As an Amazon Associate I earn from qualifying purchases. This post may contain affiliate links. If you click on these links and make a purchase, I may receive a small commission at no additional cost to you.

Welcome to the story of The Traveling Jamaican Dawta. It’s the story of a 39-year-old (that’s me) who decided to pack up her aging father, her frustrated-with-life mother, and her almost teen daughter to chase her dream of becoming a digital nomad.

My Dream of Becoming a Digital Nomad Is Now Reality

This has been a dream of mine forever. But it was just mine. It was supposed to be a solo travel thing. Then it was supposed to be a mother-and-daughter thing. How it became a 3 generational thing is a long story that I hope you’ll stick around for.

You see, I’ve always wanted to travel the world and I have long set up my life to so do. I applied to teach English in Japan when my munchkin was only around 2 years old. I was scared then because it seemed early childhood education in Japan would be costly. But I knew I wanted to do some travel, blog full-time, and make money from my blog.

It didn’t happen as my application wasn’t successful and I thought it best as traveling so far with a toddler… maybe it’s the fear of that that really held me back. Anyway fast-forward to munchkin (even as an adult I will probably call her munchkin still) being around 9 or 10 and the itch started to become really strong again.

The Travel Itch

There are a few things that contribute to this itch for me. Firstly, the kind of careers I wanted to embark on were never big things in Jamaica. I applied and was successful with an application to study fashion merchandising in Canada at one point but who had Canada tuition?

Then I wanted to become a full-time blogger and to be honest if I had continued to pursue that rigorously it would have happened much sooner. I would have been much further ahead now than I am today. But I never was able to find the balance between the 9-5 necessary to pay the bills and this creative outlet of mine.

I tried quite a few avenues of self-employment and finally, something stuck. And so I found myself working from home for a few years. As munchkin came to the end of her prep school years I got the itch for becoming a digital nomad again. I thought we could take a gap year together before she went to high school.

Then came the big Rona. Her dad wasn’t too keen on the idea of me traveling with her during a global pandemic. And to be honest I wanted to see what high school she’d get into so I didn’t push it. I allowed all the chatter to squash my plans again. And wouldn’t you know it, she got into a great high school.

OK. So now what. I’m working from home, answering to no one boss, but living life as if I am. I have a mountain of bills staring me down my face every month and I’m barely scraping by. Nothing left over to go on weekend outings as I’d like.

That nuh nice. Something has to give. I should go on the road and pay these big bills elsewhere. The bills dem done big already, why not work from Thailand, Mexico, or Bali? That was my thought process. At least someone else would be paying for the air conditioning!

My Dream of Becoming a Digital Nomad Is Now Reality

The Bali Research

So about two years ago when I was hellbent on taking that gap year I mentioned earlier, I was set on Bali. Bali was inexpensive so my online earnings would go much further and I’d be working from paradise, not from a Kingston apartment worrying about traffic.

Don’t get me wrong, Jamaica is paradise too. I do love my island nation. But the life I want to live isn’t cheap here. Me old now, mi like nice tings. Jamaica nice, but it nuh cheap.

I needed a break. I wanted a place where I could build up my passive income streams and rely less on my current online freelance work. I’m exchanging time for money. That’s not scalable. I was ready to become a Youtuber dammit! But I couldn’t afford the Youtube lifestyle in Jamaica.

So I was set on Bali. It seemed like that was everyone went to start their journey of becoming a digital nomad. And I started the process. I sold my nice nice mirror and end tables, still so vex bout that. Because of course, I didn’t go. It just wasn’t time. I even tried to sell my SUV at that time and got maybe one call. Or two. No bites really. It’s like the Universe was saying be patient my child, your time will come.

So I took a chill pill and buil’ back as we’d say in Jamaica and continued the course of building up my online freelance work as well as my coaching business. Both those streams were going really well and I was on a roll.

So what did I do? I increased my lifestyle. Nuh must. Noooo I didn’t build up any kind of nest egg first who does that? So practical. Not me.

And everything was going fine too. Until.

The Deciding Factor

There I was, living a wonderful life in Kingston. I had a very cute, very spacious 4th-floor apartment in the middle of where I wanted to be with views to live for.

I was making good money and having fun going out with my friends multiple times per week. Munchkin was settling into high school life, albeit kinda bumpy as she was having trouble making friends all over again. But overall, everything was good.

We took mother-daughter trips regularly to the country to look for my parents and go to the beach. We were building our bond while living on our own again for the first time in a couple of years.

But underlying all of that, I was freshly single and wondering what now. I was acutely aware that again I was building a life I didn’t want. How far into it was I gonna go this time? Was I ever going to get on with becoming a digital nomad?

Well, it didn’t take long for the universe to force my hand. 

My father’s health issues hit a peak and he was now unable to live on his own. I was running out of places he could live too. He’d ultimately have to move back in with me.

My Dream of Becoming a Digital Nomad Is Now Reality

New Apartment or New Life?

Munchkin and I were in a 2 bedroom. I needed one more to accommodate my dad. Summer break was fast approaching…all my options ran through my head.

Maybe I could sublet my apartment and dip my feet into travel. Seemed risky unless I found someone trustworthy.

Maybe I can put all my things into storage and we travel for two months. Or a year.

That last one I went back and forth on heavily. Two months or a year? Two years?

As I watched my father’s life turn into a series of days filled with nothing but watching Youtube on my couch and cooking breakfast each day, my answer became clear. 

I had to take him on the road with me. He deserved to see more of the world. I had the desire to show him some of the wonderful life he’d shown me when I was growing up.

So, with little more than a month until the start of munchkin’s summer holidays, I decided we were going to move to Mexico.

Things happened quickly once I made that decision. I sold my stuff, found somewhere to store what I wanted to keep, friends chipped in to house us until it was time to fly, and off we went.

Adding My Mom to the Mix

When my plan was firm in my head and I had already decided that even though I didn’t know how long we would be staying, we were going, my mom added herself into the equation. She called me out of the blue one day, not knowing yet any of my plans, to say she wanted to move to Mexico.

She was tired of the rat race, tired of Jamaica’s crime issues, and tired of carrying the weight of others on her shoulders. She wanted to retire and do something else. Live somewhere else. She had been to Mexico and other Spanish-speaking countries before and loved the lifestyle. She was watching Youtube videos on becoming a digital nomad and how affordable it was to live in Mexico and had made up her mind.

Except, she didn’t know how she’d get there, what she’d do when she got there, and how she’d afford it all. So I added her to my plans. Two heads are better than one and hopefully, two breadwinners would make this all more affordable.

My Dream of Becoming a Digital Nomad Is Now Reality

Becoming a Digital Nomad

That’s how we became The Traveling Jamaican Fam. The story of why we ended up in Panama and not straight to Mexico can be found in this Youtube video

In Panama, we didn’t do much exploring. That’s because this big last-minute grand plan didn’t include a lot of emergency funds. I earn enough money for us all to live a good life in these Spanish countries, but I am cautious about spending on excursions right now as I’m working on building up that emergency fund. 

Never know when you’ll need that.

We were only in Panama for 11 days. I considered extending it so we could explore more, but I found Panama’s prices to be very close to Jamaica’s. Maybe it’s because of where we were in the heart of Panama City.

I decided to give Colombia a go. All the YouTubers say it’s quite affordable. And you know what, it is. I am eating here much better than I’ve ever eaten consistently and I’m doing it for an average of US$50 per week. And listen, I WISH my food bill was $200 a month in Jamaica. And I definitely wasn’t eating as healthily as this. 

My little keto heart is loving all the fresh vegetables and protein I’m eating. I have salmon twice a week whereas I had to save up for that once-a-month luxury back home. Not to mention all the fresh fruits and berries munchkin indulges in for breakfast with her plain greek yogurt sweetened with honey.

On $50/week? Chiiiiiiilllllllleeeeeee

I’m just praying that Mexico is as affordable because Colombia only gives you 90 days to stay and honestly the cold weather and I aren’t getting along. 

Maybe the next city will be better. (Update: Read my first Merida living post.)

Anyway, that’s enough of the back story. Catch you on Youtube every Sunday as I document this journey of finally becoming a digital nomad.

My Dream of Becoming a Digital Nomad Is Now Reality

How to Become a Digital Nomad with No Experience

So how did we do it? How are we affording the lifestyle? And what might be the first steps you take if you want to do something similar?

The first thing is figuring out how you will support yourself and whoever is going with you. My income is already from online. I make the bulk of my income as a freelance writer and a full-time blogger. If you work 9-5, you’ll need to see if your employer will allow you to work remotely.

If not, your first step is figuring out a remote job or learning the skills you’ll need to earn an income online. I teach people how to make money blogging and I write content for businesses who need this content for their websites. What can you teach people? What services can you offer remotely?

If your income is sorted, then the next step is researching where you’d like to go. You need some criteria for yourself:

  • cost of living of the country (depends of course on your income)
  • ease of entry (will you need a visa? how long can you stay?)
  • weather
  • racial tensions (it’s a thing for us, IYKYK)
  • food, culture, things to do

And then you’ll need to weigh all these things on some sort of internal scale. For example, the cost of living in Colombia is cheaper than in Mexico but it isn’t as safe to live there. The weather was nice in Bogota though. What’s more important to you? I’d also only be able to stay 90 days before having to move on vs 180 days in Mexico.

My Dream of Becoming a Digital Nomad Is Now Reality

Once you’ve decided on a country, joining a few expat groups on Facebook will help you to get a look into the lifestyle before going. You’ll see what kinds of questions and complaints come up often to judge if the place really is for you.

I joined one for black expats and one for moms as well as general expat groups. This allowed me to get answers to things specific to my lifestyle. You can seek out spiritual groups, LGBTQ groups, vegan groups, digital nomad groups etc. There are groups for all sorts of people looking to move abroad and these groups are valuable resources before you go and help you build community once you’re there.

I have a lot more to say on this topic and lots more tips to give but will leave it here for now. If you have questions ask them below and I’ll flesh this all out more for yah.

My Dream of Becoming a Digital Nomad Is Now Reality