I don’t remember my first slice of humble pie, but I definitely can recall my most memorable one …
In 2011, I was still working for Costco Travel. As the Inventory Control Specialist for the Caribbean Buying Team, one of our responsibilities was to accompany other Travel team members on familiarization trips to Caribbean islands. The Dominican Republic was our biggest sales destination therefore a frequent training destination.
I had to fly here to be served this fine piece of humble pie.
FAMs, i.e. familiarization trips, were a privilege to travel and represent Costco Travel.
Or at least when I worked there. Each trip followed a similar itinerary: fly there, hotel site inspection, welcome group dinner, then sleep. Next morning, group breakfast, hotel inspection after hotel inspection until the end of business hours between 5pm – 6pm.
Afterwards the FAM leader, generally the Buyer of the destination, would either gather up the team for group dinner or cut us loose for the evening with THE EXPECTATION OF AN EARLY START the next day.
This was usually 7am – 8am.
I’m not certain why I carried the reputation of the ‘party boy’ but the leader would always side-eye me. “Don’t be late, ‘los“, they would quip. I shrugged, and thought:
Why call me out, yo?
Karaoke at 8pm
I hustled to my hotel room to dress down as a tourist. I understand that I’m paid to work, inspect these resorts / hotels, and report back but a grip of free time was expected.
It was usually after dinner, too.
As I hit the lobby area of the resort we were staying for the night before moving on, I spied a sign: Karaoke at 8pm, sign up at the front desk.
I had been karaoking at Malarky’s for a hot-minute so I thought I could flex the golden pipes in the D.R. I would survey the gathering crowd before picking out the song lyrics I knew forward-back, upside down and right side up.
After I signed up, I immediately became nervous and anxious. I thought, dude, you don’t know any of these people, and never will see them again. Just go up there, have fun, and let it be.
Naturally, I did what any red-blooded American that’s about to sing in public: I drank alcohol.

The host asked if I wanted to start off since I was first to sign up. I eagerly accepted the offer. At least I don’t have to ‘follow’ any latent superstar / American Idol contestant / authentic singer that’s sharking.
The open-air patio area of resort had been filled in with chairs. The performing stage was legitimately big enough for shows, events, etc.
I was asked my song finally. After I hear and observed some folks from the South, or ‘dirty South’ as they put it … I replied Garth Brooks’s Rodeo. I performed my song, I got that particular party to stand up and dress in the audience.
Once done, I strolled off the stage to join the audience. And enjoy the rest of the singers.
The next fella was a larger black man, picture Notorious B.I.G. or CeeLo. The song, Sledgehammer by Peter Gabriel, starts. I thought, interesting song to choose. I was judging the book by it’s cover, per se.
His first couple bars lets everyone know he has a big voice, and knows this song. It’s a polished performance for sure. By the middle of song, he had EVERYONE except for me, standing up, dancing in the aisle, and singing with him.
I was so #butthurt that I didn’t get this type of reaction with my song and performance! There I continued to sit, forced to eat this humble pie. I don’t remember any of the other singers, or really the rest of the night.
The next morning, after check out, I wheeled my luggage through a shortcut near the VIP lounge to the hotel lobby. In the heated pool was THAT SAME FELLA with a beautiful girl on each side of him!
I commented, “Hey man, that was a great performance last night.”
“Thank you, I’m glad you enjoyed,” he replied.
I can only assume that his golden pipes lured those lovely ladies over to him. I’ll never know for sure, but I learned that night to remain humble even in my thought process.
‘los; out