Back in 2016, I sold most of my belongings, packed the rest, and booked a one-way flight to Europe to become a digital nomad. Bound for Prague, the plan was to land some freelance design work, teach English, or maybe work for a design agency.

But freelancing was a rollercoaster, I didn’t enjoy teaching, and agency life ate up the time I wanted for exploring.

So my wife and I started our own agency, and everything changed. Because remote work isn’t just about avoiding a commute or wearing pajamas until lunch—it’s about designing a lifestyle that balances achievement with adventure.

Over the past ten years, I’ve learned that thriving remotely comes down to three things:

Intentional Planning

In my freelancing days, chaos reigned. I worked anytime, anywhere, with no real structure. But when we built our agency, we put systems in place, created SOPs, and—most importantly—brought on talented remote team members who aren’t just looking for a gig; they’re invested in our culture and want to create a fulfilling remote life of their own.

The big kicker? Boundaries. We take every weekend off, give our team paid holidays and mental health days, and stick to systems that keep projects flowing. As creatives, we have to leave room for our minds to focus on things that inspire us, whether it’s travel, music, sports, or anything in between.

Planning isn’t about rigidity—it’s about protecting time for the things that fuel you.

Creating Space for Flexibility

Remote workers are often told, “You’re so lucky to work and travel like that.” But it’s not luck—it’s preparation. Flexibility comes from setting expectations and designing workflows around life, not the other way around.

That flexibility is constantly expanding. We have the power of Slack, ClickUp, and Google Workspace literally in our hands. When you make it easy to keep work on track, it stops derailing your other plans and becomes another part of the journey.

Some of our best memories came from working while on the move: landing a major project over breakfast in a Lisbon hostel, executing a brand launch from a café in Galway, and kickstarting campaigns by the pool in Croatia. With flexibility in focus, you can say yes to adventure without guilt.

Integrating Adventure, Learning, and Connection

Not every day is a grand adventure. Most days, you have to seek out sparks of creativity. For us, that meant daily walks in Prague and Berlin to soak in the architecture, art, and cultures around us. These days, we’re hiking in the Blue Ridge Mountains, but the principle is the same. Our walks are non-negotiable because of their impact on our mental and physical wellbeing.

Community matters too. Abroad, we attended Creative Mornings; back here in Asheville, groups like AVL Digital Nomads and 1 Million Cups connect us with people who inspire and encourage us. Groups and events like these can be found just about anywhere, and they’re golden opportunities to learn and create relationships as you travel.

Why Not Both?

Intentional planning, flexibility, and adventure aren’t extras—they’re essentials for thriving remotely. If you don’t want to choose between achievement and adventure, design your life so you can have both.

Here’s your challenge: try one small shift this week. Set a boundary that protects your time, plan an adventure that inspires you, or join a community event to connect with like-minded people.