The one trait you need: resilience 💪

Howdy friends,

Sorry for missing last week’s newsletter. 

My partner and I spontaneously found ourselves traveling through Sedona, visiting the Grand Canyon, and trekking through Antelope Canyon before making a last-minute stop in Vegas. Without going into the details, I lost $60 in 60 seconds playing the one slot machine I always swear by, so I’m considering that my karma for skipping a week. 😉

This week’s story is from the #1 Nomad Accommodation Guy, Chris. He knows a thing or two about not only finding the best long-term rentals but living a life on the road, full-time. This week, he’s sharing his story about the one theme that ties all of us nomads together: resilience.

But before we dive in, I wanted to share a little bit about our first sponsor:

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Hey, this is Kelsey, and you’re reading the SiteSee newsletter. Think of me as your Big Sis when it comes to travel, inspiring you to keep going places. You can expect an email from me every Friday filled with nomad stories, tips for living a location-independent lifestyle, and the gear to get you there.

Travel Story✍️: Nomad-ing takes resilience

In 2016, I heard the words “remote work” for the first time.

Fast-forward to 2018, and I was all in on living what I later learned was a “digital nomad lifestyle.”

In that year, I spent 10 days working from Madrid. And it changed my entire life: New lifestyle. New view of the world. And the start of my own business.

That was six years ago ... But how did I end up finding myself working online in Madrid?

To understand the now, we have to go way back.

—

Growing up, I was fascinated by the world. But I wasn’t a well-traveled kid—adventure and exploration were huge aspirations for me.

In the meantime, books and TV shows were my only chance to get a sense of what was out there. But we’ve all had those moments, right, where we take a photo and think, “Yeah, that just doesn’t do it justice”?

I knew that books and TV shows just wouldn’t be enough to satisfy my urge to travel. I had to get out there and see things with my own eyes.

So after university, I started traveling more. But then I felt the pressure to tick that “Get a Job” box, and I ended up settling down in London.

That’s where I met my girlfriend. 

She loves to travel, too, so it wasn’t long before we started talking about taking the show on the road.

The only problem was her job. It wasn’t remote-friendly like mine was.

Back in the day (2017), remote-only jobs were a rare thing. But eventually, she found one.  

Looking back, I remember that moment as being the ultimate cinematic turning point. It was like we’d just poured a gallon of fuel on a fire.

Wooooooosh.

But in hindsight, we had no idea just how significant that moment was. We didn’t know that it would change everything about our lives and ultimately set the course for our future together.

—

For about a year, we were drinking from the work-and-travel firehose. Constantly moving: Three weeks here; three weeks there.

Think Europe. Then America. Then Australia. Then Christmas in Bali—and New Year’s in Asia.

All while we were still working full-time UK-based jobs.

We even branched apart a little, too. While she went to explore South America, I hung out in Hawaii, hiking, and learning to surf.

That year was one of the most exhilarating in my life.

It was also one of the most exhausting.

—

Pretty quickly, we learned that we needed to slow down if we really wanted to take it all in. 

I think this turning point is becoming more common for a lot of digital nomads. There’s a pivotal moment where you realize you don’t have to see and do everything.

After all, there’s no rush. Unlike a 9-to-5-er’s vacation, you don’t have a return flight “home” to catch the next day.

In a way, the first year of being a digital nomad is like trying to eat a party-sized chocolate cake in one sitting: It’s all fun and games until you feel like you’re going to throw up.

The key to sustaining nomadic life over the long term (e.g., two years or more) is learning to go slowly. 

It’s also important to check your “why.”

Why are you doing this? What’s your goal?

If you want to get a good dose of travel, maybe you don’t need to go through a whole lifestyle change.

But if you are looking for a complete lifestyle overhaul … Ask yourself, “Why?”

And if you can’t fully articulate why you’re ditching it all for remote work on the road, then, in my opinion, you probably aren’t ready to take the leap. 

At first, my why (our why) was just: “More travel, yay!” 

But then we discovered a community of people with a set of values and a life philosophy that made returning to our old norm really difficult. 

(more on that later)

—

A year into our on-the-road journey, I started an email newsletter to share curated accommodation offers with other digital nomads.

At that point, we had started staying in places for a month or more—and we noticed that as the length of stay grew, prices tumbled. Tumbled like getting 70-80% off of a month-long stay.

After the whirlwind experience of my first year traveling, I wanted to share these deals with the nomad community.

So Remotebase.co became my passion project for the next three years—all while I continued to work full-time. 

But after COVID-19, I decided to give up my day job and take it to the next level. That meant focusing on growth, launching a premium service, and looking for sponsors.

Plus, transitioning from full-time remote work to working for myself meant a new wave of many new things to learn. I quickly realized that balancing work, travel, and downtime is a totally different ballgame when you’re working for yourself.

For me, it was a lot harder.

—

One key thing I learned as my digital nomad journey evolved was that change really is the only “stable” thing in life.

Everything is always changing. 

• Flight prices

• Temperature

• Timezones

• Languages

• Currency

• Energy levels

• The desk you work from

• The bed you sleep in

The list goes on and on. 

At first, all of these changes are new and exciting, and the adrenaline of this new lifestyle can push you through any discomfort or pain.

But then time goes on. The adrenaline and the novelty wear off. And you realize you have to learn how to become more resilient if you want to keep going.

In the beginning, I never really thought of resilience as a characteristic of nomads. But one day, it hit me: My nomadic network is made up of some of the most resilient people I know. 

They actually get bored without the challenge of change.

Learning how to manage all of the changes and unknowns has become part of the inspiration for my latest project.

Over the last year, I’ve noticed that trip reports are being shared across different corners of the Internet. They’re really popular on Reddit and even on LinkedIn, where I’ve shared some of my own experiences (to strong reception).

But I’m only one person. I wanted to amplify the power of trip reports beyond just me.

So at the start of 2024, I launched DigitalNomadTripReports.com, a weekly newsletter sharing community-sourced, verified trip reports covering popular nomad hotspots.

—

Over the years, one thing has stood out to me about the nomad community.

Back “home,” our relationships are mostly circumstantial. Think about it: Your circle of influence is usually limited to the people you work with, play sports with, or grew up with.

Those relationships (at least most of them) are skin-deep. At best, they’re driven by mutual interest. At worst, they’re a product of pure circumstance.

But when I meet fellow nomads, I know that, while we might have different interests, our core values are much more likely to be aligned.

Values like freedom, exploration, and travel. The kind of values that keep you open-minded.

And I don’t know about you, but that’s exactly the kind of life philosophy I want my circle of influence to bring!

—

Ultimately, the digital nomad lifestyle is a constant choice.

You have to regularly ask yourself, “Is this still what I want to be doing?” 

And right now, I choose this nomadic life! 

—

To get in touch with Chris, you can visit his website, Linkedin, or Instagram.

Gear Check🧳

I've been loyal to Nike for as long as I can remember. Specifically, I've stuck to black-and-white Nike running shoes for years. But everything changed when I discovered these lightweight Vasque shoes. 

A part of their fresh Re:Connect line, these versatile shoes are suitable for hiking, running, and walking. Plus, they're crafted from sustainable materials for enhanced comfort and feature trendy colors that can easily spice up any travel outfit.

Airport Reads🗞️

• I loved this podcast episode about building confidence from my good friend, Maria. There were so many important takeaways—and it inspired me to keep on discovering my craft and learning my playground.

• Check out this etymological map of the US with the literal translations of state and city names.

• As with any week-long road trip, I learned I could be better at communication 😅 So even though I already have the Nonviolent Communication book in my Audible account, I also decided to buy the hard copy so I can write my own annotations.

Last Thing✨

As always, thanks so much for being here. Have a wonderful weekend, and I’ll see you here next week! 💫

Onwards,

Kelsey

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