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There are plenty of travel sites that tell you how to do things the right way — but as every traveler (and credit card game player) knows, sometimes things go wrong. In his bi-monthly Mistake Monday series, TPG Contributor J. Keith van Straaten invites you to learn from his mistakes — his many, many mistakes.

Missing a big bonus can lead to intense head-grabbing. Photo courtesy of Shutterstock.

I don’t remember exactly when I discovered that maximizing points and miles was a thing, but I do know that I started maximizing mistakes shortly thereafter. It doesn’t seem like I could make a mistake when getting a bonus on a credit card offer — after all, bonuses by definition are free! — but I somehow found a way …

In the fall of 2012, I was relatively new to the game and eager to learn more. I attended a Frequent Traveler University weekend in Los Angeles. The university campus was nestled in the bucolic splendor of two ballrooms at the Sheraton near the airport. I dutifully took notes as I gained all sorts of tips for acquiring and spending points and miles.

A Meeting Room at the Sheraton or a University Campus? (Photo courtesy Sheraton Gateway Los Angeles)
Turns out, a meeting room at a Sheraton can serve as a university campus. Photo courtesy of Sheraton Gateway Los Angeles.

I had a lot to learn, but at least felt assured that I was on the right track. I had heard of all the credit cards being recommended and was already implementing a strategy that worked for my goals. Then I heard a speaker bring up the Chase United MileagePlus Explorer Business card. “Oh, great!” I thought. “I just got that card. I’m ahead of the game!” But when he casually mentioned the sign-up bonus of 50,000 miles and a $50 statement credit, my face went flush in a wave of panic.

I’d only gotten a bonus of 30,000 miles — and no statement credit!

And just like that, I was struck with a case of Applicant’s Remorse: the discovery of a better credit card deal after you’ve already applied.

Just to be sure I heard correctly, I went to find the speaker afterwards, and he confirmed that the same product I’d gotten was available with a 65% larger bonus and the $50 credit. Seeing my crestfallen expression, he then proceeded to talk me off my metaphorical ledge by suggesting something I never would have considered: Send a message to Chase through the Secure Message Center and ask them to match the current offer.

Use the Chase Secure Message Center to communicate with Chase
Use the Chase Secure Message Center to communicate with Chase.

I couldn’t imagine this would actually work, but what did I have to lose? I logged into my Chase account, opened the Secure Message Center, and sent a message explaining my situation. And wouldn’t you know it, within 24 hours I had a $50 statement credit and 20,000 miles on the way to my MileagePlus account! It took several minutes for my shock to pass; I couldn’t believe my mistake had been erased so quickly.

Why would Chase do this? Were they legally required to match an offer within x days of my account approval? Did they have pallets of MileagePlus miles taking up space in their warehouse? Did they know that a few years later I would be writing for a popular travel-and-points site and publicly praise their service? Whatever the reason, I’ve continued to be a Chase customer since then, and to be on the lookout for the best bonus offers.

The Lessons

At the top of this very page, you will find an easy way to find the best current offers.

Research. Before applying for a card, see if you’re getting the best offer. TPG has a handy way to show you the current top credit card bonus offers. It also has a handy search function, which you can use to look up the history of bonus offers for each card; same with online forums like FlyerTalk. While there’s no guarantee that any offer will be increased or repeated, you can get a sense of what’s possible — or even available.

Ask. The most valuable takeaway I’ve gotten from my experience with banks and travel is that asking for a break can yield hidden treasure. (As The Points Guy himself says, it never hurts to ask.) I have received literally thousands of dollars and tens of thousands of points and miles that would have been otherwise lost if I hadn’t simply … asked.

Follow up. Even after you’ve received a new card, look around for what bonuses are being offered on the product. I wouldn’t have known what to ask for if I hadn’t known what was available. And don’t limit your search to increased offers of mileage and points. Banks often add other perks for new applicants (discounts on travel products, lowered/waived annual fee, etc.) that you may wish to request.

Socialize. No traveler is an island. Participating in the community of mileage-and-points enthusiasts is not only fun; it’s profitable. Whether attending events like Frequent Traveler University, engaging in the comments section on posts like this one or interacting with people on Twitter (you’ll find TPG at @thepointsguy and I’m at @J_Keith), you’ll learn more tips and get more of your questions answered than by merely going it alone.

Have you had any experiences trying to get a better bonus? Share your story in the comments below!

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Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.