Lisa-Gaye Shakespeare remembers being glued to the television as a young girl growing up in Clarendon, Jamaica. The television was her window into other worlds and other cultures. By the time she managed to leave the country, she was slack-jawed. “I remember my first trip with my mom to the Cayman Islands. I was amazed there was this great big world out there outside of Jamaica.” The travel influencer, content creator, and trip host, whose Shakespeare Agency Instagram account inspires wicked wanderlust, has had the travel bug for as long as she can remember.
Winding Path to Success
There was no straight-shot path to her current profession. It never occurred to Shakespeare to monetize travel. She earned a bachelor’s in communication and later broadcast journalism, where she identified an inherent love of interacting with people. “I’m a people person, I’ve always been curious about others. I want to know what makes people tick. Why do you dance the way you do; why do you eat the food you do; how are you similar to me; how are you different from me?” Shakespeare had a brief stint as a broadcast journalist for a local station, but found herself bogged day with the day-to-day tedium of reporting news and politics – topics that didn’t drive her.
So, she pivoted, and it wouldn’t be the last time. She worked as a college recruiter for almost eight years. It felt right, she says. Who better than her to help prime would-be students coming to the US? She had lived through the same experience and made it out the other side. It helped that the job had a stellar perk – Shakespeare was able to travel all over the world. The job led her to Trinidad, the Dominican Republic, Germany, and Morocco, and all reignited her passion for traveling. She’d keep a running blog everywhere she went. “I’ve always been a writer, I kept diaries when I was little,” she reflects.
Finding Her Way
The moment that put everything together for her arrived serendipitously and fittingly on a trip – a birthday vacation. While falling in love with another country, Shakespeare encountered a Black tourist group. At this point in our interview, she breaks the story to expound on a topic she has a limitless passion for, de-stigmatizing travel for members of the African diaspora. “There’s a stigma that Black people don’t travel,” she explains – even providing an example, many members from her home community in Clarendon have never even left the Jamaican parish. To Shakespeare, this Black travel group was an anomaly, and so she was magnetized to them. She inadvertently spending most of her trip as an impromptu guide. That group was from the UK-based tourism company, the Wind Collective. They were so charmed by her personality and impressed by her skills as a hostess, that they proposed a partnership, taking Shakespeare on as a guide.
The idea of being paid to travel and experience countries around the world never occurred to Shakespeare as a career path, much less a viable one. “I was like, ’Sorry, what? Are you serious right now?’” she reenacts. Straight away she left her day job and dove in full time. “My schedule for 2020 was insane. I was going to host over 30 trips all over the world,” she explains.
A Stumbling Block
Was. For Shakespeare, it’s a word is tinged with regret. For her, 2020 was a difficult year, for reasons obvious reasons, of course. When the novel COVID-19 pandemic hijacked our lives and took many from us too soon, most of us had to adjust to a new reality. Pandemic lockdowns forced those still employed to transition to a new work experience – work from home – to varying degrees of success. For Shakespeare, there was no transitioning. You can’t be a travel influencer and a guide from home. The Wind Collective had to let her go. “Here I am, 4-5 months after quitting my good professional full-time job with a good salary, I have nowhere to live, I have no money coming in, and I’m living on my friend’s couch. Great decision Lisa.”
She can joke now, but it was a harrowing time. Shakespeare had already given up her apartment and moved back home to Jamaica with her mother, thinking if she was going to spend most of the year traveling the world, she might as well live where it was cheaper. However, the lockdown protocols caught her in Miami; she was stuck. With no income, she flirted with returning to corporate, but could not commit. It’s hard to taste your dreams and then go back to vanilla.
Bringing It All Together
Instead, she created a new plan. “I wrote down all the things that I love – travel, writing, social media, and dancing – a completely crazy mix I know. I threw it all together into a business plan and called it Shakespeare agency.” She held dance fitness classes online, taking in around US$10 a head. She wrote copy for businesses and agencies, and did anything to stay afloat.
When Jamaica re-opened borders, she sped home, but was not content to sit around and wait for the pandemic to roll over. In an incredible display of initiative, she cold-emailed various resorts along the north coast with a proposition – put her up for a few days, a weekend, and she’ll document her stay drumming up the excitement to her sizable Instagram following. To this day she’s still surprised by how many of them followed up. This period was when she saw her most drastic increase in followers. Thousands wanted to know where they could go as lockdown rules relaxed, and even more just wanted to live vicariously through a beautiful Black woman making the most of disaster.
Riding the Momentum
With the worst of the pandemic hopefully behind us, Shakespeare has ridden her momentum to new heights. Just about any post on her Instagram will command over a thousand likes and countless more views. She lives between the US and Jamaica, and is working with The Wind Collective again to showcase diverse parts of the world in one-of-a-kind experience packages. The pictures might seem relaxed and carefree, but she takes great pride in her work. She details her process of creating an experience. First, she’ll never host a trip she has not taken ahead of time. For Shakespeare, she must wear both shoes – the tourist and the host. Scouting missions allow her to identify hotspots and unique experiences to build her tours around. Next, she’ll partner with local restaurants and reach out to a country’s tourism board to maximize her guests’ escapades.
So, where does she want to visit most? She still carries a childlike wonder about travel – a bit of that girl who dreamt of being a flight attendant and was glued to the television. “I want to visit everywhere in the world,” she laughs. “But…my focus is Africa. To me it’s the motherland. It’s home; it’s where my roots are. It’s where I connect most whenever I travel there.”
