The Stranger and the Rolex

Don't you look at me so smug
And say I'm going bad
Who are you to judge me
And the life that I live?

I know that I'm not perfect
And that I don't claim to be
So, before you point your fingers
Be sure your hands are clean

—Bob Marley, Judge Not

Five years ago I participated in my first 10-day silent meditation retreat, in the Berkshires. Days of silence coupled with a lack of human interaction left me alone with the never ending stream of thoughts, emotions, and body sensations, noticing as much as I could process of my inner world.

During a break from our chores and meditation one morning, a balding, middle-aged man strode toward me, where I sat in the grass, contemplating my experience so far. He was fit and appeared comfortable in his Lululemon athleisure. There was a confidence and lightness to him. As he walked past my perch, I was immediately drawn to the Rolex on his wrist. It glistened in the sun and screamed pay attention to me. I bet it was at least $30,000.

Who the hell wears a Rolex to a meditation retreat? What a pretentious and entitled asshole! I thought we were instructed to leave valuable possessions at home, I didn’t even bring my wedding ring! As the mental chatter and judgments flowed, I felt superior, righteous—I would never do ANYTHING like that. Who does he think he is? He must think he’s above the law. This is the least Buddhist thing I’ve ever seen!

A few days later, I hurried into the cool and dim bathroom after a long meditation session. I could hear the soft hiss of a shower and notice the faint smell of moldy concrete. I passed two reeking stalls and, turning in at the third, found myself utterly floored. The man with the Rolex was crouched over on his hands and knees. Once my eyes adjusted, I saw he was cleaning the toilet. We locked eyes for a second, I gave him a gentle nod, and quickly turned to find the next open stall.

In the moments that followed, I tried to process what the fuck just happened. Here was the guy I was mentally bashing for being an egomaniac and now he’s cleaning piss and shit off the toilets as a service to the community. Holy crap! Suddenly, I got it: I was judging someone I literally knew nothing about other than the fact that he wore this watch. Maybe he was given that watch by his dying grandfather and wanted to honor him on the retreat? Or maybe his preference for expensive watches didn’t mean that he wasn’t a good person. I didn’t know. But I sure as hell knew I hadn’t volunteered to clean the bathroom that day or any day for that matter. Was it me, not him, who was selfish and egotistical?

For the remainder of the retreat and the weeks following, I questioned the mental models and operating system that guided me. There was a glitch in my thinking—I was prejudiced, operating with a never ending stream of judgments based on barely any information. In my fourth decade it finally dawned on me: people are fucking complex and judge each other all the time!

Judging Is Universal

Even those who are away on a meditation retreat seeking enlightenment judge others. To judge is to be human. Everyone does it every day whether they realize it or not. Who doesn't judge strangers, loved ones, friends, co-workers, and themselves? Maybe highly evolved humans like the Dalai Lama, but I honestly haven’t met one. Those who say they don’t judge are lying. Let’s judge them for lying!

We do all of this judging because it makes us feel safe, powerful, and righteous. According to Dana Harron PsyD., “If you are the ‘better person’ in a given scenario, you don’t have to worry that you might be the ‘worse’ one. You don’t have to reckon with potential feelings of inferiority, shame, and generally not being good enough.”

In other words, we put others down and place ourselves higher on a pedestal to comfort ourselves, validate our self-worth, and mask negative emotions. We ultimately get addicted to the mental and emotional payoff.

Because of this pattern of mind, it feels much easier in the moment to remain unconscious of our judgments than it is to take a breath and get curious about the person we are judging. Carl Jung summed this up perfectly: “Thinking is difficult, that’s why most people judge.”

The world we live in, especially in the West, demands that we see our relative worth to others and attempt to improve it based on the standard. We need to know where we stand and feel good about our relative position in society. If we feel “less than,” the only way to feel “more than” is by putting someone down by attaching negative labels and fabricating stories about them. This standard tends to be driven by what we value and worship: money, influence, work, beauty, fashion, health, politics, religion, and so on.

Ian Maclaren said it best: “Be kind, for everyone you meet is fighting a hard battle.” What we’re exposed to is often the very tip of the iceberg. Judging someone on a data point would be like trying to make sense of the Milky Way by looking at our sun. Like galaxies, humans are complex, dynamic, and adaptive, swirling with emotions, personalities, beliefs, and experiences.

We don’t always have the tools to ask questions—understanding others isn’t taught in school or by most parents. In the absence of information, we supply our own context, assuming things about other people that leads to further disconnection, contraction, and distance, compounding that isolation. The ego’s drive to feel “better than” ultimately separates us. When this happens we lose the opportunity to learn about others, ourselves, and the world. Curiosity and appreciation is destroyed. We abandon learning and the pursuit to see possibilities. We close our hearts. What a shame. We remain in our tiny corner of the Milky Way—missing its vastness, intricate constellations, and hundreds of unexplored solar systems.

The Downfall of Judgment

There’s a cost to remaining unconscious, judging others and justifying our words and behaviors.

We judge others to make ourselves feel better—but this actually makes us feel like shit. Judging makes us angry, resentful, and nasty most of the time (which is why I recently took a six month break from Twitter). Sometimes it makes us feel “less than” because we see in others what we don’t have. And it can actually lead to our assumptions becoming reality in our minds–creating a nastier, angrier world.

When another person becomes aware of our judgments, they often go on the defensive or even the offensive, launching their own judgments at you. We tend to hear, that’s not me or fuck you. Or the judged person can feel like an outcast, rejected and misunderstood, and move closer to the fringe. They ask perhaps there’s something wrong with me. Still others will contort themselves into the roles you make for and force upon them, in response to the way you treat them. Imposing labels on others becomes a self-fulfilling prophecy.

When we judge someone, we only see and experience them based on our judgements, making them unwhole and imperfect in our mind. It gives us a skewed perspective of how wonderful, generous, and interesting people actually are, ourselves included. As a result, we miss out on seeing what we can learn from them, and what is beautiful in them.

Judging might be our default, but it’s not an easier way to live. We create a world that is worse than it could be, a harder world to move through, to be happy in.

Our Judgements Reveal Who We Really Are

What we judge often says more about us than the people we’re sizing up or berating in our heads. As I just touched on, our judgements reveal what we worship and value, which is largely driven by our environment and relationships. If you value and worship beauty, you’ll notice what other people look like. If you value and worship achievement, you’ll notice the amazing accomplishments of those around you and tell yourself that you haven’t accomplished anything. If you value and worship possessions, you’ll notice the nice things that people have—like Rolexes—or the things they lack. In his excellent essay How We Judge Others is How We Judge Ourselves, Mark Manson takes this one step further: “The way you measure yourself is how you measure others, and how you assume others measure you.”

When we step back and notice our judgments, the parts of ourselves that are repressed or disowned begin to emerge and come into focus. I have a Judger part that enjoys watching strangers in Washington Square Park, criticizing what others post on social media, and embellishing elaborate stories about people I don’t know. Getting to know these judging parts is essential if we want to understand ourselves, our motivations, and uncover why we judge. For example, I recently walked by a woman, likely in her 50s, wearing a bright pink hoodie. My first thought was, why is she trying to remain young—clearly a judgment. I then realized that I have a part that badly wants to remain and appear young.

Through my own exploration, I’ve observed that every human has a duality built in. When we wake up to this universal dynamic, we can loosen the grip of our judgements directed towards others and ourselves. I’m patient and I’m a time cop. I’m focused and I’m scattered. I’m kind but I’m an asshole. I’m attracted to women and men. I’m spiritual and I’m an atheist. I’m generous and stingy. I’m frugal and frivolous. I’m full of pride and marred by shame. I’m courageous and scared shitless. Once we discover this duality in ourselves then we can begin to appreciate our wholeness and relate to the vast majority of humans.

Looking in the mirror to understand how we relate to others and the world can be difficult and conjure up pain, anger, sadness, and even shame. Through this process we can even judge and scold ourselves because it might reveal that we’re unhappy, uncomfortable in our own skin, or unsure of what to believe. We might not like what we learn about ourselves and our experience—and this can be disorienting. When we’re able to stop judging ourselves we can finally discover who we are in our wholeness, which leads to self-acceptance and self-compassion. This ultimately creates connection and dissolves judgment because we see deep down inside we’re not as different from the people that we’re judging.

I’ve witnessed this “in the rooms” of AA countless times when someone I perceive to be the opposite of me—based solely on appearances—has very similar stories and lived experiences. When I see them I feel disconnected because they look different, but when I hear them I realize we’re more alike than different, thus connecting and relating to them on a new, different level. It’s mind-blowing and special when we allow ourselves to see this again and again and again.

Really getting to know others, and especially ourselves, is a practice that requires patience, attention, awareness, compassion, and energy–all skills of a great leader. It also requires courage because we don’t know what we’ll discover in the process—not just about the other person but also ourselves. More often than not, we tell ourselves that we “know” someone, even those closest to us, when in fact we really know very little of what’s possible—this isn’t because we’re uninterested or ignorant but because people are complex. To buck this trend and understand others and ourselves more clearly, we have to resist the gravitational pull of old patterns, cultivate curiosity and start the process of asking questions. From that place of wonder, every interaction and judgment morphs into a rich learning opportunity.

Waking Up Is A Process

It was the perfect day on the southern coast of Portugal. The sun was shining so bright that I had to squint to make out the palm trees and the lush green grass in the distance. I could hear the hum of a lawn mower and the crackle of a weed wacker in the background. I reached for my sunglasses to see what I was hearing. In the distance, there were two landscapers grooming the impeccable grounds of the sprawling resort I was visiting. Something drew my attention to them. And then the thought appeared: why did they get the life they have and I get the one that I have?

For the remainder of my vacation this question rattled around in my head: Why did I get a better life? I meditated on it. I took walks. Writing in my journal later, I realized that I couldn’t answer the question because it was the wrong question. As I wrote, the truth came out: Who says I have a better life? What does that even mean? I knew literally nothing about these landscapers aside from their profession on that particular day. I didn’t know their names, ask them a question, or stare into their eyes. They remained in the distance.

Despite my experience at the retreat many years ago, I was still making generalizations and drawing made-up conclusions about these strangers, their quality of life, and myself. When I took a step back, I remembered the beauty of the grounds, the array of tropical plants, and the exotic birds, and suddenly the realization was blinding: 'Someone made this.' A man who planted, watered, and trimmed. A man who walks these grounds and cares for the growing things and the creatures. A man who deeply understands and respects nature. An artist. Or a laborer working for his own growing family. Or all these things and more. What feelings or traits do we have in common? What did I do? And what did I make?

With the benefit of hindsight, I made wisdom.

When we make space and take time to question and reframe our judgments, we can cultivate wisdom about others, ourselves, and our experience. Wisdom is vastly more powerful than knowledge, which is often what we regurgitate after reading a book or taking a class. Because it comes from direct, lived experience, wisdom is embodied—we can sense and feel it not only in our minds but also our bodies and hearts. When we don’t have the wisdom or the time to attain it, the only way forward is through elders, mentors, or advisors who have walked the path before us. Once we have the gift of wisdom, we’re able to discern what is true, false, or “just is.”

Despite being fully committed to this process and honoring the wisdom I’ve gained over the years, I continue to catch myself in the act of judging myself and others. There are profound moments every day where I realize I was ignoring the practice of wisdom, containing myself within judgements instead of moving toward someone openly to understand them or myself better. But that’s ok. We can notice the judging, wake up, do the work, only to find ourselves repeating this pattern. Waking up over and over and over again is the work—otherwise we’re just sleepwalking through life.

So don’t shut down when you notice some part of yourself being judgmental. Recognizing our judgments and faulty assumptions opens the door for curiosity, discovery and, eventually, wisdom. Once we’re on the other side, we can mindfully observe our thoughts, appreciate our differences and similarities, and see everyone, ourselves included, as whole. We commit to this practice, not because it’s politically correct or "wokeness" is in vogue, but because it leads to liberation from ignorance and aversion, and a more pleasant existence for us and all beings.