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Keystone moments

My sons,

It has been said that life is a series of moments. These moments can vary across many dimensions. They may vary in duration, in intensity, in importance, and in their impact on the overall trajectory of our lives. But it is these moments, strung together with some invisible string, that guide us, that give us meaning and purpose, and that ultimately define who we are and who we will become.

When we take the time to look back and be introspective about the strings of moments in our lives, we often discover that there were some moments that seemed more important than others, more prominent in our memory. They may not have seemed important at the time, or may even in retrospect be small or unremarkable, yet they nonetheless are critical moments that we remember as having some strong impact on us.

In the 2015 Pixar movie Inside Out, the writers propose the concept of core memories. These memories hold higher importance, and are memories that strongly shape our personalities and our character traits as we grow. But they don’t explore why these memories are important, why they become core memories for us.

I believe the reason is that these memories are memories of keystone moments in our lives, moments that hold strong value and have an overall greater importance than the rest. But what are these keystone moments and why do they have such a strong impact? I’ll define the following:

Keystone moments are moments that bring clarity to all the little moments along the way, causing us to introspect and compelling us to decision and action.

If it is true that our lives are indeed a string of events, a series of moments, then keystone moments are the ones that bring clarity, understanding, and unifying themes to some series of seemingly insignificant and disconnected moments along the way. They are moments that light up individual moments and allow us to see patterns and derive meaning from the otherwise endless and continuous stream of moments along our path. And they are moments that bring sharp attention and focus, compelling us to consciously examine ourselves and actively decide what path to choose next.

Very often, a keystone moment may not be immediately obvious. We may fail to notice their significance at the time of the event itself, only recognizing their significance later on. Often it is when our minds are quiet, when our hearts are at peace, and when we’ve got the head space to reflect that we then notice a significant moment has occurred.

At first glance, these moments may not seem significant - a note from a friend, a feeling of peace after a storm, opening your first piece of mail at your own home - but in context, they become incredibly important. They allow us to elevate our thinking, to see our lives in perspective, and to step back and look at the big picture. Perhaps the note came at the end of a long series of struggles and conflicts, the peace was hard fought through a long stormy period, the mail symbolized your first touch of freedom. Regardless of the context, these moments are the culmination of a set of experiences that have deeply impacted us.

Keystone moments cause us to introspect and evaluate

A trademark of a keystone moment in the making is that when it happens, we are compelled to introspect and evaluate. Maybe you’re like me and like the dramatic and romantic thought of looking out the window at the evening city lights with a glass of scotch in your hand as you reflect, or maybe you prefer sitting in your PJs wearing your favorite robe with a warm cup of coffee on a quiet Saturday morning to think. Regardless of your choice of dramatic underscoring, keystone moments nudge us towards rumination.

These moments strike a chord with us. They are moments that reach through the veneer of everyday life and touch some deeper vein of consciousness within us, begging us to turn off the autopilot of our lives and to strongly consider the implications of what we’ve just experienced. They resonate with our core values, perhaps contradicting, perhaps amplifying, but always causing us to pause and evaluate.

keystone moments allow us to strongly pivot and change course

Some years ago, I was at yet another work conference in Vegas, staying at my favorite Vegas hotel, the Wynn. One night after some conference events, I found myself at a bar next to the casino floor with two friends, drinking and chatting way into the night. This itself is a fairly common event for me - working in Big Tech, I must have been to two or three dozen conferences in Vegas by then. This night was like many others - a couple of friends, a thinning crowd at the bar as the hours wore on, and of course, several rounds of drinks which led to deeper and more meaningful conversation. Again, nothing new.

Eventually, 5am rolled around and we all decided that we should head back to the rooms in order to make it to our 8am meeting the next morning (unsurprisingly, two of us didn’t make it), so we left the casino to escort our one friend to the hotel next door where she was staying. Walking out the front door we immediately felt tired, and attributed it to the myth that Vegas hotels pump oxygen into the casinos to keep people awake (they don’t). We all had a good laugh at that, and that was that.

Some years later as I prepared for my transition out of that company, it dawned on me - that night in Vegas was more than just our typical after-conference evening. Something about that evening that to this day I’m not perfectly clear about impacted me. For some reason, that night solidified my understanding that the thing which mattered most to me was not the work. It wasn’t the brain stretching problems, the perplexing people management puzzles, the exciting new product ideas, or even the inspiring visions for how the world ought to be, how it could be. No, the thing that mattered most to me was the people. It was the relationships. It was the friendships.

From that day onward, I changed the way I thought about my career, about the roles I was willing to take, about the team environments that I sought out. That keystone moment brought about a clarity that allowed me to pivot, to change the way I behaved and the paths that I pursued.

One of the realities of an increasingly connected world is that the strength of the current of the path expected of us gets ever stronger. With an almost nonstop scrutinization of our lives in the form of friends, social media, professional networks, and public personas, the force required for us to adjust course is almost insurmountable for most.

It often requires some large event, some crisis moment that shakes us loose and forces us to move and to pivot. Those moments are one class of keystone moments that cause us to action and give us the leverage we need to pivot.

In 2019, we had a global event that caused crisis moments for virtually every person on the planet. This global pandemic had many, many negative impacts, but for some, for the thoughtful, the intentional, and the mentally strong, it also created a flurry of keystone moments that allowed for a strong pivoting of their lives.

In the comically light hearted movie Deadpool, Colossus is trying to convince Deadpool that being a hero doesn’t mean living a life with a perfect track record. He shares:

“Four or five moments. That’s all it takes to be a hero.” - Colossus

Four or five moments. Four or five keystone moments where we pivot hard and make the hard choice to be better. That’s all it takes. I love that.