Cashing In Q&A columns

Personalized help for maximizing your rewards


If you’re not comfortable deciding which cards to purge and which to use, technology and professionals might help

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QuestionDear Cashing In,
I have numerous credit cards with good credit lines. I have gotten all of the sign-up bonuses I’m allowed, but I know I’m not using my cards day-to-day as strategically as I could. I’m also paying too much in annual fees by not knowing which cards are my true winners based on my purchases and knowing which cards to cancel.

I cannot seem to do the math on how to maximize my strategy, regardless of how many how-to articles I read. I really need some personal help, and I’m willing to pay for it. Do you know where I can find someone with the skills I need to get me streamlined, more efficient and smarter about my credit card usage? Thank you! — Jane

AnswerDear Jane,
I empathize with you. A lot of times, when it comes to rewards, people start slowly. But before they know it, they have a half dozen or more cards with different due dates, annual fees, bonus-spending categories and ways to redeem points. Keeping up with it all can become confusing very quickly.

You have probably heard the saying that the first step toward solving a problem is realizing you have a problem, and you have done that. If you are uncomfortable with the amount you are spending in annual fees and believe you are not using your cards to their highest potential, then by all means you should make a change. You are right to consider paring the number of cards you have and reallocating your spending onto cards that offer you the most rewards.

You’re also correct that there are no cookie-cutter answers. The rewards you value might differ from the ones I value, so we can’t make blanket statements about which card is superior to others.

Generally, you should regularly examine each card you have and assess if it is still worth the annual fee. For instance, if you have the Citi Hilton HHonors Reserve card (annual fee: $95), you should consider how often you stay at Hilton properties and whether the space-available room upgrades and free breakfast (at certain locations) that come with having the card is worth $95 to you. If you travel frequently, racking up Hilton points by staying there and using the card, it probably is. If you seldom travel, probably not.

If you are uncertain how to assess your cards, the next step might be to turn to technology. Wallaby Financial offers an app that takes all your card information and recommends which cards to use at different locations, based on rewards. It also has budgeting and tracking tools. The main app is called Wallaby. offers a version powered by Wallaby called WalletUp. (Disclosure: Wallaby is owned by’s parent company, Bankrate Inc.) You might find that useful.

If not, you could turn to somebody knowledgeable about credit card rewards to sort everything out for you. I’ve never used such a service and can’t personally recommend one. But if you are interested in this and don’t know where to look, you might start with people who run award booking services. In an article I wrote in 2014 on these services (“Professional award bookers promise ‘free’ flights for fewer miles“), I found that many people who book awards on behalf of others also are happy to consult with people about reward strategies, for a fee.

For instance, one of the companies I mentioned in the article is First Class and Beyond. Its website says it offers “premier consultations” at a cost of $125 per hour.

Also, since you mentioned you have read articles about reward credit cards, if you have any blogs that you particularly enjoy on that topic, you might ask the blogger if he or she would be willing to offer a consultation. Many of these bloggers, like award bookers, know the ins and outs of reward credit cards and are probably willing to help someone less knowledgable, especially if you offer to pay.

I hope you get all your cards sorted out!

See related:Chasing rewards points backfires when debt piles up, Privacy or rewards? Some card programs force you to choose


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