My Biggest Travel Mistake Ever

Big Mistake

A few days ago I wrote about my misadventures in Mongolia—the primary misadventure in that case being evicted from my guesthouse after midnight. That experience was certainly not fun while it was happening, but in the end, things turned out rather uneventfully.

As a follow-up, today I thought I’d tell you about a misadventure that was entirely of my own doing. I can blame no one but myself for this (I’d love to blame United Airlines for being so inflexible, but that would be somewhat beside the point). This misadventure is pretty much the biggest mistake I’ve made in 80+ countries of traveling. Oh, and it happened about three weeks ago.

Yes, just three weeks ago. You might expect that my biggest mistake occurred a long time in the past, when I was a young, naïve traveler. Oh, how I wish that were the case—but I’ve committed to giving you the whole truth in all my writing, so that’s what you get.


The morning started well, with a 12-mile run through the streets of Warsaw. It was a rest day for me, with no flights or buses or any other kind of transit after a weekend in Kurdistan and an upcoming connection to Asia. After the run and a nice breakfast, I went up to my room to make some phone calls with Skype.

The first call was to Singapore Airlines, to confirm my meal request for a flight from Tokyo to the U.S. that I was supposed to be on the following week. Manifesto readers may recall that I wrote about the flight over to Tokyo in the last section of the Brief Guide to World Domination. I had another way back from Asia on that trip, and had planned to use the return leg when I came back from the Baltics and Beyond journey.

Anyway, I was looking forward to that flight more than usual. Singapore Airlines is nice in any class of service, and they usually have at least three separate vegetarian meals that can be requested in advance. I had booked this flight in Business Class with Frequent Flyer miles, so that was even better—in addition to the huge menu they give you on board, you can also use a cool service called “Book the Cook” to request one of nine extra-special meals that they will prepare just for you.

Take a look here to see all the options – it is an awesome concept, although on my first flight using this system, they lost my assigned order and had to improvise something else. I was looking forward to giving it another try so they could hopefully follow through on the great idea.

In Warsaw that morning, I rang up the Singapore call center and spoke to someone about the meal request. They had a hard time finding my flight details, so after searching under my name and frequent flyer number, they asked me to look up the ticket number. “No problem,” I said. I pulled the confirmation printout out of my laptop bag… and instantly realized the first part of my big mistake.

Instead of listing July 17 as the return date – the date I had in my calendar –the date of August 6 was listed. Hmmm, this didn’t look good.

“I’ll have to call you back,” I told the agent, and hung up.

I immediately looked through all my printouts and my calendar again, trying to figure out what happened. I knew I had a flight back from Tokyo in August as well, but I thought that was with American Airlines, on the beginning of my next Round-the-World trip with OneWorld.

The more I looked at all my flight reservations, the more worried I became. I did have another flight from Tokyo in August, and in fact it was booked on the same day as the Singapore awards flight. There it was – August 6th, NRT-ORD, connecting to Seattle. And on the other paper, it said August 6th, NRT-LAX, connecting to Seattle.

As the reality set in, I could hardly believe it — I had double-booked myself on two long-haul flights that were each completely non-changeable.

The funny, or not-so-funny, thing about this is that roughly 50% of my flights can be changed at any time with no fee (thanks to the Round-the-World tickets), and another 25% or so can be changed for a $50 or $100 fee. But in the worst possible outcome of travel planning, both of these flights fell into the bottom 25% of being completely non-changeable. I could not move the date up for either one, and thus I was double-booked.

The Singapore Airlines flight could not be changed because it was a Star Alliance Awards ticket. Once you have traveled the first leg of one of those, the return leg is unchangeable for any reason. You miss the flight, that’s it—say goodbye to 90,000 miles or whatever it cost to book.

The American Airlines flight could not be changed because it was the first of a 20-segment Round-the-World ticket. The 19 following segments are completely changeable with no fees… but you absolutely have to make the first one.

This was truly the worst of all possible ticket-mistake combinations. The second part of the mistake (yes, it gets worse) is that I now had no way to get home from Tokyo… in just a few days.

When I realized this, I sat in the chair by the desk for a long time. How could I be so stupid?

I am the travel guru. I am the one who goes to 25 countries a year and fields questions from everyone else about how to get around this nice planet we live on. My friends send me text messages that consist of questions like, “What is the best way to go from Bangkok to Tehran?” and “Should I fly Jet Airways?”

(Answers: Fly to Istanbul or Dubai first, and yes, Jet is great.)

Image by pivic

My Best Excuses

In my defense, I do have 50+ flights a year to all kinds of far-off places. Using a combination of Round-the-World and Awards tickets to keep costs low means that I often have a series of open tickets at any one time, for up to a year in advance.

On this trip, for example, I returned to Europe using a Delta Awards ticket I had booked nearly a year ago, then resumed the Star Alliance trip I also began a year ago (but re-issued twice), then planned to end with the Singapore Airlines return flight that I first went out on in March.

I realize that the system is a little complicated for non-travel addicts, but it usually works well for me. My average flight price is around $300, and it helps me get to places like Northern Iraq and Mongolia that would otherwise be very difficult and expensive to travel to. I’ve used the system to go all kinds of fun, out-of-the-way places, including Malta, Burma, Indonesia, Bulgaria, Easter Island, and so on.

(On second thought, Burma is not really that fun. But I’m glad I went there, and I’ll tell that story later.)

Obviously, however, something in my six-sigma system broke down somewhere, and I encountered the perfect storm of flight planning—two long-haul flights on the same routing, booked on the same day, that were both completely non-changeable.

Sigh. To my credit, I’ve never done this before, but of course that didn’t help me when I was sitting in my Warsaw hotel.

How I Solved It

I wish I could tell you that I knew a secret trick to fixing my mistake and getting my original flight back, but then it wouldn’t be the biggest travel mistake ever. The only thing I could do was accept the reality of the situation and move on. But more specifically, here’s what I did:

1. Allowed myself to be mad for a while. In the end, I had to let it go as I always do, but I am not going to say that I was happy about it. I had made a big mistake and there was no easy way around it. This misadventure was no one’s fault but mine, and I am my harshest critic.

2. Used logical thinking to figure out how to get home. I went through my options—I could try to book another Awards ticket and use the return leg in the future (not so good because my supply of Frequent Flyer miles has been dwindling recently), try to change one of the “non-changeable” flights (sometimes that can work, but it didn’t this time), or play around with the return dates and airport options in hopes of buying a relatively cheap one-way ticket. I ended up booking the flight back from Seoul, which was $400 cheaper than Tokyo even though it connected to a Tokyo flight. I was already connecting in Seoul to go to Mongolia, so that helped a little.

3. Decided to tell you all about it. The one bright spot in thinking through the problem was realizing that I would have to tell you all about it. I don’t mind sharing my mistakes, and I hope that someone can learn from them. Perhaps you won’t encounter the same situation with double-booking yourself back from Japan, but if you’re out to do something significant, you’ll probably make some significant mistakes along the way. Even if you feel like giving up, don’t do it.

The stakes are too high.

Your personal goals are important.

People are counting on you.

Etc, etc. Don’t forget.

And then in the end…

Because of the flight changes, I ended up getting back to Seattle two days early. I have an especially busy travel summer, and had only planned to be home a week before leaving again… so it was nice to have more time at home before I took off.

In another great surprise, I was able to see my brother at the Sea-Tac airport for about an hour. It turned out that he had to visit the Seattle area for work on short notice a few days prior to my arrival, and he left to head back to the East Coast on a United flight two hours after my own United flight arrived. I don’t think that was a coincidence, and I was really glad to see him.

Still, though, I can’t believe I made this huge mistake. If you’re traveling through Tokyo on August 6th and your name is Chris Guillebeau, you’re welcome to use my free Singapore Airlines flight back to LAX. Enjoy the great five-star service and lie-flat seat at my expense. You can even call them up to reserve your choice of nine different meals.

Just remember to not book another flight the same day.


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  • Linnea says:


    I’m glad you found so many positives in this. Thanks for the encouragement (and the good example)!

  • Katharine says:

    Do you have a post somewhere about how you got to Easter Island cheaply? I looked into it a while back and it was ridiculously expensive…

    On another point, do you have a post somewhere that explains how you travel cheaply?

  • Metroknow says:

    Wow Chris – thank you for sharing this – I think it makes all of us feel a bit better knowing that even people dedicated to the travel task make mistakes like this.

    My worst I think? I booked a flight to Palau in the 80’s, and waited too long to work out my passport, so I was stuck in Guam for a week, just waiting for the mail.

  • kalex says:

    That is a rough story, and I’m sorry to hear about it, but there’s one thing that really struck me:

    Why didn’t you use the Singapore Airlines ticket with the five-star service and lie-flat seat if you had both tickets?

  • I think it takes a lot of courage to admit a mistake like this – I know I would have been hesitant to share it. I am really enjoying how you tell such interesting stories about the seemingly dull, such as the double-booking of a ticket.

  • Diana says:

    Thanks for sharing your ‘oops!’. For anyone who travels, little or lots, we all have our Moments Of Duh! And you found the brighter side of the experience, which is cool. Is there anyway you can sell the ticket? Or is it non-transferable? Probably not, since you used flyer miles? I wonder if you can donate the ticket (at least it would be a write-off) to an organization that needs the transport, like adoption or a church, or something. Singapore Air may go for that, at least.

  • Ben says:

    Great story, thanks for sharing!

  • kelli says:

    Hi Chris!

    Thanks for sharing this story, it was good to hear it from your perspective and how you handled it. This post adds such depth to your other posts and helps me to realize that we all make mistakes sometimes, and most of the time it means more by the way you handle it and own up to them.

  • Kay Ballard says:

    Great story, Chris. You are such a talented writer that reading this post made me feel uncomfortable. Your dilemma became tangible to me–not the kind of vicarious experience I would ordinarily seek. (smile) And the way you resolved the problem was instructional. I assume the fact that you didn’t attempt to negotiate a different solution means that you have found that it doesn’t ever work.

    Your acceptance seemed genuine and I believe that is why it actually qualifies as a solution. That was my takeaway.

  • Svetlana says:

    As they say, the optimist isn’t the one, who has no problem, but the one who can solve it!
    And of course, nothing is coincidentally 🙂

  • William says:

    I’m still impressed that you can coordinate all the flights everywhere… My worst mistake is when I booked a domestic flight the wrong way (non refundable/rebookable of course). When I looked at the ticket a few days in advance, I realized the flight was leaving from the city I was supposed to go to.. Luckily it wasn’t that expensive to buy a new one.

  • john park says:

    We made a similar mistake on a paris, berlin copehagen trip not too long ago. Cost us hundreds of dollars to fix it for a family of four.

    Here’s the question What is the best way to avoid this mistake?

    obviously, one can double check and triple check the calendar. But sometimes these mistakes happen also when one has written it wrong on the calendar in the first place

    Does anyone have any tricks they use to avoid these simple mistakes?

    It also brings to mind what I”ve heard some hospitals do when operating on a arm or leg, to make sure they are operating on the correct one (i.e. right versus left)
    The obviously the medical chart will say if it’s the right or left leg that needs to be operated on, but for additional redundancy, I”ve heard an orderly will go into see the patient and not just ask them which arm/leg is to be operated on but also to ask the patient to point to it as well and then the orderly marks the arm/leg with a marker pen. Good redundancy.

  • Cathy says:

    Great story, Chris! The hardest part, as a frequent traveller who made a mistake I shouldn’t have was the kicking myself part! Now that I have learned my lesson I won’t be kicking myself or maybe just not for as long as I did! Thanks for pointing out that one does need to be mad – but then one should get over it and regroup!

  • Great story and maybe I’m weird but I always love telling my travel stuff ups just as much as the stories that make me look cool. And with the amount you move around and the ticket juggling you do, I’m surprised this doesn’t happen more often.


  • Chris says:

    Hey everyone, I’m in Pakistan now. Great place! I’ll write more about it in a week or two. Thank you for all the comments – you are reading while I am sleeping, so thus the delay in reply.

    Yeah, I wasn’t thrilled with this either, but I figured there might be some value in sharing the experience.


    No, unfortunately I can’t sell, donate, or transfer the ticket. I would love to do any of those, but none are allowed according to the strict conditions of the awards ticket.


    I would also like to do that (use the SQ ticket to go home), but then my RTW ticket would be invalidated. I need that one for the rest of the year and early 2009.

    I’ll get to any questions I missed later this afternoon.

  • Chris:

    As usual, I enjoyed your latest adventures or perhaps I should say “mis-adventures”? Truly, when we allow ourselves to be transparent, we confirm that we are indeed human and that humans are bound to have “interesting experiences” along the way.

    Thanks for sharing your OOPS – they make you even more real and authentic.

  • Nomadic Matt says:

    a sign maybe you travel too much….or at least need an organizer?

  • Matt says:


    What are your tips for accruing an maximizing frequent flyer miles? Can you do a post on that?

  • Alex Fayle says:

    I’ve done things like that, but always on a much smaller scale. I put it down to being overconfident and not thinking I need to double-check things. Now I triple-check things just to be sure.

    Glad you worked it all out – and it’s great that you saw a good opportunity to learn something from it.


  • Erica says:

    My dream is to travel like you do, Chris, all over the world, all the time. Thanks for sharing this “oops” of yours. I’m taking notes.


  • Saravanan says:

    Great to see you admit that you made a mistake.

    This post of yours reminded me the following sentences which I read, when I was in School.
    The most important 6 words in life:
    ” I Admit I Made A Mistake”

    Great articles, Sorry lately I have not been able to comment on your articles. But I make sure I read every article of yours. It is moving my life in a way which is traveled by very few. Your articles are helping me to decide my path. I am enjoying my new life. Thanks to you Chris, I owe you.

  • jackie says:

    Hi chris.. I just found your site and i love it.
    … I’m about to go on an abroad program for my school and am always reading for inspiration- Its a trip around the world (semester at sea) and I know it will be life-changing. But i want to start a business from it that helps people, which is a yet to be determined business haha- but your entrepeneuriship posts are so helpful.
    For travels Ive been using Its a map/journal site where you can plot and leave comments on restaurants, museums, stores etc. that youve visited. I thought you’d find it helpful in not forgetting where you’ve been..and you can link directly to specific maps from your blog.– Just a tip 🙂
    keep having fun! and check out my blog once my ship sets sail september 1

  • John says:

    I love it!
    “The morning started well, with a 12-mile run through the streets of Warsaw. It was a rest day for me…

    Just reading your blog exhausts me! 🙂

  • Thanks for sharing Chris.

    I admit I have to have a document listing my upcoming flights for reference, and check against this when making or changing flights. My schedule, like yours, is too complicated to trust to memory alone or calendar/diary notes. At any point in time I typically have 100-200+ future flights booked. Thankfully so far I have not double booked myself although I am sure it is bound to happen. Closest I came was double checking my document just before clicking the payment button for a trip to catch up with some friends in Australia only to find I was already booked on another continent for the same days.

  • Chris says:

    Hey guys, checking in from Narita before flying home.


    That sounds great! I’m sure you’ll enjoy the semester at sea. I know the ship that does those programs.


    Yep, the plan is to do a full ebook about that subject.


    Well, I know it sounds weird to a non-runner, but running 12 miles can be a great way to relax. 🙂

    @Global Traveller,

    Wow, 100-200+ future flights! You have got me beat with that. I usually only have 10 or so open at any given time.

  • jes billings says:

    Loved this. It’s the kind of thing that happens to anyone who travels any amount. You probably know they have time zones in Europe, but it never occurred to me…

  • Chris says:


    Time zones, yes, they do exist. 🙂 I try not to get involved with scheduling cross-continental meetings, because I am usually off by at least one hour.

  • I use the meeting planner on which is usually fairly accurate.

  • neil keleher says:

    Hi Chris, linked to this via your article about running. Must have been a bad end to the run.
    Maybe the real value in making mistakes is being able to share them (and maybe laugh about them?)
    Also reference running, I used to run along time ago and loved my long runs. When I lived in Dover (uk) used to run along the cliffs there. Now I live in taiwan, not so much fun but i am finding places. But wrt injury, just bought “chi running,” had some nice tips for running injury free.

    And maybe the mistake wasn’t a mistake, just what needed to happen so you could see your brother.

  • Julia says:

    Oof — I am now going to quadruple-check all my travel stuff from now on! I am so glad it worked out, though.

  • I actully adore your post. I read your siote pretty regularly and you’re
    always coming out with some great stuff. I shared this on my FB and my followers only loved it.
    Keep up the great work!

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