My apologies for this Note coming so late in the day—back when I started writing these, it was in the afternoon for the same reason today is late, and the next few days will be as well; we’re on our annual vacation for New Year’s. My routine is different while we’re away this week, and my Note writing shifts to the afternoon after we’ve returned to the room to rest and prepare for the evening.

But, this year’s trip almost had a delay, or worse, it didn’t even happen–as I alluded to in yesterday’s Note.

We arrived at the Indianapolis International Airport a little after 4:00 and arrived at the Southwest counter to check in and drop off our bags. Thanks to a personal and business credit card combo, we have A-List status, which gives us priority at check-in and some other nice benefits, so getting there before 4:30 for our 5:45 flight was more than enough time for the Indianapolis airport.

I was feeling good and probably the most excited of everyone in my family for this trip–this trip is the one time a year I really get to step away, 95% disconnect, and spend my days in the sun, water, and in nature.

But a woman at the Southwest check-in had different plans for us.

After I handed our passports to her, she requested to see our forms from scanning the QR code on the side of her desk. Having no idea what she was talking about, she told me we had to fill out a form before we could check in for Jamaica–it’s one of the few countries with an online requirement. This was news to me, and before I had a chance to ask more about it, she told me to step to the side to complete the form and make sure to have our bags back an hour before boarding time—which was 15 minutes.

It’s been a minute since I have left the country, so I’m not up on all of the international policies, and I just followed her orders, scanned the QR code, and went to fill out the form.

And this is when I lost all optimism, became anxious, and was convinced our trip was screwed.

The form she said we needed was the customs form, which I should have known once I started filling it out that we didn’t really need and challenge her, but I was too flustered because the page was loading slowly, I had to find the hotel’s address, I’m watching the priority line fill up, and I have to try and complete five forms.

At one point, I just stopped, put my hands in my head, and conceded—it was 4:45, and the second form was circling, waiting to process.

I was defeated.

Proudly, Leo told me it was ok and everything was going to be ok—he was the calm one.

And so was Ang.

Thankfully, she returned to the desk to ask if we needed to wait to fill out the form until we were rebooked since we had to fill out our departing airport–and an angel greeted her.

Our angel asked Ang why she was worried about filling that form out, and when she heard the story, she told her to get me immediately and that she would get us on our flight. She rushed to print our luggage tags, rebooked our connecting flight by accident in the chaos or because she wanted to make sure our bags left Baltimore with us, and got us on our way–her departing word was “run!”

Leo and Ang’s positive energy saved us and brought us our Southwest angel.

Their energy also brought us a very short line at TSA, no bags pulled to the side (my camera almost always gets me flagged, and to our gate after a run before the A group even began boarding.

How we caught our first flight is a miracle, and I know it would not have happened if it weren’t for Leo and Ang; my energy was setting us up to head back home for the week for a staycation—which I’m not proud of because the calm and optimistic role is one I naturally fill. But at that check-in counter, I felt helpless and in one of the few situations that make me anxious–running late.

The downside to the chaotic morning was having a four-hour layover instead of the ninety-minute one we were supposed to have, but getting there later was way better than not getting there at all.

I didn’t know it, but that four-hour layover would provide some much-needed time to arrange transportation from the airport to our hotel.

Since we were getting in late and on a different flight than I had arranged for our transportation, I called the hotel to let them know and see what I needed to do to update that information. During this call, I realized that while I had an email response that the hotel was setting up our transportation, I never received a confirmation email from the third-party transportation company.

We did not have transportation after all.

Not having transportation isn’t nearly as big of a deal as the near miss of our flight, but transportation from the Montego Bay airport seems chaotic—the only times I’ve been to Jamaica, we’ve had transportation already arranged–and after the morning’s stress I didn’t really want to have to negotiate rates, hope that we get a good taxi company, and deal with unwanted stops along the way to the hotel.

After researching on Tripadvisor and Expedia, I found a reputable company and secured a ride on their website, which looked like it had been built in the early 2000s. It made me a little nervous that I was on a fake site. When we arrived in Jamaica, we'd find out if we had a ride or if I’d negotiate in the airport lobby.

Even less of a deal, but still a possibility for an inconvenience on our way down to the island was losing our A group seating when we were rebooked to our new flight. Because our new flight was so full, and we were rebooked hours before, we ended up in the C group—again, a three-hour flight with our family split up is hardly a big deal, but still not how we would have wanted it to be.

When it came time to board, I took Silas with me to board in the A-list priority right before family boarding and strategically sat in the back to try and save seats for Ang, Roman, and Leo. I hate trying to save seats, and if anyone had asked for any of the seats I was trying to save, I would have given them up, but my strategy worked out. I put Silas in the window of one row and my headphones on the middle seat (the one I was saving for Ang), and my bag on the aisle. If someone asked, I would have taken the aisle seat and told them the middle was for my wife—I’m pretty sure no one would have fought for that middle seat. I sat on the aisle of the row next to where Silas was sitting, and there was already a man in the window seat–I was betting no one would want that middle seat, and when Ang, Roman, and Leo got on, I’d have those two seats for the boys. I’m pretty proud of that strategy and glad that we all got to sit together.

In Jamaica, immigration and customs were a breeze (I completed our forms on the plane ride from Indianapolis to Baltimore). When we reached the lobby, I sent a WhatsApp message to our transportation company and waited for a response. Within a few minutes, I got a message back with a license plate number and description of the van—it was like their own version of Uber.

I was still uncertain about our transportation until I met our driver, and his infectious smile and warm laugh greeted us. Our short ride to the hotel was filled with his laugh, tons of history lessons, and a lot of great conversation. We could not have been luckier with our taxi driver/tour guide.

The final unknown and opportunity for things not to have worked out for us on the trip was our room situation. This year, I had to reserve two separate rooms, and while I requested that they be close to each other, the hotel made no guarantees. I was optimistic that the hotel would be able to make it happen, but I wasn’t sure after the transportation was not set up.

I’m sure you can guess how this story ends—we ended up having rooms right next to each other to make spending time together easier, despite being in two rooms.

Everything worked out.

Leo was right; everything was going to be ok.

But, it could have gone south quickly.

Had Ang not kept calm and returned to the counter, we would have certainly missed our flight.

If we had made a big deal about the woman’s mistake and forcing us to get out of line to fill out a form that wasn’t needed yet, we would have certainly missed our flight, and that negative energy would have spilled over into the seating on our second flight and our transportation.

If I had gotten angry about the transportation, then whatever transportation I would have eventually secured would have been a disaster, not the kind driver we got.

If we had been nasty and negative as we navigated the morning, we certainly would have ended up with rooms at opposite ends of the resort.

There were plenty of opportunities and reasons to be angry, blame others, and carry negative energy with us. After all, the mistakes were not our fault (although there are things I could have done differently, like confirm the transportation). And that negative energy would have been rewarded with more negative events—the law of attraction would have kept the hits coming.

Instead, we avoided further chaos and crisis by maintaining an optimistic outlook—even lifting each other up when needed, and we were rewarded by everything falling into place the way we wanted it to.

I know inconveniences while traveling to Jamaica is a very privileged problem to have, but the entire day is an excellent example of how the way you choose to receive what happens to you in life will directly impact the outcome.

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See you tomorrow and keep pursuing,

JC