Shoftim: The Uncomfortable Leader

I love being uncomfortable. Whether it’s on the trail hiking or in a boardroom teaching, I bask in the feeling I have when my heart quickens and my gut tightens. It seems weird, I know, but to me being uncomfortable is one of the most important feelings we have. That’s because when we feel uncomfortable, it means what we are about to do or say matters. Our body tells us when something important is about to happen, whether a breakthrough in a relationship or a sacred moment in a family. We get nervous, we sweat a little, our mouths dry out. We get uncomfortable. Feeling uncomfortable is the foundation of creativity, of purpose, and most importantly, of growth. Holiness is uncomfortable, and so is being fully alive. 

I learned it from my gunnery sergeant, a true leader if I have ever met one, who trained me to feel the difference between pain and discomfort. On a long hike with seventy pounds on my back, I was starting to fall behind. I wasn’t sure what was going on; I usually am near the front on a run or a ‘hump’, but that day I was slipping in my line. Gunny looked at me and said, “Sailor, you better get back in line!” Not wanting to disappoint, I pushed ahead only to fall back again a few minutes later. He came up right beside me and said, “You in pain?” I said, “yes,” feeling the heaviness of the pack and the strain on my legs. “You sure, son?”, he said, “Because, pain is the feeling that something is broken, like your body ain’t working right. Is your body working?” I said, “yes.” “Then what you are feeling is discomfort. And that’s not happening here.” He tapped my legs. “That’s happening here,” he said, as he thunked my helmet. “Get your head right, and your legs will do the rest.” He was right. We walked another few miles before resting. By the time I took off my pack, I was sweaty and exhausted, but I never fell behind again.  

I love feeling uncomfortable because it means I’m feeling most alive.

In our society, most of us are allergic to feeling uncomfortable. We spend billions a year trying to be less uncomfortable, through self care products, cozy clothes, drugs, alcohol, and thousands of other distractions. Don’t get me wrong, I love a good scotch in the evening on my sofa, but when our craving for comfort keeps us from apologizing to someone we love, or not putting in for that promotion, or demanding more support from our partner, we make the choice for short term comfort over long term growth. Refusing to be uncomfortable even for a moment allows us to slink away from each other and keeps us from growing. We fall behind in the line because we can’t get our heads right and we never fully live a life that really matters. 

This is especially true of leaders who fail to understand what it means to lead. Often CEOs, presidents, and managers feel they need to “be right” all the time because they are covering over their vulnerability, the root of feeling uncomfortable, with toxic stuff like machismo, anger, or emotional scapegoating. I was speaking with a friend who is a CEO of a corporation who told me that in their younger years they felt being right was the way to flex their position and to lead. Except their team experienced high turnover despite the amount of pay, vacation, and training that went into the workforce. They told me that it all changed when they stopped assuming that they had the best idea or that they were the only ones who could solve the problem. Saying to me, “When I was willing to be uncomfortable with my own leadership, I became a leader. My team’s talents flourished, and we all did better.”  

What this CEO was telling me, and what I learned from my gunnery sergeant, is that when comfort is mixed with power, we hold ourselves back, we hold others back and we ultimately hold back society.

In the Torah, Moses understood the power of vulnerability and feeling uncomfortable. For forty years, Moses led the Israelites across the desert in search of the promised land. As the new generation arose, Moses knew his role with the people had changed from being the fiery magic maker and plague bringer, to that of the prophetic revealer of the law, and now, on the last day of his life, he had evolved to being the sagely teacher. In this week’s Torah portion, Shoftim, he tries to outline a peaceful and just judicial system of magistrates, judges, and priests, forming the basis of the Western legal system we have today.  

But Moses knows that the populace one day will not want a teacher, a priest, or a judge – instead they will want a king. “If, after you have entered the land that YHVH your God has assigned to you, and taken possession of it and settled in it, you decide. “I will set a king over me, as do all the nations about me, you shall be free to set a king over yourself, one chosen by YHVH your God…” (Deuteronomy 17:14

While the people were free to set a king over them, it’s not the preferred method of leadership, because kings, like many leaders today, are as equally uncomfortable with being uncomfortable as we are. Moses knew that a king would probably build immense wealth (Deut. 17:17) and become corrupted by the excesses of power. Later in the Bible, the prophet Samuel was distraught that the Israelites wanted a king, until God explicitly sanctioned it. (1 Samuel Ch. 8

To hedge against the narcissism that comes with this kind of leadership, Moses instructs the people that when they do have a king, this king must carry a copy of the Torah with them at all times, “so that he may not elevate his heart above his brethren and deviate from the law…” (Deuteronomy 17:20) What Moses is teaching here is the same leadership lesson mentioned above. He knows that each of us can fall into the comfort of our station and believe that we and our power are the measure of all things. The purpose of the Torah is to show each of us that if we want to grow, we have to be uncomfortable with ourselves just enough to have the humility to know that we can’t do it all. The Torah shows us in nearly every chapter how jealousy is murderous  – like Cain and Abel, how unfettered power corrupts –  like Pharaoh, how anger strips us of our future as in the incident of the water and the rock, and how justice must be infinite and not simply pragmatic as it is in this week’s Torah portion. The Torah stands as a bulwark against hegemony, by decentralizing power from the king to the one thing the entire community can carry with them – the law.  

When we are willing to be uncomfortable in our leadership or at any other moment in our life, we can open up avenues of growth for ourselves and others. Instead of always trying to be perfect or being right and as a result shutting out others from our lives, we can be more open. We can get feedback; we can empower others by seeing them and hearing them. We can be as Moses wanted us to be; to know that more important than our own place in life is this thing that is between us.  

Our relationship.  Our covenant. 

That’s how we grow, that’s how we unleash talent in ourselves and others, by sharing with each other, and by getting uncomfortable. 

Shabbat Shalom

One comment

  • Wow!..never heard this commentary before. New ways of thinking, beng and living. Thank you so much. I love you. Diane

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