I was late to “leadership development.” My earliest life experiences were in low-income areas with little influence around me that would be considered “great leadership” — then or today. That is not to say that my experience growing up was bad — we are comfortable with that which we know, and find it hard to adapt to that which we don’t. All of this is a disclaimer that this article will be more focused on my lived experiences and a bit less on the academia that has been produced around Leadership Development.

“I didn’t know why I wanted to play music, no one else around me was a musician or performer, but I knew it was what I wanted to do. “

Coming up in Boston, MA in the 70s and 80s, I was surrounded by other kids. Many of us learned early that it was better not to depend on the adults around us. They’d be late, drunk, not show at all, or leave altogether. There was a necessity to become self-sufficient quickly and at a young age. My own father — by my memories and all accounts — was smart, creative, and funny. He also suffered from depression and substance abuse and killed himself when I was 8 or 9.

Music IS Education

By the time I was 13, my focus had begun to move from sports to music. I didn’t know why I wanted to play music — no one else around me was a musician or performer, but I knew it was what I wanted to do. Music would end up being the vehicle that delivered the true formative and deepest education in many areas of my life as it exposed me to a plethora of different views, cultures, challenges, and opinions.

I didn’t understand the language or lexicon of things like values and motivators during those early times, but I learned through my experiences that my values were fluid, quite dramatically sometimes, and I was motivated toward discovery and understanding — new people, places, and ideas. Though my music “career” never took off, it has been and continues to be the outlet for the creative “noise” in my head — and still a regular avenue for learning new concepts and ideas while expanding my knowledge.

I met and played with some very talented individuals, but few of us truly understood the business side of things. We did not have mentors to guide us, and our “lottery numbers” never turned up – no one with any pull ever heard us and / or liked what we were doing. A lot of frustration and jealousy was born out of those failures, but it was also where I learned about ego and how to utilize it appropriately — when to let it go a bit, and when to rein it in.

Music connected me with people from all walks of life in the early-1990s. Some of whom introduced me to computer-based work. I’d, to that point, been an offset printer — a gig I was able to land through the help of a band mate who’s stepfather ran a press shop — with the broken knuckles and ink-stained fingers to prove it. The consumer internet was still in a nascent state, but I understood how design and layout worked with regard to printed materials, and decided that it was time to stop torturing my hands with chemicals and metal, and instead take a shot at doing it via keyboard.

I’d never have known that these paths were an option for me had it not been for my experience with music. Building, leading, and maintaining bands is a constant challenge and it means that you are constantly adapting to and accepting changes – members, music styles, goals, and all the rest that goes along with “chasing the dream.” I also don’t feel that I’d have been comfortable making what, looking back, seems to be a pretty big leap from analog to digital, but my music experience gave me the confidence to know that I had the ability to take on change and be successful in a number of different environments.

“But my music experience gave me the confidence to know that I had the ability to take on change and be successful in a number of different environments.”

Unknowingly, at the time and well into the future, I’d also had my first mentors through the avenues introduced to me off the main music path. My print shop manager had turned his life around, after struggling with addiction, and though he could be a tough boss at times he showed empathy and support to the entire team. He expected a lot from everyone, but he also led by example — there was nothing that he’d ask you to do that he’d not do himself, including cleaning the bathrooms. He held us all accountable, daily, but never as much as he held himself accountable.

When I moved into the digital world, I took these lessons with me. It turned out that I am not the greatest designer … nor programmer. But, I was acceptable at times and I was always good at the interpersonal side of things and willing to put in the hours to meet deadlines. I took the “wins” where I could — one of my favorite compliments I’ve ever received was, “I like you because I only have to show you how to do something once!” — and learned that as long as I could deliver and build relationships, I didn’t have to be “the best” to be “successful.”

What I had done so well on the music side of my life — leadership, creativity, and support — turned out to be what I did well in general. I now understand why it was natural that I moved closer to the customer over time. The rise of Product Management gave me very interesting opportunities – the ability to work creatively across various functions, while focusing on building relationships and supporting customers. It was the crossroads where my values and motivators met in the corporate world.

Becoming more reflective over the years, it also became very clear that what I’d really lacked in my formative years: truly understanding myself and others and making decisions early in my life based on those understandings.

Because of that, I have consciously made time to support young people over the last decade or so – particularly young people who may be unsure of what they want to do. The why is important, but it is so complicated and treacherous, and I lack the training to even begin to tackle that within my own life, never mind another’s.

My efforts have taken various paths: whether volunteering with organizations specifically designed to connect students with mentors or creating my own cohort of students and giving them the opportunity to do what I did when playing in bands — lead, build, collaborate and produce without “adult” intervention (though ensuring that they have the necessary safety and support to succeed or fail). I’ve come to truly understand the value we can all deliver when we are available, open, and honest with those less experienced, and supporting them sincerely even for a short period during their own journeys.

But, and this should be very clear: This is not a selfless act, and we should not paint it in such a light. I am not a fan of the terms “mentor” and “mentee” as, in my opinion, if the relationship is one-sided then it’s likely being done less effectively than it could be.

I’ve learned just as much from those less experienced as they have from me. It’s made me more empathetic, better able to understand the world as it actually is and not how I think it is — or want it to be, and to also take personal satisfaction when someone else finds success of their own. To keep my own ego in check and build it up in someone who likely needs it more. In short, it makes me a better leader and, more importantly, a better person.

But, and this should be very clear: This is not a selfless act, and we should not paint it in such a light.

Those who know me have often heard the phrase “stories are the true currency of life.” It is something I heard someone say — wish I remembered who, and I really connected with it. You can swap “stories” with “experience” if you prefer and it may sound a bit of a cliche, but I sincerely believe it. As I get older, it becomes even more apparent to me that the things we spent much of our time chasing are often not those that deliver the most value. To us, or others. The more open and authentic I allow myself to be, the more I share with those who are sincerely seeking knowledge, and the more time I invest supporting others, the more valuable the outcome of my own time.

I’m not, nor will I ever be, perfect – not even close to it. Hosts of a community-focused podcast I record in my studio give me a hard time because when they introduce me in ways that make me a bit uncomfortable — giving me far too much credit, in my opinion — I always throw in that they need to add “complete failure” to the list. It’s a good bit of fun banter between friends, but also completely true. Without being a complete failure I’d likely not have had the opportunity to produce so many decent stories to share with those who are able to learn from them, laugh at them and, hopefully, not repeat them.

When we, as more experienced leaders, consider themes such as Leading to Repair and / or Conscious Leadership, I don’t believe that there is a path to broad success without a heavy focus on younger generations and how our own pasts and presents impact them. In my time working cross-generationally, heavy doses of self-awareness and authenticity have allowed me to communicate better and more honestly, build stronger and more trusted connections with others, and learn much more than I’ve been able to teach.