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Welcome

Friends,

Travel across North America has been tough this past week, largely thanks to springtime weather.

Tonight, I wanted to share a quick story and reflect on the reality of not being where you want to be.

665 words—let’s get going.

Links

A thoughtful commentary by a long time airline insider re:Southwest.

Massive bonus on the Citi AAdvantage credit card right now.

Story

In the winter of 2015, my wife and I found ourselves stranded in the Omaha airport for ten hours. We were flying back to Dallas just after Christmas, and had seats on United’s morning flight to Denver where we would catch an easy connection on to DFW.

Everything was good until it wasn’t. Just as we were about to board, the ground crew realized our pilots were missing. Their inbound flight from O’Hare the night before had been canceled—and we were still waiting for their replacements. As winter weather across the midwest continued to snarl the airline’s operation, we waited.

And waited.

And waited.

It was like a Steve Martin movie—one where everything keeps going so hilariously wrong that you spill your popcorn laughing (except we weren’t laughing).

Our pilots did finally arrive, and because United needed that A320 back at a hub the flight did not cancel. So we took off, ten hours late.

We could have driven to Dallas in the time we spent waiting.

And then we missed the last connecting flight of the night, so we got to spend the night at the Westin connected to Denver’s terminal.

There are worse things, and that is the point of my writing tonight.

Over the past week, weather across North America has caused long delays and meaningful frustration, particularly for spring break travelers. Airlines are materially complex and travel is this general act of releasing control.

Especially when the weather is bad.

When you have somewhere you hoped you’d be but have not arrived yet, that is genuinely frustrating.

I could make a joke and go on and write about earning two points per dollar with your credit card. But rather than pivot to points and miles, let’s sit with this for a moment.

Travel can be difficult, and that is okay. It is a part of the journey.

Once, I was on a British Airways flight bound for the USA that turned around just south of Iceland. I will save the full story for another time, but we ended up landing back at Heathrow eight hours after departing. It was a literal flight to nowhere.

And it felt kind of like spending 10 hours waiting on pilots in Omaha.

This can feel maddening, but it can also be received gratefully. The two are not mutually exclusive: if I am going to get mad about the bad then I can also remember the good.

I need to slow down, to wait, and to take a deep breath before recognizing how remarkable it is that most of my life is not spent on flights to nowhere. That no journey—travel or life—is a straight line.

And I am not in control.

I believe—on most days, at least—that’s a good thing.

Big Picture: Not being where you thought you’d be—whether in travel or in life—can be really frustrating. But that doesn't mean you're on the wrong journey.

Happy flying.

Remember, this life you are living has meaning. Thank you for reading. I am grateful you are here and would love to hear from you. If you'd like to write me a note, simply reply to this email. Otherwise I'll see you in the next one.

Be well today. -Tommy

P.S. If I can ever help you plan your next travel adventure (slash help make your points go farther), I’d be delighted. You can schedule time together here.