In June 2020, my husband and I packed up our 2 cats and started what has become a 9-month journey across America. With no mortgage, no kids, and pandemic-driven remote jobs, we figured, when else would we ever have this opportunity?

Our first trek was a drive from our home in North Carolina to the Adirondack Park in upstate New York. We intended to stay for a few weeks — much longer than our typical 1-week stay.

We didn’t leave until mid-August.

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Photo by Maria Leonardi (author)— Adirondack Park, New York

As we worked on the deck overlooking the lake one warm sunny day, I asked my husband:

“What if we just kept traveling? We aren’t going back to the office any time soon.”

He definitely looked at me like I was crazy. I don’t really blame him.

But, he didn’t say no.

We didn’t set out to live life on the road, but in 9 months we’ve traveled nearly 7,000 miles and lived in 6 different locations (safely social distanced).

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Google Maps Screenshot — Adirondack Park, North Carolina, Santa Fe, Sedona, Sonoma, Hawaii

As we trekked across the healing red rock landscape, sipped cabernet in Healdsburg, and enjoyed the Paniolo lifestyle in rolling Hawaiian ranch-lands, we soon wondered, could we work remotely forever?

The answer is, a resounding “yes.”

With the rise of remote work, people can choose to live and work where they are most happy. Whether you stay where you are, travel the world, or relocate to your happy place, the choice is yours.

My husband and I have chosen to live and work in beautiful, rural, remote locations where traditionally stable jobs are scarce.

After the first few months of Instagram posts, the comments started rolling in.

“How is this possible?”

“I wish we had thought to do that.”

“How did you [fill in the blank…]”

I was surprised by how many people wished they could do something similar but didn’t know how to make it happen, though it was too complicated, or told themselves that they “couldn’t possibly.”

The thing is, it’s uncomfortable to take a risk and try something new.

Digital nomad life has been around for quite some time. But this is different. Traditional office workers don’t get to choose that life.

The pandemic has changed everything.

If you’re one of the ~40% of workers that have the privilege and ability to do your job from home, you now have the power to take control of where you want to be.

We went on the road with 2 traditional corporate desk jobs. Here’s how you can too.

Remove ”shouldn’t” and “can’t” from your vocabulary

While living life as a digital nomad or remote worker is not a new concept, it sure is alien to traditional office work culture.

Doing things differently from the norm can surface some serious unhelpful thoughts and self-doubt.

There were plenty of times during the planning stage when I thought that we couldn’t or shouldn’t go forward with our plan. Unhelpful thoughts like “this is crazy,” or “we shouldn’t be doing this right now,” or “I can’t do this and maintain my career” surfaced all the time.

When this happens, take a deep breath and consider where the self-doubt is coming from. Is it a legitimate concern? Or are you jumping to conclusions or catastrophizing?

For me, it was mainly the latter. At the end of the day, it’s important to remember that you always have a choice.

You may think it through and decide to stay where you are and that’s okay. Just don’t let self-doubt take away your choice.

If you’re still on board — continue reading!

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Photo by Maria Leonardi (author) — Sedona, Arizona

Be an amazing employee

Be honest with yourself. Are you a huge slacker at work? If so, keeping your job while embracing remote work is probably not in the cards. If you’re underperforming, take some time now in the planning stage to line something else up that you can take with you on the road.

Trust is essential between employers and employees in a remote work world. Even the best of employees may have a hard time with distrust from above when going remote.

If you were an in-office employee, make sure you build a rapport with your boss. Don’t burn yourself out trying to be the “best” or overcompensate to win them over to your new dream, but meet your deadlines, be communicative, and be dependable.

You shouldn’t have to work more or perform above and beyond to go remote, but you do need to be competent. And when you head out on your journey, overcommunicate. Don’t hold back. Tell them what you’re working on, let them in on your progress, and tell them what’s on deck on your workload.

Plan ahead

Despite what you may see in digital nomad photos and posts about last-minute destination decisions if you’re traveling with dependents (pets or kids) or have any type of rigid work requirements, you need to start early.

We started planning nearly months in advance of our first destination and months ahead of our current destination. I wish I had started sooner.

Start by writing down what’s important and meaningful to you. What is a requirement and what’s a “nice to have.”

For us, we required high-speed internet, comfortable space for our 2 indoor cats (this meant square footage, screen doors, and habitable outdoor areas), and a kitchen to cook our own meals.

Our nice to haves which we, by and large, met at each stop were, the ability to receive packages, access to good ingredients for cooking, quiet surroundings, and easy access to hiking trails or pleasant walking paths.

Our path might be a nightmare for you if you thrive in a walking community, don’t cook, and are traveling alone and don’t like solitude.

This is why you need to look inward and not just at the thousands of posts about how you should travel as a nomad or live as a remote worker.

Identifying what’s important to you can make or break your journey.

Double-down on housing research

Of the hundreds of hours we spent planning, roughly 90% was spent on finding places to stay.

With pandemic-driven remote work, rentals filled up quickly.

Ask for exactly what you need

If you will lose your job without dependable Wifi, ask what speed internet they have. If you need items shipped ahead of time, make sure the owner can accept packages without you there. If you’re traveling in a car and don’t want to park on the street, ask if they have a driveway.

“Pet friendly” means “dog” friendly

If you are traveling with a cat, ask specifically if the owner accepts cats. Most of the time pet-friendly homes only accept dogs. This was a major source of heartburn for us and delayed our ability to book.

Look at Google Maps

You can’t always see the specific address, but you’ll usually be able to see with enough accuracy to know what type of neighborhood a home is in. If the owner says it’s quiet but it’s bordered by 2 highways, it’s probably not all that quiet. If they say it’s in a nice residential neighborhood but there are warehouses on all sides, you probably won’t be getting much of a cozy residential feel.

Read the reviews

Read the entire description and every review from the last year. Weed out the ones that sound unreasonable. For example, if a guest leaves a terrible review complaining about the rustic feel of an off-grid Redwoods home you can probably throw that one out. If someone gives a detailed account of how the “private” home is actually shared with 4 other guests, you might want to heed that warning.

Leverage monthly discounts

We used Airbnb and leveraged the up to 30% discount some homeowners offer long-term renters automatically. If you use another service like VRBO, ask the owner for a discount. You’re providing them with a steady income stream at a higher price than a typical long-term rental. It’s in their best interest to lock you in, even at a lower rate.

Housing takes a lot of time and effort, but trust me, if it’s important to you, your job, your partner, your pet — it’s worth it to find a place to call home while you’re on the road.

Don’t ignore the details

Make sure you think through the requirements of each stop you plan to make. For example, we had to prepare 4 months in advance to take our cats (dogs are the same) to Hawaii. The process involved lab tests, health certificates, medication, a permit application, and inspection arrangements to skip the quarantine.

If you plan to travel internationally, make sure you understand the visa requirements ahead of time.

If you have pets, identify a veterinarian at each stop so that if there is an emergency, you aren’t scrambling on Google to find one with reputable doctors.

If you absolutely need to receive your mail, line up rented P.O. boxes at each location. We used UPS so that we could receive both packages (wine!) and USPS (USPS only accepts USPS). Rent the smallest box available — they’ll still accept any size package.

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Photo by Maria Leonardi (author)— Waimea, Hawaii

Get your finances in order

We didn’t do this on a whim without thinking about the financial consequences. Both of us had stable, well-paying jobs, an emergency fund, and a strong idea of our typical monthly expenses.

Before you do anything, make sure you have your own budget (for your current, non-remote work life). Once you have that, make a list of all the possible expenses you could incur above and beyond this number.

For us, it came down to additional rental expense, emergency cash for healthcare, pets, and vehicles (we had both a pet and a vehicle emergency that cost us upwards of $3K), and transportation (gas, flights, etc.).

Take into account the cost of living in each location. For us, North Carolina (our residence) is much less expensive than any destination we went to across all categories — housing, food, gas, etc.

Set your average monthly rent before you start looking for housing. It’s okay to go up or down in an individual month as long as you’re hitting your goal on average. If you decide to rough it in one place, feel free to splurge in the next.

Be realistic about what you can and can’t afford. You’re going to feel like you are on vacation, but you can’t spend like you’re on vacation the whole time. Budget for additional entertainment (like hot air balloons in Sedona or wine tastings in Sonoma).

Keep track of your expenses. It’s easy for them to get out of control when you’re having fun! But the point of living this life is not to live beyond your means, it’s to live within your means in the place(s) that make you happy.

Don’t overpack

Seriously, don’t overpack. It is unnecessarily stressful to try to stuff your life into the back of an SUV and do not understand how you ever got it all in there in the first place. We left our car in storage in San Francisco before heading to Hawaii and will likely have to rent a U-Haul trailer to get everything back across the country.

Don’t be like us.

Do pack the essentials. If you love to cook, bring your favorite cast iron pan. Keep kitchen essentials and cleaning supplies with you on an ongoing basis (if you travel by car). If your pour-over coffee maker brings you bliss, bring it.

You know what those essentials are. You’ll also recognize what is not essential by what things are shoved out the door last minute because you have an extra square foot of space in the car. Don’t bring those things.

Get to know the environment

Read about the environments you’ll be traveling through. Changes in altitude and climate can impact your health. If you’re going from low altitude to high altitude, know that you might feel foggy for a week (or worse). If you go from a wet to dry climate, remember to drink lots and lots of water.

Understand the different critters you might encounter. We’ve never lived in a place where there are creatures that have nasty bites or are poisonous. But, on our journey, we’ve come across centipedes, scorpions, tarantulas, and an insanely large toad that can kill a cat in minutes (yikes).

If you have kids and pets especially, know what to look out for.

Roll with it

Planning a long trip with multiple destinations takes time and is hard work. Don’t let that discourage you — it’s well worth the reward.

Once you start, just roll with it. You’ve done what you can.

Let it happen. Enjoy the ride.