Transition: Where is the Puck Going?

I have not written much about my current transition as I’ve been deeply engaged with ensuring it’s successful. In shamanism we call this a bid for power, when one sets out to acquire more power, to “level up” by accomplishing some task. Bids for power usually come with tests to challenge us and ensure that we are ready to rise to the next level. That has certainly been the case with this transition. 

What transition? After much consideration I have decided to leave the role of Director of Business Development at AppFolio, “the world’s fastest growing company.” It has not been easy to arrive at this decision. I have, above all else, built many close relationships over the last five and a half years with humans I truly enjoy and appreciate. Some I expect to be friends with until my sun sets. AppFolio is truly a phenomenal world-class company and I keep reflecting how blessed my life is that I get to leave such a great place because I know there are more great experiences and opportunities waiting for me in the world. 

I have learned and contributed much during my time as a manager and director. I am humbled by the words shared about the contributions I have made to the people I have led and coached. And our results speak for themselves. An average of 107% quota attainment across 22 quarters amidst the company growing at a CAGR of ~30%. Not too shabby. 

Why leave? There’s nothing wrong at AppFolio. In fact, much is right. I reflect back to when my close friend and the previous director gave Socrates’ famous words, “know thyself”, as his final advice before he too walked out of the door leaving greatness to pursue his heart. I have been investing deeply in this knowing of myself for many years now and I’ve learned key attributes, values, and needs about myself:

  1. I am far more creative than I have led myself to believe in the past. 
  2. Spaciousness is required, an exploration of the void, in order for me to fully bloom.
  3. It’s not about the money. 
  4. Life is short, use it wisely. Time is the most precious resource in life. 
  5. I require and thrive with variety. I am fundamentally interdisciplinary and my college degree was more reflective of my instincts and modes of learning, being, and operating than I once realized. 
  6. I enjoy thinking, strategy, and operationalizing that strategy. I easily create structure. 
  7. I love speaking about the things I care most about. 

It’s for these personal reasons that I see these primary needs best met in another pasture. “Greener” pastures assumes a better/worse relationship, laden with hierarchy and judgement. Life’s not about greener pastures. It’s about other pastures, the simple opportunity to experiment and bring forth new experiences into one’s life. Good and bad are relative. It’s all one point on a spectrum, each point as valuable as the next. Life is experimental. And as I mature I become more clear that truly, life is short, from just about every perspective that I look at it. 

When the offer came for a promotion to Senior Director with a substantial raise to match the responsibilities I was already performing, I immediately knew the answer was no, no matter how much cognitive dissonance existed between society’s definition of success (which I was clearly achieving) and the knowing in my heart about what I am called to. 

As reflexive and self-conscious as I can be at times, this decision is not just about me and my internal machinations.

Skate to Where the Puck is Going 

Those of you that know me personally know that the best I can muster about sports is my shallow attempts at sports humor by trash talking about things I have no clue about or purposefully using the wrong sports vernacular. However recently it is the words of the great hockey player Wayne Gretsky that I have spent significant time pondering. 

While I wouldn’t have worked at AppFolio if I didn’t find SaaS and the real estate market interesting, I do wonder, “where is the puck going?” 

As I look out at the world, I see crises and realities that require all of our earnest attention if we are to co-evolve as a human species from this dangerous precipice upon which we now teeter. The puck is moving towards:

  • The arriving climate disaster and sixth mass extinction. The health of the entire living earth system, our trees, soil, air, and water, is in rapid decline at the hands of the suicidal tendencies of modern extractive capitalism and the mindset of Cartesian reductionism that fails to account for the complexity of the systems which sustain life. There are many reasons to be hopeful and there are plenty of reasons to fear that we are not doing enough. What is one’s role in securing life for the next seven generations?
  • Emergent technologies beckon our close attention for the many benefits and risks they pose. Between blockchain, Web 3.0, artificial intelligence, biotechnology, and much more, the intersection of new technology with our wicked problems represents enormous opportunity – and danger – as each is capable of accelerating or decelerating our growth towards dystopian or utopian futures. If we’re honest, Homo Sapiens has a fairly dubious record of treating our environment, “lesser” species, and even one another. How can these new technologies be harnessed for productive, life-positive outcomes that unfold more vitality, viability, and evolution?
  • The two bullet points above necessitate a global cultural rotation and reconnection to community as a primary organizing principle. With the high level of complexity and interconnectedness of our global economies comes more fragility (when not thoughtfully designed or cooperated on), a reality recognized by the shocks to supply chains and economies through the pandemic. Now is the time for the preeminence of place in how we relate to our world. As much as global problems direly need solutions they are most effectively addressed at scale by a series of bio-regional or local solutions. How do I take care of my backyard with my neighbors and assist you in building your own capacity to take care of yours?
  • Everywhere I look the signs are evident – human consciousness is rising. The Archaic Revival talked about by Terrence McKenna is unfolding, a natural, even carnal response to the downsides of modernity. Cyclically speaking, when observing the prophecies of long-time calendar traditions like the Mayan (Toltec) and Vedic Yugas, our lowest is behind us and ahead of us is a golden age of consciousness. We’ve turned the corner. Right now we are building the foundations for the mass expansion of our spiritual faculties on a species-wide and planetary level and this will continue to accelerate far beyond our human lives. What is my role in this healing?
  • All of this requires shifts in three primary systems:
    • Education is a first mover to every bullet point here. Building the capacity to expand these many ways of thinking (regenerative, complexity, holistic) is a necessity. Ensuring that on a societal level we raise functional, whole humans will solve so many issues and free us up to work on what’s most important. 
    • Consumption is rapidly ceding mind-and-wallet share to the experience economy, a principle first written about in 1999, a book I’ve yet to read. The evolution of understanding and connection can be facilitated through experiences designed to touch the heart and align the mind with it. 
    • Culture is our most powerful technology creating the very container in which human evolution takes place. It was Western culture that enabled the Enlightenment, Industrial Revolution, and Technological Revolution, for better AND worse. 

As I consider these realities as where the puck is going, I realize that I’m not “leaving such a great place because I know there are more great experiences and opportunities waiting for me in the world”. I am embarking on my dharma, this life’s sacred duty to be fulfilled. I am motivated by this deep knowing that I am responsible for applying my talents to being of service. 

I have spent many years building a set of skills which I am now ready to apply to the tasks of which I am called to. Calling is an interesting concept. Some say it is a myth. I perceive that for me, there are the right endeavors at the right time and that there will be many of these opportunities (callings) throughout this life. One door closes. Another opens. To transition with power, grace, and clarity of heart even if the vision is not crystal clear, these are my tasks at hand. To complete the harvest such that I am capable of service in the next endeavor. It sometimes requires silence to hear the next calling. 

I cannot devote my time to all of these issues. The question is, what is the next right divinely-inspired action I will take? Off the cliff I leap, trusting in myself and the universe, that I will hear a call, the one I’ve been praying for and calling in. I am ready and I will answer with passion and gusto.


This next article (coming soon) in this series on Transition is “What’s the Responsibility of Privilege?”

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