“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” - Mr Twain
I come from a family of sailors and a family deeply entrenched in the US Navy so the idea that I do not know how to sail has always been unsettling for me – but so is the idea of not having a job in a few months when my MBA runway comes to an end. That whole reality thing seems a bit daunting.
And then I was faced with the decision to spend a weekend thrashing through consulting cases and calculating profitability potentials….forward and backwards….or go sailing in Italy…..It really is surprising how quickly I made up my mind!
Yeah, I postponed selling my soul to case cracking for just one more weekend – with admittedly very little hesitation. I quickly booked a ticket to Milan and set out the travel details with a few other classmates. I did sign up with a moment of trepidation - I had never officially sailed where I had any ounce of responsibility. Surely this wouldn’t be an issue.
The event was sponsored by Rolex and was organized (in the finest of fashions) by SDA Bocconi from Milan. As I thumbed through the instruction pack I breathed a sigh of relief when I saw the packing suggestion list. Within 5 minutes I had ignored it completely and packed as if I was headed out to sea for the next three years. The next sigh came when I saw the regatta (did I mention there was a racing element involved??) schedule – two divisions – A and B. Great. I sent a report back to the States to let my parents know about my upcoming induction into the family – but not to worry I was just going to be cruising in the B Division. False. Apparently we had agreed for the serious racing. I was going to have to take this seriously so naturally I went back to the sports store and bought a pair of sailing gloves. I felt like the kid that shows up on the first day of school with bright white runners (I tried to not let anyone see me rip the price tags off on Day 1).
The venue was amazing. Santa Margherita, Italy. After a bit of a delayed arrival from Milan, we took a quick 2km taxi ride from the train station to the boats – 2km for 20 euros. Seriously? Seemed a bit arbitrary on the rate, but our driver gave us the most enthusiastic driving tour of the village pointing our each bar with unmatched fervor. We said a quick hello to our floating home for the next four days then headed up to a little villa that happened to sit atop a hill with finely manicured landscaping and sweeping views of the harbor. Nearly 500 MBAs (with a sprinkling of Alumni and Masters) chatted away before we moved the party down the hill and eventually to a boat.
I am not really crazy about the idea of alcohol and boats and me, so I had decided to take myself to bed which required disembarking the party boat that swayed slowly as people danced with amazing energy for the hours we were keeping. Lucky for me I had a few gentlemen helping me back to fixed land. Unlucky for the few gentlemen. Right before the last step I took someone said ‘No that’s not a step’. Indeed a step it was not. And fresh harbor water it was not, but swimming I was – as was the poor guy that tried to avert disaster for the both of us.
Things were off to a great start or you could say they were going quite swimmingly. Then this whole racing thing started and guns were going off and countdowns started and I felt like I should have brought along a copy of ‘Sailing for Dummies.’ Thank goodness we had 1. A great Italian Skipper – Leonardo 2. A great and extremely patient Italian Skipper - Leonardo.
You could argue that we had the fastest boat and that it was completely disadvantaged by its crew. As we passed boats going upwind they coveted our fancy racing sails, as they passed us flying their Spinnakers on the way back it was a role reversal. No one coveted any part of our boat when we finally unveiled our blue and white Spinnaker sail…..horizontally. At this point I don’t know much about sailing, but I did know that we had done something wrong. We couldn’t take it down fast enough – the committee boat did manage to sneak in a quick cell phone photo and a good laugh.
And this was just Day 1. After three races we anchored up near Portofino Harbor and went for a swim. Like a true professional, I was fascinated with the clarity of the water so it clearly made sense to open my eyes underwater to take a look around. That would be the last time I saw clearly as I donated my last pair of contact lenses to the Sea. Last pair as in I have one left and am stuck with just one in my right eye as I wait for a new delivery from the US. It’s been a real bang-up 24 hours for me at this point, but nothing in me wanted to be anywhere else than on that boat.
