I was 19. Jamaica. I was traveling with an older friend, Rino.
My mom was a flight attendant, so I was flying standby on her employee pass. Free flight — if there was a seat. No seat, no flight.
A few days before heading home, I checked the flight. Looked wide open.
It’ll be fine.
So, naturally, I did what any 19-year-old would do: I spent my emergency money. More Red Stripe. Souvenirs. Whatever else seemed like a good idea at the time.
Then I got to the airport.
Overbooked. That means I’m not getting on the flight.
ZERO
My brain went into a spiral.
Avraham, you’re so stupid. Why did you do that?
Then the panic: What am I going to do? I’m all alone in Jamaica. Where am I going to sleep? The resort might not even take me back. What is my mother going to think?
And finally: Those pilots better say yes. I’ll beg if I have to.
I had zero money. Not “low on cash” — zero. And I was stuck in a foreign country with no way home.
Rino? He had a confirmed ticket. Paid in full. He shrugged. “I’m sure it’ll be fine.”
It was not fine.
I begged the agent at the counter. Back then, you could sometimes fly in the cockpit — the jump seat. She said it wasn’t up to her. It was up to the pilots.
I had no control. I just had to wait.
They said yes.
I don’t remember much after that. I crashed the second we took off and woke up at landing. The stress had wiped me out.
MOMS ALWAYS KNOW
Here’s the part I found out later:
My mom knew me well. Mother’s intuition. She was working another international flight at the time and got her pilots to send an ACARS message — basically a fax between planes — to my pilots.
“Is my son on your flight?”
They sent one back: “Yup, he’s here in the cockpit. Crashed out and snoring. Looks like he had a good time.”
Moms always know. ✈️
FAST FORWARD 18 YEARS
I’m 37. Married. Kids. Flying internationally with my wife for our 10-year anniversary. Her first time on a standby pass.
We were staying with family friends — incredibly generous people who made the trip affordable.
We had a plan. Daily spending allowance — portioned out ahead of time. Emergency cash set aside. The flights looked open, but I knew better than to trust that.
Good thing.
First flight: “Sorry, the plane is over its weight capacity with cargo.”
Second flight: Same thing.
My wife was crying. We had kids at home being watched by other families. This was supposed to be a getaway, not a stress test.
But me? I was calm.
NOT CALM BY NATURE. JUST PREPARED.
Not some moment of enlightenment. Just years of doing this. Of knowing that “it looks fine” means nothing. Of having been the guy with zero dollars and a racing heart — and deciding I’d never be that guy again.
I had money. I had a buffer. I had a plan.
We got on the third flight. We overstayed at our hosts’ place by about five days — they were incredibly gracious, even though we felt awkward inside. (If you’re reading this, thank you again.)
We made it home. No panic. No begging.
And here’s the thing — we didn’t miss out on anything.
We did the touring. The restaurants. The relaxation days. The daily spending plan had flexibility built in. We came home feeling reenergized and responsible.
That’s the goal. Not restriction. Freedom with intention.
TWO VACATIONS. TWO VERSIONS OF ME.
At 19, I thought “it looks fine” was a plan.
At 37, I knew better.
Here’s the thing: Things come up. Flights get bumped. The car makes a sound it shouldn’t.
The unexpected doesn’t take a vacation just because you did.
The question is: are you planning your next trip like a 19-year-old or a 37-year-old?
(Age has nothing to do with it.)
Not sure which version you are? Let’s find out.
Avraham
Your Financial Coach
P.S. My friend Raphael just got back from Arizona. Drove 3.5 hours to the Grand Canyon with his kids. Last time he went, entry was $35 per car. This time? $100 per person — unless you’re American. (They’re not). Vacation surprises don’t have to be dramatic. They just have to be unexpected. Budget for them. 🏜️
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