I’m not sure how interesting this story is, but a couple of folks asked me to share it on Twitter. I think the idea is that sharing how I think about dealing with travel as it happens (and as it goes wrong) could be interesting and useful.

There’s rarely going to be a ‘right way’ to approach irregular operations. Bad weather especially, lots of things going wrong, you’re playing percentages and also playing hunches based – hopefully – on years of experience in travel.

Yesterday was a bad weather day for an American Airlines flyer, especially one transiting Dallas but really across much of the system because delays and cancellations in a major hub cascade across the whole system. A flight cancelled out of Dallas doesn’t make its next city, and can effect wherever the aircraft was supposed to go next. You might have been heading nowhere near Texas, yet you find your flight cancelled due to weather (and it’s clear outside!). That’s just how it works.

I was on the 3pm flight from DC to Dallas. My connecting flight cancelled around 10am Eastern, and I rang up American to find a telephone wait time of at least 50 minutes, and that’s calling in as an Executive Platinum (100,000 mile flyer). I’ve never waited more than three or four minutes even during bad storms.

Instead of having them give me an automated callback, I opted to wait on the line. About forty minutes in I dropped the call. I should have chosen the callback. I always worried I might miss the call, but it turns out American’s systems will try you back a few minutes later if you don’t pick up when they call you.

In the meantime, I was auto-rebooked on a flight that would have gotten me into my destination an hour earlier than planned. I originally booked a two hour connection because it was cheapest. I was put onto a one hour connection. Perfect!

I was far from confident things would work out, and indeed my inbound aircraft for my flight to Dallas was delayed so my hour connection was starting to look like 25 minutes with a change of terminals.

Right as we were about to board for Dallas, my connecting flight cancelled. I quickly got a club agent to rebook me onto a later flight.

Heading to the gate I called Hyatt. I have an expiring credit card annual free night, and figured that I would burn it for a room at the airport if it was available. This is the point at which you need to make a speculative bet: at 3:30pm in the afternoon there are still airport rooms left. Do you want one? You may not need it, but you won’t know until it’s too late to cancel, and you’ll be on the hook to pay.

I really do prefer the Grand Hyatt DFW, attached to the terminal. I’d have happily given up my free night certificate on the chance I would need a room there. The agent told me it wasn’t available — all they could offer is a “Business Plan” room for $351. That was too rich for me to book speculatively! The Hyatt Regency wasn’t available as an award either.

We boarded and I resolved to check other airport hotels online once in the air. I could have booked a Starwood award online, for instance. (The Hyatt credit card night had to be booked over the phone which is why I wanted to check on it before takeoff.)

But inflight Gogo wireless internet was slower than I’ve experienced in a year. It was virtually unusable. And things were looking good for my later flight. So I didn’t worry too much about the hotel.

Upon landing in Dallas (delayed) I now had a 2.5 hour connection so I headed over to the American Express Centurion lounge. Funny thing, I’m not exactly famous but I’m famous in airports and especially in lounges. It’s hard to visit a lounge without running into a blog reader who recognizes me! That’s really fun.

The flight continued to show ontime, so I headed to the gate for boarding. We boarded just a few minutes behind, and once boarding was complete the captain came on to let us know we’d be sitting “for about a half an hour” before heading to the other end of the airport for de-icing. I knew we’d be de-iced, and the wait didn’t surprise me one bit. Freezing rain was coming down.

After half an hour when it was clear we weren’t going anywhere, the aircraft doors were opened to allow passengers to get off. That resets the clock on the three hour tarmac delay rule. You never like to see an airline proactively ‘resetting the clock’ on a potential three hour tarmac delay!

Another half hour goes by and someone from first class gets off. I had been upgraded on my original flight, but was now in coach. An agent came on board to move me up.

I sat up front for about 45 minutes, when passengers began getting e-mail updates from American that the flight had cancelled. As is often the case, we knew before the pilot.

At this point all of the airport hotels were fully booked (with the possible exception of a couple of low end places without real-time online availability). What’s more, an accident was apparently preventing cabs from getting through. No hotel rooms, no cabs, and no hotel shuttles either. This was going to be ugly.

The first step was to find a ride out of the airport, I knew it would take awhile so I ordered up a driver via Uber. They called to say it would be half an hour. That was fine — in 30 minutes only 3 or 4 cabs made it through and baggage claim was stuffed wall to wall with people.

While doing that I booked the Sheraton out by the Galleria, 4000 points, done. The check-in clerk said they had been getting calls all night, they had rooms, but no one was booking because they couldn’t come pick up folks. It wasn’t a cheap ride (about $80) but I feel it was worth it.

American protected me on the 8am flight. Since I was going to miss a morning meeting regardless, I decided not to start off so early. Weather was still going to be bad. So despite my rule of thumb to get to the airport and take the earliest flight possible, I opted to try to swap flights.

The first American agent told me flat-out no — this was the flight I was protected on, they put you on the next available flight, so anything else would be a voluntary change. Seriosuly? I had three cancelled flights, I wanted to get some sleep before trying again.

So hang up, call back. The next agent happily set up a later flight for me. But driving out to the hotel I decided to check the status of things and it appeared that I was back on the 8am! A call to American confirmed that the first agent made notes in the reservation not to allow me to switch flights! I pushed back hard, the agent rebooked me again and this time it stuck.

I slept hard. Woke up in the morning and the 8am had cancelled anyway. As I was about to head to the airport my flight cancelled too. American’s systems wouldn’t accept calls, and then wouldn’t validate status so were dumping me into the standard queue and informing of wait times “over 2 hours.”

Then American sent me a re-booking email, about the best of what was available, so I headed to the airport and back to the Centurion lounge. While most flights today are cancelled, later ones are looking good.

• Status matters, if only for jumping phone queues and getting better access to inventory whether through proactive agent help or automatic rebooking.

• Play the odds but at some point get a hotel speculatively. Most hotels are sold out tonight already. I decided I didn’t want to leave the airport area tonight if I wound up stuck again, so I have a speculative booking on points. If I don’t need it I waste points — but that’s ok, on balance I’m coming out ahead because it means I’m getting where I’m going.

• Act quickly and decisively, and budget with the assumption that you’ll incur some unexpected costs. I realize that’s a tough thing to say, and for many it can be a hard thing to do. But I was happy to order up a car and get a hotel on my own dime and simply head out there. I’m fresh today, fully able to work, an reasonably comfortable.

• Plan to work, be comfortable, or entertained no matter what happens. Assume you need power sources and whatever other supplies to make the most of a situation. I’m fortunate that I can pretty much be productive anywhere, as long as I have a laptop and a phone, an internet connection, and a power source.

• At the airport you’re better off getting help inside security than in the lines outside. You’re better off getting help in the club than the main terminal. And you’re best off getting help from everyone you can. Multitask. Get on the phone while standing in line, if one person doesn’t help you move onto the next.

• Check everything. When someone tells you that you’re set, it pays to ensure everything is re-issued properly. The more lead time you have to know any problems the better you’ll be able to adjust and correct.

And you can do everything right — and still wind up stuck. Because in the end all you’re doing is playing the odds, not betting on a sure thing. But you’ll be more comfortable and more productive wherever you are at least.

---

You can join the 30,000+ people who see these deals and analysis every day — sign up to receive posts by email (just one e-mail per day) or subscribe to the RSS feed. It’s free. You can also follow me on Twitter for the latest deals. Don’t miss out!