My Strange (Travel Booking) Phobia

We all have phobias, right? Spiders, heights, snakes, planes, snakes on planes – there are few of us who are immune from having irrational fears about things that either can’t hurt us or which are unlikely to do so. I’m not scared of planes, heights, or snakes (though spiders still freak me out). Instead, my phobia is a bit strange: I’m afraid of booking travel in advance.

Earning miles and points for shopping online with a credit card

This isn’t some cutesy attempt at making a normal habit seem slightly more peculiar. I actually get massive anxiety about booking travel in advance. The strange part is, I don’t even have any kind of negative experience to back it up. It’s not like I’ve ever booked a trip, had to cancel, and then lost all my miles or cash. I’m not even sure where it comes from, but it’s there and I can’t seem to rationalize it away.

For starters, I have the worst time deciding on hotels. It’s probably because I enjoy the research phase a bit too much. I knew I was going to stay at the Conrad Makkah during Umrah, but still couldn’t pull the trigger on the actual booking until I was in the car, driving towards the airport. The same goes for airfare. When I flew to Europe last summer, I had my AirBerlin business class seat on hold until 3 AM of the morning I was supposed to depart. When I had packed my bags and was ready to doze off, I finally called AAdvantage to finalize the booking. This past week, I’ve been driving my dad crazy because he keeps asking when I’m going to book the flight I’ve got on hold for him that departs in two weeks. Uhm, don’t worry it will get done. 

Some of this anxiety might come from booking so much group travel. It can be challenging when you’re redeeming points from different accounts and the airline doesn’t allow holds (i.e. Alaska). When that’s the case, I’m paranoid about booking a bunch of people on one flight and then losing the remaining award space for the rest of the group. Yes, there are ways to circumvent this (i.e. hold the award with a partner airline and release it just as I’m ready to book) but all of that makes me anxious to the point where I can’t even pull the trigger on single award bookings until the last minute.

All of this is compounded by a fear that I’ll book a multiple night hotel stay and be unable to cancel it if I end up being miserable there. I know you’re thinking the solution to this would be to book refundable rates or do what Elena suggested in one of her blog posts: Make separate reservations for each night so you can cancel one if you end up at the Bates Motel. So that’s kind of what I do. I book a hotel for 1-2 nights and then book additional nights if I want to stay longer. It’s still not enough to alleviate my ridiculous booking phobia, but it worked out well in New York, where I found the Kimpton Ink 48 to be a nice hotel but the Andaz 5th Avenue was a better fit on the last two nights when I needed to be closer to midtown.

Anyway, I’m trying to be better about this by addressing it and making an effort not to worry about ridiculous scenarios that won’t even come to pass. But I want to know: Does anyone else have this problem when it comes to booking travel? Or any other travel-related phobias for that matter? I’d love to hear from you in the comment section.

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  1. Two questions. If you book at the last minute, as their any risk that the number of points required will increase? Also, if you wait until the last minute to book, aren’t you risking the seat not being available? That would certainly cause me angst.

    • The number of points won’t increase, unless you’re redeeming Arrival Miles and the cost of a stay/fare has increased. However, if you’re booking a flight with an airline program that imposes close-in fees, then you do have a $75 per person fee to deal with. What I tend to do is put flights on hold when they become available. And then I keep them on hold while I let my anxiety brew and eventually finalize the booking. 🙂

  2. I’m just the opposite. Right as the booking window opened up I got 6 of us booked from various cities to China but for my personal flight I could only lock in the longhaul flights. So I need a positioning flight for October and it’s killing me that I haven’t booked it yet. Rationally I know I have time but it just leaves me a bit unsettled.

    I think that comes from traveling for many years with a group of folks on ski trips where all the details were ironed out by July so we could make installment payments and have everything covered well before we left home.

    • It’s funny because with my 2015 trip to Asia, I was in the same situation: I found (and booked) award space to my destination 6 months in advance. Then I was freaking out for 6 months thinking, “What if they don’t open up space on the return?!” So I totally get your anxiety about not having both segments booked together.

  3. I only get nervous if it is a no-cancellations allowed booking. I worry about a last minute sickness or family emergency.

  4. Sounds like a good time to make a post on cancellation policies by different airlines. From what I understand, some airlines let you re-deposit your award miles for only nominal fee; others ( like Korean) allow long holds

  5. Felix A.

    I completely understand have the same issue, especially when traveling in off-peak time. I’ve finalized booking on my way to the airport before and had 3 different reservations on hold at same time. The biggest anxiety was the 3 airlines were at 2 different terminals at airport so had to decide before arriving.

    I think it hits other people worst, especially when traveling with friends and family because they have more anxiety and continuously asking if bookings confirmed. I’ve learned to deal with it by booking hotels then working backwards to arrival the departure flights. I like building and confirming the trip backwards.

    • Wow, you’ve got me beat! I definitely fall into that group of people who books for others and then gets anxiety from the constant questions as well as the work I have to do on my end. I can see how building a trip backwards (if you can find award space) could work to eliminate anxiety. I’m always more stressed about how we’re gonna get home anyway.

  6. Russell Levinson

    Very interesting. I thought I was bad, but you have it worse! I am still working on my final trip as an AA executive platinum with my last two free upgrades. I wanted to maximize my chances of getting upgrades and studied all the Asia routes for weeks. I booked and cancelled one trip to Tokyo within the 24 hour window, and then booked a similar route a few days later for slightly less. I then added a flight to Singapore a few days after that! Still working on hotels daily, and I feel like I’m insane.

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