The Paul Simon Method of Life Transitions
Have you heard about the 50 ways?
It’s funny when you set your sights on something, pine for it, plan for it, wish&hope&pray for it and then….magic! You achieve your desire. Success. Bliss. And then it’s time to move on—for Time is always moving onward, arm-linked in lock-step with its pal Change (I’ve seen them do the “Hey, hey, we’re the Monkeys” walk on several occasions… whippersnappers: google it).
You enjoy your dream fulfilled until your focus changes and *POOF!* you’re onto the next something with equal planning and passion as if the earlier something was just a rehearsal. Of course, that’s assuming everyone is as fickle and flighty as myself. Mea culpa?
When hubby and I decided to exit, stage left, the American dream for tropical island living, capital-R Research became my vocation. From international health insurance, to work permit requirements, to the best part – traveling to multiple island locales on reconnaissance trips – I plotted and planned. Christopher read and researched. Decisions were made from the information we cultivated.
It paid off when we moved to a Bahamian island surrounded by teal waters and outlying cays, even landing work to pay for our pending dreamlife. I say pending because it didn’t quite pan out…the whole catastrophic hurricane flattening the island and forcing us back to the States thing.
But that opened the door for a new dream, a blank slate upon which we’d sketch whatever life we could imagine with renewed vigor. Because returning to the hamster wheel just wasn’t in the cards. It never will be again. That ship had sailed…annnnd segue.
Only the Rich and Famous own boats, and no one lives on them full-time. Yachts are for summer holidays in the south of France, or weekend jaunts to Southern California’s Channel Islands. Or so I thought ‘til YouTube taught me regular people were doing it. Selling all their possessions, their homes and cars, and sinking (uncomfortable pun) everything into sailing catamarans to live on the sea. And adventuring, exploring tropical islands at will. I wanted adventure. I still wanted tropical islands. We’d already sold everything and thankfully hadn’t bought in the Bahamas before the storm, so we had the funds. Barely, but we managed it.
Buying our (non-sailing) boat was my next obsession. Eight-hour days of hunting online listings, comparing models with amenities with age, and of course, price. Once we lucked into our beautiful floaty home, learning how to live and maintain and, well, move our transient island was all consuming, requiring a level of hyperfocus reserved for air traffic controllers. On Thanksgiving weekend. We were responsible for EVERYTHING one needs to live, aka the systems dirt dwellers take for granted like fresh water, sanitation (eww, sewer stuff), generating electricity. Tons to learn. I think I’ve earned a masters in maritime, and my brain couldn’t absorb any more.
Almost four years after moving onto my dream home on the water, the sale closed and the new owners took over.
Last week we moved half of our earthly possessions off the boat, pulled the remainder from a storage unit we’d paid into for years, and hit the road, which is new. We’ve done very little driving since our “car” was an eleven-foot inflatable dinghy named “BOB” taking us from the mother ship to the shore.
Embracing our newfound lifestyle of full-time travel, we decided to overnight in New Orleans. The Big Easy on a Saturday night is an experience I hadn’t yet enjoyed, so why not? As we walked down Canal Street from our hotel to famous Bourbon Street, I gazed at the sparkling marquis above the Saenger Theatre. In concert: ‘60s folksinger/pop rock icon Paul Simon.
Serendipity.
Last week, a song popped into my head. To be fair, that’s not a unique occurrence. My mantra: a song for every moment; a moment for every song. Random songs I haven’t heard for yonks often play in my mind’s background. My brain must be pissed I canceled that Spotify subscription and creates its own playlists. In the sleepless wee hours the first night off the boat, in an Airbnb on a bed that didn’t bob or sway, my widdle bwain amused itself with a Paul Simon tune from the mid-seventies, drafting its own lyrics to capture my recent life change. The needle dropped on 50 WAYS TO LEAVE YOUR LOVER.
Apologies to Paul Simon:
“I’d like to help you with your struggle to be free
There must be 50 ways to leave your boat life.
Just jump off the deck, Beck(y)
Make a new plan, Jan
Then hop into BOB, Rob
And listen to me.
Get off the hook, Brooke
No need to look back, Mac
Just leave ‘em the keys, Lee
And set yourself free.”
That’s enough ways; I’ll spare you the rest.
The aloofness that emerged with this insomniac earworm experimentation surprised me. I expected lots, LOTS of emotion with this change. First because I loved this boat. I loved the lifestyle, the freedom, the sunny days and salt air and dolphin escorts and island hopping. But also because transitions are challenging, even the ones of our own choosing. Change may be the only constant, but that doesn’t make it easy.

We are emotional beings, and I made space for the tears and grief I knew would come. So far, they haven’t. A solitary moment immediately after disembarking, but since then zippo. Perhaps it will come later, when the transition phase is complete, when we’ve booked our tickets and stored the few items we decided to keep but can’t take with us on our yearlong expedition to we-still-don’t-know-where. Though that in itself speaks volumes.
In choosing an unconventional life of adventure and exploration over of rooting to one place, I don’t know when this transitional phase will be complete. Life is forever changing, forcing us to adapt and deal with whatever crosses our paths. So, aren’t we humans always in transition? Maybe age and lived experience are finally teaching me to embrace the unknown twists and turns. As my forthcoming memoir illustrates, one thing’s for sure: no matter how much planning and choreography and best intentions, sometimes life cartwheels instead of waltzing, turning those plans on their head. Learning to accept Change on its terms, with as much grace and patience as we can muster, might be the best way to keep Moving Forward. I’ll keep some space for the feels, in case they show up sometime.
Question: What earworms invade your psyche, and do you encourage such activity by, say, rewriting lyrics or anything fun? (AKA should I contact a mental health professional? LOL)





Wonderful essay, Wendy!! My song last week, when I had to give the dog a bath at 10pm and then clean out the tub: Bobby McFerrin “Don’t Worry Be Happy”
Music runs through me too; it comforts me and motivates me.
I sheltered at a friend’s Brooklyn apartment each weekend night while my hubby stayed in NY for his shift at Sloane Kettering before returning to CT for work. I had the sleepover shift of Sunday through Thursday. I would lie on the floor under her grand piano , listening and feeling the tunes from Phantom pulse through my body. I felt I was in the safety zone there, before I had to return to brightly lit hospital corridors and my daughter’s phase protocol (read: experimental therapy). The “Music of the Night” floated all around me. Breathe.
Now in my later years, music still keeps me going. I swim every morning with tunes from Simon & Garfunkel resounding in my brain. And Joanie Michell and The Corries push me along too. Breathe.
I am searching for music to guide me through these uncertain times now. It will need to be powerful, I think.