Defining Success

“The path is made in the walking of it” - Zhuangzi

At an intimate work dinner I attended this week in Austin, the moderator started the conversation with this question “What was the moment in your life that you felt like you had finally made it?” 

A beautiful and completely unexpected question. What does it mean to make it? How is that defined? 

This was a professional setting with people I’d never met so the easy answer was work related. 

And indeed, a professionally related response came to mind quickly. 

Reflecting on that moment, I see how often we define success by external markers—chasing something we’ve been conditioned to pursue without questioning it for ourselves

And even if we have identified something more personally meaningful, how reluctant we can be to share. 

I was the last of ten people to speak, and as my pulse quickened and butterflies surged, I shared my two part response.

Pt 1: The Easy Answer

At age 30, after five years of working my way up through supporting roles in the advertising sales world in NYC and Chicago, I received an offer letter from the FX network for my first Account Executive job. 

The base salary was six figures, close to double what I was making at the time. 

For a lower, middle class kid from Cleveland who never had his own bedroom growing up, this was it. I made it. 

It was more money than anyone in my family had ever earned. 

Years of striving and achieving through school and work in pursuit of external validation, professional status and security had been rewarded. 

I had no access to my real motivation at the time. Only now do I understand that I was driven by fear. 

Fear that I wasn’t enough in some foundational way.  That I needed to be and do more. To prove to the world that I was worthy. 

Fear that if I slowed down or stopped, something would catch me. Reveal me to be a fraud. 

A child in an adult costume. 

The Path

With my professional and financial validation,  I continued unconsciously down the well trodden path of “success.”

I enjoyed more accolades at work, got married, had three amazing kids, bought a condo and then a house in the burbs. 

I had everything I had ever been chasing in life by the time I turned 40. 

As my success and responsibilities mounted, so did my need to escape the invisible but subconsciously felt pressure to do and be more. 

More of what? I couldn’t have told you then. I had never defined my own life vision. I never paused to reflect on what it was all serving.

There was no time for reflection. I was either working, parenting or partying. 

For all those years, alcohol soaked every social occasion and many work ones also. Not just alcohol. I had been a professional partier since college. 

Despite my penchant for excess, miraculously, It never really interfered. 

But it did. 

It kept me from understanding my true motivation and realizing my full potential. 

I was playing small. Satisfied with acting out the script that had been written for me by the world. 

Waking Up

I think of those years now as if I was living under a spell. Unconsciously living my life on autopilot. 

The catalyst to my awakening happened in the fall of the year I turned 40. We spent a month in the hospital with my son Silas, who has epilepsy caused by Sturge-Weber Syndrome.

He was five years old and hadn’t had a seizure in over three years so his doctor suggested we take him off his medication. 

Within 72 hours, he was having non-stop seizures in the hospital; status epilepticus. He recovered only to start seizing again on and off, with no medical answers for weeks. 

We lived in the PICU for a month and on a couple of occasions, we weren’t sure we’d bring him home.

That experience shattered me into pieces and changed me forever. I was completely and utterly vulnerable.

No amount of striving or achieving could change my beautiful boy’s circumstances. For a month, we had no choice but to stop everything in our busy lives and simply endure.

That experience pushed me deeper on this path of personal introspection I continue to walk. 

And mercifully, that chapter ended . We survived about the worst thing I could have imagined.

And I I became less afraid. 

Vulnerability is Strength 

Making it through that traumatic experience gave me a new perspective. 

The vulnerability I felt helped opened me up to explore more of the parts of myself that were hidden from my conscious mind. 

Not immediately, but an awareness began to grow.

And several years later, I started working with my coach who gently guided me through a process of self exploration that unearthed powerful insights about my mind.

I connected dots between my adult behavior and the needs of an inner child that weren’t met. I began to understand that it was my responsibility, and mine alone, to heal my wounds. 

I learned to sit with my discomfort instead of running from it and numbing myself with alcohol and other recreational escapes.

A new clarity began to emerge. Layers of internal narrative, once accepted to be truth, were revealed to be false. 

I found a confidence and courage in myself that had been lying dormant my whole life. 

Pt 2: The Real Answer 

I called on that courage to be vulnerable this week in front of this group of strangers. 

I shared the moment of my professional “making it” and went on to explain how I had come to realize that moment was in service of my ego.

I mentioned Carl Jung’s wisdom about the second half of life being about your soul. There was a subtle shift in the energy. It felt as if my fellow guests leaned in a little more. 

I talked about how I’d felt the tug to write my entire life, but listened to the voice in my head that said nobody would care about what I had to say. I mentioned how I accidentally fell into coaching and how it had opened the door to being of service to other people.

I shared the wisdom all of it has afforded me; what other people think really doesn’t matter in the slightest.

Ultimately, I pointed to the moment of sharing my first weekly reflection with over 500 people who had donated to our epilepsy fundraising efforts in January 

It was that moment that I really felt like I had made it. Because I was honoring something that was deeply important to me, and only me. I didn’t need anyone else to tell me congratulations or reward the effort.

And I feel that same sense of fulfillment every week when I hit send and these words travel out into the ether. 

It does make me happy to hear from people that say my words have a positive impact on them. But I don’t chase that validation anymore. 

I know I am enough. Just as you reading this are.

So this week I leave you to ponder your own definition of success. How would you answer the question? How do you define “making” it? How did you arrive at that definition? What might a more personally defined version look like?

Powerful questions open the door to a deeper understanding of ourselves. The real challenge is having the courage to step through and embrace what we find.

-Coach Kris

P.S. My coach Dennis shared this quote with me in 2023 “Your playing small doesn’t serve the word” It hit me like a 2x4. It was a moment of clarity. It’s from a longer piece of work that aligns with these week’s topic. Maybe it will resonate with someone else as deeply.

“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. We ask ourselves, 'Who am I to be brilliant, gorgeous, talented, fabulous?' Actually, who are you not to be? You are a child of God. Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won't feel insecure around you. We are all meant to shine, as children do. We were born to make manifest the glory of God that is within us. It's not just in some of us; it's in everyone. And as we let our own light shine, we unconsciously give other people permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.” - Mariane Willaimson