Sailing Into the Abyss Part 2: Facing Doubt, Fear, and Humility

Sailing Into the Abyss Part 2: Facing Doubt, Fear, and Humility 

This story is a continuation from Sailing Into the Abyss: Facing Doubt, Fear, and Humility (Part 1) which you can read here

I’ve always felt quite proud (and I must confess even arrogant at times) of my ability to learn new skills quickly and naturally so I went into the sailing intensive looking forward to the challenge. I knew it would be hard but I assumed that the normal rules for how I’ve learned in the past would apply here as well. The class curriculum was laid out clearly on the Nautilus website: in seven days we would learn and be tested on all major aspects of motoring, sailing, anchoring, mooring, docking, emergency response, boat maintenance & repair, and navigation while becoming certified in three sailing levels (ASA 101, 103, and 104). What I did underestimate though was how sleep deprived I would become (after the second night with the wind incident my nervous system had hung on by its fingertips), and how poorly I would handle my feelings of incompetence and overwhelm (which I would unfortunately come to feel on a regular basis). 

On the third day, tired and slightly pessimistic, I did my best to walk through the lessons wearing my big girl panties. I listened intently to our instructor, Tim, passed the second test with a near perfect score again, and gave everything an all-out effort. Despite doing everything “right” though, I couldn’t shake those nagging thoughts of incompetence and doubt; the darned buggers had conquered the castle and were feasting in the grand hall. As their kingdom expanded, my confidence retreated into hiding. To make matters worse, Andrew seemed to be having a fine time with no struggle to understand the material. Our internationally awarded instructor explained everything skillfully with the patience of a saint, which only solidified my belief that I was severely deficient and incapable. I began to catch a whiff that my life long goal of learning how to sail may not come to fruition. 

That night the wind howled again. Regret took a chokehold and played a slow motion movie on a loop from 2am-6am of all decisions, sacrifices, and tens of thousands of dollars that had led me to this pinpoint in time. Learning something new, from scratch, and with very few points of familiarity to anchor to can be quite humbling. Compounded by that was a fear that I had made a huge mistake and that perhaps this whole sailing was just too hard, too uncomfortable, and just beyond my reach. I could see that I was being overly dramatic by making conclusions just days after beginning, but something deep inside had been stirred and there was no rationalizing my way out of it. 

On the fourth morning, despite two cups of coffee and a valiant attempt to emerge into the cockpit with a positive attitude, it became evident that all cheer and optimism had abandoned ship. Early that afternoon, with the winds blowing about 15-20 knots, Tim announced it was time for our “circumnavigation sail”. We peered into the San Jose Channel beyond our peaceful anchorage and saw the menacing teeth of white caps awaiting our arrival. A circumnavigation sail had been mentioned a few times in the previous days. The goal was for students to work as a team and make their way around Isla San Francisco, incorporating newly acquired navigation, sailing, and seamanship skills, all without the direct assistance of the instructor. But not for a second did I think that we were even close to ready for this exercise. If nothing else, the wind gods had not cooperated during our first days of instruction, emerging only at night and retreating in daytime.  

Preparing a sailboat for actual sailing takes a bit of time. Items which may fall off open shelves must be stowed, hatches closed tightly, gimbal on the stove released so it can sway with the motion of the waves, etc. Because there were white caps on the sea and winds were predicted to increase, we set up safety jack lines and donned our life jackets. After our full systems check, we turned the ignition on and motored towards the fast moving channel without any sense of where to even begin the sailing process. 

Many of the events that transpired over the next two hours are a blur. I vaguely remember raising the mainsail and then the genoa, releasing jib lines while tacking, and Tim’s voice gently guiding us (once he saw how unskilled and unprepared we were he gave us step by step instructions for our safety and his). What I do remember clearly though were large swells picking us up on their backs and then tossing us carelessly, boat rails nearly skimming water, dogs wining at full panic below (they weren’t allowed atop for their own safety), and the sails whipping violently each time we altered our angle to the wind. And most clearly, I remember feeling utterly incapable and inept. I couldn’t make any sense of what I was supposed to be doing and worst of all, why. 

By the time we screeched back into the shelter of our starting cove, I was fried. Any enthusiasm and optimism I’d been able to muster days before exhausted. I retreated into our cabin and curled into fetal position. I was done. Cooked. Toast. Brain exploded inside my skull. Clearly we had made a terrible mistake in buying this stupid boat. Andrew’s gentle caress on my head and his soothing words were unable to pacify my gloom. I felt trapped because our beautiful and safe home in Oregon had been sold and I now wanted to abandon this new one. 

Sleep that night, like the others preceding it, was fitful. As one nightmare would fade into stardust, a new one would burst on the scene. Our alarm went off at 4:30am and we departed anchor in the dark to get some practice motoring without the sun’s aid. I emerged into the cockpit a zombie, unable to fake niceties and too defeated to care. Andrew and Tim sensed my affliction and gifted me a wide girth. I was left in the company of my own negative thoughts. My mind wandered; I fantasized about selling our brand new boat the moment we returned to shore. I imagined returning to the US with my tail tucked between my legs. I’d been so arrogant to think I could join the realm of sailors and the sea; this place did not belong to me. 

By the time my thoughts began to bore even me, the sun had risen high enough to gently span its long arms along the horizon line. In the silence of that moment, I’d felt the smallest crack in my misery and self pity. Within 15 minutes an army of dolphins had marched directly towards our boat, the froth of their movement visible from 1/4 mile away. Journey had become surrounded by this super pod and a speck of magic had found its way into my heart. A half hour later we had seen our first of 20 humpback whales. The sea had come alive. 

Sometimes we are our own worst enemies. Sometimes we find suffering even in paradise. Sometimes though, despite our best efforts to resist, benevolence and love find their way to us. And sometimes, life is so beautiful we simply can’t help but succumb. The sunshine, the kindness and patience from Andrew and Tim, the dogs’ sweetness, and all of the sea creatures emerging from the deep were enough to pacify my self-attack. I was reminded of one of the most valuable lessons I’ve ever learned…even when things feel terrible, the experience and perspective WILL shift. Love has a way of finding its way back to us, no matter how hard we try to turn our backs to it. This experience was no exemption to that rule. 

Post Script: It’s been nearly three weeks since graduating from the Nautilus Sailing program. We worked hard during that week, gave it our all, and in the end were rewarded with a certification that allows us to charter a sailboat anywhere in the world. We said a fond goodbye to Tim who practically feels like family now. It was a bonding week and we couldn’t have wished for a better human to baptize us as sailors. I swear our dogs were gloomy as they saw Tim walk away with his suitcase. 

andrew and gabriella on sailboat We made passage on Journey by ourselves from La Paz to Puerto Escondido just three days after graduating.  The trip took 25 hours in total which we broke up into three days. We got to apply everything learned and managed to navigate, motor, sail, and anchor without major incident. We saw more humpbacks, a blue whale, and a pod of dolphins swam along our bow as we departed anchorage. The sense of accomplishment we felt as we attached Journey to our mooring ball in Puerto Escondido was out of this world. It’s truly incredible that when we boarded on February 3rd, we literally had zero experience with boating (other than being passengers on a few boats in our youth). That Nautilus was able to get us from that point to being independent (and safe) boaters is a miracle of epic proportions. 

Since being in our new home marina, we’ve had some lovely sails (and some not so fun ones). We’re still adjusting to living aboard full time but the community of folks here has welcomed us with open arms. When we have a question, all we have to do is ask! We’re getting to that point where certain tasks are building into muscle memory; it’s nice to not have to think about every single step quite so hard and to feel more confident out on the water. We’re SO glad to be where we are and doing what we’re doing. Neither of us would trade it for anything. Learning something new everyday is a gift and one we feel very grateful for. We are finally at the point where we can call ourselves “novice sailors” and for that we are very proud. 🙂





22 Responses to Sailing Into the Abyss Part 2: Facing Doubt, Fear, and Humility

  1. Mark James Pupillo March 5, 2018 at 11:41 am #

    I graduated from California State University Monterey Bay in 1997. In the spring of 1996, I took a sailing class off at the university. It was a incredible, spending Thursday afternoons on the Monterey Bay.

    • Gabriella March 6, 2018 at 9:15 am #

      That’s neat to hear Mark! That’s not a super easy place to sail between conditions and high boat congestion! I’m SO grateful we are in a relatively uncongested cove…it’s intense enough without having to mitigate boat traffic criss crossing every which way!

  2. Pam Westra March 5, 2018 at 12:28 pm #

    Great story Gabriella!!! Keep them coming. Your such a great writer. Loved this! Glad you are both safe and settling in. Oh to see all those whales! What fun!

    • Gabriella March 6, 2018 at 9:13 am #

      Hi Pam!! A little more fun each day lol!

  3. Margi March 5, 2018 at 1:12 pm #

    Thank you so much for sharing your story .. do you have a blog to follow or fb page with your adventures and where you’re planning to sail now !??

    Brilliant .. just when you think you can’t .. the universe rewards you with sights sounds things to make it all worth while …

    • Gabriella March 6, 2018 at 9:13 am #

      Hi Margi! Thanks for reading! Right now this blog is best place to read about our escapades sailing. 🙂

  4. Lissa Buzzelli March 5, 2018 at 4:36 pm #

    Love being part of your adventure. Be safe and follow your dreams

    • Gabriella March 6, 2018 at 9:12 am #

      Thank you Lissa!!! <3

  5. Jake March 5, 2018 at 8:44 pm #

    Was that Playa La Gringa I saw in the video?? 2:25

    • Gabriella March 6, 2018 at 9:12 am #

      Hi Jake! Great to hear from you! Nope, we are just bit south…traveled from La Paz to Loreto. Looks like Playa la Gringa is in LA Bay area? Have never been up that way! When were you there?

  6. Greg Brooks-English March 5, 2018 at 8:48 pm #

    Touching post and video. Inspirational, all. Love the raw honesty and overcoming of inner obstacles.

    • Gabriella March 6, 2018 at 9:10 am #

      Thank you for reading Greg. So appreciate your support and encouragement <3

  7. Macy Miller March 5, 2018 at 9:52 pm #

    Yeah! Way to go!

    • Gabriella March 6, 2018 at 9:09 am #

      Macy!! <3

  8. nickyabrami March 7, 2018 at 6:00 am #

    This is the first-ever Indian circumnavigation of the globe by an all-women crew.order a custom essay

  9. Grant and Sierra March 7, 2018 at 6:12 pm #

    Your story is super inspiring, and it’s great how you are able to articulate both the ups and the downs of the sailing lifestyle. It really gives a true sense of your experience.
    We were fortunate enough to attend your tiny house workshop in Ashland and it has certainly affected the course our lives forever. Our trailer has just officially been ordered from TinyHouseBasics and we couldn’t be more excited!!!

    Thank you for all your help and inspiration 🙂

    We wish you all the best on your new journey!

    • Gabriella March 25, 2018 at 6:17 pm #

      Yay Grant and Sierra!!! Hugs!

  10. J. McCart March 22, 2018 at 8:39 pm #

    Once again…awesome story there Gabriella. Loved the videos too. Well done for the both of you. Give my regards to Andrew.

    • Gabriella March 25, 2018 at 6:15 pm #

      Thank you J. McCart!! 🙂

  11. Knox March 27, 2018 at 12:46 pm #

    Bravo! The enthusiasm and courage to leave one paradigm and embrace another completely outside of your comfort zone. You two are inspiring.

    • Gabriella March 31, 2018 at 11:21 am #

      Thanks Knox! <3

  12. Kate April 20, 2018 at 2:29 am #

    Such a great read and a peek into the reality of learning to sail! Congratulations on your first successful passage! It is so nice to read of others doing what we are working towards, We are trying to learn as much as we can before buying our own vessel hopefully at the end of the year.
    Keep your stories coming 🙂

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