Journey to San Jose (Pt. 1): The Not So Calm Before the Storm

Always have a backup plan

Sep 05, 2025

It’s a few hours before our flight is supposed to leave.
We’re feeling good about everything.
We just got our exit trip tickets to Puerto Rico.
Now we can relax.
Or so we thought.

Then it happens.
Something that completely shakes up even the best-laid plans.
Something we all dread when flying.

We get an email notification with the subject:
IMPORTANT! The departure time of your flight has changed

As if that wasn’t bad enough. Our flight changed from 11pm to 4am the next day!
Your flight is now scheduled to depart from Miami International Airport at 04:00.

Delays are annoying no matter when or where you’re flying. But a delay until the wee hours the next day, when you are flying to another country, with all your possessions, and your dog in tow? That’s an entirely different level of stress.

I might usually be the stoic one, but this time around, it was Anita's turn.

Airports are one of my least favorite places. Everything about them makes me uneasy. I even dropped my laptop at the Copenhagen airport and shattered the whole screen there.

I start rambling out all the things we need worry about:

Should we leave at our regularly scheduled time?
Should we leave in the wee hours of the morning?
What do we do with Pookie that many hours at the airport?
What do we tell Anita’s sister, who’s also helping us with this trip?

Meanwhile Anita is sitting next to me cool as a cucumber. She is texting her sister about the situation, and they get right to action.

Grace is already at the airport where she’s able to physically go to the airport hotel, and check their availability – my earlier attempt looking online went nowhere.

While I’m still frantically running scenarios through my head, Anita and Grace coolly book the hotel room.

Anita turns to me calmly and says “Grace found a room available at the airport hotel. We are going to book it.”

I finally calm down. All that self-inflicted stress gone in an instant. I’m so glad Anita and I are doing this together.

We really are the perfect team — picking each other up, balancing each other out.

Sometimes I hear people complain about their partners. “We always argue,” they say. Honestly, I don’t know what that’s like. I can’t remember us having a single real argument.

Moments like this remind me how good I really have it.

Bzzzztttt. Ugh. The dreaded sound that means it's time to get up. I usually snooze it at least a couple of times.

But theré’s no time for that today. Even though we only got a few hours of sleep, it’s time to go. Ít’s 1am and our flight leaves in three hours.

We went scouting the night before to see where we could get a quick breakfast. The only thing open is a 24 hour Subway. Not really my idea of breakfast but it will have to do.

After finishing our subs, we make our way over to the check-in counter. It’s in another terminal so we have to push all of our luggage across the terminal.

Anita and I are pushing two checked bags.
One of my check bags has my carry-on bag sitting on top, the other has my backpack.
Anita’s checked bags have her carry-on and Pookie’s carrier sitting on top.
Grace has the last checked bag with Anita’s backpack on top, and her own carry-on bag alongside.

I wish I could’ve heard the thoughts of the people who were watching us. It must have been a sight.

If that weren’t embarrassing enough, Pookie starts going crazy inside his carrier.
He’s spotted another dog, and he’s not having any of it.

This is the thing we feared most when flying with Pookie. How do we control his barking when nothing works under the best of scenarios?

Luckily, Grace just happens to have a blanket in her arsenal. So we quickly throw it on top, and just like that the barking vanishes. But we need to have a better plan for the flight itself.

When we arrive at the gate, it’s around 2am, but there’s no one there to check us in. An hour goes by and finally gate agents arrive. We only have an hour to get through security and to our gate before the flight leaves.

We’ve made it through security and it’s time to give Pookie the other half of his pill.

We go to one of the mini markets.
Buy a string cheese.
Stuff the pill into the cheese
He gobbles it up.
Let’s see if that works.

Pookie’s relaxation medicine is a little miracle in a bottle. Part dachshund, part chihuahua, 100% barker — and yet, with one tiny pill in a piece of string cheese, he melts into dream land.

Weeks later, it would come to the rescue again, not for barking this time, but to calm him after an allergic reaction made him itchy and miserable.

But for now, it’s just helping him get through a flight we’ve been dreading for months. He slept like an angel the entire way.

We are landing at the San Jose airport. And it’s been one of the smoothest flights we’ve ever been on. After all the struggles, hard work and delays, we are finally here.

The thing we worried about the most, Pookie’s behavior on the plane, was not an issue at all. We’re finally here. The day is still young and there’s so much to do!