lessons from the sea

how (not) to choose work

In spring 2005 I joined the crew of a 42-foot sailboat as it was departing the US for a round the world voyage. I met the boat and crew in Florida, and we aimed to arrive in Fiji within five months. Our journey required that we pass through the Panama Canal. Gaining passage through the canal requires payment, and the canal charges by the length of the vessel. At 42-feet long, we were far from the top of the list. Priority was given to the boats that commanded a higher fee, that were designed to take up the full 1050-foot long length of the canal locks. Small sailboats waited turn, hanging out in a marina misleadingly named The Panama Canal Yacht Club, right outside of Colon, Panama where guests were casually warned not to leave the guarded gates unless in a taxi, or risk being mugged and knifed. Its main draw was a restaurant where the burgers were tasty, the beer was cheap and cold, and the crawling insects outnumbered the paying clientele. It was a place to spend time because there was no place else to go.

During the three weeks we waited, I spent most of my free time walking the docks, looking at the boats and speaking with other waylaid sailors. Boats flew under the flags of many different countries. The occupants were families, retirees, bootstrap sailors finally embarking upon a deferred dream, paid crew working for wealthy, absent owners, big groups, single handlers, all. During the day they made busy with repairs, reading, helping each other diagnose this or that issue, or arguing about routes, recipes and best practices. Everyone was doing their best to make good use of the time and make friends, but were impatient to be given passage to move through.

A few weeks into our wait, while walking the docks, I came a cross a beautiful boat, unusual and striking enough to cause me to absentmindedly stop and stare. All wooden, meticulously maintained, the line drawn from bow to stern, where the water met the hull, seemed perfect.

There’s a reason boats are rarely called “it.” Boats have names. They are referred to with gendered pronouns (most often female), and are often lovingly taken care of. They are at once, home, work, means of transport, and refuge. For sailors, for anyone who takes the time to notice, whether or not they know anything of boats, the lines of a beautiful vessel invoke a visceral reaction. This boat did that to me; it made me stop and stare.

“You like her?”

A voice, thick with Catalan accent, came from the bow. Feeling a bit like I had gotten caught staring at someone else’s sweetheart, I must have turned red, but tried to recover. “Yeah. She’s beautiful.”

He invited me to step aboard, and I did. As he showed me around, every detail up close better than those glimpsed from the dock, we traded sailor basics—where are you coming from? Where are you going? How long have you been waiting to go through the canal? How long have you worked on boats? And more. He was a far more seasoned sailor than I, single-handling a boat over 60-feet long for an owner & employer he spoke of with affection as a good friend. In contrast, I was sailing along as a part of a dysfunctional crew of five on a seaworthy, yet ungraceful vessel. He had experienced multiple ocean crossings, while I anxiously anticipated my first. He represented so much of what I aspired to become at the time. As I was about to depart, I told him, “Thank you. She’s beautiful. This is the type of boat I want to work on one day.”

My new friend paused, then looked at me hard. In the same thick, Catalan accent he challenged me.

“No….no. You have it wrong. It is not the boat that is most important.” Confused, and a bit surprised by his change in tone, I listened.

“There are three things that matter in seeking, in choosing, work. First: people. Who do you work for? Who do you work with? This is what matters most. You could be on a beautiful boat, going some place incredible, but if you have a boss, or a captain, that makes your life miserable? If you are sailing for a captain who has bad judgment? Bad skills? This is a place you do not want to be. It won’t matter how beautiful the boat.”

He continued, “Second – second is the project. You have a good boss? Good crew? Great. Yet if you are stuck sailing places you have been, over and over….? If your role never changes, if nothing is challenging, nothing is new? You will be bored. When you are bored, you will not care how pretty the boat. You must be excited about the project, challenged by the project.

“Third…third is the boat. If you work with good people, and if you have a project that’s exciting to you, then as long as your boat is seaworthy, you will be happy and interested and enjoy what you do.”

He paused again, and then finished, “Do not choose a job because you think the boat is beautiful.”


Long after I left my sailing days behind, I still employ this three-step process in looking at work, and when I haven’t, I’ve made poor choices. Boats make the choice more clear-cut. On a boat, you can’t exit if things get messy, you can’t jump ship (yup – maritime roots on that overused phrase) in the middle of an ocean.

On choosing for people: Choosing a bad captain, or a bad crew, may not only make for an unhappy experience, it can be dangerous. Working in a company for an unethical boss, working alongside people who you don’t enjoy, having direct reports for whose work you are ultimately responsible, but who are found to be untrustworthy, are potentially dangerous as well. At the end of the day, our experiences and our reputation are our greatest assets. Like our physical safety, we should be cautious of putting them into the hands of unknown people too readily. And this is before considering whether or not they are people you enjoy or learn from; work is where we spend the majority of our time.

On choosing for the project: Does the day to day of the work make you excited? Are you learning knowledge or skills you can use in the future? Are you gaining experience that is valuable? Is it something you believe in? That you are proud to be a part of? If not, as my wise Catalan captain friend said, you will be bored. And it’s hard to do good work, work we are proud of, when we are bored.

On choosing for the boat: Boat can be replaced the organization you are joining. Like the boat, how these appear from the outside, is what matters least. Yes, it needs to float—have a working business model, be financially solvent, we all need to get paid to live – yet at the end of the day, it doesn’t matter how impressive these seem if you don’t have the first two right.

The job that had led me to the mouth of the Panama Canal, where I met the Catalan captain: the boat was fine, the project was incredible–sailing around the world was a dream of mine, and then to get paid to do it?! I felt I had stumbled into something incredibly lucky. Yet the people I sailed with made it tough to enjoy. As a group we were a mess – different values, different communication styles, complete lack of trust and appointed leadership who insisted on power yet didn’t, wouldn’t, work to make the dysfunction better. I realized all of this one week into the journey and thought, “I should get off this boat,” but I had told everyone back home of my incredible, lucky, awesome adventure. I had given up another great opportunity for this one. I ignored my gut. I figured I could suck it up, tune it out, adapt.

I stuck with it, yet, I lived for time ashore. I grew to dread sailing, a lifelong love and passion, except when it was my turn to stand watch at night, when everyone else was asleep. When my contract was done and it was time to re-up, I declined. The opportunity wasn’t worth the day-to-day experience. In signing up I had neglected step one: work with people with shared values.

Without regrets, I flew home from Fiji and returned to Outward Bound, to work I believed in, to people who challenged me to be better at my work and made me believe I could do it, to a purpose I wanted to work hard for.

1. People, 2. Project 3. Boat. I’ve learned this lesson a few times. Yet, when I’ve gotten the order right? It’s been awesome. Work doesn’t feel like work, work is fun.