Question:

Should I be humble or should I be assertive? These are both supposedly good things to be, but one precludes the other, doesn't it?

Answer:

There are many reasons for being humble. Here are some of the common ones:

  1. You think you're kind of ugly and stupid.
  2. You perceive that people like you better when you are humble.
  3. It's just your nature to be humble and keep your mouth shut.
  4. You keep on falling on your face, so what's there to be proud of?
  5. You didn't sleep well last night, so you're kind of depressed.

There are also many reasons for being assertive:

  1. You think you're real handsome and smart.
  2. You perceive that people listen to you and do what you want when you assert yourself.
  3. It's just the way you are.
  4. Nobody but you knows how to do things right.
  5. You didn't sleep well last night, so you're in a barking mood.

Looks like humility and guts are not compatible bedfellows. So that's not going to work. Is there an alternative?

There must be. Moses, the Torah tells us, was the "most humble of all men upon the face of the earth." Yet he had the spunk to stand up to Pharaoh and even argue with G‑d Himself. King David sang, "I am a worm and not a man." He meant it from the bottom of his heart, but you should have seen him swing that sword on the battlefield. Rabbi Eliezer ben Hyrkanus was known for his humility—he would never say a word of Torah that he did not hear from his teacher—yet he was in constant altercation with his colleagues and stood his ground to the end. The same with Rabbi Akiva, who was so humble he sat in a class of small children at the age of forty—and yet stood in fearless rebellion against the awesome Roman Empire.

So how did these guys manage to swing two opposite attitudes at once?

Turns out there's an alternative form of humility. A humility that has nothing to do with self-deprecation, sheepish nature or even insomnia. It also turns out that the same humility comes with a sense of power—but not the sense of power that comes out of ego, pushiness or indigestion. Quite the opposite.

It's the sense of, "Yes I know who I am, what I can do and what I can't. But I stand in the presence of something much larger than my little self, so much larger that there isn't any room left for any vestige of my own ego. Something before which a thousand universes are less than dust and from which all things extend. Something which is infinite, transcendent and yet pervades all things."

Sensing the presence of the Infinite is kind of humbling, just like, say, standing before some incredible genius, superhero type you really admire. Only that this is Infinite. That's big. Very big.

Sensing the Infinite is also very empowering. Because you can't sense the Infinite without becoming absorbed within it. And filled with infinite power, yourself.

There, in that space, humility and guts don't struggle with one another. There, all your faculties are united as one to fly high above any challenge, smash through the most impervious obstacle, take on the entire world without flinching. And yet, all of you is but a transparent window for the Infinite Light to shine into the world.

Like Moses, like King David, like Rabbi Eliezer and Rabbi Akiva. Transparent heroes.