Success Redefined

 “I can do this, I can do this, don’t forget the preventer,” whispers the voice in my head as I stare at my reflection in the mirror, brushing my teeth. Wide eyes, full of fear, look back at me. Closing them, I wash my face, trying to wipe it away. “I can do this, I can do this, I can do this,” I say in a shaky voice. It becomes a mantra. My voice becomes stronger with each repetition.  

Heading to the salon, I go over my checklist. Confirming my tablet is charged, I see the time and realize I am behind schedule. Suddenly, there is a pressure in my chest. I stop and sit. I force myself to take three, slow, deep breaths.

“It doesn’t matter if I leave 15 minutes or even 30 minutes late. Take your time Cindy. Do each task methodically,” I tell myself aloud.

I place my tablet and its bracket on the pile of items to take to the cockpit. I harness and leash Hecate, my feline mate. Sliding open the companionway, I climb to the top stair and look out over the mooring field. Lights from the nearby cargo dock cast a sparkling reflection across the water. The beauty compels me to pause and appreciate living on the water. 

The rocks in the pit of my stomach slow their tumbling as I transfer the equipment to the cockpit, fire up the electronics and start the engine. I move my dinghy to the aft cleat on the port side and secure it. Untying the preventer, I congratulate myself for remembering. 

Following my departure routine creates confidence and the rocks in my stomach transform into butterflies doing battle. I can do this.  

It’s time. I drop the mooring lines at 6:25 am. The first ray of morning light breaks through the dark as I leave the mooring field and head into East Gregory channel. I remind myself that courage is doing something despite fears and insecurities. I laugh. My grip on the wheel relaxes slightly, and the butterflies calm down. I am doing this, my first solo sail.

The last time I headed into this channel flashes in my head. My friend and I were heading to Guadeloupe for the 2025 hurricane season. It was my first real test as a captain, planning and executing a multiday sail across open ocean. I was responsible for a vessel and lives. It’s a wonder I didn’t have a heart attack from fear leaving that morning. But we sailed to Guadeloupe and made it back with both the boat and our friendship intact. Remembering that experience reduces my fear.  I relax my stance, excited energy filling me as I motor through the channel. 

Once out of the channel, I turn into the wind, tap the “AUTO” button and adjust the autopilot slightly to put Endurance, my 42’ Morgan Classic, directly into the wind. Using the electric winch, I watch the main sail rise until it’s near the first reef. I climb over the coaming to reach the mast then loop the first reefing ring over the hook on the boom. Back at the winch, I start to raise the main again. 

“Shit!” The ring fell off the hook.

“Do I need to lower the main?” 

I return to the mast and put the ring back on the hook, pulling the reef line taunt by hand to keep the ring engaged while making my way back to the winch. It worked! With the main raised, I take control of the helm again, releasing a huge sigh of relief. After setting Endurance on the plotted course, I re-engage the autopilot to pull out the jib. 

Checking that the furling line and port jib sheet are free, I pull on the starboard jib sheet. There is too much tension. The jib doesn’t move. 

“Please don’t do this today,” I beg the cranky furler.

On the Guadeloupe trip I learned a temporary fix for the furler. I crawl on my hands and knees to the mast then uncleat the jib halyard, wrap my hands around the winch, slacken the line slightly and re-secure it. Back in the cockpit, I let out the breath I have been holding. I pull on the sheet, and the jib opens, immediately filling. I am filled with relief as the sound of snapping sheets fills the air. Acting fast, I pull on the jib sheet and the noise dies, replaced with the quiet of well trimmed sails. 

I turn off the engine. It’s 6:53 am.

“Woo Hoo! I am sailing,” I shout. 

I settle myself at the helm, ready for the long sail. Before long, I notice Endurance is slow, fighting to make headway despite full sails. “Should I shake out the reef?” Remembering that an island can block the wind, I decide to wait until I pass Buck Island, with the islands of St John and Tortola behind it, in case they are blocking the wind. As Buck Island slides past my port side, Endurance heels over with the increasing wind. Although she handles rough conditions well, I am grateful I didn’t shake out the reef. The butterflies prepare for battle.

Every few minutes, I stand, peeking around the equipment box blocking my view, to watch my dinghy ride up and over the swells. Dread rises in my throat each time. Then gratitude replaces dread as the dinghy rides safely over them. I scan the horizon and check the sails before returning to the helm. A roller coaster of emotions wracks my body. I force myself to breathe. It takes a conscious effort to release my clenched jaws.  I do this repeatedly.  

I don’t need a number to feel the wind increasing. The butterflies are attacking again. A gust puts Endurance’s toe rail inches from the water. Panic rushes through me, freezing me in place momentarily. 

I adjust my heading to a beam reach, but nothing changes. I want to reduce my sails but I’m struggling to move around the cockpit. Going to the mast to put another reef in the mainsail is not a safe option. I decide to shorten the jib. With the jib sheets ready, I release the furling line and pull. It won’t budge.

I ease the load on the jib and try again. Nothing.

Another gust slams Endurance. I glance at the toe rail, nearly licking the water now, as I slide across the seat. I don’t panic this time. I decide to see how things go for another half an hour, not knowing what else to do. 

The minutes tick by, the wind blowing like snot, the gusts heeling Endurance over to an unnerving level. I dissect the situation. I must find a solution. NOW!

In hindsight, I should have repaired the furler before this trip. But here I am, and I must deal with it. Even if conditions improve, which is unlikely, I don’t want to deal with the furler in water I haven’t sailed before. I can’t keep sailing in these conditions for another eight hours. Without another thought, I tack 180°, put Endurance on a beam reach, adjust the sheets, check the main, and head back toward St Thomas.

Instantly, an overwhelming wave of failure washes over me, threatening to drown me. I’m sobbing. Rivers of tears wash away my vision of sending a picture of Christiansted harbor saying, “I did it.” 

Failure is crushing me. I can’t breathe. I struggle to regain control of my thoughts.

Slowly, like honey dripping from a spoon, it dawns on me that I executed my first solo tack when I turned around. It is enough to stop the downward spiral. Breathing deeply, I regain control of my thoughts and evaluate the morning’s events. Aloud, I list what I accomplished.

“I overcame the urge to backout and started to sail to St Croix. 

I found a solution to keep the reefing ring on the hook.

I overcame the difficulty getting the jib out.

I handled my boat in 25 knot winds.

I executed my first tack!”

Feeling less like a failure, I notice the sun splashing on my face. Endurance is flying across the water on a pleasant beam reach, reminding me of how wonderful sailing is. The question of failure or success rears its ugly head again, but I know the answer now. If the goal was to sail to St Croix, I failed. But that was not my goal. My goal was to take my first solo sail. “Well guess what Cindy — you took your boat out and went sailing, ALONE, in stiff winds and successfully handled it.”

“Got it! Not a failure but a SUCCESS.” 

“Hold on, there’s more. Why did I turn around?” Because seamanship is about making decisions that are best for the vessel and passengers. Safety first. I recognized my limitations and those of my vessel and determined the best option was to turn around. The butterflies have flown away, my decision feels “right”. 

The first buoy marking East Gregory channel comes into sight. Grabbing my cell phone, I call my friends, Jono and Keith, for assistance and prepare to deal with the jib. With false hope, I pull on the furler. Nothing. Going to the mast, I do the temporary fix again and return to the cockpit. Taking a calming breath, I pull on the furling line and get three wraps of the jib. “Okay, that’s better than nothing.” I repeat the process, gaining another three wraps. Halfway there. 

I am running out of room to safely drift so I reposition Endurance. Then I repeat the process, gaining another three wraps. It’s enough to prevent the jib from affecting control of Endurance while I drop the main. I head into the wind, set the autopilot, release the clutch and the main sail drops beautifully into the stack pack. My entire body relaxes slightly. One down, one to go. 

“Shit!” The jib came partially unwrapped while dropping the main. I’m losing patience with the furler, yet I have no choice but to keep working at it. This time I put the furling line on a winch before slackening the halyard. I get four wraps of the jib. And that’s it. No more. I motor towards the mouth of East Gregory channel.

My grip on the wheel loosens and my heart stops pounding when I see Jono speeding across the water. After securing his dinghy, he climbs aboard to help with the jib. Keith meets us at my mooring and with his help, Endurance is soon secured. I am home. And I am grateful for dedicated, caring friends. I shout my thanks to Keith as he pulls away. Before Jono leaves, he tells me “I am proud of you for going sailing alone today. You made the right decision to turn back. You did a great job dealing with the jib, staying at it even though it was difficult.”  His words dissolve the last dregs of failure I had sticking to me. 

As I move around the boat, returning it to “home” mode, the morning plays in my head like a movie. I re-evaluate every step, every choice I made, asking questions that I don’t have the answers to. Today reinforced important lessons. A captain cannot rely on perfect preparation or ideal conditions. Being a smart captain, a good captain, depends on recognizing when things go wrong (and they will) and taking the time and patience to make adjustments that fit your abilities as a captain and those of your vessel. If I had had the funds, the furler would have been repaired and with a more flexible sailing schedule, I would have waited for better conditions before heading out. Lessons learned.

Worry, excitement, exhaustion and emotional overload bring sleep easily as the sun slips below the horizon. Waking at 2:00 am, my mind starts another round of evaluation, not only of yesterday’s events but of my future. “Why is this crazy desire to sail alone tugging at me?”  Because the adventurer in me yearns to travel the world by sea. So, I will continue sailing alone (once the furler is repaired, of course), building my skills and ensuring Endurance is in good shape.  Next year, solo sail to Guadeloupe? I can do it!

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