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If you have spent any time around the Wisconsin Skydiving Center dropzone, you probably know Charlie Rogers. He has been involved with skydiving since 1975 and in fact, has been at the DZ from the very beginning. Most astoundingly, Charlie has over 3,000 tandem jumps and at least 1,000 fun jumps to his name. That’s a lot of jumps, some seriously vast knowledge and mad, mad skills.
What Charlie adores most about the sport though is his role as a tandem instructor. Most TI’s will tell you they love the thrill of simply sharing the skydiving experience with first-time tandem jumpers — yet Charlie is just a little bit different in his reasons for showing up every weekend. He feels a need to give back, and this is the best way he knows how. Plus, the sentiment of being a part of an event that most people will consider an all-time top experience in their lives is pretty amazing too.
If you spend any time talking to Charlie, you quickly realize he shows a deep personal drive to bring something positive to the world. And that’s not accidental at all.
Though he grew up in a loving family in Cottage Grove, Wisconsin — where he still lives now — he had a not-so-positive early encounter with military life. As a 19-year old, he was drafted and chose to enlist in the Air Force. Having been raised to be part of the team and finish what he started, he flew over 90 combat missions in Asia in 1972, receiving two Distinguished Flying Crosses and seven air medals for his service.
Like many others involved in the South-East Asia conflict, Charlie was left with more questions than answers and a lurking discomfort about the whole debacle. However, those years spent in the belly of war also left a mark that eventually altered his trajectory and pointed him to a much different, yet vastly better place. That place was skydiving.
Recently, Charlie lost his brother Ted to cancer. When he speaks about Ted, he always mentions how amazing a person he was. His brother was a basketball player of some fame, a motivational speaker, life coach, and just a super inspirational human overall. Ted fought esophageal cancer bravely for three years despite being given only six months to live. What he left was a compelling legacy of empowerment.
The practice of inspiration and motivation seems to run in the family — only Charlie offers his version of empowerment through skydiving as a tandem instructor each weekend. That quiet confidence he exudes helps students find the motivation to make that leap and push those personal boundaries.
Skydiving can also become a type of magical meditation for people. As it turned out though, the sport gifted Charlie with something far more rewarding – ultimately, it introduced him to the love of his life.
The humble nature Charlie displays can be a bit surprising — given the ballsy, competitive sport he’s immersed himself in. Maybe it’s what came through most clearly though on the day when his now-wife Jenny was taking her first tandem skydive. Though she was partnered with another tandem instructor that day, she never forgot the impression Charlie made on the group. If you want to know what happened after that first tandem, Jenny’s side of the story is definitely worth a read — but you can guess the outcome, right? The rest is history, as they say.
Charlie and Jenny have since shared a life of travel, conquering many countries together. Thailand is one of their favorites – not just for its scenic beauty, but also for its peaceful and kind-natured people. Costa Rica and Mexico are frequent destinations as well, providing not just friends to visit but also the opportunity for the couple to experience different cultures, foods, and lifestyles.
Then there is Charlie’s collection of Shuttle Launch Passes. He readily admits to being a NASA nerd, and it’s a definite point of pride. Like many Americans who grew up in the 1960s — an era of NASA prominence — Charlie looked to the sky for the next big adventure (it’s really no wonder he found skydiving). Witnessing the growth of companies like SpaceX today is encouraging for him, and makes him feel there is indeed hope for further space exploration.
So you see — there are many sides to Charlie Rogers: daring skydiver, seasoned traveler, witness to shuttle launches. His day job writing parking tickets does not engender a fan base either, but he deals with it as just being one of those roles in life. And through it all, he remains stoic and humble to his core.
How does he prefer to be defined though, you ask? Without a doubt his favorite role is husband. Every bit of his reserved nature disappears when the subject of Jenny comes up. Charlie never misses a chance to mention how much he loves her. And it’s obvious that despite all the amazing events life has provided him with, his partnership is solidly rated Number One in his Top Ten experiences.