Andi Masengarb posted a positive review about her third tandem jump with Skydive Chicago at the end of June. She also mentioned that the tandem was a surprise birthday gift, and her girls were there to watch the skydive from start to finish. 

We decided to reach out to her about the three tandem experiences and find out who had gifted her with the most recent surprise package. It turns out all three tandem jumps have been with Skydive Chicago, all three have included video and pictures, and all three have a story. 

Andi made her first tandem skydive in July of 2009. She had recently reconnected with a group of old friends and joined them at the last minute when they invited her along to Skydive Chicago. Her second jump in August of 2015 was a fifth wedding anniversary celebration with her husband. This latest tandem was a 41st birthday gift from her awesome husband, and this one was the best because she was all about the altimeter and managed to deploy her canopy.  Using the experience from her two previous jumps, she was relaxed, engaged in the process, and focused on her surroundings.

Having a video and the photos from all three tandem jumps is very important to Andi. Taking the time to chronicle significant events is a way to take stock and build family memories. With so many of the same faces year in and year out at Skydive Chicago, it is also fun to keep track of everyone over the past decade.

The girls, ages 6 and 8, were able to watch the jump from loading into the plane to watching their mom come in for a landing. They were pretty blown away with the whole experience. The entire family is active and involved in outdoor sports, so now the kids can’t wait to be old enough to start skydiving. 

Interview With Andi Masengarb | Skydive Chicago

The bucket list discussion came up in conversation. Pretty high on the list is bungee jumping, but snorkeling and SCUBA diving have been checked off. With love for both Major (GO CUBS!) and Minor League baseball, seeing a World Series Game in person is on the table. Before Serena Williams and Roger Federer retire, she would love the chance to attend a national tennis tournament to see both compete. 

Playing catcher for fastpitch softball and sand volleyball are just a few of the competitive sports that have kept Andi active. She enjoys running and took up golf a few years ago, so basically, anything outside and busy is how the family prefers to spend their free time. Both parents coach their daughter’s softball teams and love the family-oriented small-town atmosphere where they reside. 

Interview With Andi Masengarb | Skydive Chicago

There is no doubt Andi Masengarb believes in less talk and more action. She signs her correspondence and emails with Carpe Diem, which turns out to be the family slogan passed down from a beloved Aunty. When faced with the reality that the only time spent with extended family was at weddings and funerals a solution for getting everyone together just for fun became a priority. In 2016 she found the perfect spot, sent out the invites, and just recently celebrated the 4th annual family reunion and colossal camping weekend. Even the Aunties with walkers and canes show up to celebrate the joy of family in the great outdoors. Never sigh out loud and mutter someday around this dynamo!

When it came time to have children, the pre-school style she had in mind did not exist in her town.  A few months after giving birth, she graduated on Mother’s Day with her Master’s Degree in Education. She put that degree to work and opened a business where she could provide for her girls and other like-minded parents. Those same families continue to be treasured friends, and the sense of community she gained from owning the business is immeasurable. 

Her current work is HR for the DODEA. In plain English, it is the Department of Defense Education Activity, tasked with finding educators for placement in schools serving military families in the Pacific region. Her department is responsible for filling teaching assignments in Japan, Korea, Okinawa, and Guam. 

Interview With Andi Masengarb | Skydive Chicago

Next on the to-do list: a sign-up sheet has been posted inviting her co-workers to spend a day at Skydive Chicago for a team-building opportunity. With nothing but praise for the drop zone facilities and family atmosphere, she feels everyone will find something fun to do. With her Carpe Diem approach to everything in life, we won’t be surprised to see this group at the DZ soon!

What about the potential for skydiving solo? It turns out a savings plan has been set up to do just that. She is most interested in participating in the A License In A Week program, which suits her busy lifestyle and feels like the perfect next step. 

Like the majority of tandem jumpers, the response to the excitement of freefall and the canopy ride is a top ten experience.  Coming in second on the list is the birth of both daughters, but only because labor was not as fun as jumping out of a plane. With a fearless mom leading the way, we can’t wait to see if both daughters choose a tandem to celebrate turning eighteen. 

Everyone at Skydive Chicago wishes the entire Masengarb family nothing but Blue Skies and, of course, Carpe Diem! 

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