The Ultimate Leadership Skill

Last weekend I attended Harilaos Stavrinadis’s bachelor party in Chicago. Hari, who will soon be godfather to my forthcoming son James, is getting married this summer on the island his family originates from – Icaria, Greece.

In addition to Stamos, Bartokomos, and healthy yet delicious cuisine, the Greeks are also well known for telling pretty good stories chock full of valuable life lessons. This post is based the legend of Icarus, the mythological Greek for which Godfather Hari’s home island is named:

Daedalus conceived to escape from the Labyrinth with Icarus from Crete by constructing wings and then flying to safety. He built the wings from feathers and wax, and before the two set off he warned Icarus not to fly too low lest his wings touch the waves and get wet, and not too high lest the sun melt the wax. But the young Icarus, overwhelmed by the thrill of flying, did not heed his father’s warning, and flew too close to the sun whereupon the wax in his wings melted and he fell into the sea. Daedalus escaped to Sicily and Icarus’ body was carried ashore by the current to an island then without a name. Heracles came across the body and recognized it, giving it burial where today there still stands a small rock promontory jutting out into the Aegean Sea, and naming the island and the sea around it after the fallen Icarus.

Hubris slays another Ancient Greek. “Pride comes before the fall,” says the bible. Gatsby was ruined by his own opulence and swagger. People have been warning other people through stories to stay humble for a long long time now.

Easier said than done. Power corrupts, and absolute power corrupts absolutely. And we all have egos.

How can we avoid the fate of Icarus?

Humility is the antidote to hubris. I also think humility might be the key leadership quality that breaks nauseant middle management careers through to the executive level. How?

Well let’s consider how a humble man behaves. The humble man…

  • Works hard because he knows how hard his competition is working.
  • Commits to learning and practicing because he knows he knows nothing and couldn’t learn all there is to learn in 1000 lifetimes.
  • Is grateful for whatever fortunes come his way, because he knows others are being dealt misfortune, like he inevitably will be someday.

But a man blinded by hubris…

  • Believes he has earned the right to work less for the same or more reward. He thinks his work is worth more than anyone else’s work.
  • Is done learning and doesn’t need to practice anymore. His glass is full and he does not believe in or need any new approaches or technologies.
  • Believes he deserves more. He compares himself to others and is filled with jealousy and envy when he thinks about all of the things he ought to have but doesn’t.

Humility is like any other skill- it requires deliberate attention and practice.

Some days I do a pretty good job staying humble. Other days I find myself thinking, “I’m special… I’ve arrived… I deserve…” These are evil thoughts – sirens leading us to shipwreck. When these thoughts creep in, it’s time for an attitude adjustment.

Here are some common forms of hubris along with my personal go-to thoughts and strategies for avoiding each pitfall:

  1. Company Hubris – My company is the best and will never be beat. In my current favorite business book, Exreme Ownership, Navy SEAL Jocko Willink talks about “the man in the cave” – an imaginary enemy Jocko pictured waking up early every day working to get stronger and planning to destroy Jocko whenever they would inevitably rendezvous on the battlefield. Every company has that man in the cave out there (it’s Amazon). Someone or some team out there in a garage or at a startup or at an old rival is plotting your demise. Your company has a rendezvous with this upstart competitor. Will you be ready?
  2. Career Hubris – This company can’t survive without me. Yes it can. Want proof? Go to a job fair and look around. They fill stadiums with people just like you, who thought they were indispensable. And their former employers are doing fine. I’ll never forget interviewing former $250k+ earners for $50k jobs during the recession long after they ate their humble pie.
  3. Intellectual Hubris – I’m the smartest guy in the room. Either you’re not, or you’re in the wrong room. Whenever I’m feeling like a smarty pants it’s usually because I’m getting too comfortable in my environment. So I get out of my comfort zone and expand my horizons. I visit with new people who work in different disciplines.  I’ll pick up a classic book written by a master like Tolstoy or listen to a podcast by someone like Dan Carlin. It doesn’t take long for Plato’s famous line to come back to me: “The only thing I know is that I know nothing.”
  4. Physical Hubris – I think I’m tough. There’s always someone tougher, fitter, or stronger. I get a twice per week reminder of this at Jiu Jitsu class. Other humbling athletic events are road races or attending a pro sports game in person. It’s amazing the commitment the pros have to their craft.
  5. Financial Hubris- I can afford a life luxuries. No you can’t. There are no multi-millionaire readers of this blog that I aware of, which means even if you can find a way to pay for a gardener, a Tesla, and a $700k house today, you are setting yourself up for a hard fall when any of the above categories go wrong. My financial advisor Mr. Money Mustache helps correct me if I ever get a little too spendy.

There’s one more side to this story. Remember what Daedalus told Icarus. He also said “not to fly too low lest his wings touch the waves and get wet.” Flying too low, or being timid or complacent, is equally as dangerous as hubris. Like most aspects of life and leadership, the right path is somewhere in the middle.

Be confident, aggressive, and act with speed and urgency lest you get swallowed by the waves. But stay grounded, hungry, and humble, lest you fly too close to the sun, melt your wings, and drown in the sea of a billion fools who came before you.

Chicago bachelor party weekend.
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