When a Well-Planned Dream Turns Into a Beautiful, Stressful Nightmare

Posted by Alejandro Hilton


I once told my cousin — who had seen every twist and turn of my musical journey:

“If I get confirmation for my gig at Hard Rock, I’m off for three months.”


At the time, everything was almost set. The only piece missing was confirmation for the first show of the tour. Two weeks before my planned departure, I finally got the green light. What was supposed to be a 3-month tour transformed into an unexpected 7-month adventure—packed with music, chaos, surprises, and lessons I carry to this day.


But let me rewind a bit.


That year, my son’s mother had moved with him to a town ten hours away from mine. It hit me hard. I felt stuck, powerless. So I turned that pain into momentum. I started reaching out to towns along the way, offering to perform—thinking, “If I’m going there anyway, why not share my music too?” Slowly, it evolved into something bigger. I thought, why stop at the region? Why not tour all the way down to Argentina?


And just like that, a dream tour began to take shape—completely independent, fueled by donations and goodwill from each venue.


Now, people often think I’m well-off because I travel and play music. But the truth? Back then, I barely knew how to use a smartphone. My camera had only 2 megapixels. I had no Google Maps, no mobile data, and I could only access the internet when I found free WiFi. I looked like I had it together—but I was winging it every step of the way.


When the first show was confirmed, I booked the earliest flight to Playa La Miel, a place I’d heard was filled with stunning beaches and hills. But I was in for a surprise.


I showed up at the airport thinking I could just buy the ticket and fly.

Wrong.

They told me I’d have to wait three weeks for the next available seat.


Still, I believed not every flight could be full, so I returned to the airport every day from 7AM to 3PM, hoping for a cancellation. On the fourth day, it happened—I got on the plane.


It was hilarious—people thought I was staging a peaceful protest. Some even joined me, sitting in silent support. That moment, with total strangers rallying around a musician trying to catch a plane, was oddly beautiful.


I finally arrived in Playa La Miel, but I only had two days there because I’d already lost a week. On the flight, I met a group of biologists who shared fascinating insights about the region’s flora and fauna. Life was teaching me to stay open, even in chaos.


From there, I hopped on a night bus and reached Medellín at 6AM. I was exhausted. The hotel manager noticed and, with incredible kindness, let me crash on a couch in her office until check-in at noon. That small gesture felt like a good omen.


In Medellín, I met travelers from everywhere. One guy really inspired me—he was riding his bicycle from San Francisco to Ushuaia, Argentina. That kind of courage fired me up.


Then came the night of my first international show—Hard Rock Café Medellín. I stayed in El Poblado, invited everyone I had met, and… of course, we hit some technical difficulties. But the sound guy worked his magic, and somehow, everything came together.


In the VIP room, it was just us. I didn’t even know I was allowed to bring guests—everything was so new. But we laughed, ate, drank, and celebrated. It was messy and magical. That night changed me. It killed my fear of traveling alone.


Sure, many things went wrong later. But that night? That night showed me I was on the right path.


This tour wasn’t polished. It wasn’t sponsored or planned by a big agency. It was just me, my guitar, a secondhand phone, and a heart full of hope.


People sometimes say I’m lucky, or that I live an easy life. But the truth is: I survived on WiFi, faith, and shared experiences. And every little win—every smile, every show, every shared meal—meant the world.


And the story doesn’t stop there. I’ll be sharing more as my memories pop up—especially those flashbacks that Facebook loves to remind me of, 11 years later.



📸 Want to see the real journey?

Click here to visit my Instagram and check out the photos and videos from the road. Every picture has a story behind it.


📖 Love this story?

Grab a copy of my book to read the full story—uncut, raw, and unforgettable. Click here to buy it.



Thanks for reading. And remember—sometimes the best stories begin when everything starts to fall apart.

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