My New 3rd-Favorite Podcast, and Island Life

why didnt they laughI have a new third-favorite podcast (let's face it, it will be tough to unseat "The Moment" with Brian Koppelman and "WTF" with Marc Maron). My new third-favorite podcast is "Why Didn't They Laugh?" The show is hosted by Owen Benjamin, who may be the smartest comedian out there today. The podcast's premise is to explore humor and comedy and what makes or breaks a joke. In the process, Benjamin (a concert pianist and damn intelligent guy) deeply but coherently explores psychology, neuroscience, astrophysics, music theory, relationships, race relations, evolution and an amazing array of other topics. It's OUTSTANDING, and I recommend it highly. (Not always clean, but always funny and thought-provoking.)

A recent episode featuring guests marketing expert Brian Sussman (Twitter: @briansussman) and comedian Natasha Pearl Hansen (no relation) easily met the high standard Benjamin has set. During the episode, Benjamin and Hansen realized they both sometimes kick around the idea of leaving it all behind and moving to an island.

BYC CoverAs a small token of my appreciation for the podcast, I thought I'd pass along to them (if they ever see this) some hard- and fun-won experience on the topic of leaving it all behind and moving to an island. This is an excerpt from my first book, Build Your Castles in the Air: Thoreau's Inspiring Advice for Success in Business (and Life) in the 21st Century, touching on Thoreau's take regarding what we might really be chasing when we leave it all behind, as well as a recounting of the shot I took at island life.

As with the rest of this book, the entry below starts with a quote from Thoreau's Walden, and then I add some thoughts. So, for what it's worth Owen, Brian and Natasha, here you go, and thanks.


Find Your Calling

To the sick the doctors wisely recommend a change of air and scenery.  …Yet we think that if rail fences are pulled down, and stone walls piled up on our farms, bounds are henceforth set to our lives and our fates decided. If you are chosen town clerk, forsooth, you cannot go to Tierra del Fuego this summer: but you may go to the land of infernal fire nevertheless. The universe is wider than our views of it.  Yet we should oftener look over the tafferel of our craft, like curious passengers, and not make the voyage like stupid sailors picking oakum.  …Our voyaging is only great-circle sailing, and the doctors prescribe for diseases of the skin merely. One hastens to southern Africa to chase the giraffe; but surely that is not the game he would be after. How long, pray, would a man hunt giraffes if he could? Snipes and woodcocks also may afford rare sport; but I trust it would be nobler game to shoot one's self.


In 1987, three years out of college and adrift in life, I bought that previously mentioned one-way ticket to St. Thomas, figuring that if I was going to drift through life, I might as well drift on down to a tropical paradise and live my directionless life under the palm trees.

Seven months and many rum cocktails and Caribbean adventures later, I had an epiphany while sitting on a topless locals' beach, sipping a beer – I wasn’t fulfilled. It was fun, certainly -- drinking margaritas every night, dancing on the bar till sunrise, scuba diving and sailing and playing grown up games in what amounted to an adult amusement park set in paradise -- but I wasn’t fulfilled.

I had answered Thoreau’s question: “How long, pray, would a man hunt giraffes if he could?” For me, the answer was seven months.

It begged another question: what was my calling? If I wasn’t fulfilled living the life of St. Jimmy of the Caribbean, then what would fulfill me?

The answer turned out to be political communications. In my gut, I knew that’s what I could do and would be happy doing.

I also knew that a resume highlighted by a 2.oh-man-I-nearly-didn’t-graduate GPA and a dozen different jobs in three years (the most recent being as a bouncer in a Caribbean saloon) wouldn’t get me there. So I quit hunting giraffes, left the islands, and eventually made my way to graduate school in San Francisco. Within three years, I was the press secretary to Congresswoman Susan Molinari in Washington, D.C., and since then I’ve served as the communications director for the Virginia Secretary of Transportation and speechwriter to Governor George Allen of Virginia.

My calling has changed since then, and I’ve tried to follow it faithfully, leaving political communications for corporate communications, marketing communications and speechwriting for CEOs and senior management in three Fortune 500 companies -- right up to this moment, as I work on my first book.

But the lesson remains with me: finding your calling, being the best at what in your heart you know you want to do, is the most powerful motivator of all – whether for yourself or your employees. Self-actualization, Maslow called it. Find that one thing in your gut that you want to do and to be the best at, follow that calling, and success, happiness and fulfillment will result.