I'd rather risk missing a flight than waste my time at the airport
We've all had close calls. For some, it's missing the last shot in a sports game. For others -- like me -- it's nearly missing your international flight.
I was scheduled to fly United to San Jose, Costa Rica (SJO) the Friday before Christmas. As a rule of thumb, I like to minimize the amount of time I spend in airports before domestic and short-haul international flights. That almost always means skipping the lounge and going straight to my gate. And thanks to my American Executive Platinum and United Premier 1K status, I can bypass most lines.
I'm a creature of habit, so when I arrived at Newark 57 minutes before departure, I knew it was going to be close. Having taken over 100 flights last year, I've gotten really good at timing my departure from my apartment to ensure that I get to the airport with just enough time to spare. December 20th was no exception -- until my Uber driver took the wrong exit from the highway, adding 15 minutes onto my trip time.

Since I was flying on a one-way international ticket, I couldn't check-in online, but that didn't matter much because I was checking a bag for my two week trip. United has a 1 hour check-in cutoff for international destinations, so I wasn't shocked that the kiosk told me that the flight was closed.

Time was ticking, and I knew I needed to find an agent to ask the gate to manually re-open the flight for check-in. The airport was jammed, but I navigated my way to a friendly 1K agent, who called the gate and issued our boarding passes. She tagged my bag, and wished us luck sprinting it to the gate.
Fortunately, I've got Clear and PreCheck (and you should too), so I made it to the gate before they even started boarding. Though I made it, the checked bag showed up the next morning, one day before my Panama Canal cruise.
https://www.instagram.com/p/B6yg0EilxOi/
As we taxied out for departure, I wasn't mad that I nearly missed my flight or that the bag would be a day late. And here's why.
As an ultra-frequent flier, I already spend lots of my time in airports. That doesn't bother me since I love all things aviation, but I also don't like wasting time. And personally, I have a really hard time getting work done with all the stop and go in the terminal. So, it's no surprise that I like to show up just in time for departure.
If I wanted to guarantee that I make every single flight, I'd probably have to add about 30 more minutes to each of my trips. Over the course of 100 segments, that'd be like spending two more 24-hour days in airports on top of all the time I'm already spending in them.

Sure, it's hard to predict when an Uber driver takes a wrong turn or there's some other unexpected delay in getting to the airport. But personally, I'd rather miss a flight than spend so much extra time waiting around.
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This logic isn't foolproof. If there's only one daily frequency or if I'm headed to an important meeting, then I'll be sure to add in a little extra buffer time. But, United has four departures to SJO, so I wasn't too worried about getting stuck in Newark.
And if you end up arriving too late, most airlines have generous "flat tire" policies that waive change fees and fare differences to get you on your way. Plus, if you use the right credit card to purchase your ticket and miss a connection, you'll have trip delay insurance to help you recoup some out-of-pocket expenses.
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I once heard a colleague say if you've never missed a flight, then you're wasting too much time in airports. I haven't missed one yet, but I got awfully close this time. I'm not even mad about it because I'd prefer to spend more time at home with loved ones than waiting around aimlessly at the gate.
But, when it does happen, I'll be reassured that I didn't waste more than two days of my life guaranteeing that I didn't miss my flight.
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