There are few things more satisfying to a sailor than flying all the canvass.  Every stitch of sail, drawing and pulling your craft.  Your own private cloud tacked to your deck like a giant cluster of balloons that magically draw you along your chosen path.  Each scrap of cloth held in status.  They tug at your rigging like a fathers thick-fingered hand, guiding a child over wave after wave after wave.

I have a particular taste for traditional sailing rigs.  They are more work yes.  They are also more versatile and readily repaired at sea than modern rigs and when it comes to bending on all the cloth; The more masts, stays, booms, halyards and sheets, the more beautiful and powerful your private cloud will be…  The more complex, the rig, the more challenging, rewarding and beautiful they are under sail.  There are days.  There are hours and there are moments where it is time to let it all hang out.  To dig deep in the sail locker for the last musty old bag, and bend on the last yard of cloth you can fly.  There are times to send it all up for glory sake and take your ship to her potential.  There is a time to let it all breathe. Let that sailcloth stretch and cleanse itself in the fresh ocean breeze and spray.

Though we may want all days to be like that, we must weigh our balance, moment by moment.  Watch by watch.  We must carefully measure how mush cloth we cast into the sky, so that we may sail aggressively, but in safe control.  Sailing amongst snow-capped mountains in freezing spray is a beautiful experience if well executed and deadly if not.  Cold wind is more powerful than warm wind due to its increased density.  It is thicker, creates more lift and bights to the bone.  Protective clothes and gloves make your jobs harder.  Frozen lines misbehave and a windlass encased in ice is useless until beaten free. This is no time to fly all canvass.  This is a time to reef ahead of the weather.  Sail slowly, surely and watch for that gremlin that wants to throw a wrench into your tempo, water in your heater and ice in your eyelashes.

Regardless of the day, be it flying all canvass, or reefing and beating ice, we need to find a rhythm. We need to feel out the sea, the ship and most importantly ourselves.  Our eyes must be trained to look 3 steps ahead.  Our ear tuned to the radio traffic, warnings, and weather.  Our bodies need to be hydrated, fed, warm and ready. Our mind should be processing a hundred, scenarios using what is called “If then” thinking.  Such as “If we lose steering, then I will insert the emergency tiller” Then you are reminded of the emergency tillers location, or urged to locate it and have it on hand, should the need arise.  “OK good” you say “Now if…..” Etc.

This is how we prepare ourselves and stay tuned in to our surroundings.  This is how we become better sailors.  Always prepared for the worst.  Always planning for the best. 

By far, the most common question I am asked is “When do you reef?”  Of all the skills a sailor should have, the most underutilized is the reef.  Simply put,  “Reefing” is a way to make a sail smaller and more flat.  It decreases the effectiveness of the sail, so that it cannot overpower the vessel.

I am not going to answer the “When to reef” question for you because it is not my place to answer.  I will however share with you 2 particular experiences with reefing.  The first story took place at the onset of my sailing career.  Within 3 months of my first sailing experience.  The second being my most recent, just a few days before writing these words.

March…ish, 2006.  Ketchikan Alaska

After a trying day at work, followed by disturbing personal news, all of which complimented a particularly challenging portion of my life, I decided to take a sail I had been planning.  I knew my vessel by now, but had very little skill in sailing.  In the few months I had owned her I had done her delivery, mostly under power and a few evenings of light air sailing and fussing with the rigging, under mild conditions…. Sail, study, sail repeat.  I was a student, but still very green.  Regardless of this fact, I had decided that exploring under sail was for me.  There was a towering wall of skill I desired badly.  But was merely scratching at the base like a puppy.  I was impatient and full of fire to change the path of my life.

Having decided that I already had my eye looking out for a much larger vessel.  A platform for research contracts and the like.  Some way to blend my passion with my livelihood. My dreams were born in these days and they were beautiful.

I had heard of a vessel that may fit the bill and my budget.  It was moored in a nearby community called Thorne Bay.  I had my dive gear loaded onboard and was set on diving her hull as a part of my little survey attempt. The excuse was sufficient and so I set my mind to go se her.

 The best way I can describe what I am about to tell you is this.  That day, I tried to dig under the wall of skill and knowledge.   Circumvent its formidable presence, tunnel under the foundation and emerge from the other side victorious….  I’m sure by now, you see where this is headed, but suffer me to share.  In hindsight this is a grand explanation, of what not to do., and a hard lesson worth sharing.

I rushed home to Empiricus, and set about haphazardly preparing.  I was in a rush as the days were short and I wanted the daylight in my favor.  I checked the oil and changed the fuel filter (A prior hard learned lesson I never forgot) I started the engine and let her warm while listening to the weather.  The weather was bad, but I put all my confidence in the ship, having made rough passages in January after her purchase and gaining confidence in her abilities.  But in my ignorance of the area to be traveled, I did not follow the forecast thoroughly.  I did not do my homework and as I later learned, a wicked blowing Gale beset the area between points Ketchikan and Thorne Bay, well beyond anything I had yet tasted.

I was not so ignorant however to realize the general weather pattern and my lack of skill would push my limits.  A pit was forming in my stomach as I assessed how to better my chances of success.  My lifelines were in disrepair, strung but not mounted on the portside and weakly fixed on the starboard.  A fantastic decoration of unpreparedness.

I felt a strong urge to compensate for this blatant disregard for preparedness and convinced myself that completing some other, simpler project would suffice.  So I installed the little plastic autopilot I had never tested.  I flipped it on.  It seemed to work.  Feeling satisfied with that, I glanced at the autopilot, book, pulled out the chart and cruising guide, marking a page for Thorne Bay and made the decision to go.

Motoring into the wind, I set all my canvass.  Everything from stem to stern; Genoa, Jib, Gaff Main and Mizzen.   All flying full and unreefed.  Wing and wing with a centered jib and genoa.  I fell off the wind, shut down the engine and EMPIRICUS came to life! I scampered for the North entrance of the Tongass Narrows with an uneasy speed to which I was not accustomed.

Never had I sailed her like this! I was astonished by the power of the wind, now working with me and for me.  The wind was harnessed to me like a wild animal, I felt as though the boat and I were a tiny jockey, perched on the back of a thoroughbred race horse! Charging on through the green broken water, we trounced from peak to foamy peak.  I was so alive inside!  One with my vessel and stretching her legs!  This was truly magic!  Why mine was the only boat to bee seen was beyond me.  “Fools”, I thought to myself with pride….  “Look what they are missing”.  I reveled in my moment of conquest, only to be rudely interrupted by humility. And a sight I shall never ever forget.

Like the windblown hair of a wicked old witch, the ocean loomed before me.  Her scream whistled through the rocks and trees, which guarded the cape.  The cold, cutting fury, carving a clean line in the ocean, where adventure ended and terror began.

You see, just around the cape was a body of water unprotected by land and perfectly aligned with the Southeasterly Gales that accompany an offshore low-pressure system in Southeast Alaska.  Of course I knew none of this.  I had not cracked open that file in the wall of knowledge.  Nor the one that showed how just such a channel, which met the confluence of another would cause a tide rip just ahead, causing the witches hair to stack and snarl before me, like a row of parked cars.   Believe me.  I could go on and on and on about why I never should have been in that position…  I had got myself stuck under the wall of knowledge.  It pressed down and shifted.  Locking me in.  Pinning me down.  Pressing out my stubbornness and impatiens, to make room for what I was about to learn. 

The fact is, I could not have stopped that boat if I tried.  I was frozen by fire.  The rollercoaster had left the gate and I was strapped to the hood, of car #1.

Now as scared as I was, I knew Damage control was the order of the moment.  I locked the helm and clamored to the deck, dumping the Genoa on the way, stuffing it into the bag.  I scratched my way to the cockpit, just moments before rounding the cape and piercing the welcoming wall of a tumbling chaos.

 Empiricus leapt forward beneath me, main boom groaning under the load. The noise was incredible.  A wolf den of howling sang from this moment forward while her hull was washed in a meringue of foamy sea.  The waves were not large due to lack of fetch.  Maybe 5 foot but stacked tight like dominoes set in line and tipped.  The sea was made of them but no pattern could be discerned, for the top 2 feet of the waves were beheaded by the wind, like a million icy pressure washers, spraying in one direction.  White streaks of decapitated waves, smeared out the length of the hull.  The vibration beneath me coupled with the slapping hum in the rigging was incredible to behold.  Tension was in every gust, every wave, every line, every pin, every fiber and every bone.

EMPI’s heavy narrow hull began to plane once I passed 9 knots of speed, and I just held on.  Making record time for Thorne Bay had taken back seat to “Making it to Thorne Bay”.  Yet speed rained champion, in my wide-eyed world, so I embraced it.

Just as I was slowing my heartbeat enough to adjust to this upscale in the day’s activities, a weak seam was found by the wind and the mizzen let go.  Rent in two with a mighty “BANG!”  The halyard ran free because I did not have it tied at the bitter end and I was dragging the whole mess behind me. Boom and all were cutting a messy furrow in the “witch hair” seas astern. 

Aha! My backup plan was in need.  “Good thing I thought of the autopilot” I croaked to myself as I switched on the power.  It did the trick, and steered her perfectly! For about 4 seconds…….  Poof…. Blew a fuse and took out the depth and speed instruments along with it… Fantastic I thought, palms held to the sky, shaking my head in disbelief.   Thinking it through, I carefully locked the helm and bounced back and forth between towing in drenched torn sail and steering the boat.  Every violent gust would send her rounding up and required counter steering.  (I later learned this is called weather-helm and is, at its onset a red flag to reef.)  So on I went with this dance as I drug the mess onto the stern, wrapped it all around the boom, fistful at a time, and lashed it down solid to the stern-rail.  It should go without saying that I used choice language of all varieties during this process. Like an audible mirage of frustrated companionship, I fired a barrage of creative slander skyward, only to be swept away by this full scale wind tunnel testing I volunteered myself for… Anyway, I remember speaking allot out loud.  At first to no one of course.  I was shaken not broken. Little did I know I would need more company soon….

I sailed on rails it seemed.  Like a splitting maul she broke the waves sending splinters of splattering wave abreast.  Empiricus was built for heavy weather.  But I had catching up to do.  She was tolerating me like a wise lead dog might tolerate a young musher, learning the ways of the wild.

Soon the sky began to darken as nightfall approached.  I was halfway there but the entrance was tricky and new to me.  My instruments were out.  I needed to replace the fuse and prepared to do so, disposing of the autopilot altogether, I attempted to judge the pattern of her steering and prepare to leave the helm.  I only needed about 15 seconds, but 10 was all I could get in practice, before a helm correction was required.

There are times when I wish I were more ZEN.  More fluid, smooth accurate and graceful. This was one of them.  I chose my moment, and floated down the hatch.  Body locked against the bulkhead I clung to the fuses and made my selection.  Cold water running off my hands into the spares, I wiped it quickly, popped the burned fuse out, cursed whoever wired the autopilot to the instruments, and snapped it into place, lighting the switch.  “Aha!” I cheered and bolted up the stairs, but I was not fast enough…  Bang! Smash! Etc.   The rolling smashing lurch of violence slung me to Port.  I pulled my head down like a turtle until all was clear, then poked my eyes over the hatch to see.

 I had crash gybed the full mainsail, snapping the vang hardware, leaving the main boom pinned to the Port running backstay.  I was being blown along the water in a perpetual skid that began to overpower the rudder. I jumped to the helm and buried it to port before I lost speed and steering.  The 435 square foot Mainsail and Gaff, crashed back into place, dangling vang hardware and tattered lines from the boom like bloody meat in a dinosaurs teeth, fed, but still hungry.

 I glanced at the knot meter and watched it break 11 knots!  The main boom now free to rise was kicking high in the air, billowing the mainsail into the rigging like a giant trash bag might stick in the limbs of a tree.  And yet another problem was brewing…   The entrance to Thorne bay was protected by a protruding point of land.  If I steered to clear the land, I would surely cause an uncontrolled gybe….

I have learned to describe Tacking and Gybing like this… 

Park your car in a windy parking lot, with your hood into the wind.  When you open the car door, there will be some effort, but when you let go of your door, it will simply click shut.  This is much like tacking.

Now park your car with the trunk into the wind.  Open your door and it may get ripped out of your hand, likely causing damage.  The door must be carefully controlled from open to shut.  This is Gybing. But the car door is 50 feet tall.

So basically I knew I could not hold onto the car door and did not want to risk a crash gybe.  Had I set the sail reefed, or been able to reef, or knew how to reef, these winds would not have had such an effect and I could have handled the rig much better.  In fact the gybe is now my favorite maneuver.  Done properly it is a lovely dance performed by mainsheet and rudder.  Music by Timing and pressure.

But I didn’t know that.  All I knew is that I was periodically planning a displacement hull directly toward an ever-nearing wall of rock, with no way out but a gybe. 

Ahhh what do we do in times like these?  You never really know till your there…  So I tried something I had hear about..  It’s called a Chicken Gybe.  I loosely understood that instead of passing your stern through the eye of the wind and slamming your big car door open.  You simply head upwind, tack, then fall back off the wind now headed the other direction downwind, having never gybed. 

Here we go!  I went hard to port.  Yes I went hard to port and learned something.  The ever-changing sail trim overtook me.  My sails became flags and began flogging.  The beating of the cloth sounded like machineguns on the foredeck and above me.  I could only keep up with trimming one sail and I knew the wind would eat whichever I did not control.  I paused briefly and made note that the big sail would likely cost more money and so my choice was made.  I cranked the mainsheet saving the main from flogging, but the boat had stopped cold.  Now being blown sideways and aimlessly as I tried to tame the main. 

The flogging of the jib was terrible to behold and deafening to the ear as its wind whipped silhouette blocked my partial view of the ominous rocks before me.  I just shook my head…. And as I did, the jib parted. Down the center, making two machine gun flags instead of one.  Then it literally dissolved, under a frenzied howling gust.  The fragments departed the deck and were cast into the ocean like a sacrifice to the wind and sea.  Tethered to the boat only by the sheets and a brass hank or two. By the time I dumped the halyard the jib, was unrecognizable and strung a long white mess off the Starboard side.

I crawled forward past my unfastened lines and began hauling the long skinny scrap back onto the deck.  As I did, Empiricus began sailing again.  Now directly toward the greater part of the landmass ahead.  At this moment.  I stopped.  Looked into the sky directly ahead and belted “OK!! I’M SCARED!”

I think I was asking God for help.  Or at least reminding myself that he was the boss, although I often have behaved otherwise.  Either way.  It felt good to tell someone and hear myself say it.

Now greatly humbled I dutifully hog-tied the big white ribbon pile of sail to the rail. With frozen shaking hands and scampered for the cockpit.  I let the main back out and continued my previous course, albeit closer to danger than before and only one sail remaining in play.

I looked up at the booming mainsail and its behavior along the leech.  (The leech is the edge of the sail that is opposite a mast or stay).  It is the tripping point for the gybe.  Once the wind gets on the other side of the leech, the sail will fill opposite and cross the deck (Gybe).  I was studying my options and had a new level of acceptance for damage, having lost 2 sails in as many hours.  I was moved to try something new.  Something inventive.  If it failed I would be forced to try and motor against the winds and wrestle the mainsail down alone.  But if I could just sail around that point, I could strike this monster in calmer waters, protected by the very rocks that seemed to draw me hither.

As I studied the rig, all the rules that clouded my head, the sayings and terms and procedures that yet eluded me, faded.  At that moment, for the first time, I saw the whole boat, from rudder to masthead, as a machine.  I saw and felt the reactions, the pressures and the reactions.  I saw the problem and along with it, a single possible solution, of which I was capable of performing immediately and with little risk. 

The wind charged, as hard as ever and Empi marched forward to land.  It was time…  Here is what I did.

I lowered the gaff halyard, which regardless of wind will come down under its own weight.  The gaff, (The boom holding the top of the sail up and flat) immediately pointed forward, twisting the mainsail, spilling excess wind and moving the leech further away from the eye of the wind.  This allowed me to steer clear of the rocks, which is exactly what I did, surfing the broken waves and planning at over eleven knots.  I later learned that I was “Sailing by the lee” under a “scandalized “rig.

Within minutes I was just inside the protected cove, where I started the engine, faced the easy wind and dumped the mainsail all over the deck.  By the time I negotiated the narrow passage to Thorne Bay and made fast to the dock, it was pitch black.  I don’t even remember tying up and I slept like ballast stones.

The following morning I heard some salty old timers on the dock, commenting on what a “Nasty Blow” this boat had sailed through, the night before. Commenting on the strips of sail now laying limp in peaceful rainy quiet.  Apparently this act gained me street cred with the locals.  I just laid in the bunk and shook my head.  There is a fine line between Ballsy and stupid.  I had whipped those two ingredients vigorously and salted to taste, which was decidedly bitter.

I did my dive thing and even made some money diving on other boats.  The boat I surveyed was junk.  Later that afternoon I motored home in zero wind, surrounded by rainbows. On a sea of glass…. 

OK That was then.  Lets fast forward to last weekend, October 2012.  I share ownership in a business venture property with several friends In Resurrection Bay. A few of us decided to work on the property before winter set in.  We loaded materials and tools onboard their sailboat.  We set sail inside the harbor under strong cold high-pressure winds, sailed effortlessly to our property where we anchored.  In the middle of the night, we began dragging anchor, but a responsible watch schedule alerted us of the problem.  We had to leave the location due to poor anchor holding and increasing wind.  After finding a more suitable location and a mooring, we secured ourselves, set a backup anchor and slept a bit.

The next day the winds were increasing still and very cold.  But we worked as a team and sailed very comfortably.  Having set our sails double reefed before entering the exposed area, the transition to sailing was simple and controlled.  We beat to windward 6 hours at 5 knots hull speed to gain nine nautical miles up wind.  The temps were in the low 30’s with winds at 25-30 gusting 30-35.  It was chilly but enjoyable.  I even took a nap along the way home.

Both these days and voyages were days to be approached with caution and skill.  But how do we get there?  How do we climb that wall of knowledge without being crushed by its enormity?  How do we return to enjoy the sea, which can seem so angry and fierce? 

Here is what the sea taught me.

Regardless of how old you are, where you have been, what you have done, what you have not done.  Learning to accept your mistakes and learn from them openly brings a reward sweeter than beginners luck or natural talent can bestow.  The reward of studying monumental failure, to me, is this.

As young people we watch the clock hand turn and adulthood approaching.  Unstoppable and looming.  Then one day, it has arrived.   We can try and hide from it, or throw ourselves headlong at it.  But at some point our lines are cast from the dock and our navigation begins.  We have plans to do something amazing!  Something important or just something different. So we try our best.  Tender and impressionable.  We make mistakes among the good choices and we establish a pattern.  We anchor on sunny days, sleep in and miss out.  Only to sail in the storms and see more of the worlds ugly, than we ever intended to absorb. 

We choose what we invest in ourselves.  We choose what feed our minds and bodies.  We act and react to our own decisions as we sail a chosen course, during every moment of our voyage on Earth.

At some point nearly all of us will feel like an old ship.  Beat by a storm, eaten by worms, timbers cracked, sails torn or anchor dragging.  Learn to focus, in the face of the thing, which ails you most.  Accept the fact that you need to learn how to make choices through failure.

You see the world is not out to get you.  Like the ocean, it is simply indifferent to your existence.  In order to live well, you need skills; inspect your life.  Repair what is obvious before you set out for change.  If your heart is broke, find out why… Honestly just between you and yourself ask these questions and pinpoint the pressures that upset your hull.  Then focus on strengthening those areas.   Build your skill; when to heave too, in and lay low, when to fly all canvass and how to balance between those extremes.

 If you take a proactive approach with your life, you will find what needs repair. Learn how to patch a sail, crimp a hose and splice a broken line.  Learn how to maneuver and feel the rhythm of your life.  What you can handle and what you cannot.  What adds to your joy and what causes bad dreams.  Become a student of your failures.  Be raw and honest with yourself, accepting the outcome of your choices.  Accept the consequences thereof, regardless of your initial intent or best efforts.

If you can truly learn to do this, you will not have to hide at the dock and miss out on life.  Nor will you feel the desire to ignorantly cast yourself before fury of the world.  You will find a rhythm of tactics that will carry you safely through; sunny days, hungry nights, unforgettable glory and would be terrors.  Free from the rollercoaster ride of ups and downs.  Free from slavery to appearances, or obligations of perfection.

Those who have learned of this gift, breathe easy, smile more and sleep soundly.  They fail still yes.  But the gift of being a student of your failures is found in your soul. Along with the realization that the strongest contributions you can make, in the life of another.  Will hinge upon how you process your weakest moments. 

Everybody is leading somebody.  Live well.

Captain Jesse Osborn