We were lucky to catch up with Dee Drenning recently and have shared our conversation below.
Hi Dee, thanks for joining us today. What’s been one of the most interesting investments you’ve made – and did you win or lose? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)
I would have to say that the two best investments I’ve made, in my life and in my career, were serving in the Navy and going back to school. I chose two, because I wouldn’t have been able to accomplish the second without the first. I enlisted in the Navy in 2009 as a Cryptologic Linguist and served six years. Making that decision not only secured some form of stability for myself in the future (benefits, disability pay, education, training), but also gave me a lifetime of experience I don’t think I could have gained anywhere else, good and terrible. While serving I learned to speak Persian-Farsi fluently and fell in love with the beauty in the culture, language, and people. The culture definitely brings influence to some of my works today. Outside of my training, I learned a large portion of my professionalism and work ethic from my service that has landed me in so many incredible places and opportunities. Taking those skills and gifts, and then applying them to my education after I was honorably discharged, helped me get further in college before I had my first class. I obtained an associate’s degree in Farsi that transferred over to my bachelor’s degree, and along with my GI Bill I was able to enroll and eventually graduate from University of Missouri – St. Louis.
This brings me to the second investment, school. Making the choice to go back to college at the ripe age of 27 was possibly the best investment I’ve ever made. Being older than most of my classmates, and also using the knowledge from the service, I was not as concerned about what degree was going to make me the most money. I chose to focus my educational energy to subjects, classes, and a degree that aligned with my interests and strong points. I took classes in African American studies and history, textiles, French, linguistic anthropology, and primatology as some of my electives that spoke to my interests in cultural anthropology. Once I settled on my studio arts major, I finished my core classes in studio/portrait photography, 2D and graphic design, and printmaking, as a few examples. Along with the academic portion of school, I also worked in the campus art gallery learning all that goes into an exhibition, archiving and administrative research, which has been an incredible source of experience in facilitating exhibitions and galleries. I think the greatest parts of going back for this art degree has been the connections and bonds I’ve made with the teachers and students, the safe creative space that housed my wild ideas, and learning to trust in my process and myself. The students and faculty were and are some of my biggest supporters in the work I create. The art and design group really gave us some of the best information and tools to help us get the most out of our careers and our work, and truly gave us the green light and full safety net when it came to creating. We were also around some incredible artists as teachers who, not only work in their craft and teach, but also are very well known for what they do, like my favorite print teacher, Jeff Sippel. Even working with the students has brought me so much knowledge and fortune with exhibits and coproduction. A lot of these connections, much like the ones I still have from the Navy, will last me a lifetime. Finally, learning to trust in myself and my process is why I chose these two as my best investments. The feelings I had going back to college as a veteran and a brand new mom (I started school three weeks after giving birth) at 27, were the exact same feelings I had leaving for bootcamp at 19. They both gave me a fear of the unknown, anxiety about if this was the right choice, if I was strong or smart enough to survive and accomplish this, but now I can see that they both taught me to trust in myself and trust in the fact that I can make anything happen for myself. They taught me that I will fail and fail again, and I will succeed, and fail some more, but it’s trusting that this is all a process, and I am meant to learn something from this that always moved me through the worst times, and made me grow the most. I was put in a lot of uncomfortable and challenging situations intentionally and unintentionally, and believing that on the other side of this is where growth is, has become a core life lesson. The growth, the support, the love, the gifts, skill, and talents I’ve gained from these two experiences will always be the reasons why they have been my greatest investments of my life.

Dee, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Hello to all my creative people! My name is Dee Drenning, also known as HoopsieDee. I am a multidisciplinary artist and I work in the realms of visual art (printmaking, photography, design, sculpture, erotic art), performing arts (burlesque, hula hooping, pole dance, and circus/variety arts), and community outreach (public shows, school programs, hoop instruction). My origin story began while serving in the Navy, I found hula hooping through music festivals I would attend, and later took it on as a form of movement mediation in therapy to help heal from an assault while serving. As my ADHD took my hyper focus into obsession, I started meeting other hoopers and learning tricks, and eventually got my first gig hula hooping at the Pride Parade in Augusta, GA. In 2015 I was Honorably discharged, and decided to move back to St. Louis to enjoy my newly found freedom. My roommate at the time had found an audition flyer online looking for dancers for a local burlesque venue that was to open and encouraged me to audition. I was incredibly hesitant, but I wanted to continue to be on stage, and I wasn’t opposed to learning a new dance style, so I went, and I never looked back. What started as a desire to bring hula hooping to more stages turned into an entire brand and business of many talents.
As HoopsieDee I provide services like graphic design, screen printing, painting, performances (adults and kids), hula hoop and art instruction (adults and kids, solo and groups), art administration, hoop crafting, show and event production, emcee and hosting, community outreach and event organization, modeling, and mentoring.
What sets me apart from others is my authenticity and my ability to find connections between things in life and in my creative endeavors. I am often complimented on being authentic, which was confusing for a bit, but now I have come to understand that it’s their appreciation of me living in my truth and honesty, which also goes well with the connections I find. Part of being authentic for me has been accepting how my brain works as a neurodivergent adult, and once I started accepting what worked for me, I was able to see so many disconnected things or would try and understand how the two things I’ve been given to work with translate to each other and to me or the world.
I am most proud of my desire to continue to learn, experiment, and grow. All of life is a process, and often times we tend to be afraid of it, because it is unknown, which leaves us complacent and stuck, but when we choose to be afraid and be curious to learn, we gain so much growth. The main things I want clients and followers to know about me and my work is that I love to collaborate on wild ideas, if I can’t help you with something or figure it out, I will come back to you with at least five other references and suggestions to someone who can, and I always have the hoops in my car!

For you, what’s the most rewarding aspect of being a creative?
The most rewarding aspect of being a creative is the opportunity to express myself and when people relate to my story or my work. Much of my life dealing with trauma from childhood to my mid 20s, I felt silenced, unheard, and misunderstood. I felt like i couldn’t relate to people, because the things I was experiencing wouldn’t be talked about or wasn’t given the safety to be discussed. When I picked up my first film camera in high school (I still use it today!), I wanted to show people the little things I would see or feel the mood I felt at that time, a first step in expressing what was in my head. Later I joined Latin Dance team and allowing my body to express itself was the first time I felt a release of pent up expression. All those emotions and feelings I was holding to myself, allowing them to crumble me into what felt like nothing, all coming out, being named and exposed, and released when I create. Now, interacting with others that relate to my creations and my story really brings me a feeling of community, because I feel seen, and heard, and understood.

What do you think is the goal or mission that drives your creative journey?
The biggest goal driving my journey is leaving a legacy. It’s fun performing and meeting fans and doing all these cool things, but what really drives me is the legacy that I want to leave behind for those that are coming up in this scene and field after me. I want to create possibilities and securities for someone like me who doesn’t or won’t have the same opportunities as I do. I want there to be resources for artists to find themselves, and feel protected and supported in what they do. I want to give kids a chance to try a hula hoop so that one day they remember when they first tried it and how it felt, and find a way to get back to themselves again if they are lost. There are so many artists that just want to create, and that is beautiful, but some of the most impactful ones, not even the most famous, are the ones who have left a legacy. I want to leave an impactful legacy. That is my mission.

Contact Info:
- Website: hoopsiedee.com
- Instagram: @hoopsiedee
- Facebook: @hoopsiedee
- Youtube: https://www.youtube.com/@hoopsiedee546
Image Credits
Emma Connell One Eyed Wolf Photography V Photography Jason Tucker Sonic Nation

