Rising to the Challenge — Jessi Calzado-Esponda’s story of struggle and success

Originally written for the LSSNCA Live Boldly blog.

Part 2 of a 2 part story of Jessi Calzado-Esponda’s life. Read Part 1 here.

Adjusting to life in Tampa, Florida

After six months in Guantanamo Bay, Jessi and her grandmother moved to Tampa. There, her adjustment was difficult. After all the adventure and excitement of the raft and the refugee camp, her separation from her family began to sink in. She felt abandoned and confused. “Why is my mom not here?” she remembers wondering. “Did they not like me? Why did they not come with me?”

Jessi describes several mentors, most of whom were women, who helped her succeed during her pivotal childhood and adolescent years. “These were people who looked at me and saw me for who I was, not as a sad refugee or an immigrant coming to take their job. They just saw me as a child, as a kid who needed help with reading.”

Her mentors and others in the community knew that her grandmother hadn’t fully assimilated to life in America. She couldn’t drive a car or speak English very well, so others helped to fill in some of the gaps. Jessi describes a woman named Mrs. Jennifer, who taught her how to make apple pie and other “little things that you don’t think about not knowing as a refugee.”

“Like what the heck is the Brady Bunch, and why are there so many people living in that house!?”

When Jessi developed an interest and a talent for music, she found people who supported her passion. A woman named Margie Smith gave Jessi a scholarship to Florida Gulf Coast Youth Choir, a private institution for musically gifted children. Jessi then attended the H.W. Blake Magnet School of Performing Arts where her love for music, dance, and art fully developed. Jessi says Margie both set her up for success and inspired her to do better. “Her believing in me made me believe in myself.”

Though she loved her grandmother and the support she received from her mentors, Jessi realized at a young age that she wasn’t like other people. Unlike other kids, she wouldn’t have the traditional family foundation of a mother, father, sister and brother to help her succeed. She realized that her life was up to her, and that she had to create her own success. “I became obsessed with winning,” she says. “I would set these unrealistic expectations for myself just so that even if I didn’t quite meet them, I would still be in a better place than if I hadn’t tried at all.”

Jessi’s introduction to politics and the American dream

In high school, Jessi strove for success in everything she did. She played sports, sang in seven different choirs, and was captain of her school dance team. Around that time, she met Yvonne Yolie Capin, who introduced her to a world she hadn’t even known existed. Yolie was a democratic fundraiser and councilwoman in Tampa, famous for her dinner parties and fundraising events. “She’s probably hosted every democrat who’s run in the past 10 years,” Jessi said. Yolie hired Jessi to help with these events, and Jessi would attend to take photos or lend a hand to whatever was needed. “She didn’t really need any help,” Jessi said, “but she wanted to give me an opportunity.”

Jessi says that while offering her the job probably didn’t mean much to her mentor, for Jessi, it allowed her to set her sights and expectations even higher. “It allowed me to see that there’s people out there living lives completely different from mine.” After seeing so much poverty in Cuba, the refugee camp, and even in Tampa, those dinner parties offered her a glimpse into the lives of successful people who cared about making the world a better place.

Lucky for her, two of those people were Barack and Michelle Obama. Jessi met the Obamas at a fundraising event she attended with Yolie. Months later, she was lucky enough to find herself sitting in one of the front rows at his inauguration. She describes seeing Obama walking across the stage, waving at him, and seeing him wave at her back. “I thought he remembered me, maybe he didn’t,” Jessi laughed. “But it was in that moment that I decided I had to work for his administration.”

Not knowing how to get there, but knowing she had to start somewhere, Jessi started to knock on doors. Eventually, she found herself talking to a scheduler named Lara working in the office of Kathy Castor, the congresswoman from Florida’s 14th congressional district. Congresswomen Castor was Jessi’s representative, and when she was young had told Jessi to reach out if she ever needed anything. “Well,” she told Laura. “I reached out and told her I needed a job.”

The Congresswoman’s staff fell in love with Jessi’s energy and her story, and she was soon invited to work as an unpaid intern in the Congresswomen’s office. Jessi says she was only able to land this position because she wouldn’t take no for an answer. “A lot of people live their lives thinking opportunities are things that fall into their lap,” she said. “But sometimes you have to create your own opportunity.”

She eventually turned this position into a full-time job working as a congressional staff assistant. Before long, Jessi was known as the “Cuba person,” putting together briefings, providing recommendations, and helping to prepare Congressmen to answer questions. She spoke Spanish and she knew everything there was to know about Cuba — it was her dream job. Jessi says that the thing that she took away most from her time working on the hill was that “America is a place where dreams come true, no matter where you are from.”

Rising to the challenge

After seven years working for Congress, Jessi’s dreams were interrupted. She had been driving a Congressman when a driver on the wrong side of the road hit Jessi and the Congressman head on. Jessi suffered a traumatic brain injury, and doctors told that she was 100% disabled — that she would never be able to work or do anything for herself ever again. The accident affected her memory and speaking pattern. Once an AP and honors student, she was told that she had a third-grade reading level. She was forced to leave her work on the hill for rehabilitation.

“I felt so helpless,” Jessi said. “I was 24 and wondering what I could do with my life.” She says the story of her recovery was a difficult one. “I wish I had some super upbeat, inspiring story to tell. But I’ll be honest with you, it was really hard.” she said. “At first it was a lot of tears, a lot of self-doubt.”

Volunteering with Feeding America during the pandemic.

Even during this challenging time in her life, Jessi did not set her sights on an easy career path. Instead, she chose to become an entrepreneur. When President Barack Obama announced an easing of restrictions on travel to Cuba, Jessi saw that as an opportunity to start her own travel company, Cuba Inspires. The company is aimed at supporting American travel to Cuba by organizing educational and cultural trips for non-profits, athletes, and celebrities. In the first year of the company’s operation, Jessi grew revenue to $900,000 and organized trips for multiple celebrities, including the Kardashian family. She garnered national attention for her success connecting Americans to the Cuban people, and was named one of the 100 most influential Latinas in Washington, DC by El Tiempo, a Spanish language newspaper, for her work with Cuba Inspires.

Despite her external success, Jessi was struggling internally. She was still suffering from the effects of her injury and didn’t feel deserving of the accolades she had garnered. She had such imposter syndrome that she didn’t even go to pick up the award. “How could I be deserving of this award when I can’t even remember my best friend’s name?” She remembers feeling. “How could I be recognized for this when it feels like everything is crashing down around me?”

Despite these feelings, Jessi persevered. She continued to build her company and fight to find her confidence again. What got her through this difficult time was being honest with herself about what happened and about she felt. “I didn’t pretend it wasn’t there or put on a mask.” She said. “There have been so many moments where I didn’t have control. I came over to the US on a boat with nothing but the shirt on my back. I couldn’t control that. I had a traumatic brain injury in a car accident that wasn’t even my fault. I couldn’t control that. But I could control how I reacted, I could control what kind of dialogue I was having myself and with other people.”

Paying it forward through mentorship

Jessi saw the value in the lessons she learned during this difficult time in her life. Realizing that others could learn from her own experiences, Jessi founded a new company aimed at helping entrepreneurs like herself succeed.

Through her work at Inspire Entrepreneurship Academy, Jessi has the opportunity to help other women overcome their own imposter syndrome and find the confidence to be effective leaders. “As women, we’ve been conditioned to think we’re the weaker sex.” Jessi said. “I see women all the time who are in the prime of their careers. They have so much talent, so much to offer, but they still don’t have the confidence to command a room.” Through mentorship, patience, and hard work, Jessi tries to change that. Her goal is to help women rise to the challenges they face, understanding that things will be difficult but believing in themselves enough not to buckle under the pressure. She spends her time teaching women these life skills, in addition to how to run a business.

“Women as CEOs have a responsibility to not only be successful,” Jessi says, “but to bring other people along.” She acknowledged that mentorship takes time; building confidence doesn’t happen overnight. Even so, she doesn’t plan to stop any time soon. “It’s been one of the most gratifying experiences of my life.”

Always one to aspire to even loftier goals, Jessi ultimately wants run 10 different businesses. And, of course, she wants to continue to mentor women along the way. “I’m excited to create the next league of leaders. I can’t wait to meet another refugee, someone like me.”

Jessi’s advice to others who want to make a difference in the world is to start small. “There’s so many amazing organizations and opportunities to help,” she says. “But you can’t try to solve all the world’s problems. Find something you’re good at and choose that.” She says that a great way to do this is through mentorship. “Maybe you only help one kid, but that that person goes on to help five other people. Before you know it, you’ve helped a web of hundreds of people succeed.”

Sharing her experience as a refugee

When she is not running her businesses, Jessi works to improve the lives of other refugees through her work on the Refugee Congress. “My role is basically to be a liaison for refugee issues,” Jessi said. “Whenever someone wants help understanding refugee issues, or just to hear the experience of a refugee, they call me.” She said for her, the most important thing is that refugees have a platform to tell their story.

“A lot of people want to talk about refugees, but rarely do we get to tell that story for ourselves. It’s my life, I like to be the person narrating.”

She hopes to continue to improve the dialogue about refugees in the future. “People, the media, refer to refugees as these people with incredibly sad stories, and we do have sad stories, but we also bring a lot to the table in America. We come, we work hard, and we contribute to America’s special sauce.”

Thank you for reading Part 2 of Jessi’s story. We are so thankful to Jessi for sharing her story with us and allow us to share it with you and in her own words. This blog in is commemoration of International Women’s Day! We believe Jessi is an incredible example of women overcoming challenges and empowering others to be successful. Jessi is the Washington DC delegate of the Refugee Congress. You can contact RC’s delegates by visiting their website.

You can help support LSSNCA female refugees through volunteer and donation opportunities. Some of these opportunities include: becoming a volunteer with our TEA Club for refugee women in Northern Virginia, becoming a volunteer mentor or tutor, donating supplies for expectant mothers, and other donation needs for refugee and immigrant women in the DMV. To learn more visit LSSNCA.org.