Full Circle: Kaitlyn & Angel’s Journey From Skydiving Students to Instructors

You wouldn’t expect a grad-school student from Wisconsin and an outgoing thirty-something from Mexico to become close friends, let alone teammates, travel companions, and skydiving instructors. But that’s exactly what happened when Kaitlyn and Angel met at Wisconsin Skydiving Center. What began as a chance encounter during a training jump turned into a years-long journey of growth, grit, and shared milestones. Their story is a reflection of what makes the skydiving community so special: a place where mindset matters above all else. Where support shows up without asking. And where unlikely friendships take hold. 

Their Path to the Dropzone

Kaitlyn found her way into skydiving thanks to her sister Jessica, an avid skydiver, who had gifted Kaitlyn a tandem skydive for her 18th birthday. But it wasn’t until a few years, and one global pandemic, later that Kaitlyn finally made her way back to the dropzone. In the middle of what she calls a “COVID crisis” and growing tired of Jessica’s persistent encouragement, Kaitlyn signed up for the student program in July 2020 – without telling her sister. Jessica was more than a little surprised to show up and find her sister already mid-training. 

Angel discovered skydiving in 2019 when his friend Jake agreed (i.e. was “voluntold” by his wife) to join Angel for a birthday tandem jump. Jake immediately wanted to go again, and Angel joined him. After their second jump, Jake was ready to sign up for the solo student program, but Angel hesitated. Skydiving seemed to be something you spent your whole life training for, and at 35, Angel wasn’t sure he belonged. Despite that uncertainty, he accepted the challenge and signed up. 

An Unlikely Friendship 

Kaitlyn and Angel first met on a training jump, sitting across from each other in the plane. Kaitlyn remembers feeling nervous and a little intimidated, and being struck by Angel’s calm, matter-of-fact attitude toward ‘failure.’ He talked openly about the jumps he’d had to repeat, completely unbothered by it. For Kaitlyn, who feared failing jumps meant failing as a person, this perspective was both surprising and refreshing. Angel’s mindset stood out to her in a big way, planting the first seeds of a friendship neither of them saw coming.

Kaitlyn and Angel both earned their A license in the fall of 2020. They began jumping together, and by 2021, their bond started to deepen. After their jumps, their conversations stretched beyond skydiving.  Angel shared stories about growing up in Mexico, and how much his life has changed since moving to the U.S. Kaitlyn opened up about her own challenges – relationships, graduate school, and her self-doubt as a skydiver.

Parallel Growth in the Sport

In 2022, Kaitlyn and Angel took on their next skydiving challenge together: earning their coach ratings. Angel approached it with the same determination Kaitlyn had come to admire, by knocking out his prerequisites early and charging towards his goal. Kaitlyn, with fewer jumps and more self-doubt, hesitated at first. But with Angel’s encouragement, she signed up, and both walked away with coach ratings in hand. 

Energized by their success, they soon set their sights even higher: the Accelerated Freefall Instructor (AFF-I) rating. The course to become a skydiving instructor is one of the most demanding paths in the sport – physically, mentally, and emotionally. Kaitlyn was reluctant to sign up at all, worried about failing and what people would think. Angel had his own reservations: “It was something I didn’t feel ready for and I didn’t think I was going to make it,” he recalls. Yet his resolve never wavered. His willingness to try anyway inspired Kaitlyn to do the same. 

The course was grueling. The jumps were incredibly difficult, and the classroom and ground training offered no reprieve. After every jump, Kaitlyn would open her parachute, pause, and just breathe. “There is so much to consider,” she said. “With a coach rating, you’re there to teach skills. In AFF, you’re there to keep someone alive. You can’t just think about yourself or your flying – that has to be automatic so that your full focus can stay on the student.” 

Trial & Error

The practice jumps were tough. Each student had four chances to pass three evaluation jumps. Angel passed his first, while Kaitlyn failed hers – shaking her confidence. Angel, too, failed a later jump, leaving them both with everything riding on their final evaluation together. It was a pairing they usually avoided due to their differing fall rates and body sizes. 

Kaitlyn falls slow, Angel fast. But somehow, the odd match worked – they crushed it. As soon as they landed, Angel immediately knew their efforts had paid off and they had passed. Elated, he shouted to Kaitlyn: “We did it! We freaking did it!” 

“It was one of the most beautiful and amazing feelings in the world,” Angel says. “And I got to share that memory with Kaitlyn”. For Angel, it remains one of his favorite moments in the sport – overcoming self-doubt, pushing through one of skydiving’s toughest challenges, and sharing the victory with the people who helped him believe it was possible. 

A Unique Dynamic

Kaitlyn and Angel now work side-by-side as instructors, continuing to learn and grow together. Angel says: “I’ve learned so much from Kaitlyn. She has a strong discipline, and that’s pushed me to my limits to be and do better. She’s very bossy,” he adds with a laugh, “but she makes things happen, and I respect that.”

“The thing I learned about myself, and am still learning, is that it’s okay to not be the best and embrace failure,” Kaitlyn says. Skydiving is helping her with that. And so is Angel. “He and I often talk about getting in our heads and are there to help ground each other.” 

For Angel, skydiving wasn’t something he saw himself doing – let alone teaching. “I never thought this was possible for me,” he says. “But every step has shown me that I can do more than I believed. Now, I want to help others see that too.”

Angel regularly pushes Kaitlyn to step out of her comfort zone, by encouraging her to try new disciplines, jump from bigger planes, and explore dropzones beyond their home at Wisconsin Skydiving Center. From RookieFest at Skydive Chicago to winter trips in Florida and beyond, the pair has now jumped at 10 dropzones together across five states – and they’re still adding more to the list.

Still Growing Together

Kaitlyn and Angel have already achieved so much together, and they have no intention of slowing down. Angel also earned his Tandem Instructor rating, something Kaitlyn decided was not for her – giving her the opportunity to support and encourage Angel from the sidelines. They also plan on getting another skydiving rating together, their Instructor Assisted Deployment Rating (IAD). 

In a sport where people come and go, it’s rare to find someone who grows with you through every stage. “It’s cool to look back on,” Kaitlyn says, “because Angel has been there every step of the way – students, A license, B license, C license, D license, coaches, AFF Instructors, and now IAD Instructors.”

Skydiving is quite a journey, not just because of the skills you learn, but because of the people you meet along the way. “This is honestly my favorite part about the skydiving community,” Kaitlyn says. “Without it, I never would have met so many amazing people, like Angel. We’ve all walked such different paths in life, and we were lucky enough to cross paths at Wisconsin Skydiving Center. Even though we are at completely different stages of life and from totally different backgrounds, I always know Angel is there to support me – not judge me – both in and out of the skydiving community.”

Angel’s favorite part is how tight-knit it is. “It’s a very small community where everybody helps you and teaches you as much as they can. You meet new people, and they often become your friends, or even your family.”

First Timer Advice

Thinking about making your first jump? Kaitlyn and Angel have simple advice. “I think everybody should try skydiving twice,” Angel says. “ The first time, the shock of the moment can take away from the beauty of it. But the second time, you’re more aware of what’s happening and you can really enjoy it.”

Kaitlyn’s feedback is, unsurprisingly, similar: “Try it. And if you don’t love it right away, that’s okay. I didn’t either. I did three tandems before I actually liked it. My body just needed time to understand that it was okay to enjoy freefall. You’ll hear people say they’re afraid of heights or scared of the unknown – but you won’t know if it’s worth the risk unless you try. There will always be excuses. But will you let those define you?”

Ready to see where skydiving will take you? Book your first jump at Wisconsin Skydiving today! Blue skies!