What it Feels Like to Be CEO
An ancient parable describes how it feels like to be in charge; it’s half of what you imagine.
Ever dream of being CEO? Thirty years ago, I did. Eventually, I got my wish, leading StreamBase, an MIT analytics startup founded by tech visionary Mike Stonebraker. That's when I learned that being CEO is a lot different than I had imagined.
The Sword of Damocles1 parable nails how it feels.2 A court flatterer named Damocles made light of how blissful the life of his king, Dionysius, appeared.
Dionysius offered, "do you wish to taste it yourself and make a trial of my good fortune?” When Damocles agreed, the king seated him on a golden couch and ordered servants to bring perfumes, lavish meats, and fine wine.
As he enjoyed the royal trappings, Damocles noticed a sword hanging by a single strand of horsehair overhead. Dionysius had placed it there so he would feel the delicate balance, the thin margin of error, and the constant fear of assassination that faces a king every day.
The saying "hanging by a thread" hails from this story. President John F. Kennedy used it during the Cold War when he told3 the United Nations,
"Every man, woman and child lives under a nuclear sword of Damocles, hanging by the slenderest of threads, capable of being cut at any moment by accident or miscalculation or by madness."
Like Damocles, my romantic vision of being CEO was incomplete. I dreamed it would be exhilarating, exciting, and empowering. I'd be above petty politics with peers. My word would be the last. Indeed, being CEO is all those things.
But being CEO is a double-edged sword. Your decisions impact lives. One wrong move, and your company could buckle. It’s the loneliest job I've ever had. Most roles have partners: marketing has sales, individual contributors have a team, and the board has each other. There's just one CEO.
And the threat of assassination? You might think CEOs are the boss, but we have a boss too —usually 3-5 bosses. It’s called a board. As one of my board member explained to me, "We have just one job: to hire and fire YOU." Even Steve Jobs was fired by his board4.
"Boo hoo," you say. The pay is good. You have the power. You get the glory. That’s all true.
But the CEO sword cuts both ways and hangs overhead by a horsehair thread.
That's what it feels like to be a CEO.
This story comes from my course at Modal Learning called “How to Think Like an Executive” about data-driven decision making. Thanks to Ashlyn King, Steve Wexler, and the Modal learners, who inspired this post!
POST SCRIPT: I received a DM / comment about this post from a friend who shared this slightly more modern interpretation of “The Sword of Damocles” by the Three Stooges. Hilarious!
The Sword of Damocles, History.com
I first learned of The Sword of Damocles in Ryan Holiday’s The Daily Stoic (December 6th), which I read every day!
John Sculley on the firing of Steve Jobs, Corporate Governance Institute.
Your writing is exceptional, and I love how you weave stories, references, and your own insights seamlessly throughout each paragraph.
I've met multiple founders who will refuse to be CEO again. This article definitely sheds light as to why.
Without a doubt, the most complicated job. On the other hand, that gave you the wisdom that you emanate. It is never easy to learn how to communicate upper to the board and also orchestrate the work downwards. As always, you got all my respect and admiration for how you tell the story.