From Zero Sailing Experience to Champion Sailor in 40 Days

40 days! My entire sailing career was only 40 days old and I had championship hardware to show for it! MIT Sloan has so many amazing opportunities to take advantage of and they come in all shapes and sizes. This is the story of how I went from zero sailing experience to winning an international sailing regatta in only 40 days.

MIT wins MBA Sailing Regatta in Italy

MIT wins MBA Sailing Regatta in Italy

Every year, MIT competes in a MBA Sailing Regatta in Italy. It was one of the cool things I had heard about but I never envisioned that I would actually do it, let alone win it. Two days before the Regatta was set to start, someone  dropped out of the trip and a spot opened for me. I booked my plane ticket immediately and packed my bag to leave for Italy the next day.

I had only started sailing on August 23rd by taking a class offered at MIT’s Sailing Pavilion. Most of my sailing experience before the MBA Regatta was mainly on a tiny MIT Tech Dingy with one sail that only sits 2-3 people (I wrote about this in my last blog post here-linked). My lone large sailing boat experience before the Regatta was a sail on MIT’s larger sail boats in Boston Harbor one week before the Regatta.

My skipper, Mike Easton, chose to put me on the Jib in Italy and I was extremely nervous since I had almost no sailing experience but I wanted to prove that his decision was not a mistake. The first two days were very tough. Lots of mistakes, both mental and physical. To a novice like myself, there is a lot going on all at once and you’re just hoping and praying that you understand what, and just as important, when to do your job.

Through continual feedback, unwavering support, and great communication, our team gradually improved throughout the Regatta. My personal problem area was the Spinnaker, which is a large sail that is put up when you go downwind in place of the jib sail. I so dreaded that turn to go downwind. That means it is Spinnaker time and for the life of me, I could not figure out how to properly trim the Spinnaker.

We just kept working at it though. I continually talked with Mike asking for advice or general questions about when I should do this or that. Mike was always very calm and provided great constructive feedback. Even though he was doing everything right with me, I still felt terrible that I couldn’t achieve good Spinnaker execution.

That is why our final race was the greatest feeling in the world to me. I had finally “mastered” the Spinnaker. I didn’t master it (since that would take years of sailing experience) but I understood exactly what needed to happen and when and I executed it well. Also, our team had reached the level we had been working towards the whole Regatta. We had finally executed all of our roles fairly flawlessly (at least for amateur sailors) and we were rewarded with a 1st place win in the last race and 1st place overall. It was one of the most rewarding experiences of my life! And I get the feeling that this is just the beginning of all of the amazing things that I will be a part of here at MIT Sloan.


MIT celebrates with the Trophy and champagne!

Ryan Stirling

Ryan was born and raised in Philadelphia, PA. He earned his Bachlors and Masters degree in Mechanical Engineering from Drexel University. He worked in the Aerospace and Defense Industry for the past 8 years doing both Mechanical and Systems Engineering on many different programs and then became a Lead Hardware Engineer and finally a Program Manager. His focus at MIT Sloan is Entrepreneurship and Tech. Ryan documents his Sloan experience week-by-week at his Instagram feed: ryanstirling

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