Career Makeover: From Publishing Executive to Sailor and Author

Several years ago I had notions of myself that I wore like clothes: I was a book editor. 39. Single. Relatively successful. Stable. Secure.

Not unhappy.

Double negatives gnaw at an editor, though. "Not unhappy" became increasingly not acceptable. As the walls of my office slowly disappeared behind a fleet of fishing vessel photos, I became increasingly obsessed with the dream of salty freedom. So after one bad day at work, I did it: I quit my good job, sold my tiny weekend house in Pennsylvania, packed a duffel bag of clothes, and put everything else into storage. I then sank every penny from the sale of my home into the Bossanova, a 40-foot, 30-ton steel trawler that I moved aboard without a clue as to how to run it. Nine weeks of seamanship school later, I pulled away from the dock on my very first trip: a journey up the Atlantic coast from Florida to Maine.

The happiness I found at sea, the sense of accomplishment I felt, made it clear that I was more myself, more me, standing at the helm of my little ship than I had ever been sitting in a conference room. And even though the Bossanova now spends as much time at the dock as she does at sea, the lessons I learned on her pitching decks continue to color my days.

I can't count the times that someone has heard my story and said, "Oh, someday I'd love to [insert their fantasy here]." I'm not able to tell them how to make that happen, but I can offer what I now understand about many of the great go-for-it clichés.

Take the maxim "Do what you love and the money will follow." Unless you happen to love being a stockbroker, this is not necessarily true. I, for instance, abandoned a six-figure job with an expense account, bonus package, full medical and dental benefits, and a 401(k) plan for...genteel poverty. (Taking the proceeds of a house sale and putting them all into a 40-foot, 30-ton steel boat is probably not what Warren Buffett would have advised as an investment strategy.)

I can honestly say, however, that buying the Bossanova was the smartest thing I ever did. In the end, my adventure thrilled me in a way that a fat paycheck and job security never could. And I noticed how much less stuff I needed to be happy. I stopped compensating myself for my boredom with expensive things I didn't really need and inevitably lost interest in. So by all means, do what you love, but be prepared for that to be its own reward.

No one prizes reckless abandon more than I do, but "Carpe diem" is another adage that should never be taken literally. Seize the day if you must, but do so gently and never, ever shake it. All days are not alike, and some of them are just not meant for seizing. Some days you wake up with a headache, a dentist's appointment, and a long to-do list. But that's okay. Seize tomorrow instead and today follow the path of least resistance—because deciding not to seize this particular day is also a form of seizing the day, if you follow my drift.

Likewise, whoever came up with the bright idea that you should live each day as if it were your last has probably never taken this advice. Even the most self-controlled among us might become hopelessly self-indulgent as we faced our final chances—gorging ourselves on our favorite rich foods, emptying our savings accounts for that crazy extravagance we'd always postponed, quitting our jobs, blurting out our long-suppressed dislike for a particular colleague, or confessing our inappropriate crushes to the unsuspecting. What this cliché fails to address is that the day after your imagined last day quickly arrives and transforms your grand exit into an unmitigated disaster. Now you're chubby, broke, jobless, and have really spooked your cute UPS driver. And you're supposed to live this nightmarish new day as if it's your last. You see where I'm going with this—it gets old very fast.

Better advice is to live each year as if it's your last. Pace yourself. Prioritize. Most of all, enjoy the constructive daydreaming it takes to plan your fantasy, because if you don't, you're missing the whole point: Living each day as if it's your last is really about enjoying now. Even if you're not exactly where you want to be yet, there really is a ton of pleasure to be had in stopping to smell the rugosas along the way.

And how do you know where to go? That's easy: Follow your heart. Just remember that a heart is not a GPS, and it can lead you to some pretty unexpected places. For instance, I set off to navigate the eastern seaboard. But I also wound up falling in love, working as a dockmaster, and writing a book. None of these were ports I had planned on visiting, but I am who I am because of them.

Adventure comes with no guarantees or promises. Risk and reward are conjoined twins—and that's why my favorite piece of advice needs translation but no disclaimers: Fortes fortuna juvat. "Fortune favors the brave," the ancient Roman dramatist Terence declared. In other words, there are many good reasons not to toss your life up in the air and see how it lands. Just don't let fear be one of them.

Mary South is the author of The Cure for Anything Is Salt Water (HarperCollins).