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You Get What You Pay For – The Fallacy of Maximizing Rewards and Benefits

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Maximizing Rewards and Benefits

Maximizing Rewards and Benefits

Many travel and rewards hobbyists, especially ones who read Miles to Memories, enjoy pulling as much value as possible out of loyalty programs, elite levels, and credit card benefits.  Some stretch this beyond travel.  For the past several years, I’ve prioritized everyday rewards over anything directly related to travel.  I’m also that weirdo at the Kroger fuel center with gas cans obtaining exactly 35 gallons on each fill-up.  I have a tendency to focus too much on maximization, and I need to check myself now and then.  I know I’m at risk of losing out on superior experiences due to my tendency to “chase the deal.”  I feel that we can unnecessarily limit ourselves with such behavior.  Today, I’m sharing a couple examples, one new and another old, which reflect how maximizing rewards and benefits can lead to unintentionally inferior outcomes.  I’ll then describe related matters now and in the future.


I enjoyed my whirlwind Las Vegas trip where I jumped hotels nightly to maximize benefits in conjunction with the recent MtM Diamond meetup.  A portion of this trip involved two individual stays at the Conrad in Resorts World.  It’s the only property where I stayed more than one night, and that was primarily due to stacking various Amex (Platinum and Fine Hotel & Resorts) and Hilton Diamond benefits.

On paper, the Conrad stay was a huge win.  In total, I had $104 in out of pocket costs for two nights and $482 in credits.  In reality, staying here a second night was completely unnecessary.  I had my fill with the first stay, even before completing it.  Indeed, I couldn’t possibly consume all my credits.  I wouldn’t have considered a second stay at this average property without the various benefits.  And in the end, I didn’t care much about those additional benefits during the second stay, anyway.

Maximizing Rewards and Benefits

My Encore at the Wynn stay was clearly inferior to the Conrad on paper.  I went out of pocket $98 for one night and $185 in credits.  But in reality, my Encore stay was close to perfect and put the Conrad stays to shame.  By loosening up on the travel budget just a bit, I was exponentially rewarded.  I felt and was treated like a valued guest at Encore.  At the Conrad, I was one of many being processed through the Resorts World semi-satisfied customer factory.

I felt like a slug leaving the Conrad, but Encore made me feel like a million bucks.  I was curious about staying at the Conrad and had additional reasons to be there, anyway, but I must admit maximizing backfired a bit.

International Travel

Previously, my wife and I took international vacations much more than we do now.  Years ago, I valued and maximized elite status more.  I enjoyed Hyatt stays as a top-tier Diamond in their previous Gold Passport loyalty program.  The Park Hyatt Hamburg breakfast is probably the best I’ve ever had in Europe.  The all-around experience at the Park Hyatt Milan was impeccable.  The suite upgrade at the Grand Hyatt Berlin was killer.  And we accomplished this all while enjoying elite benefits and using points according to the extremely low Hyatt chart (looking back).

But I knew I wanted to mix it up in Asia.  I generally prefer Asian hotel chains over domestic ones.  We picked certain properties where we dreamt of staying – The Mandarin Oriental and Shangri-La in Singapore, the Peninsula in Bangkok, another Mandarin Oriental in Chiang Mai.  We paid completely out of pocket for these stays, and they were worth every penny in terms of service and quality at these iconic properties.  Picking points hotels, many relatively bland in these locations, wouldn’t have accomplished our goal in the way we wanted.

I know I couldn’t take the “you get what you pay for” philosophy to the extreme.  That wouldn’t match my guiding financial principles.  We filled out the rest of our vacations at SPG, Hyatt, and Hilton properties we found intriguing with points.  Free stays at points hotels are a great tool, but we can’t let them unwittingly overtake individual goals.

Maximizing Rewards and Benefits

The Present, and Looking Ahead

I’ve spoken ad nauseum about how cash back is my favorite rewards currency.  Sure, I still efficiently acquire hotel points, airline miles, and rail points, but I don’t see cash ever being unseated as my top priority.  Tapping my cash back rewards for those “you get what you pay for” experiences definitely helps, but I know there’s a limit.  On an everyday basis, I know cash is useful for other rewarding experiences unrelated to travel.

Balancing how we maximize with our goals is an ongoing challenge.  We must acknowledge that every credit card welcome offer isn’t right for us.  I’m probably not maximizing Chase as much as I could since I quit caring about 5/24 years ago.  I may be missing out with Chase, but I’m okay with that.  Also, these days, I’d rather infrequently pay for a luxury (non-points) hotel high on my list than spend money and time on degrading elite status and related stays.

In the future, I only see my tendency to focus on a la carte travel experiences increasing.  In the meantime, I’ll focus on earning currencies (cash back, points, and miles) at high rates to make up for the perceived “extra” I have to pay to reach my goals.

Maximizing Rewards and Benefits – Conclusion

Some of you may be with me here.  I also understand others may find my philosophy clear as mud.  But I understand it myself, in this moment.  And that’s all that really matters.  We each use our rewards differently, and that’s okay.  What I do and do not earn and redeem is not an indictment on others’ habits.  It’s merely a reflection of my own goals.  Regardless if you’re into maximizing rewards and benefits or not, go after what you want and don’t let anyone else’s beliefs unnecessarily discourage you.  But do try to learn from others along the way.  I still am, and it’s a blast.

How much effort do you put into maximizing rewards and benefits?  How do you prevent yourself from taking it too far?

Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers.

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Benjy Harmon
Benjy Harmon
Benjy focuses on the intersection of points, travel, and financial independence (FI). An experienced world traveler, husband, and father, he currently roams throughout the USA close to expense-free. Benjy enjoys helping others achieve their FI and travel goals.

Responses 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.


  1. I think the key is knowing why you’re traveling in the first place, and what you value. We want nice experiences, but don’t care about fancy hotels or suites. We’re doing Switzerland next winter, and we could book rooms for nearly “free” with our CC travel credit. But those rooms are located in bland motels away from our activities. Instead, by spending a few hundred dollars, we booked good hotel rooms with great views where we can relax in comfort. But we avoided doubling our out of pocket cost (or spending points at a “good” rate) and buying a suite with a picture window because that’s not what we really need. So we’ll pay for better hotels because this is a bucket-list trip, but we won’t go broke for space we don’t want.

  2. True!!! I spend HOURS searching for best deal or something that aligns with where I want to go. Even planned trips around staying at a certain Hyatt, etc. While part of that is indeed fun, it is also more time-consuming that I probably account for. This really is the best blog. Fresh. Real.

  3. I’ll admit that much of the time I kind of half-ass it as far as maximizing value. I am OK with using a Marriott cert for a 20K a night hotel because I do not stay at that many hotels (I love Airbnb) and a free night is money in my pocket. Airplanes too. I really do not mind economy seating 90% of the time and so the points I save are there for more flights or conversions to hotel chains or whatever.

    Yeah, I likely could squeeze the beard off an Abe Lincoln penny as far as points, but I only put in the time and effort I feel like doing. For me, this all works. For others, do as one wishes and as long as we all enjoy ourselves and go places and do things, far as I am concerned, that is all that matterrs.

  4. Great appreciation that we’re on the same page with, “… We each use our rewards differently, and that’s okay. What I do and do not earn and redeem is not an indictment on others’ habits. It’s merely a reflection of my own goals.”
    But I cannot buy into the notion that cash-back is a rewards currency – as many do. It’s income, in the soft sense (versus taxable hard income). The moment you accept a cash-back benefit, be it as a cash rebate directly onto a card statement off-setting the balance due, or a cash-out that is mailed to you, those dollars have zero connection to the subsequent booking of a flight or a reward, there is simply no connection, no physical or accounting thread between the two whatsoever, and no connection in time either. The only connection is the mental notion that they are in some way associated, in some manner one got something for less or free. But reality is, at the moment you received the cash your net worth was not +$X, and that’s where the story ended. That you later decided to reduce your net worth by -$X, that’s not part of the hobby.

    I’ve spoken ad nauseum about how cash back is my favorite rewards currency.

    • DjG,

      If I paid with cash for an item, I wouldn’t earn credit card rewards. If I paid for that same-priced item with a cash back credit card, that cash back is a reward. It simply appears we have different connotations.

      But the last thing you mention is that cash back has been your favorite rewards currency? 😉

      • It was a cut and paste error, “I’ve spoken ad nauseum about how cash back is my favorite rewards currency” was to be deleted. And my typo, “at the moment you received the cash your net worth was not +$X,” was intended to read, “at the moment you received the cash your net worth was now +$X,…”

        We don’t have different connotations regarding, “If I paid for that same-priced item with a cash back credit card, that cash back is a reward.” I fully agree. What I don’t agree with is the next step – what you do with that cash (reward) – because I see the story as over and done with at that point of receipt of the cash. You connect it to traveling freely, by expanding the “reward” to be, “rewards currency, in, “… cash back is my favorite rewards currency….,” and, “Tapping my cash back rewards for those “you get what you pay for” experiences definitely helps, …” You sort of get it with the closing, “I know cash is useful for other rewarding experiences unrelated to travel….” Cash is fungible, mutually interchangeable, that removes it from being a “rewards currency,” into simply “cash from rewards.”

        Anyway, I’m along side of you with my gas cans, always maxing out 20 gal with Giant Food Fuel Rewards, jealous of the Kroger 35 gal. Then again, we can max at $1.50 off per gallon.


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