The wind blows where it pleases, wrote a mystic in the Kabbalah. But human beings can choose where they go.

I’ve always believed that empathy is one of human being’s highest qualities and highest callings. Every great man or woman in our history was empathetic; every great leader could put him or herself in the shoes of others; every great writer could imagine the pain and joy of others.

Empathy is widely believed to be the root of behavior that we call “goodness.” It is a commandment of every significant deity in human history. It is the foundation of compassion, altruism, generosity, love, self-sacrifice, and charity.

Psychologists and spiritualists both have written that a lack of empathy is the root of most destructive and violent behavior – in fact, just about everything we associate with what we call evil.

Writing in Psychology Today, Dr. Steve Taylor wrote that there are two kinds of empathy, “shallow” empathy and “deep” empathy. Shallow empathy is the simple kind, the more accessible kind: seeing the world through the eyes of someone else, walking in their shoes.

The second kind, “deep” empathy is much more difficult. It’s the ability not just to imagine but to feel what other people are experiencing. It is the ability to enter the mind of another person to try and sense their feelings and emotions rather than yours.

The space between them and us fades away; in one sense, you almost become him or her. It feels like an amazing journey to me.

I practice shallow empathy all the time in my work with the Army of Good. I  have only once or twice even attempted “deep” empathy when I did; I recoiled from the pain and torment of the other person in the same way I ran and hid from my pain.

Perhaps that is because I felt what they felt, and that can be awful.

The thing about empathy I have noticed in my life is that I tend to practice it only on the people I like and sympathize with.

But the great human and spiritual challenge and the true measure of empathy is quite the opposite: can I feel it for someone I don’t like and relate to.

From the first, I’ve seen Donald Trump as an important and challenging opportunity to see how “good” I can be, whether or not I can achieve my goal of rising to one of human being’s highest qualities.

It is very easy to talk about empathy; it is not easy to practice it on any more than a superficial level. Most people don’t wish to go there. One of the things that fascinate me about President Trump is that he seems broken in this way, he seems to be unable to feel or show any kind of empathy, even in the most tragic situations.

It is important to say that empathy is neither forgiveness nor compassion. It is, to me, a higher level of understanding, and a way to process the broken parts of me.

In his rallies and public appearances, it seems many of his followers are the same way. They call for blood, again and again, never for mercy. The absence of empathy sometimes feels like their true connection to me.

According to Harvard’s Daniel Gilbert (Stumbling On Happiness), empathy is what makes torture possible. Without empathy, a torturer would have no concept of the pain he was causing. Because he feels pain, he knows how to cause it. Some people find pain unbearable, writes Gilbert, they push it far away because they know what it is.

Today, I watched Andrew Cuomo’s press conference and saw a master of deepening empathy. He conveyed the idea – true or false – that he understood my patience, fear, and confusion, that he felt what I was feeling.

I then went and read President Trump’s wounded and furious tweets from yesterday, and watched the press conference where he frowned, crossed his arms, and quieted a New Orleans nurse who was attempting to talk about the hard life in a coronavirus ward.

I remember reading what when an animal feels unbearable pain or fear, they often lash out at the source, try to swat it away with their paws. I thought of that while watching the President. He can’t bear the pain of being himself.

I recoiled from the tweets and videos; I felt both anger and anxiety, and the rawness that comes from reading Trump’s tweets or watching his anger boil over again and again.  I can’t bear the hurt and anger.

The President has never suggested to me that he understood my pain or fear.

But I began the difficult task of imaging his.

Lots of good people love this man, and I want to see if I could feel what they feel, not so that I can support him, but so I can understand him and become a better and deeper human being in the process.

For me, this is the point of living: working to be better.

If I can feel what he feels,  enter his mind space, it will help make it impossible for me to inflict pain or suffering on other people, at least on purpose.

I listened to him and closed my eyes, and walked outside and to the quietest corner of the pasture. I recalled one of the few Jewish sayings I remember fondly: “that which is hateful to you, do not do to  your fellow.” Hating Donald Trump is simply not a healthy option for me, I can’t leave it there.

And clearing my head in this way, I did connect with this very wounded man. And I did recoil at first, and it was painful, and it did bring up much of my own anger, abuse, wounding, and sensitivity.

I’m not doing this to judge Donald Trump or his presidency, but to make me more whole and healthy, He will have to take care of himself. I felt my self-boundary beginning to melt, my moat, my walls, my barriers crumbling into dust.

My mind rushed back to the hurts, the cruelty, the fear I felt as a child, the disapproving father, the abusive mother, my bed-wetting shame, the savagery of other children, the pain of my sister,  my terror, it all came washing over me like a flood.

Criticism was unbearable, I hid in closets and cemetery crypts, I lived in a fantasy world where I was always the hero,  and could never be wrong, and never be wounded. I was consistently praised, I slaughtered and drove off my enemies and terrors every night of my life to save and protect myself.

I stopped after a few minutes of deep empathy; it was disturbing and frightening.

Yet, for a few moments, I did connect with this person as a fellow human being, and not just as a political figure and leader I fear and mistrust.  We did melt into one another for a second or two.

I was often surrounded by broken children who could not and did not care about me, who were not reachable, who could not empathize or sympathize with me or anyone but themselves.

This experiment, if I can call it that, was transformative.

It did not leave me loving Mr. Trump or excusing him; it is not for me to forgive him or accept him. But it was a powerful experience for me, as it helped me to understand him, and in so doing, inch a bit closer to the highest quality of humanity.

Real empathy, shallow or deep,  is hard work. I can’t just say it and feel it. I have to go down to scary places to find it and keep it.

The wind indeed blows where it pleases, but I really can’t. I can only choose who I wish to be.

I am learning to accept the world as it is. And to accept me.

I don’t think I can live up to the major moral teaching of almost all world religions: “treat other people as you would like to be treated yourself.”

That goes too high for me; I am not healthy or wise enough or young enough to get there.

But what I might be able to do is to understand other people as I would like to be understood myself.

I think I almost got there today.