 2019It’s really convenient. From California, we get Prime deliveries next day, from Milbridge it’s about 3-4 days. Considering the population density gap between both locations, I’d say that’s pretty good.
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