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The One Thing I Hate In This Hobby That Others Seem To Love

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One Thing I Hate

The One Thing I Hate In This Hobby That Others Seem To Love

I know I am going to be in the minority here. There is something I always kind of dread when I am going to plan a trip that others seems to absolutely love.  That thing is searching for award space. I loathe it, it drives me insane and I want to bang my head against the wall half the time.  There are alerts, checking when award space is supposed to open up, back up flights in case space opens last minute and risking everything for a close in booking miracle.  People love the rush, enjoy playing the game and savoring the win but it just feels like an extreme waste of time and complete frustration a majority of the time.

I Actually Enjoy Trip Planning

The sad thing is I actually enjoy the rest of trip planning.  Although I loosely plan my destination activities.  I have found under promising and over delivering is the way to go.  Whenever I plan a ton of stuff we end up missing some of it and then I am left disappointed.  But if I only pick a few highlights and leave the rest open to interpretation so to speak I come out feeling like I hit everything I needed to.  Plus, discovering the unexpected is my favorite part of traveling. It really is kind of magical to find an amazing place that no one told you about before you went.

Having said that, I still enjoy researching the place I am going to and then selecting the things that a top priority for me.  I also love looking at hotel reviews, even if others like to complain about them. But searching award space for flights…nah.  That just isn’t my cup of tea.

One Thing I Hate

Adding People Makes It Exponentially Worse

I should say finding flights just for myself isn’t so bad.  And even when I am booking for my immediate family it isn’t terrible since I can do it as soon as I find space.  But when you are talking about extended family (people not under your roof) or friends etc. it complicates things.  I can find the perfect space but by the time I get everyone’s okay or get them to agree to book, the award space vanishes.  Nothing is more frustrating than that!

It doesn’t take a rocket scientist to see that adding more seats makes finding space that much more difficult too.  And don’t even get me started when you are talking about trying to get flights to and from different airports that arrive around the same time. That is a pull your hair out moment right there.

Final Thoughts

I am actually kind of surprised that I don’t enjoy flight award booking more.  I usually enjoy the chase and the ultimate payoff but something about award searches drives me bonkers.  Especially when LifeMiles are involved 🤣.  There are so many hoops, rules, partnerships etc. to go through for each and every flight that it feels like I always enact the law of diminishing returns. So much so that I have picked a few currencies that work best for me and I go that route even if it isn’t the best deal every time.  It has made the process a lot less time consuming.

What about everyone out there?  Do you enjoy the chase or are award searches something you could do without too?

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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. Okay – so the million dollar question is – why are we doing this if it is sooooo hard to get payback on our miles and points? I’m seriously wondering if this is all just a shell game at this point and the CC companies are winning. I am not the most skilled at figuring out the various programs and not the most knowledgable. I also try to learn but I would benefit from some 1:1 time to help me learn as I find it hard to try to do things just by reading info on the internet. If redeeming miles is difficult for someone like Mark, who makes a living reporting on this, do I even stand a chance? I’m starting to seriously consider using an award booking service and I’d really appreciate a review of them

    • I wouldn’t use myself as your barometer. I think whether or not you enjoy the hunt plays a roll into award searches more than anything. Like I said I stick to my more tried and true options and pay a little bit more for awards just to save mental bandwidth.

      I do think the difference between using points for cash back vs travel has begun to blur more and more for sure. But even if you go that route there is still a ton of value in it all, at least in my opinion.

      Not sure we can do the award booking service review since none of us have ever used one but hopefully someone else can chime in. I know Juicy Miles and One Mile at a Time’s service are two of the bigger, more used ones so I would probably start there.

    • In my view, it’s not difficult to obtain payback (book rooms/flights), what can be hard is to book the rooms/flights you want, or to feel as if you’ve maximized your return. I’ve never failed to redeem and come away believing that I’ve come out “ahead.” Way ahead? Sometimes. A little ahead? Sometimes. But never has it been difficult to redeem. And if we exclude the extremes, if we exclude nonsense like complaining that you cannot book what you want a month or two out (we all knew long ago that you plan six months out to maximize), most of us should be left very pleased.

  2. Yep. I COMPLETELY agree and in the same boat. I’m an experienced traveler and typically travel (non-COVID) about 100 days a year. But the booking airline awards unless it’s a super simple search/itinerary I typically use an awards booking service like Juicy Miles. I try to make the most of my miles and fly Biz/First and want free stopover if possible and that kind of search typically takes me too long. Although it can add up paying $275 for 2 tickets (typically me and my wife) my hourly rate isn’t worth the aggravation for how long it takes me.

  3. Fully agree, even when paying cash, and even with just one other involved, it’s too much “is this okay with you…” involved. For miles flights, my solution is now to more often call for an agent to book. Even without the hassle of others involved, I often suspect I am not finding my best option, so at least three times (Delta, United and American) I resorted to calling for an agent to assist. With two of the situations for sure, flights that I could not find were offered to me, the agents worked hard to fit the flights into the miles I had on hand, and in all three cases the agent after our friendly chat waived the booking fee.

  4. Agree 100%. Using miles for saver space is a fool’s errand for me. A family of 5 AND traveling during peak dates due to school schedules? Forget it.

    Too much time, to much frustration, and too often coming up empty. All that time can be better spent accumulating the best travel currency of all: cashback.

  5. I couldn’t agree more- it is just too time consuming and makes me think I can be ok with coach seats as long as the flight is 6 hours or less, so maybe shorter hops are the way to go. I’ve flown first and business on and off for years and loved the experience, but with today’s limitations even in those classes I’m not sure it is worth it.

    • Something to consider for sure Judi. And first class is always full, economy can be half empty. Which is better these days? 🙂

  6. I agree entirely. For some reason I’m usually offered the 5 AM departures or overnight domestic flights unless I pay quadruple the miles, so I keep checking constantly for something that works. Takes a lot of time.

  7. Oh, can I relate to this! Even though it’s only my husband and me, and I do all the trip planning, this is the hardest part. Especially now that I’m “out of practice”, having last booked an award trip in 2019 (that was to Australia, return from NZ and one of the “fun” experiences I would not like to repeat, although it did work out very well).
    Like Christian, we have a trip to Asia in early 2022. We’ll be vaccinated long before that but who knows what the state of travel will be by that time, what with new Covid variants et al. We’re fit and healthy but we’re 70+, so it’s more concerning to us. So do I book with my UA or AA miles or transfer them to an Asian carrier where they might be “stuck” should we have to cancel/change plans, whatever? Like Christian pondered – book early or wait? I never get headaches, but this might give me one, or 2 or 3….

  8. @Christian “Do I book something that only kinda sucks and hope that something better will appear? Do I wait for a period when floodgates sometimes open? Stuff like this gives me heartburn.” hahaha that is exactly how I feel when I think about booking premium award travel for two. Half the time I give up and book Y and plan on taking two sleeping pills right after the meal.

    • LOL. An admirable perspective. Unfortunately (in this case) I’m 6’4″, have wide shoulders, a tricky knee, and weigh closer to 300 than I’d like, so that makes Y less optimal. I’m plenty cheap enough to want to pay the Y price but especially with the knee it takes a few days of pain/discomfort to recover from a long haul flight with a 32″ pitch when the person ahead has reclined. OTOH in normal life people generally choose not to instigate trouble with me due to my size, so I’m not unaware of the advantages of being unusually large.

  9. Mark — per the concusion of your post, what are the few currencies you stick with tl book to avoid multiple saver award hassles ?

    • As a Delta hub captive I always check Virgin Atlantic for Delta flights as well as Skymiles. I always check British Airways and American for AA or Oneworld. And for star Alliance I will check United and LifeMiles.

      I will deviate for specific bookings but those are my main stays. I feel like LM, Virgin and BA have the most transfer bonuses so it makes it an equal or lower cost than other options when that is taken into account but then I don’t have to have miles scattered all over the place, if that makes sense.

  10. I think finding award space has gotten harder in the past few years compared to over 12 years ago. I should say it’s harder to find *saver* award space and easier to find regular award space but sad part is it costs astronomical.

    • 100K Skymiles for roundtrip domestic economy does seem high haha. It is true – they seem to move have of old saver space into these web specials and the rest went to anytime award space.

  11. I loathe booking award flights. Even trying to confirm everything with my partner on the spur of the moment to book in seconds makes things challenging. Going places with friends is always more expensive because I usually end up paying cash on flights that accommodate everyone. There are exact dates that have to be booked. Part of the fun is starting and ending the trip together. Traveling as a group of 8 or more is impossible but when it gets up to that many people I do t feel guilty about is flying separately. I often get stuck paying cash for hotels when traveling with others too.

    • Adding in non miles and points people makes it an extra pain for sure. Often I will just book them with my points and have them pay me for it (often at a discounted rate since I am a sucker lol)

  12. I totally agree. I wind up picking a destination and season, then dealing with the ‘big’ flights in order to set the dates. Whatever I find becomes the framework to set the rest of the pieces since they’re easier and more fun.

    • That is a good plan. I often will leave the flights and trains etc. in the middle of the trip open until the very end. But I do like to book the big flights early as well.

  13. Well said. I agree completely that it’s a giant pita in so many cases. I’m trying to find two first class saver seats to Asia very early next year and while I’ll likely succeed it ultimately won’t be worth the hassle. Do I book something that only kinda sucks and hope that something better will appear? Do I wait for a period when floodgates sometimes open? Stuff like this gives me heartburn.


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