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Transitioning to Life on the Road

Updated: Oct 27, 2020

For those who don't know me, I'm originally from the Northern Virginia area - which is a collection of suburbs outside Washington D.C.. After living somewhere for 25 years, I felt creatively uninspired and used international travel to escape the routine and discontentment in my everyday life.

In 2019, I started to truly evaluate my life and where it was going. I was tired of complaining about the predictability and lack of adventure and decided it was time to finally take control of the only life I have and live more boldly. You're in charge of your own happiness in this world, and for me I knew I needed to make some big changes in order to be fulfilled everyday - not just waiting for the next big trip to escape my life. I decided to essentially turn my life "into" a vacation by traveling full-time, starting with Denver, Colorado back in June 2020.

Researching Phase

Even before the pandemic started, I was mapping out a plan for transitioning to a more minimalist lifestyle as a digital nomad - one where I prioritize traveling and exploring instead of the traditional route of buying a home and starting a family (there's nothing wrong with this route as long as it's what you want!).

I had been researching new cities and digging through reddit posts to find as much information on this lifestyle as I could. Truthfully, there wasn't a whole lot. Most digital nomads I read about left their 9-5 jobs, switched to freelance or savings, and moved to a cheaper country in South America or Southeast Asia. Unlike them, I didn't want to quit my day job - I enjoy the work I do and the benefits/financial stability are important for reducing stress for me. If you can transition your job to full-time remote like I did, then that would be the easiest way to getting started with this new lifestyle.

Part of the fun of this type of lifestyle is getting to choose where you want to go and for how long you want to be there. There are no rules really, so start by making a list of cities you want to try living in, some pros/cons, check out costs to make sure you can comfortably afford it, and then figure out what time of year you want to be there and for how long! Keep in mind that this can all change. I thought i'd want to be in Denver for 4 months and escape before winter, but I felt like my time wasn't done here yet, and just got another lease to extend even longer.

Finding a Furnished Rental

Ideally, if I was with someone, I would do the vanlife and travel that way, but i didn't feel safe or comfortable doing that on my own, so I've opted for renting out fully furnished places. This can be quite expensive, but it works for me since I couldn't bring many things in my tiny convertible. If you're looking for a cheaper alternative, you can rent out an unfurnished place and use furniture rental services for the basics (check each city for what services are offered, CORT is a popular one here in Denver).

First night in my first fully-furnished rental in Denver

I am extremely picky with where I live. I have a massive list of the amenities I need and am willing to pay and wait for the right fit. If you don't have a dog and you're a little less high-maintenance than me, then you'll probably have a much easier time. The best websites i've seen for finding furnished places are Airbnb, Furnished Finder, and just checking out if any apartment complexes have fully furnished rental units. If you're living in a van, you can skip this part.

The main amenities I look for when choosing a place are:

  • High-speed internet/WiFi - You'll need this if you have to VPN for your work or stream video/content for conference calls.

  • Pet-friendly - If you're bringing along your furry friend, highly recommended!

  • In-Unit Washer/Dryer - If you are packing light, you probably will be doing lots of laundry, so this should be convenient for you.

  • Parking - This is usually a given, but you'll need a safe place to store your vehicle.

  • Fully Furnished - You'll need there to be at least a bed, TV with HDMI ports for your Roku or Amazon Fire stick, desk for working at, and some kitchenware cooking.

  • Gym - If you're on the move, you probably won't have a lot of time to check out local gyms and get a short-term membership, it's much easier to just find a place that already has one conveniently there for you.

Packing just your Essentials into your Car and Hitting the Road

Another difficult part of transitioning your life to the road is that you can only bring your essentials. This can be hard if you have a small car like myself. I did own quite a bit of nice electronics and furniture before moving - I was able to sell lots of unused clothing and pack up the nonessential electronics into storage at my parent's home. If I had a bigger car, I would have brought along a lot more of those things.

To create additional space in my car, I purchased a "boot bag" which is essentially just a backpack for my MINI. If you have a larger car, you can opt for a roof-rack for more space. Just remember that this is a chance to clear your life of a lot unnecessary items and just bring along the things that make you feel comfortable and at home. I'll create a more detailed post on Items that i've found useful for a traveling/remote lifestyle.

Letting Go and Preparing for Hardships

The COVID-19 pandemic began around the end of a really tough year in my life. A 5-year relationship came to an end and I was starting this new chapter in my life with a new puppy, all on my own. It's hard to leave such a comfortable and safe life for one where you don't know whether things will work out, but just remember that life is about doing what you need, regardless of what others expect of you; it's being centered on yourself and your own needs. Remembering that when others judge or criticize my life decisions, has helped me immensely.

With that, leaving your hometown, friends, and family is extremely difficult. Having technology to keep us connected is critical, because it will get lonely sometimes, but when you allow yourself to let go of the things that contributed to who you were, you create space for a newer version of yourself, a version will have lots of uncertainty, but lots of growth.

Preparing for the hardships ahead is important because they'll be there, but just remember that everything is temporary and you are in complete control of your happiness and can make changes as needed.


Hi! I'm Jackie and my dog is Sora. I work remote as an engineer, but I love to spend my free time in nature and by traveling to new places. I take my camera wherever I go, and sometimes my drone.

Somewhere With Sora is a Seattle-based lifestyle and travel blog that provides helpful travel and adventure tips for all kinds of trips, with or without the dogs.

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