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The Course is Ours to Plot. Right Now.

I can’t remember exactly when this whole thing started. Maybe it’s in my Hawaiian DNA. Maybe it happened when I was a kid at Disneyland coveting the just-out-of-reach treasure of The Pirates of the Caribbean. It could have been after reading Robinson Crusoe in college. Maybe it was all of that, but for whatever reason, the fantasy of sailing, of becoming a skilled sailor has always been one of my deepest desires.

The dream of total independence, boundless freedom and self-reliance draws me to boats, and to sailboats in particular. The open ocean, being propelled by the forces of nature, becoming part of them–that is it for me.

My sister’s family has a boat. I could spend an entire day just hanging around the docks while they work on it. I feel a certain peace and clarity being near the water, in the water, on the water, under water…pick any preposition really. I decided early on that I would sail. I would get a boat, I would learn all about it, plot my own course, and live the life I have imagined.

About twelve years ago, without telling anyone, I quietly put my name on a waiting list for a boat slip. The location of the harbor was ideal for me because of its proximity to AT&T Park in San Francisco. (My thing for baseball runs deep too. I actually understand the game of baseball pretty thoroughly–sailing, not so much. Yet.) I believed that this particular harbor was my destiny.

It made no difference that I knew nothing about boats. That I did not own a boat, and did not have the means to purchase even the smallest row boat, let alone a seaworthy sail boat. I set those realities that might dissuade lesser sailors (not that there are any) aside. After all, the waiting list for boat slips was long, people were waiting anywhere from eight to ten years for their chance to rent slips at the South Beach Marina, I had time. Like any starry-eyed rebel with no real plan whatsoever, I was confident that within eight years I would of be wildly successful and ready for the opportunity when it came. I took my place in the queue and forgot about it.

Meanwhile, I finished school, taught some writing classes at the community college, moved a couple of times. In 2004 I got a job in the PR department at O’Reilly Media, then in 2006 I moved on to become the Style & Pedagogy Editor at the O’Reilly School of Technology. (I have just distilled ten years of my life to a paragraph here, but you get the idea. Life went on.)

Fast forward to 2011. A phone call came in, the caller, unknown. I never answer those (sorry, Mom.). This time though, the call came from Linda at the South Beach Marina letting me know my boat slip had become available. I wasn’t at all prepared for that. She asked what kind of boat I had (a slip can’t be rented to a person without a boat to dock in it at that harbor. Who knew?) So, playing it off like I was a totally cool and boaty kind of person, I said, ‘yes, I have a boat, it’s a…29 foot sailboat. Sure, I can have it in the slip in 60 days. As an experienced sailor, I don’t see why that would be a problem.’ A wise man once told me to, “fake it til you make it.” I am not always capable of doing that-in this case, I found the strength to be completely full of it.

Within 60 days, with the encouragement of my friends and some mildly irresponsible financial maneuvering, I purchased a 1972, 27’ Catalina sailboat. (Fortunately, the nice man I bought it from was willing to bring it across the bay for me without judgement, and park it in my new slip, since I had no clue how to move it myself.)

And there it remained. For two years. I sat on that boat, shared beer with friends on the boat, decorated the boat for the World Series, read books about how to sail while lounging on the boat. I just never sailed the boat.

AT&T from boat

I was overwhelmed by the volumes of information available about boats, equipment, techniques, wind, currents, terminology, knots, sails, rules, safety, maintenance. Books I can afford, but sailing lessons are not cheap.

Despite the challenges, (and after much haranguing by said beer drinking friends) I made my move, and scheduled an official sailing lesson. There was no turning back (at least not without a fifty dollar cancellation fee.) The sailing school directed students to some literature. We were told to read up on the basics before the lesson–I did not. I had already extracted as much as I was going to from books.

The morning of the first lesson, we spent half an hour in a room with an extremely knowledgeable instructor, where we learned to tie a couple of basic knots and identify the various “points of sail.” At last, we boarded the boat. After a safety check, pumping out of the bilge, and seeing a demonstration of the motor, we took to the San Francisco Bay. That’s when the real learning, the learning that will stick with me, began.

Over the course of a weekend, four novice sailors learned the right of way (that’s pretty important to know when you’re on a collision course), how to tack (prepare to come about!) and jibe (not to be confused with the “jib”), and to perform these tasks as either the helmsman or crew. Phrases like, “cleat the line,” “ease the main,” “fall off,” and “ease the jib,” now make sense to me. My earlier sailing research, where I read stuff like this:

When you fall off from close-hauled to reaching, you ease the sails to maintain a consistent angle to the wind. As you fall off to a run, however, you reach a point when you can’t ease the sail out any farther because the boom is against the shrouds that hold up the mast. If you want to turn farther, you will have to jibe and bring the boom over to the other side of the boat.

…was transformed from vaguely understandable and more than a little intimidating, into knowledge and confidence that I can and will become a proficient sailor.

Books can provide a foundation, but I’m learning to sail through practice and guidance from an experienced instructor (I think you may know where I’m headed with this.)

As an editor here at O’Reilly School of Technology, I spend lots of time trying to spread the word about our approach to learning, the “learn-by-making” pedagogy. I’ve spent hours at my laptop detailing the reason and philosophy behind the OST approach to learning, but in practicing what I preach, my confidence in our pedagogy has been reaffirmed. We learn everything by doing.

Because of my recent experience on the water, working with the rigging and using the language, the sailing instructional guide books are no longer overwhelming. That foreign language is becoming more familiar and I’ve begun to get momentum. I’m not quite ready to hit the San Francisco Bay alone, but I am on my way.

Beck on the bay

*It is with great personal restraint, that I resist oh-so-many tempting nautical endings here (anchors aweigh! tally ho! take the wheel, yarr!). Instead, I’ll share a few final words of serious encouragement. Imagine your future, whatever it is, wherever you envision yourself, then take action to make that vision your present. Learn something, do something, get out of your comfort zone, let other people help, be bold and be afraid. That’s when the good stuff happens!

If your next move involves learning more for a new or improved IT career, we can help.  Find out more about our learn-by-making teaching method.  All you have to do is ask the really good people who make up our Student Services team by calling, chatting, or contacting them by email.