Tips and Tricks for Your Worst Travel Day Ever

Let me tell you about my worst travel day ever trying to get back from the west coast a few weeks ago! Yes, this is definitely part rant, but definitely some good tips and tricks in here in case you are left stranded at an airport, when all you want to do is get home!

Below is a summary of the newest “Let Me Tell You Why” podcast, which you can listen to in full below, or wherever you get your podcasts from

I was in Oakland for four days, then San Francisco for two and a half. My original flight home was supposed to be Sunday morning at 9 a.m. But Saturday, New York got hit with horrific lightning, thunderstorms, flooding. So Saturday afternoon I get a notification: my 9 a.m. flight is canceled. I’m thinking, “shit, that’s so early,” but figured they must just be rearranging flights, so I went to see what else was out there.

I’m a Delta boy, so it’s pretty easy to just go into the app and change things. There was a 7 a.m. flight, so I said cool, I’ll get up early, and switched to that. I went out to get a drink in San Francisco, came back to the hotel around 8 p.m., and set every alarm I owned because a 7 a.m. flight meant getting up brutally early.

As I’m about to go to sleep, boom. Alert. The 7 a.m. flight is canceled too. And now I’m rebooked on a flight Monday at 11 a.m., which means I don’t get home until Monday night, past midnight. That basically meant my whole week could get killed. I was like, god damn it.

At that point, three Delta flights out of San Francisco Sunday morning had been canceled, but the rest of their flights still looked like they were happening. Here’s the thing about being on the road for a while, when you’re mentally finished with a trip, it’s really hard to keep going. I was just tired. I didn’t want another day in San Francisco. I had things to do at home. So I decided: I’ll do standby.

I got to the airport Sunday for the 11 a.m. standby and I was already number six on the list. I talked to the Delta staff and asked them straight up what they thought. They were honest, these flights are fully booked, they didn’t think I was making it. I said, you know what, I’m here anyway, I’ll try. Worst case, I get a hotel near the airport.

The 11 a.m. flight’s standby list crept up, I got to number three, didn’t make it. There was another one at 1:30, so I waited for that too, ended up number 16 on that list. That flight took off without me. At that point I was talking to Delta reps who were so sweet and so nice, but they were basically telling me it wasn’t happening.

I was determined to get home, so I opened Amex Travel and started looking at other airlines. I found am American Airlines flight, San Francisco to New York, connecting through Phoenix, red-eye landing at 6 a.m. But then I wasnt able to get those seats on Amex, so I wanted to the American website, and boom was able to book those seats!

I had a few hours before that flight, so instead of stressing at the airport, I figured I’d go relax in the lounge, get some work done, watch the World Cup final, make a day of it. I’m sitting there with my laptop out when I get a notification: the San Francisco to Phoenix flight is now delayed 45 minutes. Which meant I was going to miss my connection to New York, the last flight out that night. If I missed it, I’d be stuck in Phoenix and this entire plan was pointless.

So I found out there was actually another flight from SFO to Phoenix leaving in about half an hour, and I ran to that gate. I asked if I could get on it instead, and they told me no, there was no way.

I wasn’t going to just accept missing that flight, so I went back online and started looking at literally every flight from San Francisco to Phoenix. Found a 6 p.m. Southwest flight that could still get me there in time for a 9:30 p.m. AA flight from Phoenix to New York. So I called AA, made sure they could cancel the first leg of the flight, and keep the second, and they assured me I was good to go, and I could call back later that week for a refund!

My Southwest flight boarded at 6:45, but it kept getting delayed, a little, then a little more, then a little more. I was gripping the armrest thinking, I cannot have this happen, I cannot be delayed any more than this. We finally took off about half an hour late, which meant we’d land in Phoenix at almost the exact same time my connecting flight to New York was boarding.

I’d never been through the Phoenix airport, and to make it worse, the gate kept changing for both my flight and my connection, and they kept getting further apart. The airport map said it was a 15-minute walk between them, which to me sounded like basically a mile?

Knowing the flight was already cutting it close, I paid extra to board early so I wouldn’t get stuck checking my bag, and I upgraded to a seat near the front of the plane, because I needed to be one of the first people off. All these Southwest upgrades really don’t cost that much, and at that point I didn’t care what it cost me.

We landed, and I jumped up immediately, apologizing to everyone in front of me on my way off the plane. Grabbed my bag, a carry-on packed for six days plus about 30 pounds of gear on my back, plus a random plastic shopping bag, and started sprinting, or more like power-walking as fast as humanly possible, through the Phoenix airport. I was moving so fast I probably would’ve wiped out if I’d gone into a full sprint carrying all that. I was the person yelling “sorry, sorry” while cutting through people on the moving walkway, because I was not missing that flight. I would have run through them!

I ran that entire mile with all my gear on me, and I made it to the gate on time. I got on that plane, and nothing felt better in the entire world.

It took me a solid minute just to catch my breath. I run all the time, but running with all that gear on my back was a different story. I don’t sleep on planes, and this flight from Phoenix to New York was only about four and a half hours, so I was just up the whole time.

We landed at JFK at 6 a.m. I got home around 7, having not slept in over a full day at that point. I ate something because I hadn’t wanted to eat with all the stress of trying to figure everything out, slept from 7 to 9, and then went about my day. And I got it done. Nothing felt better than being home after all that chaos, the cancellations, the delays on top of delays, the connections, the red-eye, the no sleep, all of it.

Here’s the part I actually want you to take something from: this is our future. We’ve talked about how extreme weather is going to keep affecting travel, and this is exactly it, more flight delays. We used to think this kind of chaos only happened in winter with snowstorms, but look at how many crazy rainstorms we’ve had this summer. This is the new normal. Traveling is going to keep getting harder.

So here’s my advice:

• Check everything. Check every site, check Google Flights, check whatever credit card travel portal you use, check the actual airline directly. Don’t rely on just one source.

• Go to the gate. Talk to people. Call people. Whatever it takes, being physically present and asking questions in person got me further than waiting passively.

• If you think you might need to rush, sit toward the front of the plane. Being close to the front (or upgrading to be) can be the difference between making a connection and missing it entirely.

• Do not check a bag if there’s any chance you’ll need to move fast. If I had checked mine, none of this would’ve been possible , I honestly probably would’ve just stayed until Monday.

I know I can’t always control this stuff, and I got lucky that everything I needed lined up, no checked bag, an upgrade that worked out, a gate I could actually run to.

I travel a lot, so I know I’m very fortunate this doesn’t happen to me more often, and knock on wood, I’ve got a lot more travel coming up, so hopefully that’s enough stress for a while.