The Hardest Thing In This Hobby – Letting Amazing Deals Slip By

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The Hardest Thing In This Hobby

The Hardest Thing In This Hobby – Letting Amazing Deals Slip By

If you asked people what is the hardest part of the miles and points hobby you would get varying answers.  Some would say that earning points is the most difficult. Others would say getting maximum value when redeeming points is by far the hardest part.  Getting past Chase 5/24 may make it on some people’s list.  But no, none of those are the right answer, at least in my opinion.  The hardest thing to do is to pass up on amazing deals that just don’t work for you.

Knowing When To Say No

Last night the miles and points community was frothing at the mouth over some American Airlines award bookings.  You could fly from LAX to Auckland, Sydney and most of the Hawaiian islands for 10K round trip.  That is INSANE value.  Yes it is a lot of flying in coach but you don’t ever see fares like this to Aukland or Sydney.

This phenomena isn’t new though.  When Southwest first introduced flights to Hawaii they offered them for $49.  It created a lot of excitement in the community as well.  There have been amazing business class error fares over the years too that people have been able to take advantage of.

These types of deals have an extremely short shelf life which just leads to more FOMO because of the pressure. We have to make a decision on whether or not to fly halfway across the world in a matter of minutes because we know the deal won’t be there for long. Especially for a group of deal hunters like us. Finding value is our middle name so when something like this presents itself it means we have to book it right?

The Hardest Thing In This Hobby

Getting Over The FOMO

I have to admit I fell into this trap last night and was thinking I could knock one of my bucket list destinations off for 10K American Airlines miles.  Sign me up!  But the timing wasn’t great.  And flying to Auckland would be 18-19 hours in economy when it was all said and done…each way!  Still I forged on and was trying to get a flight plan together.

I wouldn’t be able to stay very long because of my kids school and my wife’s work schedule etc. That is when I realized that it probably wouldn’t work and would I really enjoy it anyway? Or would this just be me booking something because it is a deal versus it being something I really wanted to do when I wanted to do it.

Then I moved onto Hawaii and said I could get the whole family there (from LAX at least) for 40K round trip.  I said honey let’s do Hawaii for Christmas and your birthday. She gave me the look of death and said I thought you were supposed to be traveling less, not more.

She was dead right.  I had made a promise to myself to travel less over the next year.  And deals like this or once in a lifetime contests have blurred that line over the past year.  So I finally came to grips with the fact that these deals were not for me.  We didn’t have the vacation time and my next month or two are already jammed packed.  I would finish off either one of these trips just more depleted and regretting it afterwords. So passing on these deals, even though difficult, was the right move for me.

Final Thoughts

Don’t get me wrong these deals are amazing and anyone that can make them work I am happy for you! But if you are limited by vacation time or small children etc. and don’t have a flexible schedule don’t be ashamed to say no thanks.  Cramming a trip in just to get a deal, isn’t always worth it.  I would have had to fly 36 hours to spend a few days on the ground.  That would have caused stress on my wife to deal with the kids and her job and it just isn’t worth it. Plus I would have come back exhausted and way behind on work.  That would have added undue stress on me as well.  All in all it would have been a bad scene.

I should have known better from the start that it wouldn’t work for me but I got excited none the less which only leads to a feeling of letdown when I finally come to terms with the truth. So if you are in my boat don’t feel ashamed or like you are missing out.  We can’t do everything all of the time, no matter how good of a deal it is!

Mark Ostermann
Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

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  1. I think it’s like a compulsion with us! I had to tell myself not to even look. Funny thing is, I still regret it a little. Lol Balance is so hard when those deals pop up!!

  2. Totally agree with you. I just moved recently, bought a house, and now am establishing a new life with my wife, which entails developing friendships, and reconnecting with my son, daughter-in-law, and grand daughters. Sometimes, now matter how awesome the deal is, you gotta pass, because other life priorities are more important. really, as you go through life, The friends and family relationships carry much more importance than the ability to say:”that AA deal?, nailed it”.

  3. Just in case you wanted another chance to come to Hawaii looks like Hawaiian Airlines is trying to keep up. They just posted a sale starting at $300 from places on the West cost with some price increases starting further East. Must purchase by 31 OCT, travel dates between 31 Jan – 10 Mar. I tried it the sales works traveling to & from Hawaii.

    And as a bonus if you like the band Air Supply they will be performing 5 shows on Oahu Jan 21, 22, 24, 25 and 26.

  4. LAX-AKL is 13.5 hrs, not 19 🙂 Only ~2 hrs longer than LAX-LHR.

    I had a balance of exactly 6,006 AA miles in my account when this deal popped-up. Great deal & a great way to burn off the last of my AA miles.

    • I don’t live in LA, the same for most people booking it, so I added on the time of my flight to get there too 😉

  5. I see things differently. I consider passing on a deal the ultimate liberation. I’m the boss of me and having this hobby allows me to decide what to take advantage of, and what to pass on.

  6. Instead of going to sleep at a reasonable hour, I actually stayed up trying and failing to make either of those deals work from LAX for us. I was SO READY to book something but I was too late and the good deals were already gone. Such a bummer! But yes, I am also okay with getting over the FOMO and letting go of the disappointment of not seeing this one in time. I got to book the $50 / night error fare to Bellagio next month and the 15K miles for 2 people to Puerto Vallarta on Southwest (CP + no change fee) for Thanksgiving so I really can’t complain lol

    • Those are two good ones! I have my Bellagio booking still set up but not sure I am going to use it sadly. Flights for the weekend I picked are not really working out well.

  7. Mark. You’re wrong.

    JK. It is truly hard to pass up many deals, especially miles deals for me. For 6k miles and ~$27, I don’t even care if I don’t fly it and walk away if it doesn’t work. It was a book now and see if you can figure it out later moment since the cost was so low.

  8. Same here. I didn’t get even log in though! I just kept telling myself, when do we have time and my husband will not take a flight that long in economy, while I probably would, I bet I would hate it. However, then I noticed that a Crowne Plaza (?) in Auckland was on the pointbreaks list… hard to pass up but just had to do it. Too bad you all couldn’t use this deal on the FarAway challenge!

  9. I totally agree! I think I (maybe?) learned my lesson after booking ANA round trip first class for 93000 MR reward points. But I really wanted to go other places rather than returning to Japan. So finally cancelled after wasting a lot of time and some money.

    • Exactly Kate. I know people that have taken these deals even though they weren’t really in their plans just because it is a great deal. You still need to burn hotel points, money of food, taxes, and surcharges plus parking etc. That can all add up that I think we need to ask is this worth it to us. Each person will answer that differently depending on the particular deal/location. 99% of the time it is gonna be a no from me.

  10. I have Hawaii on hold and may or may not do it. Thankfully Australia and New Zealand were already on my radar for a return visit and I was able to get a nice one-ways into AKL and out of SYD (6K each) to piece together a good trip. My AA status through the Hyatt match got me MCE which factored into the decision. And of course I am close to LAX which also makes this a good deal.

    Totally understand why it wouldn’t make as much sense for you.

    • Yeah the flight to LAX was a big part of the decision. Especially on the way home – knowing I had to jump on that last leg would be killer.

  11. Mark, actually you could have booked and cancelled within the 24h free cancellation window. But tbh what you say here really strikes a chord. I’ve been doing some insane travel this year, with a a couple TK business class to MNL/SIN, the insane CX F/J error fares of which I booked several, SQ J from JFK-SIN but with a direct SIN-FRA-SIN in between the two long legs, NZ biz ORD-SYD error, a bunch of intra-Asia J class flying. Much as I love being on a plane, I’m quite exhausted and my lady is giving me the stare of death every time I go somewhere, or talk about going somewhere. It’s so hard to not pull the trigger when there’s a great/insane deal in front of you though. I somehow am thankful I sat out this NZ deal. And I think I’m gonna psych myself to be actually ok with sitting out others. It’s hard but I need to try for the sake of my sanity and my relationship!

    • Glen that is the key. Stacking these deals can lead to a big strain on our relationships if we are not able to go with the people closest to us. That is the issue I run into most with these type of deals. Since they often don’t give you much lead time and my calendar is usually booked a year out I just don’t have the time or room to squeeze them in.

  12. I tried for an hour to get thru the AA website after the deals posted, but it kept saying to “try again later.” Be glad you saved yourself that annoyance!


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