Lotoya Jackson shares how she escaped the 9-to-5 and created a life focused on travel, remote work, entrepreneurship, and parenthood
During the Laugh, Cry, Cringe storytelling series, Lotoya Jackson shares her desire to inspire, encourage, and empower women of colour to travel.

Lotoya Jackson, a guest speaker for the Hart House series Laugh, Cry, Cringe, is a traveller, educator, and storyteller. From backpacking across Asia and doing a four-day hike up Machu Pichu, to volunteering with a start-up in Cape Town and camping in the national parks of Southern Africa, Jackson has travelled to 37 different countries spread across 5 continents. 

Jackson shared that she wants to show people they can travel just like she has because she believes that “especially to people of colour, travel is one of the greatest gifts you can give yourself because travel is the key to discovering ourselves.” Jackson started her talk by asking us to keep this question in mind: “How has a lack of representation affected the decisions you’ve made in your life?” 

Growing up in the Jane and Finch neighbourhood as a child of Jamaican immigrant parents who were working class, Jackson shared that “school was not a priority, surviving was. [My parents] didn’t get a lot of education, but they still managed to come to Canada and make a living.” They preached those same values to her, hoping she would own a house with a white picket fence and one big happy family living inside it. 

Jackson was fascinated with exploration from a young age. She loved to take the bus or the train by herself and discover Downtown Toronto. She was also passionate about Asia and discovered that native English speakers would teach English in places like South Korea, Taiwan, and Japan, through the organization Dave’s ESL Cafe—an international hub for English second language (ESL) teachers. “I quickly noticed that many of these sites I was obsessing over never featured anyone who looked like me. Some of the job postings that I would see as a 16-year-old girl explicitly said they were looking for a white, blonde male or a white, blonde woman because that is what the parents of the students wanted,” she noted. The summer after graduating from York University in 2007, Jackson got a certification in teaching English as a second language—a credential required for anyone interested in teaching overseas. 

The idea of being halfway across the world, in a place that may not accept her, gave her cold feet. So, she decided to move to Montreal in the middle of the winter to teach English. “I wasn’t happy. I wasn’t in alignment with my heart,” Jackson confessed. After eight months, she was back teaching ESL at a school in Toronto, where she met Christina, her boss. Jackson was still apprehensive, so she made safer trips, like a road trip across Cuba with a small group tour. 

She went to Vancouver, and when she came back, Christina said, “Lotoya, you are going to ruin your life with regret, so I’m making the decision for you. I am giving you three months to get yourself together and go to Japan, or I’m going to fire you.” She needed this push to apply to an agency that hired ESL teachers in Japan.

You can imagine Jackson’s overwhelming emotions when she got off the plane at the airport. “I knew I wouldn’t blend in but preparing for the onslaught of attention you receive in certain countries is hard,” she shared. During her first month in Japan, people stared, pointed, and moved away from her. Jackson’s students, however, she adds, were a treat: “we had amazing cultural exchanges.” They wanted to know everything about her, and she wanted to know everything about them. But outside the classroom, it was not a pleasant experience. Every day, she went home and cried. 

But on the fourth weekend, she had an epiphany. She looked in the mirror at her sewn-in extensions and didn’t feel like herself. She cut off the extensions and expressed that she felt like “a new person had appeared again, and that day I also knew I needed to change my mindset about the situation.”

Jackson understood that locals had little experience with foreigners. She had to understand that she was there to learn about them, but they also wanted to learn about her. She said, “I was chasing geishas, and they were chasing me.” Instead of getting upset, she tried to interact with people. If they pointed out her hair, she asked them if they had seen hair like hers before; some would rub her skin, and she asked them if they had seen skin like hers before. Jackson learned to make friends in Japan by reaching her hand out first.

She discovered the field of e-learning during a free period in her class. Two boys were huddled in the corner on little devices, and she asked them what they were doing, and they said they were taking a law class online. It was a lightbulb moment for her.

In 2013, she completed a Master’s in Education at University of Toronto’s Ontario Institute for Studies in Education. “Before I graduated, I had my first e-learning developer job at Pearson, the world’s biggest education company. It was a full-time corporate job, the opposite of what I wanted for my life,” she explained. 

So, she booked a trip to Brazil for a Carnival. On this trip, Jackson bought a book that she claims changed her outlook. The four-hour work week by Tim Ferriss is “an amazingly detailed blueprint for escaping the 9-to-5,” she explained. Drawing from the book’s principle of liberation, she met with her boss to discuss her plan to work remotely since most of her clients were in the US. But her boss declined, and she resigned immediately. The next day her boss called her back and said she wanted her back, not as an employee but on contract for a 30 per cent pay hike.

This was a pivotal moment for Jackson. She had realized the benefit of taking rest and following her heart, so she began five years of checking off all the places she had wanted to go on her bucket list. She spent summers in Europe on a one-way ticket. She chased waterfalls in Iceland. She stayed on a Columbian farm milking cows. “I allowed myself to wander,” she explained.

A travel tip Jackson stresses is the beauty of boutique hostels. She says that hostels have a terrible reputation, but it’s not like it is in the movies. They can be as cheap as $30 a night, which is perfect for someone travelling on a budget. Safety is the biggest concern. She shares that you can check in with ID. You don’t have to stay in a dorm. You can ask for a private room; there’s a lot of flexibility. There are lockers for your valuables, and the community aspect is the best.

Now, Jackson is trying to balance being a mom and a traveller. She’s aware that her daughter’s needs must be prioritized, but not in the way people think. She knows that she can forge a path where her and her daughter can have the best of both worlds. Travelling gave her a depth of education. Although her daughter is starting school this year, Jackson hopes they will be able to travel. “Travelling with her and seeing her reaction to things is the best joy I didn’t know I needed,” she confessed.

Jackson is inspired by The Alchemist by Paulo Coelho. The book is about understanding that everyone is self-obligated to achieve their “personal legends.” In other words, discover their purpose, follow their hearts, take risks, and follow the omens—or signs—that will lead them to find their personal legends and achieve their destinies. Jackson says that being young with few commitments is the ideal time to experiment with life. “If you’re interested in shaking up your world perspective, gaining new perspectives, and hitting the reset button, I challenge you to see how travel can do that for you,” she concluded. 


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