My name is Richard Coleman. I’m 55 years old, from California, and most of my life has revolved around business.
I built my money in software and cybersecurity, sold two companies over the years, and eventually reached the point where work became optional. I still invest in projects occasionally, mostly because I enjoy the process, but these days I spend more time traveling than sitting in offices.
After my wife died, I started moving around constantly.
Not in a dramatic way. I just realized I didn’t enjoy staying in the same place for too long anymore.
Travel became routine.
Europe, South America, Southeast Asia, islands most people haven’t heard of. I’ve stayed in luxury resorts, rented yachts, flown private when it made sense. But honestly, the things I remember most usually have nothing to do with luxury.
It’s always the unexpected situations.
The random people.
The places that weren’t planned.
I ended up in the Philippines after leaving Hong Kong earlier than expected during a business trip.
I booked the flight almost impulsively.
At the time, I figured I’d stay maybe ten days.
That turned into nearly three months.
The country felt unpredictable in the best possible way.
Every day something happened.
One afternoon I got invited to a birthday party by people I had met only twenty minutes earlier at a beach restaurant. Another time I spent an entire night stuck near a dock because bad weather shut down transportation between islands.
Nobody around me seemed stressed about it except me.
People there adapt to situations differently.
I met Isabel in Palawan.
I was trying to rent a small boat for the afternoon and getting nowhere because I clearly misunderstood how the process worked.
She overheard the conversation, stepped in laughing, and told the guy:
“You’re charging him double because he looks expensive.”
She said it directly in front of him.
Honestly, she wasn’t wrong.
She helped me negotiate a fair price, then casually asked where I was planning to go.
I told her I had no real plan.
She smiled and said:
“That’s usually when the best trips happen here.”
That ended up being true too.
