36

As I sit here writing this, my massive Great Pyrenees is asleep beneath my desk, and my wife and kids are doing something fun in the next room. I just turned 36 and I was gifted with a particularly wicked hangover and more hairs from my head stuck the edge of my porcelain tub after a shower than I care to acknowledge — to myself that is. Needless to say, I’m in a contemplative mood.

The question I’m asking myself, as each finger strikes a key on my ancient Macbook Air is: Why am I doing this? Why am I blogging? Why am I still an entrepreneur? Why am I still pursuing making a movie and TV show? I’d probably be more comfortable just working a regular job. I’d certainly have less stress and, just maybe, I’d be in the other room enjoying whatever it is my family is doing right now.

The truth is (because you’re going to find out anyway), I don’t know if any of what I’m doing will work out or if I’ll enjoy any of it more than anything else. But I’m here, in the moment, living life, trying to avoid regret and putting my thoughts to paper, so to speak, (Even though I was told, just the other day, that blogging is so 2005.) It is with that humility that I keep writing.

I’m here, in the moment, living life, trying to avoid regret and putting my thoughts to paper, so to speak, (Even though I was told, just the other day, that blogging is so 2005.) It is with that humility that I keep writing.

So, back to what’s on my mind. Transitions. Not just because I turned 36, but because transitions seem to be happening everywhere. Of course, they always are, but I seem to be taking more notice. Personally at least. Transitions cause powerful shifts in energy and thought patterns. We may resist, but they persist. This is life.

By definition Transition is the process of changing from one state or condition to another. And as mentioned, I’m an entrepreneur, and that means constant transition.

As Prof. Scott Galloway put it in his newsletter,

“Entrepreneur is a synonym for salesperson, and salesperson is the pedestrian term for storyteller. Entrepreneurs believe their story will come true. This requires confidence … and delusion. It helps to be somewhat detached from reality — to assume that, for whatever reason, you are the one who can see into the future, and that in the new world your product/service will be needed and successful, despite overwhelming evidence (i.e. the current reality) that it’s not. A reality distortion field if you will.”

Some of the stories I have personally conceived are that the companies I founded, Naked and Kosan, would be billion-dollar successes. They weren’t. Although, I think some thought the former was, so do what you will with that. And, like the end of a good book, in entrepreneurship as in life, there is often no full-stop ending to provide simple, sweet closure when one project is complete. It’s just another transition. In my case, from the top of the Empire State Building (figuratively) to financial dismantlement (aka rock bottom) and…somewhat…back again.

As I type those last two words, I must ask myself, “Are those words just part of yet another story?”

Is coming up with a new story really the solution or does one just need to grow up and stop living the in a distorted reality. I’ve been hearing that for well over a decade now!

Like in every story, you play a character. Usually, the hero who is trying to overcome obstacles to fulfill a dream. In my story, in order overcome those obstacles the character I’ve played was “workaholic,” “hot shot,” “playboy,” “influencer,” “dreamer,” and most of those roles just led me to burn out and misery…which I always realized too late.

Desperately holding onto this idea of what I should be, I’d just end up backsliding into comparisons and self-pity. Wondering why, at thirty-whatever, it seemed so many of my peers had made better, more responsible, choices. Were their stories not like the fairy tales I’d told myself? Were they not living in a distorted reality? Why wasn’t I better at the things other people were better at?

Wondering why, at thirty-whatever, it seemed so many of my peers had made better, more responsible, choices. Were their stories not like the fairy tales I’d told myself? Were they not living in a distorted reality?

Tangentially, this “rock bottom” made me less curious about entrepreneurship and more so about the stories I was telling myself. The labels I was giving myself. Vulnerability, born of insecurities, was like a sharp knife carving up my insides to make space for new understandings. The question: “What if I had no story, no past reputation to build upon, but just a blank slate?” allowed me to rise above myself and see what may actually be there.

That question allowed for, in a word, “detachment”: A powerful tool used during transition so as not to allow the tearing apart you can feel from holding on to where you were. It allows you to go where you’re going — to move from who you were to who you are becoming.

As I’ve come to learn, transitions can be precarious. The world around us, those who know us, and know our stories seem inclined to draw us back to familiar territory. It’s easier to keep us in boxes I guess, but we need to resist being pulled back so we can discover our inner calling.

Through the unravelling of the stories, and the removal of the labels we’ve given ourselves as well as the ones other haven given as too, we move forward to a more authentic version of ourselves. We’re never quite out of the story, and the story can also serve the manifestation of our dreams, but we can make it a story that includes humility, awareness and openness. One where we meet the world exactly where we are today — not where our future self or the zeitgeist says we should be.

can we make it a story that includes humility, awareness and openness. One where we meet the world exactly where we are today — not what zeitgeist says we should be.

This led me to question what was most important to me in my work. What did I want to obsess over? What did I want to take to bed and wake up with? What will make me feel the most human in my work?

And that is why I’m sitting here typing this. This is why I stay in the practice of creative writing even when it is counterproductive to more practical work. And this is why I continue to move away from starting and running businesses, and more toward creating art.

The irony, of course, is that in my little world, the story I’d fought 15 years for — of me as an entrepreneur — was all but accepted and now I’ve transitioned into more uncertain territory.

Alas, I’ve come to accept that uncertainly is the fertile soil of which we grow and thrive as humans. As well, nothing can avoid the force of constant change, even as we enter that part of our lives where we’re supposed to build some measure of career, financial and life stability, inevitably change happens nonetheless.

The essence of creating lasting success is the ability to differentiate between what serves us and what does not. To discern who we are, what’s working, what we want to double down on, and what no longer serves us. And we transition through these pages of our life with grace, presence and reverence for the process.

All right, time to join the family!