Almost exactly two years ago to date, I stepped onto a sail boat for the first time in my life. A group of us girls decided it would be fun to cruise for our friend Amory’s birthday so we set out for the Port of Long Beach. I honestly didn’t really pay attention to much other than that the boat we rented was owned by an African Prince who paid the captain to charter the boat while he wasn’t using it for his exotic California vacations. And our captain, ironically, was a young guy about our age, native to California, pretty attractive too, in that weather beaten captain kinda way. With a free bottle of champagne and playing passenger, I was completely aloof in paying attention to what he was actually doing to captain the boat but he entertained our silly flirtatious questions about his sailing experiences and shared about his most recent return from a 28 day trip he had sailed from Long Beach to Honolulu. That was it for me. That was the moment. Time kinda stood still and voices faded into the background like they do in the movies. That was the day I decided I wanted to sail. This scruffy young captain even talked about how the crew had scouted him out- like your elementary kick ball team, but this was kinda more for a life and death adventure. This crew was critical to surviving the journey and everyone maintained an essential role equipped with crucial skills. There was even a member recruited just to entertain the crew when they all started to lose their wits over the course of the long journey out at sea- someone who could play ukulele and keep them in positive spirits. I thought if nothing else- I could hopefully fill that role! 
Hopes and dreams of cruising the high seas and visions of arriving at the white powdery sand coastline greeted with leis were dancing through my mind. Little did I know what I was actually getting into — there was a lot standing between me and that lei. A few of my friends had also mentioned interest in sailing so after the birthday cruise with captain dreamy, we somehow organized ourselves to enroll in a few classes down at Newport Harbor. I have to admit- sailing did not come naturally to me. I am horribly dyslexic and the concept of starboard and port or bow and stern just moreover confused my need to understand which hand makes the “L” as my right hand. But no matter, each week I was getting to log hours on the ocean, my favorite place to be. On heavy wind days, riding the gusts of wind at 15 knots kept us heeled over felt like we were surfing swells on a giant surfboard. That part was fun. I met some interesting people and saw dolphins, seals and maybe a whale or two. We progressed through the classes and seasons of wind change from the smaller lido boats up to the 32 foot shields. With each class it became obvious that I was a weaker link. My friends were picking up this new sailing language and concept much more easily than me. And as we turned in our final exams to complete our keelboat certification, I barely passed. The reality of that test score turned into a dark cloud of doubt taunting me that the next course was a gamble for me. In fact, I hesitated to enroll back in the school because that taunting cloud seemed to point and laugh at the idea of me passing this next class, much less making it to my big dream of sailing the high seas to an exotic island.
Right about now you might be wondering why I am wasting my breath on this story. I am writing about this because I am passionately and deeply in love with the ocean. I also love participating with creation and enjoy being active in this big outdoor playground called the sea. But it is crazy to me how easily I would avoid something that I LOVE because I might, MIGHT, not succeed. How often in life are the things we want the most the very things we shy away from because we aren’t 100% sure of the outcome. We avoid the things we desire and dream about because we can’t visualize the path to get there. Fear, doubt, worry or anxiety cloud our vision so sometimes, sadly, we don’t even try. An incredibly gifted artist struggles to put their art on display for fear of rejection or criticism even though it is their greatest gift to the world. Someone who deeply desires connectedness or community fears going to a party or social gathering alone even though all they want is a new friend. It’s a strange dichotomy.
So how the rest of this story goes is this; I enrolled. Convincing myself this is my only shot, singing Eminem in the back of my head, I began the Basic Cruising course with three other friends on a 42 foot sailboat called the Betty. Betty is designed as a performance cruiser with a ball bearing mainsheet and a Genoa staysail. Below decks, Betty sleeps eight people in four cabins including a spacious salon and galley for leisure. Basically, she’s a big boat.
Being the only girl in these classes is kind of fun but also extremely intimidating. (I have to note I have loved every single instructor I have ever learned under in these classes, a few of them women). Overall, all the guys in all my classes have been nothing but HUGE cheerleaders and encouraging – but feeling a little inferior adds to my self defeat. A few of the classes I was really struggling and beating myself up for not understanding some of the practical skills and the next thing you know- the final exam to this course was right around the corner. I know I am dragging this story out- so I’ll shoot you straight. I studied pretty damn hard and took that exam with plenty of sleep and maybe even some caffeine… but on my freaking birthday- I didn’t pass the written test.
I didn’t pass. I failed.
A lot of people knew about this exam and on my birthday, every single person I saw, I had to tell them: ‘I didn’t pass.’ This left me with all kinds of disappointment but mainly lots of feelings of unworthiness. That feeling of not just, ‘I failed this exam,’ but also battling the inner dialogue of, ‘I am a failure.’ YUCK.
I was really curious at my reaction to the feeling of failure. I wanted to hide, withdraw, not show up. I had trouble moving forward in other areas of my life that week. But in that failure, I was reminded by some close friends: I am still Kristin, I still love just as hard, I still laugh just as loud, I still work tirelessly to help others, I still belong to the same family, my name is known, my passions are known more and the story doesn’t even end here. I know these are the most obvious statements, but come on- you’ve failed too and felt the same heart-sinking feelings. You’ve been confronted with the same self-doubt- maybe you got laid off, maybe you got dumped, maybe someone you deeply care for offered you some criticism and it cut to the heart. But here is the thing, we are gonna fail. In fact, only the people who dare to fail are going to be the ones who succeed greatly. Only the ones who dare to get on that boat are gonna be the ones to get to the exotic island. The people who think that story is for someone else but not possible for them will be stuck watching from the shore and looking at pictures of those who dared greatly in the newspaper arriving on the shores of paradise with leis.
And I might not make it to paradise on a 28 day sailing adventure but I’ll tell you this: I failed that test, hung my head and thought – EW failure is not fun – but it ain’t over. So I hit the books hard, asked for help from friends that did pass, I dared to show my face again, I went in there and took that test again and I aced that mother effer. Yep! 96%
So what’s next? In less than two weeks this little lady is setting sail on the Betty for a 5 day trip to the Channel Islands and the next course to check off the list. I still have my sights set on paradise but first let’s conquer the California coast. And for you- what do you desire the most? What keeps you up at night? What story or adventure or accomplishment can you not escape the thought of? I dare you to try- because who knows, you might actually do it.
The best sailing crew a girl could ask for. Thank you for these photos Cameron!
Be Free 