Accommodations, Remote Work, Solo Travel, South Africa

From Remote Worker to Entrepreneur: My Journey Building a Location Independent Career and Lifestyle

I started writing this article from a little cafe overlooking the white sand beaches of Cancun, and luckily I could be writing this from just about anywhere.

Cancun beach

(Cancun beach)

Over the last 3 years, I’ve worked on creating a location-independent career and lifestyle. Since I was a teenager, I knew that I wanted to explore the world – to try unknown foods, live with friendly strangers, and see alternative ways of living- regularly. Once a year for two weeks was not going to cut it. As an adult, location freedom and cultural exploration are where I find my bliss. I also love to create things. Learning all the ways I can combine my passions and turn them into income is my mission and one that I hope to continue chasing for all my years.

Everything around you that you call life was made up by people that were no smarter than you and you can change it, you can influence it, you can build your own things that other people can use. Once you learn that you’ll never be the same again.” – Steve Jobs

I’m currently location independent and a part-time nomad. This means that my income comes from work I perform remotely, and with this freedom, I travel often and take my work with me. My home base is Toronto. My aim in sharing my journey and lessons is to inspire others to chase those dreams that often get buried in the name of conventional living, or the “deferred-life” plan.

My Remote Work Journey

When I decided that I wasn’t going to spend my life in a cubicle fighting for pension benefits and waiting to earn another week of vacation, I knew creating an alternative career wouldn’t exactly be easy. Plus, I decided that if I were going to work remotely, I wanted to do it successfully. For me, this meant earning a comfortable income and being financially free, not minimally making ends meet.

I was also aware that it would be a work in progress as I tried different ways of making this dream come true. My experience has looked something like this:

The start. After completing my B.A, I lived and taught English in Tokyo. This magic experience ignited my love of slow travel and exposed me to people who were living very unconventional lives. It’s also where I discovered the field of e-learning and quickly realized that it combined my passion for education with my love of tech. It’s cutting-edge education that by its very nature didn’t require an office to do. I was hooked!

Lotoya and Japanese students

(Karaoke night with my students in Japan)

When I returned to Toronto, I enrolled in a master’s degree program in education and started working on building my new career.

Independent freelancer. In 2013, after a year in my first e-learning role at the world’s largest education company, I was over it. My daily commute was daunting. After returning from Carnival in Brazil, I scheduled a meeting with my boss and channelling Tim Ferris’ and his Four Hour Work Week, laid out a plan for remote work. She refused, so with my remaining courage, I resigned. I had no plan, I just knew I couldn’t continue. Luckily within a day, the company returned with an offer. They wanted to hire me as an independent freelancer, where I’d maintain the same responsibilities and clients plus I could set my own rate. Ultimately, I ended up with a 10% pay raise and total location independence – not bad for resigning! Eventually, the contract fizzled and I had to focus full-time on writing my thesis.

Full-time, in-office, employee. Shortly after completing my M.Ed, I gave in when the opportunity to work at a large airline came around. I still thought that flight benefits and the attractive compensation could be enough to quiet the parts of me that dread this type of office job. Turns out, even the tease of cheap travel wasn’t enough to make it bearable. I bolted and headed to Ecuador determined to make a living picking up e-learning projects on sites such as Elance and Fiverr. I did manage to earn enough income to minimally keep me going. However, I wasn’t hitting that measure of success I had set.

Full-time, remote employee. In the fall of 2014, I landed a full-time, remote job with a government training company. Initially, this was my dream job – doing something I enjoy from anywhere and with full-time health benefits. However, as time has gone on, I’ve realized there’s a cost to this. I’ve stopped making significant progress toward my bigger goals and even worse, it’s become apparent that my location independence is tenuous. Even though I’m outside the office, I can’t escape the bureaucracy, politics and other unfortunate realities that come with working within an established, government agency.

Entrepreneur. Cutting what’s left of my employee relationship is the final step in what seems to have been a gradual process of dislodging myself from the security of full-time work, and my leap into self-dependency. Again. However, this time I have an e-learning service business focused on the emerging video niche that’s gotten some momentum. In addition, this year I plan to launch my first travel course, Solo Female Travel: how to see the world safely, cheaply, epically, which has been in the making for years along with at least 2 other courses on unique topics curated from my travels around the globe.

Finally, the morning after my last day as an employee, I’ll be boarding a plane bound for Cape Town to live out a part of my grand vision for the kind of impact I want to make in this world. I will be volunteering my expertise and learning from others at an education startup. Working with a team on e-learning projects in international contexts has been a dream of mine for years. I’m excited to be making that happen now!

Life on the Road

I will be living and working from South Africa for nearly a month before beginning an overland, camping trip from Vicotria Falls, Zimbabwe to Johannesburg, South Africa. 

Travelling for an extended period of time while working remotely can be challenging at times depending on location and requires discipline, and a bit of a schedule. It’s also inspiring and motivating.

When I first started working on the road, I didn’t have much of a process and I’d walk around my new location looking for coffee shops or other spaces where I could work. However, I discovered that internet connections too weak to support a Skype call, or too slow to upload files are far too common. When it comes to getting stuff done, tapping into the right resources from the start is key. And as the number of digital nomads grows, this is becoming easier to do.

Work Resources. When I’m not working at the startup, I’ll be using a coworking space to work on other projects. Coworking spaces are in virtually every city and are usually equipped with strong wifi, comfortable work areas, unlimited coffee, and most importantly for me, brilliant minds interested in talking about their work. Some such as La Cocotera which I visited in Tarifa, Spain, and PodShare in LA, also offer ‘co-living’ accommodations.

coworking space

(NeueHouse, New York City)

Schedule. I’m not a huge fan of scheduling creative work, however, I’ve found that while travelling, organization and predictability are essential. There will be daily distractions and without a firm grasp on work times, it’s easy to get derailed quickly. Studies show that we are most creative immediately following sleep, so I’ve gotten into the habit of every night identifying the most important creative task for the next day and tackling it first thing in the morning. I then usually have an afternoon break to do something fun, before resuming work again.

Accommodations. Airbnb is my go-to resource for finding a place to stay when travelling for extended periods of time (anything under two weeks and I’ll usually book a hostel room). I usually rent a room in a house which allows me privacy but also the chance to connect with my hosts and other locals. In South Africa, one of my Airbnb hosts is an educator at Cape town University which will hopefully translate into some interesting local insight.

Social. When I go somewhere new, I like to immediately plug into locals and expat communities. I’ve used with success in Colombia, but more recently I’ve connected with others through relevant Facebook groups with active events. Within a day of landing in Tarifa, Spain this summer, I had dinner with new friends I had connected with in a digital nomad facebook group before my departure.

The Biggest Lessons

1. Perseverance is everything. My remote work journey has clearly taken many paths, and at moments, I’ve felt defeated. Luckily though, I never lost sight of my goals, and I’m grateful for all the professional experiences I’ve gained. Every time, I’ve taken a big risk either to reset my course, or jump at an opportunity (and felt my heart in my throat), the results have been unimaginable. I’m certain that you simply cannot give in when things get frustrating and tough, if you really want to find success and uncover your purpose in life. The rewards are for those willing to be uncertain, uncomfortable, terrified and still determined.

2. Finding your unique values, skills, and mission and putting it to work is the best way to secure your future. People have asked me what are some remote jobs that would allow them to travel and work. Many people are looking for an easy answer but the truth is many jobs can be done remotely, so the most important decision is what do you want to spend your most valuable resources of time and money doing. Every one of us has things that make us tick and it’s up to us to spend all the time (and experiences) required to figure out what those things are.

“You can get fired from a job, but you can’t get fired from your gift. So find your gift and you will always have work.” – Anonymous

3. Aim for a diversity of income streams. I like to think of my work and life in terms of projects – some revenue generating and others mission-driven. In addition to my full-time remote job, I worked on my side business, set up a profitable Airbnb property and started creating my travel e-course. This diversity of income allows me to achieve the financial goals I’ve set and keeps things interesting.

Thanks for reading my journey! And what about you? What are you going to do with your one and only life? Comment and share your journey!


  1. So inspiring. Lotoya you are a boss 💪👏👏👏

    I feel ya about nurturing your gifts to build your own work opportunities. I’m looking to start a business relating to fitness and boxing conditioning.

    I love that I have entrepreneur homegirls to exchange ideas with.

    Enjoy your new experience lady. Can’t wait to hear about it in the future-ish.


    1. Lotoya Lotoya Author

      Thanks so much Kay! I love your boxing and dance videos – that’s the perfect example of combining your gifts and finding your niche. Let me know if you want to have a brainstorm session!🤓


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