Gabby Beckford joins our pre-scheduled Zoom call from Dubai. Behind her are two suitcases—one to check, one to carry.
It’s March 2021, and while most people were working from their homes, Gabby was far from hers.
That’s just how she likes it. With her dad in the military, Gabby moved often as a kid. She loved living in Japan the most.
Eventually, though, her family settled into a small town in Virginia—and stayed there.
Gabby is not a “stay there” kind of person.
Eventually, her wanderlust became unbearable.
After her senior year of high school, she saw her chosen college offered a summer trip to Iceland and called to ask about joining the trip—even though she wouldn’t technically be starting until fall. Gabby seems completely unafraid of ever calling, applying, or asking for anything.
As long as she had a student ID, the college staff said, she could go. The next thing Gabby knew, she was hopping on a plane to Iceland at only 17 years old.
How was it, I ask?
She was terrified of flying by herself, afraid of not knowing the language, and fearful of being the only Black person she’d see on the trip or in the country (she was).
But she signed up and boarded the plane anyway.
Once the backpacking part of the trip began, she realized she forgot her sleeping bag. Too embarrassed to tell anyone, she slept inside her tent, in the wilderness, freezing, night after night.
While the discomfort and fears were real, so was the awe. Gabby remembers thinking:
This is amazing. Being terrified [of leaving my comfort zone] is better than being safe.
[I love] that feeling of being so present in the moment, whether it’s good or bad. Even when things go wrong, it’s still a moment.
After that trip, she knew traveling would be a lifelong priority. She planned to get a degree in engineering and then get a job that included international travel or save up to travel during her time off.
Why engineering, I ask? “My dad,” she explains. “He’s first-generation Jamaican. I did not have a choice: engineer or doctor.”
“I didn’t have crazy expectations.”
While Gabby studied engineering, she also started a travel blog to help share her passion. If the blog happened to lead to one free trip, she’d be ecstatic. “I didn’t have crazy expectations,” she explains.
She eventually got her first sponsored trip—to Chattanooga, Tennessee. But instead of that trip fulfilling her dream and closing a chapter of her life, it opened a new one.
That trip, along with the scholarship she won to study for a year in Dubai, made things clear: Gabby didn’t want to do her travel blog on the side anymore; she wanted to do it full time.
She didn’t know how, and she didn’t know when. All she knew was her dream was getting bigger, and she didn’t want to talk it down to size.
For a time, Gabby let that dream live quietly in the background. “I wanted to work and save money first,” she tells me.
She moved forward with the opportunities in front of her, graduating college and finding an engineering job in Baltimore.
Every day she woke up at 4am to work on her blog, “writing” during her commute by recording posts on her phone. She traveled during her time off, going to Italy, Japan, and the U.S. Virgin Islands.
By the end of 2019, after six years of blogging, the money she was making from brand sponsorships steadily rose.
She was 24 years old and knew she could stay on her parents’ health insurance plan until she was 26. “If I’m ever going to quit my job to travel or be irresponsible, it should be now.” She decided it was time to go all-in on her dream, so she quit her job to take her travel blog full-time.
Her last day at her engineering job was February 14, 2020.
How did her parents react? “My mom was super supportive. My dad was like, ‘Are you ill?’”
Her first trip was to chilly Chicago for All-Star Weekend. She remembers hearing whispers about COVID, but it still seemed far away.
Next, she took a short press trip to Savannah, Georgia. On the flight there, there wasn’t a mask to be seen. On the flight home, everyone wore masks.
Airlines canceled most flights. Airports seemed all but shut down.
Gabby’s dream of travel blogging full time was going to end before it even had the chance to begin.
Except that isn’t at all what happened.
“It might not be good, but I’ll have an idea.”
Overnight, it seemed like travel was dead.
But travel businesses still needed to stay alive. Many looked to freelancers with ideas for what to say during this strange and scary time. They required fresh content to keep their websites and social media platforms alive—and keep their businesses from falling apart.
They were looking for ideas, and Gabby is never afraid to share hers.
It was like, whoever had an idea, got the bread. And I was like, “Oh, I can have an idea. It might not be good, but I’ll have an idea.” So I was just pitching myself so much because I knew people needed content and ideas about pivoting.
She pitched about 50 outlets on topics like virtual travel using Google Maps, using your suitcase at home, making vision boards, traveling locally, and going on road trips. She relentlessly followed up on each pitch, sometimes sending three or more emails to the same editor.
One of her first gigs was making videos on traveling from home for Lonely Planet. More media outlets saw her on there and reached out to work with her: “It just snowballed.”
There were, of course, days when she cried. Days when she panicked. She even still kept in touch with her old boss, checking in every so often in case she might need to return to engineering.
She also was coming to terms with the fact that the industry she’d just launched herself into was about to change forever. Once she got past the grief and panic, she thought:
Okay, the way travel blogging was before is gone now. So I shouldn’t even worry about my old plan because it’s obsolete now. I’m ahead of the game because I’m so easily throwing away my old plan.
“If your Instagram gets blocked one day, you need to have those two things.”
Gabby’s freelancing business was growing, but the sponsorships, which had been making up 30% of her income, were dwindling. She decided her new plan needed to include a direct connection with her audience.
The more she engaged with her audience, the more she realized how many people were desperate to learn how she could travel at such a young age—especially young people who didn’t have a lot of access to travel, money, or opportunities.
Her answer? Scholarships.
Gabby learned to apply for things when she learned about poetry contests as a kid. She wasn’t a poet, but she was competitive and maintained her lifelong childlike sense of “I can do that.”
That same mentality helped her fund her college degree and scout paid travel opportunities like the year she studied in Dubai.
She wanted to share those kinds of opportunities with the people in her audience, and her email list seemed like the perfect way to do that.
The Instagram algorithm will change daily. TikTok came out of the blue, and suddenly you’ve got to learn that. Social media is so variable. It’s hard to rely on it as a source of income.
She started a newsletter to curate funded travel opportunities.
Once I started doing my weekly newsletter, that’s when I saw consistent traffic to my blog. That’s when people began to respond to my emails, being like, “This is amazing.”
People started talking about her email newsletter on social media, tagging her, and telling friends.
Since her newsletter features many funded travel opportunities for people ages 16-30, I ask her how she finds their response to email, considering most assume Gen Z to be a social-media-only generation. Her response?
They love it. I probably have gotten three DMs today saying like, “Hey, where can I sign up for your email newsletter? I heard that you have paid travel opportunities every week.”
I think when it delivers value, people will use whatever method they can.
Initially, she started an email list because of her fellow travel bloggers’ advice when she first started. They told her:
You need a website and an email list. Those are the two things. If your Instagram gets blocked one day, you need to have those two things as the bread and butter of your brand.
She also loves automated email sequences as a way to help people with their most frequently asked questions; she’ll often respond to a question with a landing page that leads to a helpful email series.
It’s also just a great way to just introduce people to my brand. They can get introduced to me slowly, and I can attach videos and social media.
It’s like having a conversation with me over time, which you can’t do anywhere else. People miss your Instagram post or miss your TikTok, or they can’t see it every day.
She saves all her favorite email replies in a folder. Many of them come from subscribers who won scholarships and opportunities they only learned about through Gabby, excited to head off to places like Qatar or Japan, places they would never have visited without her.
While Gabby loves traveling herself, opening those same doors for others is just as thrilling.
Soon, they would return the favor.
“As featured on…”
Back in October 2019, Gabby visited many incredible Black-owned restaurants during a trip to San Diego. Ever the curator, she began wondering why there was no list covering all these unique businesses—so she decided to make one herself.
The following year, in the summer of 2020, that list went viral.
Someone had taken it and turned it into a graphic that was being shared by major media outlets everywhere.
Her audience noticed. They’d seen that list before—and in the same exact order. They came together and told the media outlets where the content originally came from, calling on them to credit Gabby as the original source.
After that, outlets like Good Morning America and the New York Times were sharing Gabby’s content.
What meant the most to her, though, was the attention it brought to the restaurants in San Diego. Many of them reached out, saying how many orders they had coming in thanks to her list. One popsicle stand she’d featured said they’d sold out of their popsicles via online orders for the following year.
“I am rejected way more than I am accepted.”
While Gabby appreciated her brush with virality, it didn’t change how she continued to run her business. She continued pitching and emailing, and pitching and emailing some more—the same habits she teaches young people when it comes to applying for scholarships and opportunities.
I am rejected way more than I am accepted.
I try not to let it get me down because I’m like, “This just wasn’t an opportunity for me. This was meant for someone else.” It’s not like it was against me; it was for someone else.
But I definitely have the emotional part where I’m like, “Am I even good at all?”
But when that happens, I don’t beat myself up. I think it’s just part of being human.
Even at my worst moments, I’m like, “I’m alive. And to feel this sad or this scared means I’m having a human experience, and I can appreciate that.”
She also finds strength in the statistics and encourages her students to remember them:
I know statistically that half the people who see opportunities won’t apply, and a third of the people who see them will start applying and not press submit.
Statistically, you are way more capable and likely to win than you think you are, even if you don’t feel it.
Recently she surveyed her audience. One of the questions she asked was why they don’t apply for specific scholarships or opportunities. Almost everyone said the same thing: “They just don’t think they can win.”
Many feel that way about almost anything they dream of pursuing. Sometimes it’s easier to not apply at all. To avoid that first rejection—the one that seems to say, you were right the first time, you’re not enough, you can’t win.
So what does Gabby share with her audience to help them get through that? And how does she get through that?
I try to lead by example because it’s so easy to talk to me, see my personality, see the TED talk [on delusional confidence], and be like, “She’s just so confident. She never has cried in her life.”
I cry every day.
But I try to share the rejections as much as I share the successes. And I’ll just screenshot my opportunity tracker and show them how of the 50 things I applied to, 40 were nos, but the 10 yeses added up to six figures and two years’ worth of deals.
You don’t need everything to be a yes; you just need the things meant for you to be a yes. I think the thing about making it a spreadsheet and seeing it analytically is that it shows you that rejection is not personal.
If you’re rejected from something, it’s nothing against you. It doesn’t mean your business idea isn’t good; it doesn’t mean you’re not incredible.
I love to say there’s no such thing as once in a lifetime: the guy, the house, the deal, the scholarship; there’s another one right around the corner, so don’t even sweat it.
One rejection I hope shouldn’t keep people down because you’re going to be rejected from so much in life, and it will be a blessing. It will be a redirection of where you’re supposed to go.
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