Let’s be clear. I know you could care less about my vacation to Jamaica. Nothing annoys me more than when friends come back from vacation all excited and want to show you all their pictures. I love you, but I’m jealous. I’m also a member of the “it must be nice” club, so I get it if that’s what’s on the tip of your tongue right now.
But if you’ve been part of my INNER CIRCLE for any length of time, you know I talk about trips differently. Not so much what I did or saw, but what I learned. And what I want to remember. Some of which might be useful for you too.
Jamaica has been one of our favorite places for years. Trip #5, in 2022, was the best. We went to an all-inclusive at Secrets in Montego Bay with two of our adult children. We vowed to come back here for #6. Sadly, the kids can afford to travel but don’t have the PTO or the bandwidth. Since we’ve seen most of the touristy stuff on Jamaica, we decided to do a lot of nothing. Barb had workout plans to create for clients, and me and Silas Kane are collaborating on some short stories. Work out in the morning. Some work. Then nothingness. And lots of time staring at the ocean, thinking about stuff.
So, here’s some of the stuff I thought about.
This Vacation Felt Different
It was the first since I retired. Honestly, I’m not a vacation person. We took exactly three vacations when I was a kid, all just one or two nights. My first wife’s family took long, frequent vacations. It seemed ridiculous and extravagant for folks who didn’t appear to be working all that hard.
Then came divorce and debt and working two jobs, trying to get kids through daycare and school. Vacations started happening, but I always felt guilty for taking time off and spending money we didn’t really have.
And of course, I traveled for a living, so vacations were just an extension of work. I had a hard time relaxing.
As the kids grew up and left home, and as we had the means, we started taking more vacations. COVID slowed that down, but once it passed, we resumed.
Even then, vacations didn’t feel justified. My business slowed and I didn’t think I’d earned one. I always stressed over getting home, unpacking, and hustling to get business going again.
Watching the chicken man serving up some authentic jerk chicken.
This trip was different. I told myself repeatedly (and Barb reminded me too) that this was a retirement trip—and I earned it. And I made myself believe it. Each time I felt guilty sipping endless refills of Evan Williams on the rocks while watching the shimmering turquoise water, I reminded myself it was okay.
As I thought about my son and daughters wrestling with life, relationships, and everything else that keeps them awake at night, I remembered one rainy night in Chicago…
It’s 10:59 p.m. and my flight lands at O’Hare, two hours late. My connection to BWI left an hour ago. United automatically books me on the 6 a.m. flight. Now the dilemma: do I get a hotel for a few hours of sleep or just gut it out in the airport? I opt for the latter.
The airport is empty. As I walk through that long, illuminated tunnel under the runway, Gershwin’s Rhapsody in Blueplays over the intercom. United’s theme song. It always sounds regal and pompous to me, since I’m a Southwest guy.
It keeps playing. Over and over.
I find a quiet corner near my gate, pull out my jacket, eye mask, and Bose noise-cancelling headphones. Except—I forgot to switch them off. The batteries are dead. No spares. All the Hudson Books are closed. Without noise cancelling, the headphones are useless.
The floor is hard.
It’s cold.
My back hurts.
My legs go numb.
My shoulders ache no matter how I roll over.And the fucking Rhapsody in Blue plays on. And on. And on.
I barely sleep. The next morning, I get coffee, fly home, and leave a few days later to do it all over again.
That’s when I realize this trip is different. I’ve earned this vacation. And the next few. And I guess anything after that.
Habits Matter
In 2023, I adopted mindful eating and fast walking, along with some HRT. The mindful eating was the hardest. Well, maybe not as bad as giving yourself a testosterone shot in the ass once a week, but as a compulsive overeater, it was rough.
It took time, but I got results. I went from 224 pounds down to my average of 170. I walk three miles, four times a week, to my son Dustin’s house mixes. I rarely finish a meal. It became a habit I stuck with—even on RV trips.
And it became the expectation for this trip.
We walked nearly every day, Barb hit the gym, and we enjoyed the buffet breakfasts, light lunches, and dinners. The food was great, but I never finished a plate. I didn’t feel deprived. I certainly took advantage of the bar.
The morning we packed up, I stepped on the electronic scale in the room: 170.9.
Because fitness became a habit, I could adapt it anywhere. Even at an all-inclusive resort.
Cold Plunges Are Painful—but Good for You
Barb loves massages. I don’t. I went for a pedicure instead, which came with a pass to the wet spa.
Steam room, jacuzzi, then the cold plunge.
“Please Rose, can you share the headboard? The water is really cold.”
“What’s the password?”
In Titanic, Jack Dawson said falling into a frozen lake felt like a thousand daggers. He’s wrong. It’s more like a thousand needles. I went under up to my ears and counted to eight. That will get you a buckle at the rodeo so I figured it was good enough for the cold plunge. But Barb said you need two minutes. No way. And no way Jack Dawson delivered those lines to Rose while freezing to death on that damn headboard she wouldn’t share.
But afterward? I felt great. Slept like a baby. So good we went back again a few days later.
If you ever get the chance to try a cold plunge, do it.
Observation Brings Surprises
Most mornings, we’d get in PT gear and reserve lounge chairs, though it wasn’t necessary in September—Jamaica is quiet this time of year.
On my power walks, I zoned out to DiscoDust mixes, but also noticed things: cloud formations, a tiny black kitten I wanted to pet, workers spraying for mosquitos, an older couple strolling.
And then I saw The Nose.
A man with the biggest nose I’ve ever seen. Jimmy Durante had nothing on him. It might’ve had its own zip code. Impressive. Terrifying. More on him later.
Jimmy Durante. Big Nose was bigger.
Later that day, Barb and I passed a woman in a white t-shirt and backpack… and nothing else. Or so it seemed. For a moment, I worried she was in trouble—alcohol, maybe even something worse. Barb and I were trying figure out how to intervene when we noticed she was wearing flesh-colored shorts. Relief.
Amazing what you see—and assume—when you’re paying attention.
Service Providers Need Love Too
People rave about Jamaica’s vibe—friendly, warm, welcoming. But imagine the toll of serving unlimited alcohol to endless waves of tourists.
Bartenders at all-inclusives have a thankless job. They must serve without overserving. They also put up with bad behavior. First-timers drink like sailors on their first liberty after a long deployment. Second-timers bring the same attitude along with big Yeti cups for greater efficiency. Veterans like us know the alcohol isn’t running out—pace yourself.
So, when I go down to the bar to refill my bourbon and get Barb’s champagne, I see Big Nose giving the Jamaican bartender a hard time. He’s eastern European from what I gather from his heavy accent. His hairy back and shoulders are covered by a tank top that is struggling to wrangle his man boobs. His large nose is pitted and dotted with blackheads. She’s trying to communicate and he’s putting up a fuss about a green olive in his drink or something. Finally, he’s happy and leaves. She shakes her head and mutters something under her breath. The she looks at me with exasperation.
“What can I get you, mon?”
“Evan Williams on the rocks. And a champagne.”
Then I lean in.
“Hey, didn’t that guy have a really big nose?”
Shock. Curiosity. Grin. Then laughter. Hard, uncontrollable laughter. Tears streaming, almost falling over. She tells me I’d get her fired. We laugh together.
The next day, I see her again. I smile, tap my nose and wink. That’s all it takes. We laugh again. Good medicine.
The Value of Getting Away
It’s nice to step away—from routines, from people, even from pets. From the news cycle too. World events will unfold whether I read about them or not.
But none of it happens without a change of scenery. A change of perspective. Both are healthy.
And finally—set goals for your vacation.
When the kids were growing up, vacations often felt like FOMO. We took them because neighbors did. No goals.
In 2023, we went to Aruba with friends. Barb wanted athletic adventures. I wanted rest. Disaster. Now, we get aligned first.
This year, the goal was rest with a little work. We agreed—and it worked. Same with our last RV trip. It prevents arguments and disappointment.
Vacations are expensive, not possible for everyone. But if you get the chance, make the most of it.
Now, as our flight descends into Nashville, I’m thinking about unpacking, groceries, laundry, mowing, blowing leaves, picking up the dogs, and making peace with my cat Athena—who’ll be pissed I was gone a week.
Reality sets back in. But it’s tempered with knowledge and perspective I only gained because I took time to notice. Maybe that’s the best way to celebrate a vacation.
So, what trip are you planning next? And what do you hope to learn?