Going from IT to the Outdoors: The Ultimate Digital Nomad Starter Kit

The freedom to travel the world is pretty damn incredible. The ability to control where we spend our time is a luxury unlike any other.

And I should know. My wife and I travel full-time in our 30’ Airstream travel trailer.

We also maintain a growing YouTube channel called A Streamin’ Life and work on online projects almost every day. We get to pick and choose exactly where we lay our heads down at night, but we also need to be online every day.

It wasn’t always this way.

I worked 14 years in information technology, answering to bosses with varying levels of expertise in the very field that they were managing until, one day, I got to be the boss. As the Director of Information Technology, I was tied to my job. And, I never got to work from home.

I worked a very traditional job in a high-paying career field. But in 2016, I quit that traditional job.

I traded in the 9-5, predictable existence for the life of a digital nomad.

What is a digital nomad?

Just as the name sounds, a digital nomad is someone who moves around but uses telecommunication to continue engaging with work—typically outside of the set schedules of a 40-hour work week. For me, it means I travel full-time around the country with my wife and two dogs, and we’ve learned a thing or two about staying connected on the road.

Here’s something that you probably didn’t expect me to say: It’s not always easy.

And, you need to be prepared to work from just about anywhere. For example, I’m writing this article from a laundromat (that’s right - even as a digital nomad, life still happens). Clothes still need to be washed. Bills need to be paid. Cars need maintenance. Things still happen.

We aren’t always strolling through beautifully-architected European cities or sunbathing lakeside or overlooking the Swiss Alps or sipping Margaritas as we watch the sun dip down over the Pacific ocean.

I wouldn’t trade this lifestyle for anything. But, it’s not always roses and sunflowers either. In this article, I’m telling you exactly what you need to know to be a successful and happy digital nomad.

Here are the top five things that you need to know before hitting the road as a digital nomad.

To work from the road, you need to be a special kind of person. Believe it or not, it’s not always great. Yes, those pictures that you see on Instagram of millennials lakeside, pointing bare toes into the air with a laptop on their laps does not always accurately represent what it’s like to be a digital nomad.

1, It’s not always easy to stay connected.

We live in an incredibly connected world. We can map from one place to another using our phones, browse the Internet almost everywhere and communicate with virtually anyone with just a few taps on our phones.

But, let’s face it: most digital nomads aren’t ditching their traditional office-type jobs so they can hang out in crowded, well-connected cities.

In fact, it’s quite the opposite. They are working on the road. And, others still have devised incredibly innovative passive income streams to help fund their traveling lifestyle.

The point of becoming a digital nomad is to see beautiful things and get in touch with nature. The amazing power of some freakin’ solitude is indescribable, and if you’ve worked for decades or more in information technology, that’s probably exactly what you are looking for.

Unfortunately, there still remains a remarkably big dead zone where connectivity through a cell network, much less a WiFi signal, is downright impossible. If staying connected is a part of who you are, you won’t be able to go just anywhere. At least for long.

After traveling full-time throughout the United States for a couple of years, I learned three primary things (the hard way!) about the “connectedness” of our country:

1. There are so many dead zones out there, especially around the most beautiful areas of our nation (like National Parks)
2. Even when there is a signal, it may not be enough to be productive, and
3. Less sophisticated areas of the country are easily susceptible to cell tower overload during peak hours

It’s frustrating, but still very much a first-world problem. But, sometimes I feel like punching a hole in the wall whenever my Verizon MiFi device “sees” cell signal, but I can’t seem to do anything online.

It’s not always easy to find Internet on the road, and when you do, it’s not always dependable. Hotels, restaurants, and other public Wi-Fi options are notoriously unreliable. And if you’re hanging out in a campground, you might as well not even try to connect to their wireless network. We’ve only noticed a handful of campgrounds with reliable Internet access.

Pro tip: Use coverage maps available from virtually every major cell phone provider to get an idea of what areas have coverage. But remember that even if there should be cellular coverage in your area, that won’t mean it’s going to be fast - or dependable.

Here's more on how my wife and I stay connected as digital nomads.

2. Can you handle the solitude?

In a hectic information technology career, it might seem attractive to escape the hustle and bustle of city life; of running from problem to problem. Fixing this. Debugging that.

I know, it’s relentless. And, it can be tough to keep dragging your butt into the office.

Those weekend getaways plant the seed that solitude is good into your head - but, not everybody can handle the solitude or the lack of resources at your disposal.

You probably won’t have the same sense of community that you enjoy living a traditional life in an office and working around the same people and building relationships among friends. After all, digital nomads travel. Most travel often.

Will you be able to handle having nobody to talk to on most days and nights?

3. You need to be prepared.

Here is one thing that you can’t do if you’re looking to become a digital nomad: Just up and go. For most digital nomads, it doesn’t work that way. For most, it takes a lot of preparation.

For example, where will you sleep? Are you a #VanLife sort of person or are you pulling in enough dough to crash in swanky hotel rooms? Maybe you’re an RV-type person. Great, but what type of RV will you feel comfortable with and do you have the proper vehicle to tow it?

Also, how will you stay connected?

A lot of digital nomads rely on cellular technology through the use of Jetpacks (MiFi) devices. You’ll need to spend the majority of your time in places with signal (and, as I previously stated, is tougher than it might appear to be). Don’t rely on publicly-available wireless Internet if your job depends on you being connected each and every day.

Do you feel comfortable planning your travels?

In other words, how will you decide when to leave and where to go? You’ll need to park yourself (and your car/truck/RV) somewhere every single night. Street (stealth) camping isn’t always possible - at least legally. What if campgrounds are full and hotels are booked?

These problems won’t always be the case, but they will happen...eventually. The most successful digital nomads manage stress well and have backup plans as much as possible because they aren’t coming home to a dependable and stationary house.

4. Being a digital nomad requires a LOT of discipline

When you’re out there in the middle of nowhere (or even in a busy city with a lot of distractions), you have nobody to rely on but yourself. When deadlines creep up, you’ll need to summon the energy and motivation to get your work done.

And, that is a lot easier said than done for a lot of people.

The buck stops with you when you’re a digital nomad. You won’t have coworkers or friends there to keep you on track. For most digital nomads, they set schedules for themselves and stick to them to help ensure productivity throughout the day.

For my wife and me, we worked the mornings and explored during the afternoon. That scheduled ensured that we always got our online work done before venturing out to do something fun. The mornings happen to be when we are the most focused.

Set a schedule that works for you. If you’re most productive in the mornings, then create a schedule that prioritizes your digital activity in the morning.

Some digital nomads need to be online during certain periods of the day because that’s when their coworkers or customers are online. Obviously, those requirements will heavily dictate how your schedule will look.

The bottom line is to create a schedule that works for you and stick to it.

5. The grass isn’t always greener as a digital nomad

One of the biggest draws of a digital nomad lifestyle is how much better it’ll be.

The stress of the 9 to 5 will suddenly melt away and we’ll get to sit on a beach or on a hotel balcony with huge views of the Alps and plow through some remote work that keeps the money rollin’ in and the smile on our face.

Because, well, that’s what the photos show. Don’t believe everything that you read and see on Instagram about being a digital nomad.

Here’s the problem: Nothing about the art of making money suddenly changes or gets easier just because you’re living a life on the road.

Being a digital nomad is still life. If you’re running a business, you still need to square that against life’s demands. Build relationships. Sell. Provide customer service. Of course, product development.

Even with websites like Fiverr and Upwork, which are services specifically designed for remote work, most of those jobs don’t pay nearly enough to live a lifestyle as we see on Instagram.

They provide income, but that might only enable us to live in our cars or vans and eat ramen.

We probably won’t be staying in hotels and eating gourmet meals every night designing 150px by 150px logos for small businesses.

Is Being a Digital Nomad Right For You?

The ability to travel the country and work from anywhere is an amazing feeling of freedom and adventure. But, wanderlust isn’t always a wonderful experience. It’s still real life. And, it takes a person who is prepared for a new set of challenges and can go with the flow.

If you’re that kind of person, then being a digital nomad might be right up your alley. Or, street. Or trail :)

The Ultimate Digital Nomad Starter Kit

If your goal is to live a digital nomad lifestyle, there are three basic tools that’ll help you to maximize your livelihood while on the road:

1. Internet access (without this, you’re kind of just a nomad)
2. A vehicle (to travel and, most likely, live in—or at least sleep in)
3. Resources and a way to power the digital side of your nomad adventure

1: Internet Access. Most digital nomads need to stay connected, at least some of the time. In the United States, Verizon tends to have the widest coverage areas, though you’ll find some areas where another network might provide better coverage. I’ve known many digital nomads to subscribe to multiple cellular service providers (like Verizon and AT&T) to maximize their chances of an Internet connection anywhere they happen to be.

Also, cell boosters can be purchased to help enhance the cell signal. We use a system called WeBoost, but there are any number of options out there. A directional antenna will tend to be stronger than a bi-directional antenna, but it’ll also require finding the right angle based on the location of the closest cell tower.

2: A vehicle (or means of travel). Whether you’re a vanner (#VanLife) or feel more comfortable in a large motorhome, you’ll need some sort of mode of travel - especially in the United States. Remember that digital nomads will need enough storage for their digital equipment (computers, routers, cell boosters, etc). Your method of transportation must account for that.

If you aren’t sure what vehicle (if any) will work the best, consider renting first before buying.

3: Resources (power, etc). Lastly, you’ll need consistent power for your computers, monitors and anything else that you use to get your job done. RVs can provide power through built-in 12v power systems, but remember that batteries need to be charged regularly.

Protip: For the utmost autonomy, consider fitting your vehicle with solar power. We're able to power our Airstream entirely using solar energy allowing us to re-up our devices from anywhere on the planet where the sun is shining without a plug! (Of course we still have backup for those cloudy days.)

If you prefer a hotel or hostel route, you’ll also need to ensure that you have a comfortable working environment. Desks and comfortable chairs are a must, but you may not be able to control those resources without a dedicated living arrangement like an RV.