Updated from 3/3023

Whether you are trying to hack one big trip, or you’ve jumped into points and miles with full abandon, you’ll quickly find that it is a game of rules, details, and a lot of fine print. As Tom and I got more into travel hacking, we found ourselves learning from small mistakes and missteps. While there is no one right or wrong way to do this, there are things that we found out along the way that we wish had known because it may have changed our strategy. Here are some of the highlights? low-lights? of our learning curve – maybe they will help you! 

Not Fully Grasping Chase’s “5/24” Rule
To be quite honest, many of the other mistakes we’ve made below are loosely associated with this concept. Chase has an unwritten rule (that is supported by many data points in the travel-hacker world) that if you have 5 or more new personal credit card openings in the past 24 months, they will not approve you for one of their cards when you apply. As soon as enough time passes and you drop down to 4 in the last 24 months, bingo, approval. They will not tell you on the phone that this is their rule, but they will tell you that there are too many cards associated with your name if you are in this camp. If you are making a spreadsheet or using a travel-hacking organization app, this is an important piece of information to track – card opening dates for any cards you have.  The goal isn’t necessarily to always be under 5/24 – but it is important to have a strategy that includes going for what you want in that family of cards first, so you don’t wind up in Chase jail like we were. This is a pretty straightforward and simple rule, and I’ll go on below to explain why it is very important…

Not Fully Grasping the Power of Chase 
I would say that we sort of understood the above rule when starting out, but what took a little more time and a card denial to really grasp is that Chase Ultimate Rewards (URs) are really useful when you’re just starting out. URs are really east to use, versatile, and valuable in the travel hacking world. Beyond that, Chase has other co-branded cards with Hyatt, Southwest, IHG, United, Marriott, and on and on. Is this the only points/miles bank you should focus on? Not necessarily. But if you are new to the travel hacking hobby, it might make sense to pick a couple of places you want to go and then familiarize yourself with what the best points currency would be to take you there. I bet 8 times out of 10 it will involve opening a Chase card. 

Adding Each Other as Authorized Users to Every Card
It made tons of sense to us at first that if Tom opened a card, he should add me as an authorized user and vice versa so that we could both easily use the card and attack the spending requirement of a bonus we were working on. Plus, marriage and togetherness and what’s mine is yours and stuff. Turns out, this isn’t a great idea for a couple of reasons. The big reason, if you haven’t already guessed, is that it will mess up your 5/24. When applying for a new card online, these accounts where you are listed as an authorized user will trigger the computer algorithm and you will likely get denied. You can potentially call for reconsideration, but this may have varying degrees of success depending on the customer service rep you get. This is how we found ourselves quickly at or over 5/24, as we each had double the accounts associated with our names. The good news is, it is easy to remove yourself as an authorized user if you are running into problems, which is what we ended up doing for a couple of cards. Certain cards have made sense for us to keep each other on as authorized users, but we’ve moved away from signing each other up every time.

Shying Away from Opening Business Cards
Turns out, if you have any minor side-hustle, even selling your old junk on Ebay from time to time, you are eligible for these cards. You apply as a sole proprietor, use your SSN instead of an EIN number, and remain very honest about your projected revenue. What’s more, you don’t even need to use it only for the business (ever the rule follower, I had to investigate this). This aspect of travel hacking was something I originally had no interest in… but Tom always is one step ahead of me and realized how many more points we could earn this way. Business cards often offer great sign-up bonuses and perks for low or no annual fee, and most of them don’t end up working against you on your 5/24 – even business cards you’ve opened with Chase. Now, if you have an established business, you obviously can use this strategy – making sure to be careful about your accounting. But if you don’t have an obvious business – maybe you should consider a garage sale or some dog-walking!

Not Valuing Our Points for their Full Worth
At first it was so exciting to get free stays and flights – we didn’t try very hard to make sure the deals we were getting on points were making sense. Overall, we didn’t do that poorly, but with time we’ve shifted our mindset towards valuing our points similarly to money. We aren’t going to spend 50,000 flexible points per night on a hotel room that only costs $200-300/night. We’ve learned that those 50,000 points can be used to book a $2500 business class flight or several nights at a much nicer (and more expensive) hotel. We don’t go crazy trying to squeeze maximum value out of every single point, but we’ve gained an understanding of what our points are worth. The Frequent Miler’s “Reasonable Redemption” resource is helpful for figuring this out.

Succumbing to FOMO
Honestly, this is something Tom and I will probably continue to do. Ahem. I’m looking at you, American Airlines card I wasn’t planning on opening. Ahem. We often will have no immediate plan to open a card soon, and then some interesting, new, “highest ever” offer will come up that makes us re-evaluate our plan. The important thing to remember is that probably next month some other bank will be offering the “highest offer ever,” so don’t fret too much if something great comes up but you can’t make it work right now. We are trying to take a longer view – a marathon view, if you will – and not let FOMO guide our decision-making. 

How about you? What have you learned along the way?