We had the good fortune of connecting with Jill Charpia and we’ve shared our conversation below.

Hi JILL, we’d love to hear about how you approach risk and risk-taking.
Risk-taking has always been essential in my life, starting from a very young age until now. I love a challenge and risk is a necessary evil. My goal is always to try to do my best to mitigate the level of risk. Some days, you eat the bear; some days, the bear eats you, but without it, life would be dull. In my much younger years, I had a much higher pain tolerance for risk, and I found so much success that it even blew my mind at how far I could go. There was a significant downside to it, but my life’s philosophy is to never give up, and keep trying.

What should our readers know about your business?
My hard-working mentality began at a very young age. I grew up on a farm, helping anywhere I could (whether I chose to or not (Thanks, ma, haha), and entered the Air Force at the age of 18. I was given significant responsibilities very young which led me to work on the guidance and control systems of a variety of aircraft.

As I moved through the ranks, making the decision to continue to progress, I pushed to finish my 4-year degree in 2 years and earn a commission. This business degree allowed me to move into a position in Government Contracting, which led me to travel to many US-based and deployed locations. Getting to learn, support, and fight for the greater good, no matter how hard it became, created the tenacious person I am now. The struggle of working in a very male-dominated political world has almost placed me in the grave a few times over, but by building my life over and over again, I am able to have a rich and fulfilled life. I’ve learned how to appreciate the small moments and the beauty of stillness and understand growth.

I’ve thankfully acquired the knowledge to move into a Travel-based role that fits my personality and is allowing me to tap into my creative side. As a Travel Blogger/Owner, working with multi-national personnel, I now get to enjoy the best of all worlds (travel, creation, business, leadership, and mentorship), all of the skills I developed within the military. One of the main lessons I’ve learned throughout my career is to never let anyone stop you from your dream. Keep pushing and find the way. The other main lesson is that if you don’t know how to do something, find someone who does what you want to do and ask a lot of questions! Don’t remake the wheel. Travel Till You Drop is my way of continuing to learn as well as teach and give back.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
In and around the Denver area, I have to say, my favorite spots are located in the mountains. I love to head up to Evergreen and spend the time by the lake, take a hike, play golf on one of the prettiest courses I’ve found, head to Morrisson to drop in and have a few sippy sips, take in a show at Red Rocks Amphitheater to hear my favorite artists and roll on up to Estes Park to see the elk cross the road.

Who else deserves some credit and recognition?
I have to send a shoutout to my family as my biggest supporters. They stood by me in the rough times, and also showed their support when the success came. They may have hated my life choices at times ( living/working in so many war zones), but they realize that I thrive in this type of environment. No matter what, they are always there, dealing with the extremes in my life, but I think they kind of like to ride the ride (from the cheap seats) lol.

Website: https://traveltillyoudrop.com

Instagram: https://www.instagram.com/traveltillyoudrop1/

Linkedin: https://www.linkedin.com/in/jillcharpia/

Twitter: https://x.com/TraveltillUdrp

Facebook: https://www.facebook.com/TravelTillYouDropp/

Youtube: https://www.youtube.com/@traveltillyoudrop

Image Credits
Jill Charpia

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