We recently connected with Stephen Dummit and have shared our conversation below.

Alright, Stephen thanks for taking the time to share your stories and insights with us today. We’re complete cheeseballs and so we love asking folks to share the most heartwarming moment from their career – do you have a touching moment you can share with us?

The story of John and me begins in Pasadena, California in 2004. I was rooming with a college classmate in the same apartment complex as John, who was living in his dad’s place. We soon became friends, which wasn’t difficult given his calm presence, easy smile and genuinely welcoming energy. It seemed he was always fresh from a thought provoking conversation, often with a complete stranger that he had befriended as if by magic.
As we got to know John over the next few years an interesting dynamic started to surface. John was often found enjoying his breakfast coffee, more accurately described as a cup of vodka with a splash of dark water. You didn’t have to get too close to smell it wasn’t Foldgers in his cup. It was not uncommon to find John passed out in the middle of the afternoon surrounded by piles of dirty laundry, fast food leftovers and empty cartridges of CO2.
Lurking behind that adventurous spirit, huge heart, and willingness to always lend a helping hand was this shadow side. While I was earning a fine arts degree, John was fine tuning his art of escapism – and he was talented at finding anything that would take his attention away from the realities of life.
Now you might get the impression that John is a shady character, but that would be far from the truth. In fact, he moved in as a third roommate when we graduated and upgraded to renting a house. We sometimes hired him as an assistant on gigs that helped to pay the bills and he was always professional on the job, despite his “off” days in between.
You might be wondering why, exactly, someone with such great qualities would dive so deeply into this self-destructive behavior. As outrageous as he could be, we found it difficult to fault him. You see, John would often speak fondly of his older brother, his idol in so many ways. An older brother who was tragically killed before John was even an adult, leaving a wound that would become so painful at times it was all he could do to cope.

Fast forward 16 years. As is the meandering way of life, I was now multiple experiences and a construction career removed from that fine arts degree. I was in my element, fulfilled in a way I had never been before, building my skills as a professional coach and facilitator.
John called me out of the blue one day and we caught up about life since we last talked. I was delighted when he shared he was more than three years sober and happily engaged. I was saddened to learn he had also suffered the loss of his father in the years that had passed. I recounted my journey of discovery, finally cutting through the fog to find my purpose – he shared that he was still figuring out his. We laughed over stories and misadventures. To be completely honest, I cried tears of joy after that phone call. Hearing how far he had come warmed my soul.
About a year later John again reached out. His wedding was in four months and he was asking for help – he wanted to be the best version of himself before he said his vows. Far removed from his wild past life, John now had much more focus and absolutely understood what was at stake. The years of sobriety had brought back his sharpness, quick wit, and sense of humor about most things in life. His magnetic personality was working for him as it always had. What he lacked was clarity about his identity and purpose. He knew what I did professionally and wasn’t asking for any favors, just that we engage in coaching. I was honored and happy to agree to it.
On day one of coaching, I asked John to make three agreements: Candor, Commitment and Courage. Candor meant he had to agree to be totally honest with me. If I asked how he was, “good” was not an acceptable answer. Commitment meant that this was going to be a process and even if he considered quitting, he was making the commitment that nothing would prevent him from completing the sessions. As for Courage, John knew that to become the best version of himself he would have to face some things from the past in his own way, but that I would be there for support.
During our weeks of coaching sessions we discussed many things, but there were two main questions our conversation would always work themselves back to: “Who are you?” and “What do you want?” The first time I asked John this, I was met with a long silence broken by a disappointed “I don’t know”. I was quick to reassure John that though these questions are very simple at face value, most people would struggle to answer them.
“Who are you?” and “What do you want?” became the mantra of our coaching sessions. I would let him steer the conversation, which would span many topics. My job was to follow with intent listening and deep curiosity. We would explore the beliefs that formed the foundation of his life. Where did they come from? Did they still serve him? Would they add or detract from his future married life? Like most people, John wasn’t used to diving into subjects like that, but he stayed committed to the process.
I watched John transform as he found more and more clarity in who he truly was. In our work together he built the essential ability to be fully present rather than trapped in his past. This freed him to focus on and truly enjoy what was most important to him: his soon-to-be wife, his healthy routines and the career opportunities open before him. His view of the future changed from defeat to delight, from can’t to could, from impossible to possible. We continued coaching right up to the day of his wedding.

John called me the morning of that special day, not out of nervousness or worry, but for the simple fact that he wanted his vows to be true to him and felt he was struggling. We reflected on everything that had taken place in our conversations during those past four months. In the process of finding his sense of self, John showed tremendous courage; in that time he not only processed a garage full of memories of his father and brother, but had to face yet another family loss in saying goodbye to his sister. This was a defining moment when it all came together for him.
He shared that no matter what he tried to write for his vows, he felt like he was trying to prove or “sell” something. I reminded John that he had already made it, there was nothing left to prove. Life had thrown him a gauntlet and he’d conquered it all to get to this day. I encouraged him to own the moment as if all his family was right there beaming from the front row. Taking his fiance’s hand meant he’d already won. This wasn’t a contest, this was a victory speech!
John fell silent. After a few moments, he spoke, “Today I am love. Today I am going to show everyone just how much love I am. I am going to be so present and full of love because that’s what I am here to be!” His voice was full of confidence, joy and conviction. I could feel his smile stretching ear to ear through the phone. His energy radiated through me and my heart was full for a friend that now knew who he was and what he wanted..
I am telling this story because John is living proof that our circumstances, our pasts and our experiences are only a part of our stories. This is not to say that they are meaningless – far from it. But what meaning they hold and how that meaning impacts our future is our choice. As a coach, my only wish is to help others find the choice that is most true to them so that they might discover the best version of themselves. John was always capable of being the person he is today, but as someone who has himself been coached, I understand the power of having a little help along the way.

Stephen, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I am a professional Coach and Facilitator. People describe me as a positivity vortex, an adventurer and a bit of an adrenaline junkie. I am constantly amazed with all the amazing experiences that life offers.
I arrived in human development through the construction industry where I owned and operated a construction company for more than 10 years. During that time, I was focused on becoming the best boss and leader that I could be. Through years of learning about leadership and working with a professional development coach myself, I grew fascinated with the world of helping people become better. So much so that I wanted to offer that growth and development to those outside of my company. I shut the doors officially on being a construction contractor and headed full-speed into helping others through individual coaching and group facilitation.
Now I get to help companies decipher the best approach to developing, aligning and supporting their workforce. I work with company leaders directly to discover their pain points – what is holding them and their people back. Most of the time the problems are centered around developing personnel, lack of a common language, the shift from independent contributor to manager and identifying what leadership looks like to their team.
I am proud to be the owner of a bespoke consultancy, Tradewinds Leadership, that creates value by establishing a relationship with our clients first. We take our time to identify a pathway for them that feels true to their unique dynamics while building on what is already working. This sets us apart from many consults that primarily offer standardized, one-size-fits-all training. This approach is fast and offers some sense of “doing something”, but often addresses symptoms rather than root issues. It takes longer to deeply understand a company’s people dynamics and the investment is well worth it for me. The result is tangible solutions that they can use for years as they grow, which provides a feeling of purpose that I relish in being able to provide.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I have had the opportunity to unlearn and relearn a great many lessons in life. One that stands out is “my past dictates my future”. For a long time I held onto the belief that the choices I made in the past limited my options to move forward. I used to believe my college major (Bachelors of Fine Arts) meant that I had to choose something in the “art” world or my degree was useless. I used to believe that since I was in construction and running my own company I had to stay doing that until retirement. Both of these beliefs were simply not true. Once I learned to let go of these beliefs and decided that everything from my past was meant to serve what I am doing now, the doors to opportunity opened.

Do you think you’d choose a different profession or specialty if you were starting now?

Absolutely! The sense of purpose that I have and the fulfillment I get helping people develop is unmatched. If I could go back, I would do it all again the exact same way. Am I super proud of how I did everything in the past? No. Do I think that everything that happened helped shape the person that I am today? Yes. Every day I get to communicate with people that are looking to grow and improve, companies that want to better their employees, and associations that serve to improve people’s lives. I wouldn’t trade anything for the ability to professionally coach and facilitate positive change!

Contact Info:

• Website: https://www.tradewindsleadership.com
• Linkedin: https://www.linkedin.com/in/stephendummit/

Image Credits

Nick Pinto (@wherespinto)