Recording this from Mykonos, Greece, as our ship pulls into port on what should have been a podcast release day. Instead, I'm taking a break—and sharing something more personal.
If you know anything about me, you know I don't like vacations. Especially long vacations. Especially vacations that take me far from home. I come to you today from Mykonos, Greece, 5,500 miles away from home, seven time zones ahead. What?!
When my wife Tywana and our friend Tom started planning a Mediterranean adventure over a year ago—three days in Venice followed by a seven-day Greek isle cruise—I'll be honest: I was hoping the day would never come. I said yes because, well, September 2025 would never come.
But here I am, sitting in Mykonos, Greece, on Tuesday, September 9th, watching the beautiful hillsides rise up from the Ionian Sea. We pulled into port in the dark. When I woke this morning, I opened the curtains to see the lights of Mykonos. It feels surreal, and I need to tell you how we got here—and why this journey has changed everything I thought I knew about taking breaks.
The Unlikely Travelers
I'm here with six of my dearest friends, including Tywana. These aren't casual acquaintances—these are people I've known for at least a decade, most for over twenty years. We've lived life together. We've weathered challenges, celebrated birthdays, attended funerals, and rung in New Years. We're all over 60 now, the youngest being 61, with me bringing up the rear at 64. We’ve had parties. We’ve had funerals.
We're a group that has faced real adversity, as have all senior citizens. Among us are people who have overcome life-threatening illnesses, someone who has lived with Type 1 diabetes for over 50 years with all its complications, and those of us dealing with significant losses.
But there's one story that makes this trip particularly meaningful.
Lisa's Courage
Five months and two days ago, our dear friend Mike passed away suddenly. Mike was 59, just three weeks from turning 60. He was supposed to be on this cruise with us. Instead, his wife Lisa faced an impossible decision: cancel the trip or somehow find the strength to come without him. Yesterday was the five month anniversary of his passing.
Lisa chose to come. But here's what makes her decision even more remarkable: the day after Mike's heart attack, Lisa had one too. So yesterday—as we explored the Greek islands together—marked the five-month anniversary of Lisa's heart attack.
Today is also another anniversary: it would have been Lisa and Mike's 30th wedding anniversary. They celebrated their first anniversary in Athens— our destination for tomorrow.
The Climb
Yesterday, my wife and I decided to tackle the famous steps of Santorini—587 steps rising about 300 feet above the sea. What they don't tell you is that these aren't regular steps. They're only a few inches high but spaced about three yards apart, creating an irregular challenging climb.
Tywana made this climb five years after double knee replacement surgery. I made it despite my own physical limitations as a 64-year-old. But when we reached the top and looked back, there was Lisa and her son, Nick. Lisa had made the entire climb just months after her heart attack.
Metaphorically and physically, what a climb we've all made just to be here.
The vertical climb of the steps of Santorini, specifically the Karavolades Stairs connecting the Old Port to Fira, is approximately 400 meters (about 1,312 feet). The staircase consists of 588 steep and uneven steps that ascend this height from sea level to the town of Fira on the cliffs of Santorini
48 Hours of Freedom
When we pulled out of port last Saturday, the plan was to spend a littles than 48 hours at sea. I have to admit, I kind of freaked out. I'm slightly agoraphobic and claustrophobic, and the thought of being somewhere I couldn't escape for two full days was terrifying. By the time we boarded, I'd already been away from home for four days—farther than I'd ever been—and we were heading even further into unfamiliar time zones.
But something unexpected happened during those 48+ hours without touching land. I didn't hate it. I didn't even dislike it.
I spent time with my friends, watched shows, enjoyed incredible food and drinks, and simply had a great time. For the first time, I understood what people mean when they say "it's about the journey, not the destination." I've always been a destination guy, always moving from place to place, trying to get to the next thing. But this experience taught me to slow down and be present.
Taking the Break
Today was supposed to be podcast release day. I had everything prepared to launch the interview I had recorded before leaving—most of the work done, so I could finish up on my laptop while traveling. But you know what? I decided not to do that. I'm taking a break. We all deserve breaks, and I'm finally learning to take mine.
Normally, by this point in any vacation, I'd be itchy to get home. But I'm genuinely enjoying this time. We still have four more days—stops in Athens and Split, Croatia—and for once, I'm not rushing toward the end.
The Bigger Picture
As I look at our group, I see people who have overcome tremendous challenges. Lisa is here with her son Nick, carrying Mike's memory with her but refusing to let grief stop her from living. Mike is here with us in spirit—we love him, we celebrate him, and we're honoring his memory by embracing this journey together.
This group is bound for life. We're friends for life.
It's Never Too Late
I'm not a traveler. At 64, I'm definitely a homebody. But I'm enjoying this trip tremendously, even though I complained about it for the entire year leading up to departure. It's never too late to surprise yourself, to discover new joys, to embrace experiences that initially make you uncomfortable.
Sitting here in Mykonos, I'm reminded that our time here on the planet is short. I spent some time alone with Lisa a couple of days ago, on the ship. It's natural to think about what we don't have—that's human nature. But whether we have a minute, five minutes, five years, fifteen years, thirty years, or fifty-nine years on this planet, whether we've been with someone for a short time or for thirty-five years like Tywana and I have been—it's all a blessing. Mike is the kindest, gentlest soul I’ve ever known, and we are all fortunate to have had him in our lives, no matter how long or short that was.
No matter how long or short our time here, the most important thing is to enjoy the ride.
The Lesson
I'll be back with regular episodes soon, but today I wanted to share this experience with you. Sometimes the journeys we resist most are the ones that teach us the most. Sometimes taking a break isn't just okay, it's necessary. And sometimes the best way to honor those we've lost is to keep living fully, to keep climbing those steps, to keep embracing the journey even when, especially when, it scares us.
Grab life and take everything out of it. The ride is shorter than we think, but that makes every moment more precious.
What are your thoughts? Have you ever taken a journey that changed your perspective? I'd love to hear from you.
