Syzygy Sailing

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!