Like most travelers this weekend, my Monday isn’t starting where I thought it would.

If you read my Friday newsletter, you might recall that I was supposed to hit publish on this edition from Honolulu. I was planning to fly from Newark to Honolulu on Sunday and spend about 36 hours thawing in the Hawaiian sun.

I was going to return from Honolulu to Los Angeles on Southwest’s final flight with open seating.

Instead, I’m currently sitting in my apartment.

After a few hours in Newark yesterday — that included sitting on the plane for an hour — my flight to Honolulu was eventually canceled.

I rebooked for this morning, but that flight also got canceled. (At least I didn’t need to waste more time or money heading to Newark.)

So now I’m just staring at the mound of snow on the street and dreaming that it’s a winter version of Diamond Head. (It’s not, and I must reschedule the trip soon.)

As for what else is going on, Apple just debuted an all-new AirTag, there’s a one-day-only double-dip opportunity, and I even have some advice for handling flight disruptions.

I’d also be remiss not to mention that today marks two months since I left TPG and started this newsletter. I’m so grateful that you’re here with me. (Why not tell a friend to subscribe too?)

Since I no longer have a boss, I also don’t get performance reviews. So tell me: what are you loving about the newsletter and what would you like to change?

Advertiser and Editorial Disclosure

If you’re flying this week, listen up.

I have a bunch of expiring free drink vouchers on Delta and some upgrades on United.

For the Delta vouchers, open this Google Drive, log in to your Google account, download one (or three), and then move the files you downloaded into the “USED” folder. (Click “Organize” then “Move.”)

For a United upgrade, fill out this request form. I’ve already processed 78 upgrades this season, and have just a few left.

Apple just released a second-generation of AirTags, and before they were even announced, I had the chance to travel with them.

The new AirTags offer expanded range and improved findability, along with a 50% louder speaker.

The first- and second-generation AirTags are pretty much identical (with a few small cosmetic changes). The price also hasn’t changed. You can pick up a single AirTag for $29 or a four-pack for $99.

I just shared a hands-on video and pictures of them from my travels.

If you already have AirTags, I’d particularly recommend upgrading the ones in your checked bags — you never know when the extra range will pay off.

As I mentioned at the start, my flights this weekend were among the thousands of cancellations that plagued much of the country.

While you can check out the recap of what happened on my Instagram, I figure it’s worth sharing some of my tips (aka the ones you won’t find elsewhere) for navigating days like yesterday.

Set expectations

This is simple, but if you don’t proactively change your flight (using flexible weather waivers), be prepared for your trip to get canceled.

That was my MO going into the weekend, and it made me far less bummed when my flight was eventually canceled.

Check other planes

When my Sunday flight showed on time, I was skeptical.

So I checked the rest of Sunday’s Newark departures and noticed that United kept about 15 flights on the schedule. (I also looked at JFK and saw Delta did the same.)

That made me more confident that United would actually try to make the flight happen, rather than just cancel it while I’m already on my way to the airport.

Create a backup list

Before I even got to Newark, I created a list of backup options that would still get me to Honolulu.

This included flights to Denver, Los Angeles, and San Francisco. The LAX and SFO flights were leaving 15 minutes before mine, so I wasn’t going to switch unless mine was proactively canceled. (A mistake, in the end, because those cross-country flights made it.)

I sprinted to the Denver gate after my flight was canceled, but after a round of deicing, it too was canceled.

Go to the gate

Days like yesterday can be the jackpot for ballsy non-rev travelers. Why? Because there are typically plenty of misconnects and no-shows, meaning that it’s easier to get a last-minute seat on sold-out flights.

The same is true for paying passengers. Although I didn’t end up using my backup options, United cleared a ton of upgrades and standby passengers on all the other flights.

Use protection

Trip Delay Protection is likely the most underrated credit card benefit.

Personally, it’s saved me thousands of dollars over the years, and it comes included on some of my top recommended credit cards.

Instead of footing the last-minute transportation or hotel bill (or redeeming points), use your credit card protections instead.

Rakuten is a shopping portal that offers cash or points back on thousands of brands.

Today, Rakuten has a 10% cashback offer (that also converts 1:1 to Amex or Bilt points) on many merchants.

If you’re a Chase Sapphire Reserve cardholder, you could even double-dip by using your StubHub credit and getting 10% back after the purchase.

If you haven’t used Rakuten yet, you can get $50 (or 5,000 points) after your first $50+ purchase. Use my sign-up link to support my content.

It was generally a quiet weekend, so sharing some other updates here.

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