Doc Diego Coaching & Advisory

I had a lot of fun with Jason on his podcast. He has a way of getting to things with his presence and questions. I feel this is a good reflection on my own journey, work, and how I support others on their journey.

Ep 53: THE EMOTIONAL LIFE OF A STORYTELLER | with Doc Diego In this episode, Doc Diego shares his journey from childhood curios...

Reflections on Sisyphus
I woke up this morning excited and perplexed. Happy, but profoundly sad about some of the things I see us doing to our neighbors. I woke up ready to go, eager to start, motivated, yet I am sitting here reflecting on Sisyphus.

It was something I felt during my meditation and then again on my walk this morning before the sun was fully out. I felt a mixture of gratitude for the moment, for the beauty I can move through, and the memory of a time in my twenties when, physically, I had reached every goal I had set.

I weighed 180 pounds and could bench twice my body weight. My body fat was as low as I knew I could reasonably get it. I remember sitting at Bally’s after benching my max. I had achieved, but I had not arrived. There was no fanfare, just a question: “Do I have to keep doing this?”

There is something in me, maybe the spirit of the Jaguar. I can be relentless in being where I want to be. I find joy in the planning, the ex*****on, and the doing. But it has always escaped me in the arriving. Pursuit gives me direction. I can organize all my energy around a goal, yet the other side of that goal never holds me for long.

There is evidence from neuroscience that anticipation, effort, and progress can be deeply rewarding, often more than the completed outcome itself. But I am not sure that fully explains what I was feeling then or what I am feeling now in this exploration.
Since then, I have learned the joy of doing and letting go of expectations. This evolved from the pain of not receiving what I put into a thing, leading me to appreciate and practice nonattachment: the joy of the activity without attachment to the outcome.

I remember dating someone once, another therapist, who wanted a clear commitment, almost a guarantee of an outcome. My position was, and is, that if I commit to an outcome or a specific future, that commitment is conditional on the outcome. Instead, if I commit to a process, I am more deeply committed to what might be possible, rather than committing to some way I wanted the world to be. The previous pain taught me about myself. I learned that I can be so driven toward an outcome that I leave so little room to even ask if it was an outcome that really fit me. So this time I approached things differently, only to encounter someone else’s drive to ensure a future outcome.

Here is the thing about being driven: it can become addictive. Everything you produce, and every reward you receive, can simply fan the flames of the quiet promise that one day you will arrive. You will achieve. You will have all you desire and take your rightful place in society once your worth is finally recognized. Yet we do not leave room to ask, is it worth it?
I think about the ancient world and why stories like Sisyphus remain so relevant to our Western world today. I look for humanity underneath the culture and the myth.

In the Greek myth, Sisyphus was punished for being clever and for using his abilities to challenge the limits placed upon human life. His punishment was to exist perpetually in a condition where all his effort could never produce the desired outcome.

It is the Kobayashi Maru in Star Trek, the no-win scenario. A test of leadership and character. How do we face the moments when our efforts do not lead to the outcomes we desire?

For Sisyphus, the punishment was to experience neither success nor failure. He could never complete the task, but he was also never released from it. There was no final victory and no definitive defeat. Only perpetual striving.

This kind of striving often goes unexamined.
It is the pressure to get ahead. To be the first to market. To reach the stoplight before everyone else. Sometimes it seems as though our entire culture is in a hurry to be somewhere other than where we are.

I feel the weight of all that effort.
I slow down and feel the effort underneath it. The same question returns:
“Do I have to keep doing this?”
These deeper questions reveal threshold moments.
We tend to over-rely on what has worked in the past. Thus, we are more equipped to persist than to explore.

A threshold moment is when something deeper opens, and wisdom offers another way. The way is in letting go and examining the doing itself. How did we first begin? How have we kept it going? It may be less about asking why and more about exploring the reasons, expectations, and hoped-for outcomes that organize the effort.

What do we expect to receive through the doing?
What do we believe will happen when the stone finally reaches the top?
These are Sisyphean outcomes: rolling the boulder uphill in pursuit of an arrival that may never come, rather than acting from meaning we have consciously discovered and authored for ourselves.

I think this is where the myth ends. We do not know whether Sisyphus believed his punishment was worth the attempt to remove the limits placed upon human beings. Sisyphus does not speak for himself.

But what would our striving say if it could speak?
What promise has it been making?
What does it believe it is protecting us from?
What does it hope we will finally receive?

We persist in action for hoped-for outcomes, but we can also persist in the absence of action. We can keep doing out of fear, and we can keep ourselves from doing out of fear.
What is it we hope to gain when we strive so hard, both through doing and through not doing?

Perhaps the medicine is not in the striving. Medicine is in the questions that bring us to the doing that aligns us with our own nature, a threshold.
When we persist in failing to do what is ours to do, this pull grows stronger. We also feel the pull when we persist in doing what no longer belongs to us. In both cases, our attention can become so fixed on an imagined future that our feet no longer strike the ground of the present.
We move, but we are not here.
We strive, but we are not participating.
We accomplish, but we do not arrive.

This is where the work begins: increasing our awareness of the organizing themes within our lives and of the larger organization of life itself. It is the deeper question of who we really are and where we fit into this big cosmic way of being.

The path to these deeper questions begins by becoming conscious of the unspoken agreements beneath our effort, the fears beneath our avoidance, and the imagined futures that draw us away from the ground beneath our feet.

Life is movement. Life is continuous movement from one state to the next. These deeper signals are signals of alignment and congruence, your threshold. Does this resonate with who I am? Does this align with my values? Is this congruent with who I really am?

When we feel the weight of Sisyphus, our boulder is the weight of misalignment.

A signal from the weight we are carrying.

Our work begins with first feeling the weight.

Together, the three elements of self-compassion - mindfulness, common humanity, and kindness - become a source of resilience, a way to hold our suffering with warmth without becoming overwhelmed.