They say you never forget your first time and Detroit native Sharolyn Wynter remembers with absolute clarity the trip that changed her perspective forever.
An expat, short for expatriate, is one who resides in a country other than where they grew up.
“My first international trip was to Jamaica where my mother was born,” she shared. “My mother is from the small, small town called Pisgah. That experience was life changing for so many reasons because the country in Jamaica is not like Kingston (her father’s hometown) or Montego Bay— the popular tourist areas. It is very remote. It’s up in the mountains, and also it’s like watching people who are really self-sufficient survive without all those material things that I thought I needed. It was like a reset almost.”
This piqued her curiosity about life beyond the United States. It was an “eye-opener” that set her course for the future. Wynter spent over ten years at Deloitte Consulting and serving as the Director of Strategic Partnerships for Girls LOVE Travel, a community of 1.1 million female travelers. She transferred to London from her U.S.-based company for what was initially supposed to be a two-year stint. She loved it and wound up extending an extra year, which was the maximum allowed on her work visa.
“For one, the people are pretty well cultured,” she explained of her desire to remain in the UK. “And what I mean by that is because there are so many different, diverse communities and cultures represented in London they’re far more open to what we would call ‘others.’ So I felt like it was easy to be your authentic self because people were already exposed to others. So if you hear people speaking a different language or are dressed in a certain way, it’s not anything to stare at.”
The moment she hit the tarmac in Washington, D.C. at the end of her stay, she felt the pull to return abroad.
“I was like, this is not it,” she recalled. “I had this whole thing about I don’t do things that don’t make me happy. I was like, I’m not happy.”
Things would take a turn for the worse a year later when her father died. Wynter also started to question her own mortality when she started experiencing fainting spells which led to a diagnosis of chiari malformation, a condition where the lower part of the brain presses on the spinal canal.
She realized that it was time to get serious about her goal of taking a year off to travel and began saving in earnest to fund her dream. Her first stop in her gap year? London.
“I could just be myself and exist. I didn’t feel like it was a constant validation exercise that I felt in the U.S. And I also felt the way that the U.S. is set up is quite toxic from the perspective of you don’t realize it because you’ve been gaslighted your whole life. So it’s normalized. And so once I had a chance to live somewhere else and then come back, my sense of normalcy had changed. Things like microaggressions that I had just ignored before, I didn’t even realize they were glaring.”
Next up on her solo journey was the southern European country of Portugal where she had visited several times before. Then the pandemic hit. She considered changing her plans but went instead with her gut and managed to get into Portugal just before the borders closed. After finding an apartment and signing a lease, everything seemed to be falling into place.
“Portugal was just an easy pick because it was at the top of my list already. I actually liked it so much that I invited my mom the second time I went to check it out. ‘Cause I just felt so good there. By the time I visited, I’d probably been to 30 countries and something about Portugal felt so much like you belong here and I can’t explain it.”
As she awaited her Portuguese residency, Wynter had another decision to make. Re-enter the corporate world or strike out on her own? The latter won out.
She is the founder and CEO of Xpat, Inc. and creator of The Xpat App, an app specifically geared towards galvanizing the Black expat community. The idea came about while Wynter was researching Portugal and having a hard time finding Black female insights about life there. She came across the YouTube channel, Driven Spice, and reached out for some information. The conversation went so well that she wished others could have listened in and have this type of access to others living abroad.
“I started doing expat chats and interviewing Black expats because when I go on other expat sites it’s kind of like I got to dig through a lot information to get to the Black people. And for me as a Black person race relations is a key component about where I’m going to move.”
The app is her first stab at entrepreneurship and creating a new life outside of the corporate world.
“I spent all these years taking all my creativity, all my skills for other people, making them money. And I know and trust and have faith that these skills are valuable enough that I can survive as an entrepreneur.”
Wynter admitted to being a rolling stone, moving every couple of years to a different state. There is no guarantee this is her final destination.
“I love change. I love new environments. I love new beginnings. I’m just super curious. I really like Portugal, but I would not be surprised if in five years I’m living in another city. But Portugal is a really good fit for me because of the vibe there. And you know, it’s a pretty country too, and I can still have access to the EU. This is a good fit for me right now, but I can’t say that it’s my forever place.”
Follow Shar as she builds her Black expat community on Instagram.
Related: The Black Expat: ‘I’m Developing A Small Apartment Community In Antigua’
