Try talking to a glass of water. Crazy, right? Then how is it that the sea seems to speak to me? I know it’s no more angry in storm than calm, that indeed it bears no emotion, and yet I wouldn’t be human if I didn’t see some meaning in its many faces.

After being diagnosed with terminal brain cancer in May, 2011, at the age of 36, I was due for a dose of meaning. Surgery, radiation and chemotherapy treatments occupied the next two months. By August I was feeling strong, but also bored and useless.

I was visiting friends at Damariscotta Lake, on a picture perfect day, when I could no longer bear to sit. I walked into the water and swam away. Miles away. I was never more exquisitely alone, between dark depths and a bright blue sky. I returned changed.

After that, I wanted only to be in the water or on the water, never mind the cost. My death would come in a year, statistically speaking, so why not enjoy what life I have? I bought a wetsuit, a kayak and a sailboard, and hurried to deplete myself in pursuit of the moment.

I paddled and sailed in Casco Bay fearlessly but recklessly, having at once a will to endure the worst and a wish to die instead. Asked “What’s the worst that could happen,” I found no answer urging me to caution. One day in late October, I tried to sail around Peaks Island but the wind died. A tidal current streaming out of Hussey Sound pushed me miles off shore. I sat on the board and waited, never thinking of calling for help, but the Marine Patrol spotted me and scooped me up, along with the board and sail.

I made a point of saying I was warm in my wetsuit. “You were headed out to sea,” said one of the officers. I showed them my strobe light. They were not impressed. I thought I might blog about it later. They just wanted to keep my name, and theirs, off the front page of the newspaper.

That was my last outing of 2011. With winter came a higher dose of chemo and paralyzing nausea. It felt like someone stuck his hand down my throat and pulled my stomach out through my mouth. Spring limped home, finally, and I began to prepare for the summer that was forecast to be my last.

The deed I chose as my ultimate test and farewell voyage was windsurfing from Portland to Bar Harbor in midsummer. A wiser person would have acquired a more capable craft, perhaps by rental or loan, but I was ever chasing ideals of self-sufficiency. The right approach, I convinced myself, was low-tech and lightweight, amphibious and adaptable.

I christened the sailboard HERON, though it’s more like a hunk of foam than a boat. I outfitted it with pad eyes and elastic deck lines for holding gear. I made a paddle (my motor in still air), a big dry box and a bivouac sack. I bought a marine radio and waterproof charts. I trained myself in the awkward task of de-rigging on the water: detaching the boom from the mast, and mast from sail, then rolling it all up in a bundle.

Despite these preparations, I continued to learn things the hard way. Soaking my cell phone in salt water (and ruining it) proved zipper-tab sandwich bags are not waterproof. Being caught on the water in a thunderstorm proved my “weather eye” needs to look out! And then there was that (other) time the wind died and stranded me. (I’d left my paddle at home!)

Perhaps the most damning of my oversights was failing to keep in touch with my windsurfing buddy, Dave. We were supposedly sailing “together,” but the southwest wind was strong and I was blown all the way to Mackworth Island. He texted to check on me, but it didn’t seem urgent and I didn’t answer.

It did not occur to me, at the time, that Dave might be concerned for my welfare. Did I not have “whatever, man” written clearly on my face, as if to ward off all reasonable concern? I de-rigged and began to paddle over short waves back to Portland.

I noticed a few unusual boats on the water, including a large Portland Fire Department boat. Then the Harbor Master’s motor skiff zoomed up to me. “Are you Bogart?” a man asked. I was taken aboard and shuttled back to East End, where an ambulance and fire engine were waiting. Including the Coast Guard effort, it might have been the greatest waste of emergency services in history that would have been avoided by answering a text message.

Finally, in mid-August, I set out in the rain on the voyage of a lifetime. The wind barely sighed. I’d covered about a hundred yards when the low sagging clouds split open and poured. I detached the mast base, laid the fully rigged sail over the board and sheltered beneath it.

The excitement of departure was still fresh, but it didn’t take long to wear off. Progress was maddeningly slow in the soft air, and the current was pushing me inshore when I needed to get out. Fog shrouded the sea lanes. Rockweed was strewn across the bay and fouled the centerboard.

I struggled to hold a course northeast between The Brothers, then pointed windward of Clapboard Island and fought for every inch. Over the course of a mile I gained only ten yards to the wind, and it wasn’t enough to clear Clapboard’s shoals. I hit a rock, lost my balance and toppled over clumsily.

It seemed to happen in slow motion. It was ridiculous and silly. I was unhurt, but there was something wrong with the rig. The mast base extension, an aluminum tube that connects the mast to the mast base, was hung up on the rock and cracked in half. My heart sank. The trip was over.

But I had my cell phone, and thought to contact a few other windsurfing locals. Dave texted back. He offered to meet me in Falmouth with a replacement!

With the exception of Dave’s valiant effort, which saved the trip, day one was a bust. I covered only four of the hundred-or-so miles to Bar Harbor. I slept on a tiny islet just south of Clapboard, near the site of my crash. Above the crowns of its two broad oaks, the orange glow of Portland’s lights in the wet sky said I had yet to leave home.

Look for Part 2 in the August issue of The Working Waterfront.