Introduction
What’s your name, how old are you, and where are you from? Where do you live currently, and how do you make a living?
My name's Zennen, I’m 28 years old, and I’m from Canada. I've been traveling for over three years now, and I work remotely as a Meta Ads media buyer. I'm currently based in Latin America but tend to bounce between a few places throughout the year.
Life Before Becoming Nomadic
What were you doing before becoming a digital nomad?
I graduated university in 2020, right as the pandemic hit. It started just before my final semester, so everything went online. Once I finished my degree, I was stuck working from my bedroom. There wasn’t really anywhere else to go back then.
I ended up talking my way into a content marketing job at a startup. I told them, “Hey, you don’t really have a social media presence. You should do a vlog. I can help with that.” They took a chance on me, and I got the job.
For the next 14 months, I worked fully remotely, teaching myself different parts of digital marketing from that same bedroom. That was my first step into remote work, and eventually, it set the foundation for becoming a digital nomad.
What made you want to make a change?
I’d always wanted to travel and make money. Combining the two just felt natural. But after spending over a year stuck in my room, I hit a breaking point. I had all this energy and nowhere to put it. I was tired of seeing the same four walls every day.
Even outside of those walls, my city didn’t have much going on. It’s not internationally known for anything, and it’s on the smaller side. I knew there was so much more out in the world, and I wasn’t going to live my life confined to that room—literally or metaphorically.
Freedom became the goal. For the last couple of years before I graduated, I was setting myself up for that. I started teaching myself digital marketing, kept my footprint light, avoided buying a bunch of stuff, and stayed away from relationships that might tie me down. I already spoke a bit of French, and I was mentally preparing to leave.
I always knew it would happen eventually. But sitting in that room for so long made the decision feel urgent. I just couldn’t take it anymore.
What was your first step into remote income or travel?
I’ve been traveling since I was a kid. My parents took me to Guatemala when I was 11 and 13. I went to Miami at 14, and later we took a month-long family trip to Israel, Egypt, and Jordan, where I got to see two Wonders of the World.
Those early trips, especially to Guatemala, really opened my eyes to how different life could be in Latin America. I didn’t speak Spanish back then, but I became fascinated by the region. It made the world feel a lot smaller—and a lot more interesting.
In 2019, I went on a university exchange to Lisbon. While I was there, I also visited parts of Spain and spent time in Rome. Again, it just reinforced how beautiful and varied the world is, especially compared to growing up in the Canadian prairies.
As for remote income, I started working from my bedroom in Canada during the pandemic. I was doing digital marketing for a startup, making around $35,000 CAD a year at first. Toward the end, it bumped up to about $45,000. But since I was living at home with minimal rent and almost everything was shut down anyway, it was a solid starting point.
Did you hit any early roadblocks? How did you overcome them?
Not at first. Things were pretty smooth early on. After I started traveling, I stayed with the startup for about two more months. Then I transitioned to a marketing agency where a few friends were already working. It was a bigger company, and they actually taught me a lot of new skills. So for the first year and four months, things went really well as a digital nomad.
But in early 2023, that changed.
I’d never been to Asia and felt like it was time. Asia just seemed like the future—massive population, tons of tech innovation, and a totally different energy. I didn’t feel super tied to my job at the time, and the company had a remote-first policy. So I booked the trip and moved.
Two weeks after landing in the Philippines, I joined a work call at 2 a.m. local time and suddenly HR and my manager were on the line. That’s when I found out I was being let go.
It was a rough moment. I didn’t know anyone locally, and I no longer had income. I felt like an astronaut who’d just been cut loose from the ship. Just floating out in space, alone.
For the next few months, I freelanced a bit for the original startup I worked for. Just small content marketing tasks for $300–400 a month. I lived off savings and tried to stay afloat. It wasn’t until around October that things started to pick back up again.
I made the most of it by tring several different things, and eventually connected with some former colleagues who invited me to work with them.
What You Do For Work Now
What do you do for income today, and how does it work?
I run Meta Ads for businesses that want to get more clients or customers through Facebook and Instagram. Most of the businesses I work with sell products, though some offer services. It’s the same kind of work I did at my last marketing agency, just in a different setup.
Right now, I’m a subcontractor for an agency. I’m not an employee with a salary or benefits. The agency is technically my client, and I manage the advertising for their clients. I take over those relationships directly, so I handle the day-to-day work for each account, but I’m still considered external.
There are some clear pros. I make a lot more money than I did as an employee. I’m not locked into a fixed number of hours. Nobody is expecting me to work from nine to five or sit at my laptop for eight hours a day. I do have meetings, and the team works during normal business hours, but there’s flexibility.
I also like that I’m free to work on my own stuff. There’s no non-compete clause, so if I want to launch something on the side or take on other freelance work, I can. When I first got hired, I was already in Bangkok, and the remote lifestyle wasn’t an issue at all.
The downside is that there’s no built-in stability. I don’t get vacation pay or sick days. There’s no health insurance, no Christmas bonuses, and no fallback if something goes wrong. I also pay all my own taxes, since there’s no employer covering any of it.
Still, I think it’s a good trade. I earn more, I have more freedom, and I’m building toward other projects that could eventually replace or surpass this income.
How much do you typically earn per month (USD)?
Right now, I usually earn between $7,000 and $8,500 Canadian dollars per month ($5000-$6000 USD). Sometimes a bit more, sometimes a bit less. Before taxes, that is.
My best month was about $14,000, but that was a bit of an outlier. That spike came from some one-off freelance work with a prospective client. It wasn’t tied to my usual subcontracting work, which still makes up the bulk of my income today.
How did you learn the skills you use now?
I started by talking my way into a content marketing job. After that, I got referred to a marketing agency through a friend. The agency liked hiring beginners because, according to them, we didn’t come with a bunch of bad habits.
They were bringing on a lot of entry-level people, so they trained us from scratch. I was given course material, started out as a junior, and spent time shadowing people on client calls. Eventually, I worked my way up and started managing accounts on my own.
It was a really solid learning environment. I wasn’t thrown into the deep end right away, and that made a big difference. I got to build confidence and develop my skills without the pressure of carrying everything myself from day one.
I never officially made it to the title of “senior media buyer” at that agency, but in my current role, I’d say I’m operating at that level. I manage a bunch of accounts and take full ownership of results now, which has helped sharpen my skills even further.
A lot of what I do also ties back to my commerce degree, along with things I’ve picked up through YouTube, podcasts, and just reading online.
Do you work alone or have a team?
Right now, I work with teams. That’s how it’s been in the past as well.
I do enjoy working alone, but I haven’t found many ways to make good money completely solo. So for now, I’m usually part of a bigger system, handling one piece of the overall service being delivered to clients.
That said, I’m actively working on building more of my own projects and bringing on my own clients. The long-term goal is to have more ownership over what I do, but this is where things stand at the moment.
What tools, platforms, or services do you rely on most?
First off, ChatGPT. It’s hands down the best money I spend every month. Total game-changer.
It can help with almost anything. You don’t need to be a Facebook media buyer, a coder, or a designer. You just need to know a little, or be curious, and ChatGPT will guide you through the rest. I use it constantly.
Besides that, I use Notion to stay organized. I dump in all my notes, plans, and ideas there. It keeps everything in one place.
I also use 1Password, since I have a ridiculous number of passwords at this point, especially for client work.
YouTube Premium is another one I gladly pay for. I watch a lot of educational content throughout the day, and I don’t want to sit through ads.
Slack is how I keep up with my team, and Google Calendar helps me manage my schedule. My tech stack isn’t huge, but it’s tight.
I use Surfshark as a VPN if I need to access something from Canada or hide my location. And I rely on Google Drive for cloud storage.
That’s pretty much it. I keep it lean.
What was your first $1K/month like — how did you make it happen?
To be honest, I don’t have a cool story about launching a product and watching Stripe notifications roll in. My story was more about becoming an employee and then taking those skills on the road. Nothing flashy, but it worked.
After six months without a steady job, I started subcontracting. That’s when things started to shift. I was getting paid per client instead of a fixed monthly salary. That felt like a breakthrough.
As an employee, your incentive is often to do less. If you’re on a flat salary, taking on extra work doesn’t necessarily mean more money. I used to manage three or four clients and make around $4,000 to $5,000 a month. It felt like a lot of work, and when they offered me another client, I wasn’t exactly excited. Most of my pay was fixed, and I hadn’t been around long enough to unlock much of the performance bonus.
But once I switched to subcontracting and got paid per client, I actually wanted more work. I started to see the path to $5,000 or $10,000 per month. It was just about taking on more clients—or doing the work faster.
That shift gave me a real sense of control over my income. If I found ways to work more efficiently, I could pocket the extra time. As an employee, saving time usually just meant getting assigned more work without more pay. But as a contractor, if I finished faster, I could either take on more clients or just enjoy the free time guilt-free.
That mindset shift was a big turning point for me.
Life As A Nomad
Where have you lived or traveled in the past 6–12 months?
Life is awesome right now. In the past 12 months, I’ve been to Japan, Korea, Canada, Peru, Mexico, the Dominican Republic, Brazil, and Uruguay. I’m also heading to Paraguay in a couple of days.
I can pretty much travel wherever I want. I’m not accountable to anyone. As long as I stay within a reasonable time zone for work, it’s never really a problem. Nobody cares where I am. The only issue that ever comes up is when I arrive at a new Airbnb and the Wi-Fi is trash. But even then, I usually have a local SIM card and can just hotspot myself if needed.
The freedom to do all of this is exactly what I’ve been optimizing for. And it feels really good to be living it now.
What are your favorite memories from the road so far?
This is a great question. I’ve had a bunch of standout moments.
I remember flying through the dunes of Huacachina in Peru on a dune buggy. That was wild. I also drove around Cebu Island in the Philippines during a bit of an unemployed stretch. I was basically waterfall hopping and went canyoneering at Kawasan with a cute Filipina girl. Definitely a core memory.
I got to go to Carnival in Rio. I visited Machu Picchu, Chichen Itza, and Christ the Redeemer. I even made it to Angkor Wat. I think that adds up to three Wonders of the World, maybe four depending on who’s counting.
There have also been slower, more meaningful moments. I spent Christmas and New Year’s in Mexico City. I reconnected with family during a trip to the Dominican Republic. And one of the most special things I’ve done was take my dad traveling with me for a few months. We visited three countries together. That experience meant a lot.
I also got to return to Japan and visit Korea for the third time. Honestly, I’ve had so many amazing experiences. The best part is that I didn’t have to sacrifice my career to have them. And I didn’t have to sacrifice the moments to keep the career going. That balance is the biggest win.
What does a typical day look like for you?
These days, I usually wake up around 8 or 9 AM. Sometimes later.
I’ll make some coffee and spend the first couple of hours working on a personal project, like this upcoming website. Around noon or 1 PM, I start my day job as a subcontractor.
After about two hours, I usually take a break. Sometimes I go for a walk or hit the gym. Altogether, I’m typically doing around four to five hours of concentrated subcontracting work each day.
The rest of my time goes toward personal projects, grabbing food, exercising, walking around, exploring new spots, watching Netflix, or just relaxing. It’s a flexible schedule, which I love.
Some days I only work two or three hours. Other days it’s closer to five, but on average it’s usually about four hours per day.
In the evenings, I might go to a language exchange, find somewhere to dance reggaeton, meet up with friends for dinner or a barbecue, or hang out with someone I’m seeing. It really just depends on the day, but it’s always on my terms.
What’s the hardest part of this lifestyle? What’s the best?
The hardest part of the lifestyle, especially if you’re doing it alone, is the solitude. You’re kind of always in this in-between state. If you’re only spending a couple of weeks in a place, it’s tough to build real connections. You might meet people, but a lot of those relationships are short and surface-level.
There are some spots where that’s less of an issue. Places like Bali attract nomads who are open to meeting new people every day. They have that same energy and rhythm. But if you go to bigger cities like São Paulo, Lima, or Bogotá, the locals already have lives. If you meet someone on a Saturday, you might not see them again for a week. If you’re only in that city for two or three weeks, you might only hang out a couple of times and that’s it.
That kind of solitude can wear on you. Maybe not a big deal if you’re more introverted, but if you’re an extrovert like me, it can get lonely.
Now, the best part? The freedom. You don’t have to sacrifice your dreams to make money. And you don’t have to sacrifice your income to live the kind of life you want. You get to build a life that has both.
There was one time I lined things up so I could spend the weekend on a remote island off the coast of Dumaguete in the Philippines. It was called Apo Island, and it was full of sea turtles. Totally isolated, but I could make it work and still do my job afterward.
Another time I got to take my dad traveling through Latin America. We visited three countries together, and I kept working the whole time. I reconnected with family in the Dominican Republic after years apart, and I wasn’t rushed. I didn’t have to leave just because I was out of vacation days.
The best part is being able to choose where and when I want to be somewhere. If I want to go to Brazil for Carnival, I can. If I want to experience Dia de los Muertos in Mexico, I can. If there’s a concert or meetup in Medellín, I don’t need permission. I just book it and go.
This kind of lifestyle wasn’t really possible until recently. People used to travel for work, not travel because they wanted to and work while they were there. Being a digital nomad has opened that door for me. It’s a whole different kind of lifestyle, one my grandparents would have never imagined possible.
How has this lifestyle changed you?
There are a couple of ways it’s changed me.
First, the world feels a lot smaller. I used to think of faraway countries as exotic or intimidating, but now most places feel familiar. I don’t really feel fear about going anywhere anymore. You could drop me in Kenya, Ghana, the Philippines, or Indonesia, and I’d figure it out. I’d probably even have a good time.
I also think much bigger now. I’ve met people from so many different walks of life, and it’s shifted how I see the world. My mindset has grown so much that I just don’t feel compatible with where I came from anymore. I’ve tried all kinds of food, learned about different cultures, and seen how people live all over the world. It’s hard to go back to the structure and thinking of small-town Canada after that.
Another big shift is how much more I question things. A lot of people just accept the way things are. They assume that because something has always been done one way, it should stay that way. I don’t think like that anymore. I constantly look for better options. I think about business ideas. I think about how to reduce taxes legally. I think about how to design a life that actually works for me. That part has been huge.
I’ve also grown in ways that feel tangible. Every year has brought a new version of me to the surface. I can track it. I can tell you where I was each month, what I was working on, and how I was feeling. There’s a sense of momentum. When I go back home and see old friends, their lives often feel like they haven’t moved much. They could summarize the last few years in a few sentences. I couldn’t do that if I tried.
And one more thing — I learned fluent Spanish while living in Latin America. That has opened up more doors than I ever expected. It’s made life richer in every possible way.
Advice, Vision, and Resources
What would you tell someone who wants to follow in your footsteps?
Here’s what I would say.
Most people who want to become a digital nomad but never do it get stuck on the idea that they don’t have any online skills. They think they’re underqualified. They focus on all the reasons they can’t do it, and that overwhelm stops them from ever taking even one small step. I get it. If you’re working a physical in-person job and someone starts talking about digital marketing or software development, it can sound super technical and intimidating.
But the truth is, you can learn anything online these days. Even if you don’t have any technical skills yet, ChatGPT can explain everything to you. It’s an incredible resource. I heard someone say on a podcast that there are no more technical barriers. The only barrier left is agency. It’s the belief that you can take action. That’s what most people are really missing.
So if you’re wondering how to get started, I’d say this: start learning online skills. Go deep into a topic for a week. Learn everything you can about SEO. Then the next week, learn about Meta Ads. Then try social media marketing. Design something in Canva. Set up accounts just to play around with new tools. Ask ChatGPT to help you build a personal website. Create a dummy email sequence even if nobody signs up for it. Code a mini project. Use Cursor. Use Replit. Just try stuff.
You don’t have to be great. You don’t even have to be technical. You just have to be curious enough to explore.
Eventually, you’ll find something you like or something you’re pretty good at. Then it’s just about knocking on some doors. Ask for opportunities. You only need to convince one person to pay you. One good client. One decent gig. One part-time job. That’s all it takes to get to $2,000 or $3,000 or $4,000 a month.
From there, you can keep leveling up.
If you had to start over, what would you do differently?
If I had to start over, and I was smack in the middle of my old city with no income, and let’s say I’m starting over skill-wise, I would start by thinking through all the different ways you can make money online.
Right now, I think the biggest opportunity is in AI. It’s still so new that there aren’t many real experts yet. Nobody has ten years of experience with it, because it hasn’t even been around that long. At most, you’re a couple of years behind. And with a few focused weeks or months of learning, you can catch up.
If I needed to start making my first few thousand dollars per month online, I would look at how I could use AI to improve the systems of real businesses. Not just tech startups, but regular mom-and-pop operations. Think landscaping companies, barber shops, local services. AI can help streamline a lot of those operations, but most of those business owners haven’t had time to explore that yet.
And if not AI, then I’d be looking at other digital-first opportunities. I’d be listening to podcasts every day, diving into rabbit holes, and learning as much as possible.
Then it’s just about getting in front of business owners and offering to help. Not asking for a job, but offering to solve problems. That shift in mindset is important. People don’t always like being asked for things, but they do like being offered real help.
If you do that enough, even for cheap or free at first, you’ll build up skills, case studies, and goodwill. Eventually, people will start paying for what you can do.
What resources (books, tools, people, websites) helped you most?
Yeah, I mean, there’s so many things.
I read The Four-Hour Work Week in university, and that really changed the way I thought. I realized there’s a different type of freedom out there, and it can be achieved through entrepreneurship. I built on that by reading some of MJ DeMarco’s books, like The Millionaire Fastlane and Unscripted.
I also went deep into podcasts. The Tim Ferriss Show was a big one early on, and My First Million is the only podcast I still listen to every episode, pretty much every week.
Alex Hormozi has been a huge help too. He’s intense and maybe a little too bro-y for some people just starting out, but his stuff is incredible once you’re already thinking bigger.
I’ve also been really inspired by Peter Levels. He helped shape my idea of what’s possible as a digital nomad. And then there’s Marc Louvion. He’s got a great course called Codefast that helped me understand how to build and ship products even without being super technical.
There’s a lot more, but those are the big ones that come to mind.
What does the future look like for you? Any new projects or goals?
Yeah, a couple of things that I’m excited about at the moment.
Number one, I’m building a cool community. It’s actually the one you’re reading this on. It’s called Nomadic Blueprint. I think it’d be really fulfilling to build a platform to help other people live this digital nomad life, which I feel has given me so much. I want to reduce the barriers to make that happen. And it’s also a great project for me to grow something of my own.
Beyond that, I’m looking to step up my freelancing and increase my income there. I’m also setting up my personal tax residence in Paraguay, which will allow me to reduce my taxes from around 25 or 30 percent all the way down to maybe 2 or 3 percent. That’s a massive savings and gives me a lot more flexibility.
Those are the main things I’m working on right now. And beyond that, I’m planning to set up shop in Latin America and choose one or two cities to use as a home base. I’m excited about that as well.
What kind of people should connect with you, and where can they reach you?
I’m interested in connecting with people who are building something, growing an audience, working in marketing, or doing anything creative. If you’re putting something new into the world or building something of your own, I’d love to connect. Those are the kinds of people I naturally vibe with.
Also, if you’re based in Latin America, there’s a good chance our paths might cross.
You can reach me primarily on Instagram (@Zennen) or Twitter (@ZennenLeggett). I’m also on LinkedIn (Zennen Leggett), but to be honest, LinkedIn kind of sucks, so I definitely prefer Instagram or Twitter.
If you really want to get in touch more directly, you can email me at ZennenRL@gmail.com. And yeah, I’ll probably get back to you there.
