08/30/2012 08:02 pm ET Updated Oct 30, 2012

Cuba: Shoot for the Stars or Settle?

I joined a HuffPost live chat yesterday. The discussion centered around our disappointment when we don't quite fully succeed in a quest.

It helped me immensely to hear from three people who threw their best selves into their respective projects over the last few years... and yet came up short of the original mark.

Donna had the beauty salon of her wildest dreams in mind. An impressive 7,000 square-foot operation. But life happened on the way. Her son took his life. A myriad of starts and starts later, she did open her shop, but she had to back off her dream concept and come to peace with a much more modest business.

Seth and his team were busting with ideas for a new social network. Smart, young Internet minds with forward-thinking steam on their side. Two years of pushing, investing, researching, designing... and yet in the end it was not to be. Back to the drawing board.

Paul and his gang pressed hard on a start-up in San Francisco. Typical 'round the clock energy went toward funding and all the back-end work that a start-up requires. They believed they had something special but one thing came after another and they could no longer move forward.

So we all got talking. We're all allowed to feel disappointment. We're human. It's such a shock to the system, to not get there, when by the inherent nature of pushing toward something ambitious, you simply must believe with every corner of your being that you will get there.

Every stroke of training I took over these past three years, every bowl of soup and concoction of electrolytes I drank, I had no shadow of doubt that I was going to swim the entire 103 miles between Cuba and Florida.

And for the 51 hrs, five minutes, I was in the water, from the plunge into the sea off Havana, I still believed, stroke by stroke, that I was going to get there.

Donna, Seth and Paul similarly were 100 percent confident that they were marching boldly toward their vision of succeeding in their particular endeavors.

So where are we all now? I was saying to Seth, many years my junior, that I can just picture him as an old man, rocking on the proverbial front porch, telling another old guy about this time in his life that he and his pals worked their butts off for a couple of years, intending to launch a state-of-the-art new social network. And, as life goes, the other old guy wouldn't ask him if it wound up a rousing success. No, he'd ask him what they all did to get it together. And Seth would regale this old guy with their all-nighters, their wacky schemes, their laughs, their wild machinations in coming up with stuff nobody had ever thought of before.

Why is it that when we end a long-term relationship, we can't seem to find the positives, to remember the joy of all those years? We dwell on the negatives and throw out typical salvage lines: "Well, we produced two beautiful children together."

Every single one of us knows heartache. It's the human condition. So do we settle for small dreams to make sure we can achieve them? Do we never test our will, our potential, for fear of failing?

I may not have reached Florida but I wouldn't trade these past three years for anything.
And I applaud Donna and Seth and Paul for reaching for their respective stars. They are each one the better for their ambitions.

As Browning put it: "A man's reach should exceed his grasp... or what's a Heaven for?" Way out there under those Florida Straits skies, our team was indeed reaching for the stars... and I do believe we had the good fortune to see a bit of Heaven on our journey.