Travel Problems Only Over-Thinkers Will Understand

Reykjavik Iceland

I was playing around on Facebook recently, procrastinating doing something or other, when I chanced upon one of those buzzy articles about over-thinkers. I clicked on it and within a couple of minutes found myself nodding in complete agreement. I’m an over-thinker, which isn’t meant in the intellectual sense per se, but rather in how people like me see the world. It’s a mindset and while not an entirely healthy one, it does have some advantages. There are certain times though when it’s a hindrance, especially when it comes to travel and I’m sure that my fellow over-thinkers will commiserate with me when it comes to these situations that drive over-thinkers crazy.

We worry about every detail

It’s our nature to think, think about again and then reconsider a few more times every possible detail of a trip. Maybe that’s why I enjoyed my recent tour experience in Egypt, I didn’t have to agonize over every detail. This of course leads to over-planning, which typically takes away all fun and spontaneity from a trip. I’ve tried to improve, but a recent trip to Iceland really showed me how much I haven’t actually changed. Before leaving home, I made a spreadsheet divided by day and then activity. I then came up with a fairly detailed list of things to do and see for each day and proceeded to worry that I was missing some once in a lifetime experience I hadn’t heard about yet. There were multiple options and contingency plans all built into the spreadsheet. That’s insane. That is what crazy people do when they vacation and I was right there with the rest of the loonies. Normal people do not need spreadsheets to relax. It’s a common issue for over-thinkers though and it takes a lot to break this cycle of maniacal over-planning.

Ample Man Berlin Germany

We imagine every worst-case scenario

Let’s take the same trip to Iceland. For about a week before we left home I agonized, AGONIZED over the weather. The forecast wasn’t good and I was worried that it would be really hard to get around. Then I worried I had selected the wrong part of the country to spend my time in, sort of wishing I had gone with Option A instead of B. Then I worried about worrying; yes, this is actually true. It’s another lovely personality trait of the over-thinker, we like to imagine everything that could go wrong so we can prepare and worry about it. I look at those young backpackers who just drift through life without a care in world and simultaneously envy them and also worry about the details of their adventure they aren’t spending time agonizing over. If I don’t have a worst-case scenario to think about, I think about other people’s problems as a sort of public service I suppose.

Tres Rios Beach Bed

We can’t sleep anywhere

This is true of us no matter where we are, but suddenly becomes more pronounced while traveling. It’s bad enough when we’re at home and have a thousand thoughts running through our heads instead of blissful and calming sheep, but these thoughts seem to only multiple when traveling. Is the trip going well? Will I make my train connection tomorrow? Will I wake up in time to make my flight home? Have I done and seen enough? Am I in the right hotel? Will someone break in overnight and steal my passport? What’s that sound? Welcome to the thoughts of the average traveling over-thinker as they attempt to catch a few hours of shuteye before starting the next day. I’m also incredibly jealous of people who can sleep wherever they are, whether it’s in a train station, on the back of a camel or on a plane. Over-thinkers lust for this ability, but we’re lucky if we can fall asleep at all much less in extreme circumstances.

We don’t believe the people we travel with

We love traveling with other people, so much so that we worry constantly about whether or not they’re having a good time. Did they really like that museum or are they just saying that to be polite? They agreed a little too quickly to that dinner suggestion, they probably want something else. We over-thinkers care SO much about our traveling companions that we analyze and re-analyze everything they do and say just to make sure they’re having a nice time. Needless to say this has resulted in more than one argument between my partner and I as we’ve traveled the world, I usually refuse to accept anything he says and instead imagine his thoughts and feelings for him. So if you find yourself traveling with an over-thinker, have some patience and be sure to constantly say how much fun you’re having.

Great White Shark South Africa

We WANT to live in the moment

Believe me, it’s not that we don’t want to enjoy travel experiences as they happen, it’s just hard to shut off our brains sometimes and just absorb the situation. That’s why when I do find that special place or activity that gives me the chance to not get lost in my own thoughts, but rather get lost in the experience it suddenly becomes THE BEST THING EVER. We’re also somewhat prone to overstatement and make attachments quickly, so those nice places become life-changing, forever endearing destinations. I think that’s one reason why I seek out amazing experiences more than anything else. Walking around old buildings is fine, but I need to DO something, I need to concentrate on something other than my own inner-monologue in order to truly have a great time.

Reading back through these, I realize that I make myself and other over-thinkers seem to be somewhat insane; perhaps candidates for medication or admittance into the nearest sanatorium. But we’re not nuts, many people are over-thinkers to some level and most of us will exhibit these traits throughout the course of our travels. I exaggerated a lot to make my points, but hopefully this post will help all over-thinkers re-think (ironically enough) how they travel and enjoy a more relaxing, and less thought provoking experience in the future.

What are some other traits of the traveling over-thinker?

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

26 thoughts on “Travel Problems Only Over-Thinkers Will Understand”

  1. Oh my god… this is me. I recently succeeded in putting together an epic group trip to Croatia with 7 friends and I could barely even enjoy myself because I was so stressed out about whether everyone else was having a good time. And I never even made the connection between my trouble sleeping and my overthinker tendencies!

  2. I don’t know that I’m an over-thinker, but I definitely am a thinks-a-little-bit-too-much (or am I over-thinking that…?).

    That spreadsheet sounds interesting. Any chance you’d share it with us? It’d be interesting to see part of how you prepare for a trip.

  3. I am definitely an over-worrier when it comes to travel- usually over things that have to do with transportation, customs, reservations etc. I will check and re-check and worry and drive Mike crazy (doesn’t help that he is a compulsive passport loser). After reading your list though I feel like I’m not so bad…

  4. This is SO ME. And ‘We don’t believe the people we travel with’ – that’s so my husband!
    Still don’t think I can totally give up my spreadsheets though….

  5. I’m a bit of an overthinker in some ways. I can get very obsessed about the details exactly how a certain transfer is supposed to go, or checking in the moment online check in opens. Most of my travel-related overthinking is about getting places. But once I’m on the plane, I fall asleep quite quickly :)

    Thanks for this post! It makes me feel better about the overthinking I do. For one thing, I know I’m not alone, and for another, I can see that it could be worse…

  6. Just an excellent piece. I do much of this also, and have long debated travelers who say precise planning (reservations, itineraries, etc) eliminates the excitement and fulfillment from free flow movement, ie, the road less traveled, etc. My wife and I have visited @65 countries, with only a few on tours. Obviously, the tours are structured and very little is on your own. Those are the trips that we liked least. Mostly, we decide on the general area we want to see (Europe, Asia, etc), how much time we want to spend (we are retired….and most int’l trips last @3 weeks), the time of year, and mode of travel (train or car). Since we have accumulated a significant amount of airline miles, we leave the arrival city to the best route for the points required…and either Biz or 1st Class. So even if we are going to Stockholm…our best route might be thru DUS. My point is that even this part of traveling requires precise planning. Last minute travel will rarely get you to your destination economically. And the same goes for lodging. We use @airbnb frequently. Waiting until the last minute is fraught with problems when wanting specific locations. Our travel process has rarely failed us, and would be lost, and a nervous wreck doing it spontaneously.

    1. Thanks so much for the kind words and the great comments! There is no wrong way to travel, but it is interesting to hear about everyone’s experiences!

  7. Yep. I’m an over-planner for sure, and it’s gotten to the point that I have to sit down with my husband for an intervention session at least twice before every trip due to my inability to settle on anything (review sites are great, but I’ve wasted more of my life than I care to admit agonizing over hotels and restaurants.) And then I have to talk myself off a ledge every time a choice I finally made turns out bad. We should start a support group.

  8. Ok. THIS. Was amazing! This is totally me! Everyone keeps saying “let go”, “enjoy the moment”. But how? Theres’s always something to worry about. I’ve made my peace with it and realised that I won’t fully enjoy a trip UNLESS I’m completely paranoid about something or the other. Good to know there are others like me out there. :)

  9. So true. I’m heading to Thailand in a couple days and cant seem to choose a ‘resort’ (hostel/budget hotel) primary because I’m over thinking the location, cost, amenities…

    That said, I’ve traveled so many times that I know I will have fun no matter where I stay. Why I over think the little things (when they truly don’t matter), I will never know.

  10. Hi Matt
    I’m an over thinker too. I’ve been thinking of doing some more travelling in Southeast Asia, but I need justify the travelling with how well my blog is doing, can’t decide if the blog is going well or not! Undecided and over thinking lol

  11. Ha! It seems like I’m in good company! I get what you’re saying. In the last couple of years, I’ve tried to be more flexible and less maniacal about planning or ‘sticking’ to a plan. It’s been a slow process. Just when I think I’m being spontaneous while traveling, I find myself reaching for my notebook, spreadsheet, or travel book to make sure we’re on track. It drives my husband crazy; he’s more of a ‘live in the moment’ and ‘go with the flow’ kind of guy.

    Thanks for posting this, though. I’m not alone!

  12. Had a good laugh with this – every one hit the mark and is probably why I travel solo more often than not. I had a 30 page itinerary for a month in africa, have contingencies in place for weather (took three days/tries to reach Table Mountain and a bit of shuffling of other activities) and feel a sense of comfort with my “crazy”. Right now, I’m trying to plan a sabbatical and keep going back/forth with a detailed plan (this city, that city, etc) or a loose itinerary and see what happens….

Comments are closed.

I help you experience the best the world has to offer!

Please enter a valid email address.
Something went wrong. Please check your entries and try again.