I love a good deal, especially when it comes to getting a good flight. Ever since I got into churning a few years ago (signing up for credit cards to get rewards), I started booking flights primarily with reward points from these credit cards. I spend more time searching for flights with good point redemptions than I'm proud of, but when you find a great flight it's like finding an undervalued company whose stock is about to pop. Or for the millennials out there, it's like finding a meme-coin for $0.000001 before Elon Musk Tweets about it. This post definitely gets into the weeds of the reward hacking ecosystem, and may be too in-depth for some. But there are some Google Sheets skills you can gain from seeing the tool I built for this episode (copy Google Sheet here).

One of the most coveted seats one can book with award miles: Singapore Airlines suites. Source: The Points Guy

Award flights: from hack to hobby

The inspiration for this episode came from multiple places. Booking award travel started off as a hack I thought was only meant for people 1) with too much time on their hands and 2) who travel for a living (e.g. writers). Over the last few years, I realized my online and newsletter "diet" is slowly being taken over by these award travel blogs.

One Mile At A Time: one of my favorite news sources for award travel.

It first started with trying to understand the lingo in subreddits like /churning and /awardtravel. I even started going to meetups where like-minded award travel hackers congregate (shout out to Spencer Howard from STTP for organizing an NYC meetup earlier this year!). Recently, I've been listening to Chris Hutchins' All The Hacks podcast who I feel brings award travel hacking to the "mainstream." While Chris is an award travel aficionado at heart, he brings this "hacking" mindset to other aspects of his life. This brings me back to knowing rules of the game you play.

Knowing the rules to "win" a game

I wrote and spoke extensively on relating games you play in life to Squid Game in episode #80. I mentioned travel hacking as one of these games, but wanted to spend this episode diving more into the rules of this game. Knowing the rules of booking award flights can help you "win" a nice business class flight. When you explore the edges or extremes of these rules, that's where you can get a really good redemption or benefit. That's what makes award flight hacking so fun, in my opinion. It's kind of like taking a model or some code and testing for the edge cases. You don't want your model to output something that's ridiculous.

You hear about these "error fares" where the airline makes a mistake and you're able to book a flight for a fraction of its normal cost. This is not the same as using the award rules of airlines, their airline partners, travel alliances, and credit cards to find these good deals.

What I like about All The Hacks is that Chris applies this mindset to things like your 401(k), shopping online, getting a low interest rate on your mortgage, etc. These are all little games you can play to maximize and optimize your earnings or savings.