My Biggest Miles & Points Regrets Since Starting The Hobby

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Biggest Mistakes With Points

Beware!  My Biggest Mistakes with Points and Miles

The points and miles hobby is filled with great opportunity for huge rewards without too much effort.  To quote the first Spider-man movie, with great (hobby) power comes great responsibility.  Particularly, there’s a responsibility to avoid mistakes and other unforced errors.  We will inevitably all make mistakes, but what’s key is to avoid the whoppers.  Here are a few of my biggest mistakes with points and miles since I started having fun with the hobby in the early 2000’s.

Closing Rather Than Product Changing

This one seems obvious to many of us.  Most importantly, we must do our homework on each of our cards to determine other card versions we may not even know about.  One card I did not do so with was my United Explorer card several years ago.  Since I wasn’t using the card for long term spend and I wanted to avoid the annual fee, I tossed this card.  I didn’t know of the no fee version which provides extra Saver award availability.  It’s still the one Chase card I wish I held (or maybe the Hyatt card), and I don’t plan to apply for a new Chase card ever again.  Always check for card product change opportunities prior to closing one.

Biggest Mistakes With Points
I loved the SPG Amex. Maybe too much.

Overly Focusing on Airline and Hotel Currencies

It was a different time when I started – I recall that the hobby was prominently ruled by airline and hotel cards.  That’s what had most of my attention, at least.  I overly focused spend on my SPG Amex and United MileagePlus cards while ignoring the growing bank point earning cards.  Fortunately, I put most of my spend on the SPG Amex, which provided great point value for SPG properties and a variety of airline transfer partners at 1.25 miles per dollar spend (impressive at that time).  Man, I loved SPG.  But I digress…

Due to my love of SPG and other traditional travel currencies, I failed to dive into bank point currencies earlier and missed out on taking advantage of lucrative (at the time) plays.  We all have only so much mental bandwidth, but always remember to have at least a minimal understanding of the various cards and currencies available.  A great idea is to bookmark and read Miles to Memories!  I know an excellent contributor there, and a few other good people… 😉

Biggest Mistakes With Points

One of My Biggest Points Mistakes – Forgetting Card Spend

This next one has been an ongoing battle for me.  Many of us have heard to always periodically spend on each card we have to avoid an unexpected closure due to inactivity.  I still don’t do it enough.  Fortunately, this only happened to me once.  Unfortunately, it was one of my most lucrative cards.  The no fee Amtrak Guest Rewards Platinum Mastercard only earns one point per dollar on non-Amtrak spend, but the points are worth 2.5-2.9 cents each.  I’ve traveled Amtrak plenty over the years, and my Amtrak Guest Rewards points balance is still very healthy.  So I didn’t have any interest in spend on the card for a while.  Bank of America closed the account without any warning or notice.  Ouch.

Excessively Valuing the Southwest Companion Pass

I don’t consider this one a particularly huge error, as I didn’t reallocate a significant amount of spend to reach the Pass.  Still, it was a waste of time and effort to obtain, simply because I didn’t think long term.  I obtained the lion’s share of Southwest points with two welcome offers, and I figured, why not obtain a bit more to meet the Pass requirements?

How many times did I use the Companion Pass after obtaining it?  Zero.  Why?  The preparation, arrival, and care of our first little one pretty much neutralized any utility we could have obtained from the Pass.  I’ve heard some refer to the Southwest Companion Pass as the most overrated rewards in the hobby.  I won’t go that far, but it’s a misguided goal if one doesn’t have a clear plan to substantially use it.

Being Overly Stubborn about Saver Awards

Early in the hobby, I focused on 12.5k mile one-way Saver award flights.  I absorbed an inconvenient connection or made alternative plans if I couldn’t find a “cheap” redemption.  Looking back, I let those attractive, “high value” rewards control how I behaved.  More than 15 years later, I probably still have some of those extra miles from these “savings” sitting in my accounts.

For years now, I’ve focused on my goals, travel-related and otherwise, redeeming accordingly to meet them.  I don’t always make the most economical redemptions, but I don’t care since I more readily achieve my goals.  And with hobby antics, we can easily earn more rewards to compensate.

Not Focusing Enough on Cash Back From the Beginning

My first rewards credit card was the Citi Dividend, which provided simple cash back rewards.  After this card, I promptly got tied up in the hotel and airline cards I spoke of earlier.  My focus was solely travel rewards then, and more specifically free lodging and airfare.  I reached financial independence at 38, but I could have met my goals earlier if I looked at leveraging cash back rewards more quickly.

I later adopted the cash back angle with more time in the hobby, though.  It’s now to the other extreme where most of my redemptions are focused on cash back rewards for travel (and other) goals.  I’ve recently focused even more on everyday rewards unrelated to travel.  I want my rewards to have the most everyday benefit for me, whether it’s cash back or non-travel rewards.  Why unnecessarily limit yourself to rewards currencies that only benefit travel, which can be a relatively minimal portion of your lifetime?

My Biggest Mistakes With Points – Conclusion

I’ve made plenty more mistakes along the way, but these are my biggest mistakes with points and miles.  It’s inevitable that we all trip up now and then with all that goes on in the hobby.  So much more information is coming at us now, and much faster with every passing day.  Every now and then, reflect on your recent hobby activity and determine what mistakes you can avoid in the future.  What are hobby mistakes that have stuck with you?  How have you prevented future screw-ups?

Benjy Harmon
Benjy is a fan of points, miles, and financial independence (FI). An experienced world traveler, husband, and father, he currently focuses on roaming throughout the USA expense-free (or close to it). He enjoys helping others achieve their FI and travel goals.

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  1. For me, it was not having a goal when I started. I just wanted miles and points, which is great, but then I had a bunch and they weren’t useful for what I wanted to do, and I couldn’t get a good chase deal because of the 5/24 rule.
    Also, not researching more. I had united miles and wanted to use them for my first ever business class flight and didn’t know that there were some awards not visible on the website. Then, when they changed my departure time by 12 hours, I didn’t know that I could have made alternative suggestions for new flights.

  2. This one I do not get: “Closing Rather Than Product Changing. This one seems obvious to many of us.”
    I thought closing to reopen the same card (or newer but not too worse or even better) was routine way to gain big boosts from sign-up bonuses. And eventually, for a moderate player, seems that you have to close some now and then to not only earn SUBs, but to be able to spend on all cards now and then particularly to gain on retention offers. Unless I misunderstand, a product change does not get SUB, doesn’t get anything, other than a different card usually a downgrade without an AF, but also without AF related typical benefits (club passes, free room, etc.). If I’m missing something, would be great to know.

  3. Biggest mistake – thinking that advising others based on my success would help them achieve similar results. Lesson learned – 99.99% of the time, they do not follow through, save your time and energy for your own rewards.

    • I don’t personally see this as a mistake because I love talking about my hobby and am happy if people even do one small thing to help their travel goals. However, it is certainly frustrating to do a whole work up for someone and have them say, “But I don’t want another credit card, I’ll just pay for the flight.”

      • I can see your point of view, however, often their lack of follow-through is not just a choice that they simply don’t want another CC, it’s a statement about the hobby after their reflection; I really do not take those excuses seriously. The most valid excuse is fear of not being able to spend at the required levels; but that they don’t ask more, and walk away, that too might just be smoke and mirrors. They may not be frank, honest, or direct, but more often than not I have found those who walk away think lowly of our hobby. Anyway, we have you, me, and others to talk about the hobby so all is good, right?

      • I also think it’s fear of making a mistake. That’s why they want hand-holding. I really think most of us don’t mind taking a risk.

  4. Transferring UR points to Korean Air when UR announced KE would no longer be a transfer partner. With a KE devaluation looming for 4/21 and KE having removed F inventory for award bookings for the foreseeable future, these miles will have a fraction of their expected value.

  5. Not using up my Latam miles which are now going to expire since they won’t extend the date during a pandemic.

  6. Before pay yourself back was a thing and when I realized after “unknowlingly” collecting these points that for one thing they were worth money, I cashed in 20,000 ur’s for cash. With only a CF card. I remember wanting those points back so bad once I realized the value of them but Chase said a loud NO. I think this is what holds me back from doing paying yourself back today. Also that I only have a CSP at this point.

    • DonJ,

      I hear you. Yes, UR could be worth more for a given travel redemption, but there’s no harm in redeeming for cash in the near term to meet other goals. And if/when Pay Yourself Back goes away, I’ll be back to cashing out UR at 1 cent per point as I was before!

  7. One of my biggest mistakes, and one that I really saw clearly when the world stopped spinning in March, is not spending my points aggressively, or not even at all! Similar to your point on Saver Awards, if I wasn’t getting an unreasonably large $/point ratio, I would just buy the ticket with cash. That Hyatt redemption would have “only” been 1.97 cents/point, so I paid cash instead type of thing. Now, I’m trying to be better “as long as it’s reasonable”. I’m not going to give Delta 100,000 miles for BOS-JFK in coach, but I’m also not going to sweat it if it is reasonably close to 1.25 cpp. At least that’s my plan if we ever get to go anywhere again ….

    • Jason,

      I’m with you there. I firmly believe finding the best redemption for a given goal is the key, even if it’s not the most monetarily “valuable” redemption.

  8. It takes a big man to own his screw ups…my mistake was transferring miles to an airline plan and en finding out the flights I wanted had sold out with no other availability.
    Thanks for the work you do and the lessons you impart!

    • Geo,

      Thanks for the kind words! I don’t think yours was a mistake, though. More like poor timing/out of your control. It happens to all of us!

  9. Hmm. None of those seem like particularly terrible mistakes. The one mistake I didn’t make was being overly abusive to the banks as others have been. I’m happy with how I’ve managed myself and the rewards I’ve earned.


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