I was fortunate to be assigned a seat next to Bill George, author of Discover Your True North and a professor at the Harvard Business School. During our dinner conversation, he told me something surprising about his experiences working closely with many Fortune 500 CEOs and high-level executives. He noticed that leaders needed to get in touch with their own deep sense of pain, vulnerability, and humility, and occasionally a deep sense of shame, in order to shift from being good leaders to becoming great leaders. At times, this was simply acknowledging the pain of being human, or the pain of feeling like they had let others down, which they had covered up, as many of us do. Other times it was the pain from difficult, imperfect childhoods, failed relationships, or traumatic events. Feeling this pain helped these executives glimpse how much more was possible by freeing up energy and

feelings that were being held close, which allowed them to be more authentic and caring leaders.

Learning to lead yourself is the hardest part of becoming a leader. That’s one of the things new CEOs and aspiring entrepreneurs come to me for. They come because they feel lonely; they don’t have anyplace else to put the feelings.

Looking back, I realize this time as the beginning of my own radical self-inquiry. My pain helped me realize that I was lost. My soul, no longer content to be ‘bruised and battered,’ took charge of my body and grabbed the attention of my conscious mind. The headaches, which continued even as the self-inquiry began, became a way for my body to say, in effect, ‘Wake the fuck up.’ For, if I didn’t wake up, my soul was going to drop me to my knees, writhing in pain.

The pain of hating our own creation is a consequence of our investing too much of our sense of being into the company, the product, the creation. When we hang our sense of self on the whisper of an idea; when we unwittingly insist that our love, safety, and belonging depend on what we do and, most important, how others feel about our feelings, our actions, and our work; then we leave little space for anything other than bitter, existential suffering.

So much of what I’ve learned about growing up came from learning to lead.

In fact, the process of becoming me made me a better leader. The two processes, becoming a leader and becoming ourselves, are intertwined and interdependent; better leaders are better humans and better humans are better leaders. Leadership lessons, then, are, at their core, lessons in humanity.

Sometimes the belief systems that are most difficult to overcome aren’t the ghosts in the machine of our childhood. Sometimes the most difficult belief systems fall under the rubric of “conventional wisdom.” Conventional wisdom, for example, dictates that, in our process of becoming warrior-leaders, we focus on the hard things. Big rocks, folks say knowingly. ‘Break down the big rocks and then focus on the little rocks.’ But how do you discern a big rock from a little rock?