The Monk and the Riddle: Leadership, Passion, and Being Human

Introduction: Komisar's Central Distinctions

Randy Komisar makes some valid distinctions in The Monk and the Riddle: The Art of Creating a Life While Making a Living. He observes the differences between leadership and management, and between drive and passion. Passion is to leadership as drive is to management — that is one of Komisar's main points. The character of Lenny serves as a compelling example of what an individual consumed purely by drive looks like: Lenny has a fixed set of expectations that must be met, and he is so obsessed with the idea of winning that doing something for the love of it is almost completely foreign to him.

And yet Komisar's argument cannot help but feel a little disingenuous at times. For example, Komisar made his way in the early days as a lawyer by annihilating the opposition in the courtroom — including people he would know and socialize with outside of work. He ignored the unspoken rules of the courtroom — respect, courtesy — in order to challenge and dismantle every single one of his opponent's points. This made his boss shake his head and gawk in awe at the same time. Komisar was driven to win, and driven to win at all costs. He did not mind making a friend who happened to be representing the other side look foolish. Was that drive? Was it passion? No doubt it was both. It was also skill, judgment, and a dash of that don't-give-a-damn mentality that often accompanies those who reach the top of their fields.

Drive, Passion, and Komisar's Own Rise

That combination of qualities is precisely what brought Komisar to the enviable position he now occupies — the position many secretly desire: the born leader, the t-shirt-and-jeans figure working deals with the suit-and-tie crowd, the man who carries no cell phone and can only be found if you know somebody who knows him. The man who has what others want. What makes Komisar unique, however, is that he retains a sense of humility despite this status. He genuinely wants to help. He sincerely wants to be a guide for those who, like Lenny, haven't a clue. That is what makes him compelling, and what makes the book so readable. We identify with his impulse to walk away from the Funerals.com pitch — but we admire him all the more for staying and offering Lenny a helping hand.

The central question becomes: how did Komisar get to that point? Did he get there through passion, through drive, or through both? No doubt, Komisar loved obliterating opponents in the courtroom, and no doubt he loved working deals in the Silicon Valley ecosystem. He had a passion for challenging tasks, but he also had the practical intelligence to know how to win, and the ability — the drive — to follow through.

Lenny as a Case Study in Misdirected Ambition

A person like Lenny is too naive and too unrealistic to see the forest for the trees. He is looking for the get-rich-quick scheme — the shortcut to success, the home run — and everything he does is oriented toward that goal. Is this drive? Not exactly. It is closer to mistaken ambition. Lenny obviously has passion, demonstrated by his relentless pitching of the funeral-services idea. But what he lacks is direction, guidance, and a teacher. Komisar senses this and, out of a kind of pity, decides to try to be a Socrates to Lenny's Euthyphro. In doing so, Komisar displays genuine mentorship — he becomes the leader to Lenny the manager, and an ineffective manager at that.