vignettes

Why we love the underdog

"It's only after we've lost everything, that we're free to do anything." —Tyler Durden, Fight Club

I love the underdog. And I know I'm not alone.

Some of the most famous and beloved stories are based on the triumphs and tragedies of the outranked, the disenfranchised, the social misfits: David and Goliath, Oliver Twist, Rudolph. These stories are translated and shared around the world, and passed from generation to generation, because they hold in them a universal desire—we all want to believe that good will ultimately win, no matter the odds.

And while the made-up stories entertain and inspire us, it is the true story that actually gives us hope, for it provides evidence of something that feels very much like a miracle, telling us that we, too, can author our own possibilities: James J. Braddock (The Cinderella Man). Robert Kearns (Flash of Genius). Ernest Shackleton (The Endurance). Susan Boyle (Britain's Got Talent). Barack Obama (President of the United States).

We love the underdog because they take the risks that we won't. Inspired from within, they demonstrate extreme levels of courage, braving the unexpected and making themselves vulnerable to other people's judgment and ridicule. They fight the good fight, and they will continue fighting long after we've all gone home. They do this because they believe that what they have to gain is far greater than what they have to lose.

Security can be a double-edged sword. The more we have, it seems, the more we're afraid to lose. Whereas the underdog is motivated by love (of an idea), the rest of us are motivated by fear (of failure).

What motivates you?

Moving on

"Winners never quit, and quitters never win." —Vince Lombardi

While this mantra may unite and inspire a team to seek SuperBowl legacy and fame, I often wonder how well it works for individuals, especially when the time horizon is sure to outlast a single football season.

As we cultivate the story of our lives, we become entangled with others. We commit to a life of growing old together (in exchange for fidelity). We commit to creating a financial return (in exchange for investment). We commit to our employer (in exchange for remuneration and experience). But even the best intentions are not always enough to sustain a commitment over time. Circumstances change, as do the people involved.

From what I've experienced, there are three tell-tale signs to help us recognize when it's time to stop trying to make things work, and time to start looking for the exit: there is the unfair exchange rate (we are giving more than we are getting), the empty well (we've exhausted our available resources of time, energy, and money), and the philosopher's dilemma (there is nothing new to learn or do).

As someone who has held on too long (to a failed business venture), and let go too soon (of a childhood love), I can't help but wonder:

How do you know when it's time to go?

What it means to be Rich

"In poverty there is great wealth, and in wealth there is great poverty." —Epicurus

We fear that which we don't know or understand.

Meet Rich, my fear. Ruddy cheeks. 65, a shock of white hair. Baggy coat. Cranky. Always carries a shopping bag. Sometimes he talks to people who aren't there.

You will find him every morning in front of Peet's on Chestnut, starting at about 7:25. And he will remain there, or across the street, or one block down, until at least 11:30. He goes there to hunt. One espresso at a time, from the people walking by.

During my Peet's phase, I would see him. And like other "upstanding" citizens, I would avoid him. As I approached the cafe, I would speed up or slow down so that he would tag the person in front of me or to my side. If I didn't have human camouflage to hide behind, I would do the next best thing—turn the volume up on my iPod and pretend that I couldn't see or hear him.

It's appalling, I know. But it's what we humans do when we feel helpless and afraid.

One day I realized that my efforts to avoid this man that I feared were creating an unexpected compromise. My world was shrinking. My morning routine had become the victim of a stranger's comings and goings. I had to do something different.

So I pulled a Judo move.

The next time I saw him, I approached him. I offered to buy him a cup of coffee, and it stopped him in his tracks. Suddenly, the hunter became the hunted, and we were equals—except he declined my invitation. He had already reached his limit for the day.

This was the day that Rich became a person to me.

How wealthy are you?