Home
 
Choose Your City
Change City

Second Shift: Insurance broker by day, sailing instructor by night

Christopher Fletcher turned his passion for sailing into a second job.

"I figured if you learn something really unique and you lean how to do it well, you should pass that knowledge on to the next generation," says Christopher Fletcher. Credit: Provided "I figured if you learn something really unique and you lean how to do it well, you should pass that knowledge on to the next generation," says Christopher Fletcher.
Credit: Provided

Our Second Shift series features people who work more than one job or have creative ways of making money. This week, meet a guy who ends the work day by sailing into the sunset - and get's paid for it. Want to be featured? Email emily.laurence@metro.us.

The Stats:
Name: Christopher Fletcher
Age: 57
Residency: Westchester, NY
Lives: Alone
Number of jobs: 2

You were able to turn your passion for sailing into a whole second job.

RelatedArticles

Oh absolutely! I was sailing with the Manhattan Sailing Club back in the '90s and had done a bit of instructing for them as a sailing coach. When I came back to New York five years ago and realized that my office was literally across the street from them, I contacted my friends there and told them I would love to teach again.

What are your sailing classes like?

I am a senior instructor for the Learn To Race program which essentially turns raw sailors into lean, mean sailing machines. I teach twice a week and teach them all about the intricacies of the sport and give them the skill set to be able to work together as a team. When people start to get their physical confidence and then their mental confidence, when it comes together it's just so rewarding as a coach.

You're an insurance broker during the day. Is it hard to leave on time to get to your second job?

No. The people at my 9 to 5 job are very supportive, which is great. When it's a Monday or Thursday and people see me in my red T-shirt, they know where I'm off to.

What do you do in the winter when it's too cold to sail?

The sailing season is essentially May 1st to October 15th. In the winter, I just try to stay in shape and look forward to the start of the next season. Sometimes I teach educational classes that aren't necessarily on the water, but are about navigation. Also, one week a year I sail a 51 foot boat down to the British Virgin Islands for the Manhattan Yacht Club and I am responsible for the nine people on board. This year, my 25-year-old son is coming with me, which is going to be great.

Sailing sounds like a pretty idyllic way to end the work day.

Oh it's a blast! I grew up in Larchmont where some of the best sailors have worked out of. I figured if you learn something really unique and you lean how to do it well, you should pass that knowledge on to the next generation. There's no reason why it should be a lost art form.

Follow Emily on Twitter: @EmLaurence

 
 
You Might Also Like