DeShawn Wynn shared their story and experiences with us recently and you can find our conversation below.
DeShawn, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What are you being called to do now, that you may have been afraid of before?
The life of a corporate event producer is behind the scenes. And I was quite comfortable with that. However, my career is now moving me to be upfront. I am doing a lot more speaking, teaching and consulting. It is stretching me out of my comfort zone, but I am loving it.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’ve been producing events for nearly 30 years and have owned my event planning company for the past 15. What excites me most is helping organizations achieve their goals by planning meetings with both strategy and empathy, ensuring that every stakeholder feels included and valued. This year, I’ve expanded my work beyond client events and launched my own signature retreat brand, Stretch to Wynn. These retreats are personally designed by me to guide participants through reflection and growth. I want to help them stretch beyond stagnation and build lives that are both strategically designed and deeply fulfilling.
Amazing, so let’s take a moment to go back in time. Who were you before the world told you who you had to be?
I would have to restructure the question. For much of my life, like so many others, I walked in the direction of who the world told me to be. It wasn’t until the last seven years that I realized I had been sleepwalking, moving through life without truly living by design. From childhood, we are inundated with expectations from family, society, and now social media about how our lives “should” look. Without even noticing, we follow that script. Only to wake up years later wondering where the time has gone and why we still feel unfulfilled.
What have been the defining wounds of your life—and how have you healed them?
The defining wound of my life was the loss of my father seven years ago. His passing gave me permission to question everything. It was the moment I took a long, honest look at my life and began asking myself why I was moving the way I was, and why I held certain beliefs. Many of those things I had never dared or even thought to question before. That loss became the turning point where I chose to live with intention, rather than simply moving through life on autopilot.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What’s a belief you used to hold tightly but now think was naive or wrong?
For much of my life, I believed there were no gray areas when it came to decision-making. Every choice felt like it had only two outcomes, right or wrong. And I would overanalyze my every move, terrified of suffering the consequences of a “wrong” decision. What I didn’t realize was that this mindset kept me living in fear. Over time, I have come to embrace Nelson Mandela’s wisdom: I never lose, I either win or learn. Bad days will come, and some lessons won’t feel good, but I now understand that every choice moves you forward. Some take you directly toward your goal, while others create detours that deepen your experience and expand your knowledge.
Okay, so let’s keep going with one more question that means a lot to us: Are you tap dancing to work? Have you been that level of excited at any point in your career? If so, please tell us about those days.
After running running a business for 15 years, adding a new business has me slow tapping. I am excited about what I am building. I love what I have built so far. But starting something new is always terrifying. So the dance has begun, I am on the stage looking a bit timid. But give me some time, the momentum is building and my dance will start to pick up some greater levels of energy!!
Contact Info:
- Website: https://wynningtouch.com/
- Instagram: wynning_touch
- Linkedin: https://www.linkedin.com/in/deshawnwynn
- Facebook: https://www.facebook.com/wynningtouch/
