09/06/2013 12:52 pm ET Updated Nov 06, 2013

5 Life Lessons of a Pathological Optimist

path·o·log·i·cal: being such to a degree that is extreme, excessive, or markedly abnormal.

I am preoccupied. Since quitting my happy life, I've been singularly obsessed with writing a memoir for my daughter. As the narrator, I've been grappling with the characteristics that define me. One consistent impetus has emerged: optimism.

You could say my optimism is pathological. I blame it on a short memory and an antipathy for "impossible." Being optimistic by default has led to most of my setbacks, but those setbacks have also turned into my greatest achievements. Below are the five major risks taken that have defined my life story:

  1. At 22, when my girlfriend Laurie was given two years to live by her neurosurgeon, her family was understandably devastated. Despite the evidence, I refused to believe it. Believing instead that what she needed was something to live for, I asked her to marry me. My reward was 10 unforgettable years (eight married) with my soulmate.
  2. At 29, I resigned my six-figure job to start a social network for investors. No start up experience. No guaranteed funding. My wife had an unpredictable condition. And then two weeks after quitting, Lehman Brothers fell, ushering in the great recession and taking the investors for my network with it.
  3. Failed start up behind me, I got in on the ground floor of the uncharted and unproven world of social media marketing. Social media has since become an integral part of every big brand's marketing mix. I quit my job for my start up, but it led me to a new passion that has defined my career.
  4. When doctors told Laurie her weakened body couldn't bear children, I refused to believe it. Even after 12 years of uninterrupted birth control, Laurie ended up getting pregnant anyway. We were all shocked and concerned for her life and the baby. We refused the medical advice. Laurie's pregnancy ended up giving her the healthiest seven months of her life. We then welcomed a 4-pound, 7-ounce miracle baby into the world.
  5. At 35, I quit a rewarding job and moved out of my dream home. I'm on a mission to South America to write a memoir for my daughter about the love story that gave her life. Without my risky gambles and ensuing lessons, there wouldn't be a love story worth writing about.

Humans are notoriously bad at predicting the future. So if the outcome is unknown, why assume it will be negative? Assuming a positive outcome keeps me fully engaged, having fun, and thus more likely to succeed. I'm not alone -- Psychology Today recently published, "What Happy People Do Differently." The conclusion is that one of life's sharpest paradoxes is that the key to satisfaction is doing things that feel risky, uncomfortable, and occasionally bad.

For me, the key is intention. It's not about the size of the risk, it's about why you take it. Take a big risk to make a lot of money and you may or may not succeed. Take an equally big risk to enrich others and the universe is sure to reward you in some unexpected way.

So I asked myself, if I write about my blind optimism in my memoir, will it lead my daughter to take unreasonably big risks? Will my pathology work for her too? I'm optimistic.

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