The Actualization Ladder

“Before enlightenment, chop wood and fetch water. After enlightenment, chop wood and fetch water.”

— Zen parable

As a recovering workaholic, the question that has plagued me over the past decade is why we continue to feel unhappy and empty despite achieving everything we’ve ever wanted. The great irony is that the higher we climb towards our calling, the harder we fall when disillusionment knocks us off the ladder.

So how do we escape this rather insidious ambition trap?

After observing people who have gone through this painful existential cycle, I realized that the answer is actually so outwardly ordinary that it hides in plain sight. What is extraordinary is how we inwardly approach life on the other side.

I developed the Actualization Ladder framework to encapsulate the three steps of this journey in hopes of shortening the distance it takes for you to reach your true purpose while avoiding the most common pitfalls.

Level 1 exists within the normal, societally accepted realm. This is where most of us get funneled into as adults. Its Four Pillars are family, house, pets, and job—give or take a few elements. This is a stable, well-trodden path: the super highway of life complete with the convenience of proverbial gas stations and 7-Elevens.

Level 2 is for the ambitious ones seeking meaning and purpose beyond the Four Pillars. This may or may not yield the typical rewards of money and prestige from Level 1, but you definitely have to sacrifice stability, leave your comfort zone, and even put your health on the back burner to pursue your passion.

For many people, this is when things get tricky because you may still not feel fulfilled. Something is still off. It comes with much frustration because on the surface, you have surpassed all of society’s expectations. You are bringing value to the world, perhaps even “saving” it, borrowing Silicon Valley speak. You are even living your purpose, the pinnacle of every self-help book.

Yet it all feels so empty.

The emotions at this stage aren’t pleasant—a mix of burnout, self-loathing, and depression. It’s the very definition of an existential crisis because we are asking, or rather crying out to the heavens, for our answer to why we are here. Why we feel like we’re losing even as we’re winning. What more must we do in order to feel content, happy, and at peace with ourselves.

I did this for years in the technology industry. The first decade of my career was marked by a hyper focused obsession with “making impact”. My self worth was completely wrapped up in the products I was creating, the teams I was leading and the events I was running.

Looking back, I had incurred a heavy cost, foregoing the opportunity to deepen friendships for loose connections to elevate my career. Yes, it was out of curiosity and passion plus a sprinkle of savior complex. I was truly loving what I was doing.

But one cold December night in Shanghai, I found myself alone in a hotel room closing deals thousands of miles from home, without any real connections to rely on for support and comfort.

This is the beginning of Level 3 personal growth, which may be triggered by a meltdown or a slow burn. But the realization is always the same: that what we’ve been chasing all this time was a mere stepping stone to what we truly wanted, or worse, has led us far away from where we wanted to be. For in the pursuit of Level 2, we may have sacrificed the very things that make such endeavors meaningful and fulfilling.

What does Level 3 look like?

It’s different for everyone. Here are two stories from my coaching work:

For Ray, it’s about connection with others—in other words, relationships, which he had cut off in full pursuit of his music career. At Level 3, he now makes music in order to build connections, thereby reversing the order.

For Annie, it’s presence. Deep presence that runs on Kairos time, which was utterly crushed in her past life as a successful CEO of a major nonprofit, even as she appeared to be crushing it to everyone else. She now chooses to move and think at a pace that is much truer to her nature.

What about me? I desire to understand and be understood. It comes from my obsession to understand the nature of things. My form of connection comes from deep listening and observation that leads to appreciating the things, both big and small, simple and complex, past, present, and future, that make someone special.

I’m an explorer of inner worlds, mapping the terrain and connecting the dots as we go in together. It took me a while to realize and accept this about myself as it involved rewriting several layers of personal narratives. But here we are.

Ascending the Actualization Ladder resembles walking up an M.C. Escher staircase. Paths that lead upward eventually loop back to their origin. On the surface, Level 3 might look similar to Level 1 and 2.

But after completing the journey, somehow, chopping wood and fetching water are imbued with new depth and meaning.