What Nomad Life Actually Looks Like Long-Term with Ebonie Finley

I’ve always believed there’s no one “right” way to live this lifestyle — and that’s why I love sharing these features in On The Road.

What does nomad life really look like after years on the road?

This month I’m featuring Ebonie — marketing pro, surfer, foodie and the creator of The Nomad Dating Show, who’s been questioning the traditional life script since 2017. We spoke about cartel-controlled Airbnbs, why every nomad needs a non-negotiable emergency fund, becoming a homeowner while travelling (and why she wouldn’t recommend it), and launching a dating show for digital nomads in 2026.

This one’s honest. High highs. Real lows. And everything in between

Hey Ebonie, tell us about yourself?

It all started in 2017 when I became completely obsessed with the idea of working remotely. I created a travel series called Nomad Generation and it genuinely changed the course of my life. I never looked back.

I’m originally from Montréal, Canada. My dad is Canadian and my mom is from the Bahamas, and that contrast basically defines my personality. I’m full of dualities. I love winter and snow, but I’m also a surfer and a total beach girl. I own a home and I’m a huge homebody, but I also can’t imagine my life without constantly exploring the world. I’m a massive foodie. I don’t trust people who aren’t obsessed with food 😂 but I’m not much of a cook. I love fashion, makeup, fresh nails… and then I’ll go wild camping in the backcountry of BC and destroy that manicure the same day. That’s me.

Professionally, I work in marketing, but I’m also a Creator and producer.

What does life on the road like for you?

Honestly? It’s a roller coaster. The highs are very high and the lows are very low.

I started travelling because after graduating and doing the 9-to-5 in a grey cubicle, I felt like I couldn’t breathe. I had this deep feeling that life had to be more than working just to survive. I didn’t want to live to work. I wanted to work to live. Travel is where I feel the most alive, so I built my life around that.

Sometimes you land in the perfect destination with the perfect apartment and it feels like you’ve hacked life. Other times, despite all the research, you end up somewhere that doesn’t feel safe or aligned and you still have to show up and work.

We once booked an Airbnb in Puerto Viejo in Costa Rica that turned out to be in a cartel-controlled area. We had to leave immediately and lost thousands of dollars just to get somewhere safe. That was one of the hardest moments.

But then there are the highs. Costa Rica everywhere except Puerto Viejo, Panama, Mexico, Bali, Thailand… and right now Cape Town. We are absolutely on a HIGH here. I’m falling in love with this place. Life on the road is fun, exciting, dreamy, but also full of challenges and hard moments as well.

What does Nomad Generation mean?

Nomad Generation is about freedom at its core.

It’s the belief that our generation is questioning the old script. We don’t just accept the life we were told to live. Whether someone travels or not, I believe everyone deserves more freedom. Freedom of time, freedom of movement, freedom to design their life.

For me, it’s about living as a global citizen, mixing cultures, ideas and experiences, and finding your people around the world. It’s idealistic, yes. But it’s about creating a space where we say yes to a life with fewer limitations.

How do you balance work, travel, and downtime while constantly moving?

I’m still learning 😅

I try to choose destinations where my day-to-day life feels good. Walkable neighbourhoods, good food, access to nature and a gym, and a strong nomad community. If the base is right, everything else flows better. I try to keep downtime for when I am home and fill my weekends up with adventure when I am on the road.

Life on the road sounds dreamy, but it’s not without its challenges. What’s been your biggest nomad insta vs reality moment?

Becoming a homeowner as a nomad was probably my biggest misfortune so far.

On paper it was the dream. Passive income, a base, financial growth. In reality, managing tenants from the other side of the world has been incredibly stressful. I love my home, but unless you plan to settle or can afford to leave it empty, I don’t recommend it for nomads.

For anyone dreaming of a nomadic lifestyle, what’s your number one piece of advice?

Have a solid emergency fund. Non-negotiable.

Things will go wrong. Not if. When!! They will!

You need fast access to at least $5k for safety situations, last-minute flights, new accommodation, real life emergencies. And get travel medical insurance. I once paid $2k for emergency stitches on a trip where insurance would have cost me $30. That’s just a bad decision. In 2025, I had to buy a return home flight because of my tenant and it was almost 2k. I always make sure to top up my emergency fund to 5k and I never travel without insurance.

Where do you think everyone should add to their travel bucket list? 

Cape Town. It has EVERYTHING.

The food, the beaches, the mountains, the energy, the people, the nomad community. I kayaked with wild dolphins and swam with penguins on a random Tuesday. It doesn’t make sense how magical it is and it’s becoming so HYPE. I think people should come before it get’s out of control, which the prices for accommodation already are, so sooner rather than later!

What does 2026 look like for you? Any fun projects coming up?

I’m launching The Nomad Dating Show, and I’m beyond excited. It’s a dating show for digital nomads to help people find their forever travel partner. The community needs this, and I am super excited to produce and launch the show.

And I’ll be travelling full-time all year, if no emergencies bring me home, of course!

Where can people find you?