Syzygy Sailing

What a change.  For the past four years I’ve been part of planning a two year sailing adventure.  Now, I’ve been spending time planning a new life-long adventure.  I’m expecting a baby! And with a girl that I love!.  Wow.  You sure can get some unseen huge curves on that road-of-life thing.

My relationship is not analogous to some random islander hook-up.  We are very much in love and very much together for the long haul.  Rather than run off to the next port-o’-call like they might have done in previous centuries, a couple of months ago I left Syzygy.  Upon arriving from Colorado, I was at Syzygy only briefly before I learned the news and headed back to Colorado to be with my girl-friend.  Contrary to being punished, I feel rewarded. My life has traded one option for the equally incredible one of raising a child.  Of course, this was definitely unexpected. I mean, I was planning on sailing around the world for Christ’s sake!  So it was a heady choice, though definitely the right one for me, and I am very much excited.  A baby!  I’ve always looked forward to the idea of kids.  Soon after I found out, a friend relayed a story that struck a cord.  He talked about how he had always thought about having kids but probably would have never gotten around to doing it.  But it happened unexpectedly to him and now he just couldn’t be happier.  I think, in the first half of that thought, there’s some truth to that for me and I fully expect that the second half will ring spot on.

It was extremely hard telling Matt that I was having a baby, moving back to Colorado and not going sailing.  I was still a mess of emotions at that point.  My fear of the unknown was high;  I didn’t know how he would respond and so I feared the worst: his reproach, his disappointment, and the weight and the burden such a response would have on my already frazzled emotional state.  His opinion carries so much weight with me and his opinion of me is incredibly important.  It would have been crushing to me if his reaction was intensely negative.  When I broke the news though, my fears did not come to pass.  Instead congratulations came and the reassurance, “I’m not mad at you.”  It speaks to his character that despite his disappointment, which I knew was there, despite his sadness at how our lofty goal would not be shared, he chose, perhaps because he knew I needed it, to stand in support of my decision and where my choices are taking my life.

With that fear overcome, I felt enormous relief.  I knew telling Jonny would be, while difficult and emotional, immensely easier.  A couple of hours later, as I put away a few beers, Jonny and I talked well into the night on it.

I know I’ve chosen to miss out on an incredible adventure: attempting to sail around the world.  But I also know that this is clearly the right choice.  And there will be plenty of adventures for me in the future.  They might not be the sailing-around-the-world type, but adventures will be had.  I’m going climbing this week-end.  I’m planning a trip to France in December.  So adventures will still be had.  I feel some guilt though that I will not contribute to finishing work needing to be done on the boat.  We were on a tight timeline even before this event.  Now, minus my labor, the to-do list looms larger.  And as is usually the case, while some items get checked off, new ones get added.  It has been tough to listen to Matt and Karen describe working on the boat.  Karen told me of her excitement at refinishing the deck:  laborious work, but extremely fulfilling to see it look so nice.  I had pangs of envy wanting to be there to pitch in and enjoy.  Matt vented and despaired at new work to be done, and I despaired because I can’t say, ‘well let’s you and me double down on our efforts.  Let’s make a big push.  We can do it.’  I can’t say that because I’m not there.

However, I certainly was not the critical component to this trip like our captain Matt, and my departure from the plan will not doom the trip.  My sailing skills are still, unfortunately, much to my chagrin and to put it nicely:  limited.  Living in Colorado has not allowed for nearly as many opportunities as I would have liked to get to know my boat: sailing her, the systems, and the work put into the boat.  I have to admit that I have never taken the boat out sailing without our captain on board, Matt and I agreeing that my skills simply were not quite up to par.  Depressing perhaps, but I willingly admit it to be true.  So my bailing certainly isn’t an impediment to Matt, Karen and Jonny going forth on an amazing adventure and doing what we began planning four years ago.  Sailing the world is still a consummate adventure filled with endless potential.  People beg off trips all the time, including many trips that Matt, Jonny and I have been on or led, and those that stay on still get to experience everything the adventure has to offer.

We’ve all had six weeks to sit and chew on this.  Matt and Jonny, at my request, refrained, for the most part, from writing about this this until I was ready, a fact I very much appreciate, allowing me to announce this very personal news first.  We aren’t the Washington Post, here at our little corner of the blog-osphere, breaking news of Watergate to the world, and so I want to acknowledge the courtesy of allowing me to tell our little audience about this first.  I’m sure they both have many thoughts on it, some of which I hope and expect they will share here.  We have all used this blog as a window into our excitement, frustrations, and feelings for the last two years.  I will probably not have much more to blog (though a sail still awaits completion), this adventure ending for me as a new one begins.  Jonny, Matt and Karen, however, have the opportunity for an incredible adventure ahead.  My absence from it certainly doesn’t stand in the way of that.  Good luck to you!

Over the last five hundred years or so, if a sailor did something stupid like neglect his duties or disobey orders or insult his captain, or strike an officer, or desert the ship, or display rank incompetence or drunkenness or insubordination, or steal a dram of rum, or spit on the deck, or fail to stow his things properly or to clean his clothes adequately, there were any number of punishments that could be meted out: the sailor could be flogged, or whipped, or pickled, or cobbed, or made to run the gauntlet or to clean the head or to carry a 30-pound cannonball around the deck all day or to station himself at the top of the mast for a few hours or just to stand still until told otherwise. He could be lashed on board every ship in the fleet, or he could be tied to the mast for a week, or keel-hauled, or he could have had his feet bound and covered in salt and presented to goats for licking, which quickly went from ticklish to agonizing, because the goats don’t stop licking before the sailor’s feet have become bloody stumps. Or, if the sailor had mutinied or murdered, he could be hanged, shot, or have his head cut off, boiled, and then shoved onto a spike above decks, and left there for a week or so, to serve as an example to the remaining and hopefully far more loyal crew. Magellan preferred this latter technique. If the sailor had buggered (aka sodomized) another sailor, that, too could earn him the severest punishments. The sea was not San Francisco, man. But, if the sailor, while meeting the locals on some tropical island far away from home, knocked up a local woman, or a bunch of local women: nothing. Getting a girl knocked up was what sailors did when they weren’t sailing, like Genghis Khan, or Mulai Ismail, the last Sharifian emperor of Morocco, who had something like 1400 sons and daughters before he died. Most sailors probably never knew how many women they knocked up on their voyages.

How far we’ve come since those days. I can neglect my duties all I want; I can make fun of Matt’s mom and call Jon a cabron and not get punched in the face; I can run off to Yosemite for a couple of weeks; I can trim the sails poorly and sail us home by some unimaginably indirect course; we can get so drunk that we decide to clean up our spilled wine with spilled beer; I can drink all of Matt’s beer and Jon’s expensive whiskey; I can spit on the deck or anywhere else on the boat I feel like it; and I’m not sure if I’ve ever stowed my things or washed my clothes properly. The boat is my oyster. If I were so inclined, I could invite over all the gay guys in the bay area with one simple Craiglist post; instead, I have tried my hand at luring girls here, all the while wondering what girl would really find this sailboat alluring. Remember: according to Google, Syzygy is a janky piece of shit, and based on the information in this paragraph (swearing, drinking, spitting, dirtying), I’m no example of fine manners, either. Finally, the biggest change of all: getting girls knocked up is decidedly not what sailors do. This is the 21st century, man, even if it is San Francisco.

So I’m 31, and dating, and it’s always a mystery when and how to tell girls about the boat. They always have a ton of questions. Is it small? It’s like a New York City apartment, you know, a 400-square-foot studio. Is there a fridge, and a stove? Yup. Is there any headroom? I can’t jump up and down, but I don’t have to squat. Is there a bathroom? Yup, but I prefer to piss in the bay. Is it noisy? Seagulls squawk in the morning, and sometimes the wind howls in the afternoons, and sometimes the docklines creak as they stretch taut. I try to make it sound romantic. Does it rock back and forth? The boat moves a little bit when tied up, but nothing crazy. And get this: the boat is so burly that if it gets knocked over 90-degrees it still pops right back up. In fact, if it gets knocked over 120-degrees, it still pops right back up.  Do you get seasick? Not in the marina, but at sea, sure. Most sailors do occasionally. Is it cold? Not really, and I have a diesel heater. Sometimes I feel like a caveman, proving that I exist in modern times: yes, I have electricity and laundry and cell-phone service and an internet connection. Yes, a sailboat. Really, it’s not a big deal. It’s got a certain allure, I know it, but somehow I end up on the defensive.

And here’s how I can tell my dating life isn’t going so well: I’m sleeping with Bob Seifert. Not “sleeping with” in the euphemistic sense, but literally, as in sleeping beside the book he wrote, called “Offshore  Sailing: 200 essential passagemaking tips.” I have a hardcover copy of it in my bed, and I cuddle up to it every night like it’s some titillating classic or a book of translated swooning poems. Page 27 describes one of my favorite projects: boom preventers. As if I need those. There’s no other way to put it: it’s my boat porn, full of seacocks and cockpits and blowers and interfacing electronics and deep-cycle batteries and coupling nuts and prop shafts and large tools and lubricants and docking equipment and proper bedding techniques. Talk about a change. I should be punished for my behavior.

[Reposted from my Outside blog]

There’s a cliche about boat-owning: they say that the best two days of a boat-owner’s life are the day you buy your boat and the day you sell it. Anecdotal evidence already suggests the opposite.

First, buying Syzygy was no fun. Buying the boat — literally paying for it — entailed electronically wiring the largest check I’d ever written to some obscure bank in Seattle, while at the same time second-guessing myself and wondering if I’d made a grave mistake. Was I buying the right sailboat? Had I taken a big hasty jump too soon? Did I just screw myself for the next three years? Five years? Life? My concerns ranged from tiny to huge, such that the actual boat-buying was fraught with anxiety and concern and distress. Which is to say that the day I bought the boat was not one of the best days of my life — 99% of the other days in my life, in fact, were better. A bad day at the dentist was better, because at least there was progress. With the boat, I wasn’t sure if I was going forward or backward. I can’t fathom how the first part of this myth was born.

Second, I saw Syzygy’s previous owners a year and a half ago, when we met them in Mexico to take the boat for a sea trial, and I would testify in court that they assuredly did not enjoy selling their boat. I think owning it made them feel young, spirited, engaged, and adventurous, and that selling it only reminded to them that life’s circumstances — increasing age and flagging ability and mobility — had finally caught up with them and forced their hand. It took them three years to sell their boat, and it’s difficult to imagine that, at the end of the ordeal, there remained, as far as Pavlov could be concerned, any joy still associated with their boat. Relief: sure. Annoyance: yup. Finality: fine. But exultation? No way. That’s not what I saw.

There is another cliche about boats and money that does hold true: they say a boat is a hole in the water that you pour money into. Some say BOAT stands for Bring On Another Thousand. Absolutely. Here’s how you quantify it: You think a project will cost $500? Triple it. Even if you’ve already beefed up your estimate, added some wiggle room — triple it. It’ll cost $1500, I guarantee it. It is absurd how much stainless steel, copper, and “marine-grade” parts cost. The only way to spin it positively: at least this isn’t aeronautics.

On top of projects and maintenance, there’s the cost of keeping a boat at a marina or, if you’re really feeling flush, at a yacht club. To most sailors, this is an extra cost, in addition to rent/mortgage for a dwelling on land. When the economy sours (as California’s has), boat owners promptly stop paying their slip fees. Marinas, in turn, chain up boats belonging to such delinquents, so that the owner can’t just sneak in one day and sail away. There are a few such boats here. Apparently, you can put freedom in shackles.

I suspect that John Tierney, in last month’s NYT science column, called “When Money Buys Happiness,” was right. He examined the relationship between money and happiness, and reported that houses, higher education, travel, electronics, and fancy cars, though expensive, tend to provide happiness. On the other hand, there’s children, marriage ceremonies, divorces, and boats. These things are also expensive, but don’t provide happiness. Tierney sums it up: “Boats: very costly, very disappointing. Never buy a boat.” I wish he’d told me that a year and a half ago.

There’s a corollary rule about time that’s related to money and happiness. If you think a project will take 5 minutes, that means 10 hours. If you predict 3 hours, that means 6 days. The rule: double the number, and step up the unit – from seconds to minutes, from minutes to hours, from hours to days, from days to weeks, and from weeks to months. Accordingly, as projects abide by this rule, and drag on and on, it’s easy to see where the happiness goes. It swims for shore, headed to Colorado. Boat owners chase after it, and before they know it, a few years have gone by and the bank account is near empty. So it goes.

Perhaps the best rules of all, though, I learned last summer from Tim, a friend who also owns a sailboat. We were at a bar, yabbering on about the ongoing nature of boat projects, when someone interrupted and asked if there were any general principles to sailing. He answered immediately. “Keep water out of the boat, keep people out of the water, keep the girls warm, and keep the beer cold.”

There’s only one last important rule, lest you are prepared to lose all of that happiness, time, and money: Keep the boat off land.

[Reposted from my Outside blog]

In late November I flew to the East Coast to visit my family for Thanksgiving. It was the first time I’d spent 10 days away from the boat in six months. They gave me an earful, my family.

On a walk in the woods with my mom, she asked if I was “prepared to weather a downturn in the economy.” I hemmed and hawed, and admitted all my savings were sunk into the sailboat. Then I tried to explain that cruising is really cheap — you load up on rice and beans, and just take off and go, like a climbing road trip. She seemed unconvinced, and rightly so.

My cousin Myles asked if I was done fixing up the boat; I told him it was complicated, that the boat was sorta like his house — a huge, ornate 1880’s Victorian, perpetually mid-repair, in a historic town. He grasped the situation immediately, and said, “So you’ll never be finished.” I smiled. “Exactly.”

My cousin Joel told me to read “Adrift” — Steve Callahan’s terrifying story of shipwreck and survival — and I told him I had, and that if he thought that story was good, he should read “Survive the savage sea,” by Dougal Robertson.

This got them — my whole extended family, now — riled up, and the comments began to pour forth. Myles, reasoning that piracy was more of a threat than sinking, suggested that I acquire cannons. My dad chimed in: torpedos! Myles: machine guns! My cousin Jim: Missiles!

I opened another beer, and tried not to get defensive. Maybe I should bring their phone numbers, so that I could have the would-be-pirates call them directly to negotiate the ransom?

While home, I also added a few more names to the list of People Who Wish They Could Come Sailing With Us:

-My mother’s boss
-At least one of my folks’ neighbors
-Half of my friends, including one who’s just finishing grad school and afraid to look for a job
-At least one former coworker

Heckling and eager stowaways aside, it felt good to get away from the boat and gain some some perspective. Onboard Syzygy, it’s easy to get so involved, so focused, so lost within a project that it’s impossible to decompress or relax. At the same time, being away from the boat was also disorienting. Soon enough, withdrawn from the boat, I found myself getting antsy. I chalked it up as an urge to tinker. The urge to repair and build was so physical — like I needed to hold tools in my hands lest they curl up and wither — that I had to wonder if the sailboat thing hadn’t changed me.

I climbed up onto the roof of my folks’ house and did some caulking. I put down some new roof with my dad. I cleaned the gutters. I tried to go with the urge, but this was just regular maintenance. I still yearned to build something, and the opportunity that presented itself came, courtesy of my mother, in the shape of… a squirrel-proof bird feeder. It was no sailboat, but it was a challenge: could I use a little ingenuity to outwit mother nature? (The answer, sadly, was no. Squirrels are tenacious little things.) As I dug through the garage looking for parts, I wondered: do I enjoy asking for trouble? Do I tend to invite problems my way? In another sense, I was looking for an opportunity to solve a problem. Such opportunities are often compelling. Can I get up that rock? Can I get up that mountain? Can I get down that canyon? Can I run those 26 miles? Or how about: Can I fix up an old sailboat and sail it around the world?

I spent last week away from the Syzygy, too, visiting my family again. The urge to tinker was still there — I climbed up the Chestnut tree in the backyard and hacked off some dead branches, and sanded and painted the rusting wrought iron railings on the front steps — but even more evident was the urge to nestle in, stay put, have some coffee and just relax. After all this fixing-up-a-sailboat work, I needed a break. I needed to, as they say in the South, “set a spell.” So I sat. And that’s when I noticed the coolest thing: I’ve changed. I’m way more patient than I used to be (though still no saint). I’m way more eager to immerse myself fully in a task. And I’m more comfortable without distractions, just me and my thoughts.

This last realization occurred near the end of a six-hour, coast-to-coast flight, when I noticed the passengers near me getting fidgety, almost childishly so. I sat, knees bent, safety belt buckled, neck squished against one of those godawful airplane headrests that comes standard on those godawful airplane seats, and thought: this is nothing. This aint no sailboat, and this aint no ocean.

“I just want my mom to approve!” I huffed to my dad as we chatted one evening on the phone, a year ago, about my plans for sailing around the world.

There.  I said it.  After 31 years of doing my damndest to assert my independence from my parents, I realized I wanted desperately for my mom to approve of my future plans.

Her reception, three years ago, of this cockamamy idea to go sailing around the world with my two best friends could be termed luke-warm at best.  She was officially Strongly Against the Idea, for the obvious reasons. “You’re abandoning a career,” she’d said.  “You should stop being so reckless.  Why don’t you settle down with one of those nice girls with whom you keep finding a way to go separate ways. Why do something so dangerous?”

Her disapproval grew as our plan slowly manifested.  Shortly before we bought our boat, if I wanted to even talk about the sailing venture when i called home, I had to make sure only dad was on the line, otherwise I would face grim silence.  It only took a few times of sensing the steely look through the phone, and am pretty sure I sometimes heard teeth grinding together, before I realized to not bring up the topic.

I vented sometimes to my sister, admitting to her how important it was for me to have my mom say something to the effect of ‘go have a great time son!’

But why was it so important?  I suppose it’s obvious, she’s my mum.  I wanted them to be proud of my life, to think they had done a good job raising me, because I sure thought they had.  I wanted validation that my life is worth something, and if my mom didn’t approve, then it filled me with self-doubt.

My sister’s advice was always the same: Talk to her about it.  Let her know how you feel.

I couldn’t take it upon myself to face that conversation with my mom though.  So, cowardly, I avoided confrontation and discussion about it.

But I sensed an olive branch at an unlikely location. My mom, dad, sister, and I were in a large children’s furniture store, surrounded by baby-cribs and pint-sized dressers, over a dozen example baby rooms perfectly laid-out with every required baby accessory, shopping for furniture for the niece on the way.  My mom pointed at a large map of the world and quietly asked where we might be going.  Where was our route?  I sketched out an idea for her, mentioned a couple of places that I was really excited about like Thailand and India.  Then I gave her a hug.  I hope that hug said what I didn’t:  Thanks for asking mom.” And, “I love you.” And,  “Thanks for playing the role of parent and making the first step towards reconciliation.”

I felt better, but still uneasy.  And so a few months later I took the next step, and asked her if she and dad would come visit me in San Francisco over Thanksgiving, the winter holiday I usually spend with the fam.  She had adamantly declined previous invitations the summer prior, but this time she agreed they would come out.

Three months later, my mom stepped aboard Syzygy.  I showed her around the boat, pointing out work we had done, highlighting our safety improvements as well as some of the things I had learned along the way.

“See these wires, Mom? They’re called stays and we put in brand new over-sized ones all around the boat so our boat would be super-strong.  The deck is a little slick right now, but we are going to put down a new rough surface so that it’s safer to walk around on.  See these?  They’re called fairleads and I helped install them.  Hey Mom, check out the engine room!  This is what I love learning about.  Let me show you.”  I watched her furtively but intently, assessing her eyes, her noises, her tone.  ‘What was going through her head?’ I wondered.

I’m quiet by nature and often hold emotions inside; a trait I inherited from my mother.  So she was hard to read as she walked around the boat listening to me blather on anxiously.   But I think seeing the boat drove home that this concept I had been talking about for three years was real.  After seeing the boat, seeing the work and effort put into the boat, and hearing about the learning derived the experience, I think it came through that this wasn’t just a larger version of the carefree adventures we had taken so frequently in the past that, in the end, are individually trivial and superficial.  Jonny, Matt and I had worked hard at creating the opportunity for a life-changing experience involving enormous sacrifice and choices, and that we would emerge afterwards with an experience that would profoundly affect us; this will be a time of such greater import than the week-long climbing getaway. I think the enormity of our collective effort was made real when she saw the boat.  Or realized that I define those superficial carefree trips, but this trip, this trip will end up being part of what defines me, and by extension, a reflection of the values she raised me in me.  Values of which I am extremely proud.

The next  day, Matt and I treated my parents to a Thanksgiving dinner.  I’d never been in charge of a Thanksgiving meal before, though in the past I had taken on such important T-day duties as setting the table, making ice-tea, and heating up bread. Despite repeatedly being ordered to stay out of the kitchen under threat of being cut off from the wine, most of my pictures from Thanksgiving have somebody posing for a picture, and my mom in the background, in the tiny kitchen quietly trying to help.  In the end, Matt came through with a stellar turkey, my side dishes were generally a winner, and the meal was a success.

The next day was another big day.  We were going sailing.  Matt played an excellent role of knowledgeable captain, correctly intuiting such a role would help put minds at ease.  Not that he was acting; he was just being clear in his captain-worthiness.  This was the first time that any of us had taken the parents sailing, and the wind was perfect for it.  Enough wind that we were able to move along at 5-6 knots, but not too strong.  We rarely heeled over much, allowing everyone onboard to walk around without having to hold on for fear of falling over.

As we sailed out through the bay, I talked to my mom about the wind, the sails, work to be done and plans that we had.  We relaxed.  We drank some wine.  We laughed.  And finally came the moment that happens whenever we have someone new on the sailboat.

“Would you like to take the helm for a while mom?  I’ll be right next to you.  It’s a great feeling.”

She demurred initially, but with some more prodding from my dad and I, eventually wrapped her little hands around the wheel.  I could tell she enjoyed it.  Enjoyed the wind in her hair.  Enjoyed feeling the pressure on the wheel from water sliding over the rudder.  And at that moment, I felt like everything became O.K..  She was silently saying, “Go have a great time son.”

Happy Mother’s Day mom.  I love you.

I’ve never been much of a prankster. The furthest I ever took an April Fools joke involved telling someone I didn’t like his shirt. Yes: lame. I know.

As the day crept up this year my friend Amy regaled me with stories of epic April Fools jokes in her family. They sounded like so much fun. I felt so left out. To hear Amy tell it, April 1st was the only holiday worth celebrating.

So I got to thinking about a prank. I started by searching for a victim. An obvious target was Amy, since she so enjoyed such shenanigans. She’s a professional April-Fooler, though, and I figured she’d see right through my meager attempts. What I needed was unsuspecting victims. Someone who trusted me totally. Someone who’s known me for years, and as such, never heard me pull an April Fools caper. Oh, Matt and Jonny: I would pity you if it wasn’t me doing the pranking.

The three of us lately have been pushing our fingers into our temples, frowning in thought, throwing fake smiles every once in a while as our minds wandered toward the financial challenge before us. We have little money, a lot more boat parts yet to purchase, and (most importantly) a two year trip to save up for. We’ve tried prioritizing projects, but that only made the monstruous task before us more evident. What we needed was some levity.

So I sent them this e-mail:

—–

From: Jon Haradon
Subject: umm….news
Date: April 1, 2009 5:52 PM
To: Matt Holmes, Jonny Walman

So the Superintendent of my district swung by our school today. Apparently she didn’t get the message about me leaving. She said the district was starting a STEM (science technology, engineering and mathematics) charter school in the district and she asked if I would be interested in running it. She basically implied that if I wanted the job it was mine. It would pay a bundle, and as director of the school, I would get to decide exactly how it looks. Couldn’t be be more perfect with where I want to go with my career. I have to admit, I’m strongly thinking about sticking around and taking the job…. I’ll give ya’ll a call to talk about it tonight.

—–

I let them sweat on it for four hours while I busied myself. I actually forgot about it. Matt and Jonny didn’t. I’m not sure what happened, and they seem unable to recall the events during the time in question, so traumatized were they. I heard hints, though, of emergency meetings, soul-searching conversations, and maybe — OK, definitely — some searing words for me.

At 9PM, I called Matt.

“Hey what’s up?”

I feigned ignorance. After some pleasantries, Matt, slowly started, “So… uh… that was some bomb you dropped on us.”

I couldn’t hold the facade any longer — I told you I’m no prankster — and offered “April Fools?” I felt like a little kid lighting a fire-cracker the size of a torpedo, and sprinting away while the fuse quickly burned down.

Silence can reveal many emotions. In this long silence, I could hear disbelief and dumb-foundedness, and then relief mixed with incredulity.

“You’re shittin’ me….”

About all Matt could say after that was that I had better call Jonny. In the background, I heard Karen yell at me. She later flamed me on Facebook. I suppose I deserved it.

I called Jonny. He asked if I had talked to Matt. I confirmed, which was about all I was able to do before spilling my beans.

“Well I don’t know what he said, but I think I’m going to be a bit more harsh.”

I cut him off. Yet again, I lit the fire-cracker and sprinted in the other direction. “April Fools,” I timidly let out.

There was less silence this time. Jonny told me I ought to know how much he simultaneously hated me and was glad that we are the kind of people who are pranksters. He also said he’d need a week to get over the shock.

I hadn’t thought about what the hoax might prompt as an aftermath; I was just hoping to fool them, and definitely succeeded. It’s strange, but swindling my friends made me feel really good. Not because I lied, but because my friends were truly moved and devastated by the possibility that I might not join them. Yes, love reveals itself in strange ways.

In the next few days, Matt and Jonny mentioned that my firecracker actually prompted interesting thinking on their parts, something about soul-searching and opportunities in life and trusting your instincts and taking chances and friendship. For us to have conceived this adventure, have made it through over three years of planning, and be on the verge of leaving, there had to be some intense bonds of trust, respect, and compassion. Some serious man-love. And so while I might have severely severed that bond of trust, (and I currently don’t trust anything they say, because I know they are scheming up some way to way to exact revenge) I think I’ve nudged us all to think about what this journey means to us, together. We’ll need those bonds when confined for a months in a tiny, floating, 40-foot boat with no escape.

Unless they prank me by throwing me overboard.

Everyone at my school — students, fellow teachers, and administration — has known about this sailing adventure for a couple of years now.  So it shouldn’t have come as a shock six weeks ago when Sarah, the principal (and my boss), emailed me this note:

Jon, could you please get me your resignation letter as soon as you have a chance?  I want to start the search [for a new teacher] as soon as possible.  (Unless, of course, you’ve changed your mind : )

Thanks,
Sarah

But it did. It shocked me. The note made me pause, blink, blink again, and contemplate the magnitude of the choice laid bare in the e-mail — quit my job or not —  and how it all began with seemingly innocuous choices four years ago.

I’m about to quit my job, a job I’ve had for eight years. For Jonny, the purchase of the boat was the terrifyingly committing step. For me, this step is the extraordinarily committing one.  I think I know why. If things ever went sour or didn’t work out, I could simply shrug off buying the boat as a poor financial decision, like the decision I made to leave money in the stock market for the last six months. I wouldn’t be the first boat owner not to go sailing. But quitting my job is more undoable. I’ve got the job security of a teacher, and the comfort I derive from that snuck up on me, without me realizing it.  Why in my right mind would I let go of that?  I know plenty of other people who have asked me as much.

Four years ago, when the idea for our trip was first hatched, it wasn’t so committing.  Matt and I had just taken our first sailing course, and the idea seemed more fanciful than anything else. It was distant and intangible. As a first step, we committed to saving some money. No big deal. In fact, we treated the money-saving as a competition, and spontaneously e-mailed each other screenshots of our savings account just to rub in our positions. It was playful, like keeping track of who has done more weekly push-ups.  Jump forward four years, and it doesn’t seem like a game anymore. I’m walking away from a career.

I should have been able to fire off a resignation letter that same day in response. All it required was typing a few sentences, and after all, I’d already made the decision to resign four years ago. The decision to buy a boat took me down a path, and I’ve gotten so far along it that now much of what I do feels pre-ordained. My choices have become necessities of the circumstances I’ve put myself in, and I’m feeling swept along… and I don’t have any control.

To try and take back a little control, I spent six weeks chewing on the decision to formalize my departure from my job.  What ended up happening was it chewed on me.  One little person on my shoulder would try and call me crazy.  If acted out on TV, that would be a  caricature of my  mom.  Another romanticized the possibilities.  That little person whispering in my ear would be some amalgamation of Tom Robbins’ fictional characters.

I finally wrote the letter. I had to and felt that out-of control-feeling as I wrote it.  I hedged, however and asked for a leave of absence instead, which makes it easier for me to come back.  I also apologized to my principal for taking so long.   And even if I feel a loss of control in this particular decision, I kept coming back to the excitement I feel about what lies ahead.  About the learning that will happen, the experiences that will unfold.  Friendships created and deepened.  Now I’m impatient to get started, and scared about the scope and breadth of preparations we have yet to make.  I’m ready for the next chapter of my life. And it’s coming quickly!