Reflections on a long weekend of deals

I hope all my American readers had safe and meaningful Thanksgiving holidays, and all my other readers didn't miss me too much this weekend!

I feel pretty good about the deals I participated in this weekend, but I definitely got frustrated at various points and learned some valuable lessons, lessons I hopefully won't forget over the next 12 months! Here are three.

Plan ahead for Small Business Saturday

Going into Saturday, I had 2 American Express-issued credit cards, each with one authorized user, 2 eligible prepaid cards, each with one sub-account, and one third-party American Express card (the Fidelity Investment Rewards American Express) for a total of 9 eligible cards, or 27 transactions eligible for a $10 rebate.

I managed to make all 27 transactions, but it wasn't easy and it wasn't fun, mainly because my family insisted on coming along with me, then immediately becoming impatient as I did what I needed to do to maximize my value from the promotion.

I had a few problems repeat themselves over the course of the day:

  • Cashiers could not understand what I wanted to do. The most frustrating example of this was a cute chocolate shop which I visited Friday afternoon to go through my plan: buy a ton of chocolate, then pay $10 at a time with a bunch of American Express cards. The same cashier, perhaps the owner, was working on Saturday, and I asked for about $50 in assorted truffles, caramels, powders, and bars. When I went to pay, I reminded her I needed to pay $10 at a time and she responded, "Oh, we can't do that." I ended up salvaging the situation by having her ring up each item separately, but couldn't help silently wondering: "do a lot of your customers come in a day in advance and spend 10 minutes explaining their shopping plans to you?"
  • Technical limitations. Another merchant couldn't split transactions between credit cards. He was apologetic, but it still meant I couldn't buy anything very expensive from him.
  • Problems with gift cards. Small merchants in my hometown don't seem to sell a lot of gift cards, and the cashiers may not have much experience ringing them up (setting aside problems with split tenders!). At one merchant, the cashier slipped up and handed me an unactivated gift card. Since this wasn't my first rodeo, I was sure to check the gift card's serial number against the receipt he gave me; they didn't match, and he was able to find the activated one in the pile by his register.

Ultimately, I found that bars and restaurants were more patient, experienced, and friendly than any of the actual shops I went to. I feel somewhat ambivalent about this, since I would have done more shopping for actual Christmas gifts if the retail cashiers helping me had the same friendly attitude as the bars, restaurants, and breweries where I simply bought gift cards.

Maintain a demand schedule

The only Cyber Monday deal I participated in was the Orbitz offer of $100 off any hotel reservation of $100 or more. I have two trips planned for the next few months and was able to save $100 on each of 4 nights, canceling the much more expensive stays I had already booked.

I would have booked more nights under the promotion, but for two issues: first, most of my nights are already booked on points. While I considered canceling more of my existing reservations in order to rebook the nights through Orbitz, I already have the monthly points income I need. Canceling some reservations in order to book cheap paid stays would just increase my balance of orphaned points; I'd rather enjoy my Diamond elite status with Hilton and my last-night-free premium redemption with Club Carlson and keep those balances nice and low.

Second, the travel I have planned for later next year isn't close enough to finalized to be able to book hotel stays around it. And that brings me to the concept of a demand schedule, an idea I learned about from Sam at Milenomics, but have implemented only sloppily. The basic idea is to know, in advance, all the trips you are expecting to take for the next year, with as much information as possible about each trip. Once you have a demand schedule, whenever a deal comes along, whether it's free hotel nights anywhere in the world, first class mistake fares, or buggy airline redemptions, you know the cities, nights, and flights to search for first.

I was only able to book 4 nights through the Cyber Monday Orbitz deal, but it's not as if I'll only be traveling 4 nights next year. On the contrary, I'll take dozens of trips, and if I had already planned them out more carefully, I'd have booked all my hotel nights for pennies on the dollar this morning.

Be active on Twitter

Fortunately, this is a lesson I learned early and well. Throughout the day on Saturday and Monday I was reading updates from Twitter users and travel hackers all over the country reporting their own experiences, information I could immediately put into action. In fact, I only learned about the Orbitz promotion mentioned above through Twitter on Sunday night. If I'd missed it, I'd feel like a colossal mark.

Back in June I shared a list of Twitter feeds I think are worth following. Here are a few more:

  • @PointsWithACrew. Posts a lot of clickbait, but ignore that; he also shares some good deals, and is a decent writer.
  • @travelwithgrant. Active on Twitter and in the community, and passes along good deals.
  • @milestomemories. Where I found out about today's Orbitz offer, and many others.
  • @Drofcredit. Encyclopedic approach to bank deals, and very helpful on Twitter.

All those guys write blogs too, but I find it tough to read very many blogs, or even scan their headlines, anymore. For me, Twitter is the perfect medium: it gives you access to longer pieces if a headline grabs your attention (which is why clickbait is a cardinal sin) while also letting you interact with the authors if you have specific followup questions.

If you're interested in my own Twitter musings, you can of course follow me @FreequentFlyr.