Blogger Confessions: Really bad redemptions

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Bloggers have a tendency to write only about the ‘right’ ways to earn and burn miles. As is the case with many learned skills, it is often from the dumb mistakes we’ve made along the way that help us get to the where we are today. In the first, Blogger Confession, we’d like to share some of Points, Miles and Martinis poorest redemptions we’ve ever made as we were learning ‘the game’. Not surprisingly, all of these redemptions are still available to those who haven’t discovered Boarding Area.

1. Exchanging one years’ worth of Amex points for shirts

In my first year as a road warrior, I racked up thousands and thousands of AMEX points from my Amex corporate card and I really didn’t know what to do with them. I debated getting an iPod Photo but ultimately decided that I could use my corporate spend points as a 1% rebate for Non-Iron shirts at Brooks Brothers. Since I needed to replenish my Business Casual anyways, I traded in thousands of points in over and over again for gift cards. I knew that Amex points could transfer to Amex points to miles since I was flying American Airlines each week and they weren’t a partner, I figured there were better uses (Obviously I had yet to understand points diversification). For more than a year of my life, thousands and thousands of my Amex points were turned into shirts. Bad idea.


2. Redeeming SPG points for Amazon Gift Cards because I feared a devaluation was imminent

As the economy was hitting a low point and the hotels were releasing incredibly lucrative promotions quarter after quarter, I was racking up (what I thought at the time) crazy amounts of Starpoints. I convinced myself without consulting anyone else that this pace of points distribution from SPG was unsustainable and thus they would surely devalue the currency. I needed to liquidate so I started redeeming Starpoints for Amazon Gift Cards for a tiny bit better than a penny a piece. Bad idea.



3. Using SPG Flights to purchase two round trip domestic tickets to Austin

After draining my Starpoint account on Amazon gift cards, I let the account grow a little until I received an email describing the newly launched SPG Flights program in which you could redeem Starpoints for any airline with no blackout dates. I really wanted to go to Austin so I just pulled up the SPG Flights and booked two roundtrip tickets for 40,000 Starpoints. I thought I got a phenomenal deal until I checked the American Airlines website and found the same flights for 220 dollars after taxes. Bad idea.


The bottom line

It may seem that bloggers always use their points intelligently but this blog is proud of its heritage of making stupid mistakes. The best way to learn is by messing up so the next time you think you are making a poor redemption… probably are, but do it anyways!

Editorial Note: Opinions, analyses, reviews or suggestions expressed on this site are those of the author’s alone, and have not been reviewed, approved or otherwise endorsed by any card issuer. For details on current offers visit the card issuer’s site.

About alex

Alex loves to travel and does so a lot. Logging 100,000 flight miles each year over the past 4 years, Alex uses points and miles to power his passion. Alex is continuously striving to experience the far reaches of the globe. In his day job, Alex is a Management Consultant frequently on the road advising Technology organizations. I love thinking about, reading about, and talking about all things travel. Feel free to reach me at

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  1. Don’t feel bad. I once redeemed 45K for a first class ticket from DC to Tulsa, Oklahoma because I thought it would be neat to fly positive space. This was back when I still worked for AA, and didn’t really grasp the idea of just a few more miles getting me to Europe in J.

  2. Ha ha. We are in the process of cashing out our Chase Quicken points because it seems impossible to redeem them for airfare. Very stupid not to leverage the points for maximum value of 1.25, but heck, we can use the money.

  3. Before I started collecting points, I got Chase Ink sign up bonus…50K was applied against my balance. Then 20K later, I did it again. I still feel bad about that.

  4. Years ago I redeemed 100K CO miles for a RT ticket in coach to Athens. It was my first ever redemption with miles, and I vaguely remember there being availability at the low level – I just didn’t want to deal with a connection!

  5. I have tons of examples:
    1. Sold 200k AA to a friend for 1.3cpm because I wanted cash.
    2. Used 200k or so MR to pay for Amex travel with 20% rebate.
    3. Lets 100k miles and more points expire

  6. OK, I have a no annual fee credit card with Citi which gave 5x Thank You points for a promotion. I have a bunch of these now. Would getting Darden gift cards (we can use them at Seasons 52) be a good use? I’d hate to have to admit to this years from now as a mistake.

  7. When I was in my early twenties I redeemed miles for a round-trip flight from DFW to LGA just because it was available.

    It was my first redemption, and I assumed that award seats were much more difficult to come by, so I jumped at the chance to redeem miles for what was probably a cheap ticket.


  8. I don’t regret mine but it still wasn’t a good redemption. I was visiting my college girlfriend in Europe and had a two day stopover in London. I was planning on getting a cheap hostel but they were in the neightborhood of $40 a night plus I would have had to pay for breakfast. I didn’t really have the money to spend, so I redeemed 100,000 Hilton points to stay at the Hilton Park Lane. Prices were really low that week so it was a really bad redemption and my worst one to date, but at least I could see Parliament from my bathroom.

  9. I second Grant. We prioritize things differently as we age and at the time, you really wanted brooks brothers non-iron shirts (can’t blame ya!)
    As for me, I used to use UR points to pay for flights back a few years ago versus transferring them to a frequent flyer program and redeeming them for longhaul flights.

  10. Redeemed 25,000 AA miles for an 160$ ticket to Kansas City. But I was young and needed the money!

  11. I read your blog regularly, but I guess I’m a slow learner and not great with math. Maybe posting a question will help?! I have my first small accumulation of points from a signup bonus for SPG, almost 40,000. Do you think it’s a good idea (i.e., not a mistake!)to redeem the points at 10,000 points per night for a domestic hotel stay? Also, can you explain the math to figure out how to valuate a redemption? From a post above, it looks like $1.25 per point is the goal? Maybe your comments will help a newbie not make her first mistake! Thanks in advance. You are all so helpful, and it’s a lot to catch up on.

  12. I’m new to the game and really at a loss on some of these so call undervalued conversions.
    I’m taking a relatively inexpensive flight on Southwest using RR, to stay at 2 different locations in Illinois. 1 hotel will be paid with Barclay Arrival credits the 2nd leg with Priority Club points. At the end of the trip I’ll have a weeks vacation with probably less then $60 out of pocket. I paid nothing for the points/credits. What’s undervalued about that?

  13. I have had a few of these in my day. Like the time I exchanged 100,000 Flexperks points to give $100 gift cards to my employees. It was great for morale, but I would have been better off buying them airfare for twice the value.

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