How to Stop Overthinking Your Travel Plans to Death

 In Badassery, Planning, Skills
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Lately I’ve realized that the life I’m living isn’t mine, and it needs to change. How do I know? I haven’t left the country in over a year. And it’s totally because I don’t know how to stop overthinking the whole travel thing.

Maybe you’ve experienced this too. You dream of visiting Paris or Micronesia or Svalbard. But you keep finding reasons to file it in the “someday” category, letting opportunities pass by. You just can’t seem to commit and pull the travel trigger.

And that’s really tragic. Because when social scientists ask dying people about their biggest regrets, they almost never say, “Dang, I shouldn’t have blown all that time and money traveling.” Instead, they almost always regret the things they didn’t do.

So let’s give your dream a fighting a chance. In today’s post, we’ll talk about how to stop overthinking travel. And we’ll challenge the four biggest thought habits that hold you back from firing up Kayak and booking those flights to Svalbard right freakin’ now.

TL;DR? Here’s a hip hop poet who says it way better.

1. Analysis Paralysis

Jenny Offill, award-winning author and instructor, noticed something strange about her writing students.

Many her most brilliant pupils were the ones who stalled out and never got published. Some of them never even finished a book.

“Why do you think that is?” she asked a colleague.

The answer: “I think they were waiting for instructions.”

I can totally relate. I’m always waiting for the magic knowledge bullet that will render me infallible. It’s true in writing. And it’s definitely true when it comes to travel.

Example: for years I’ve wanted to go to Kazakhstan. (Elaborate Pinterest board here.) But first, I need to:

  • Determine the top 20 attractions by reading expat (not tourist) blogs
  • Compare AirBnB monthly rental rates against local want ads on Almaty Craig’s List (translating ads if needed)
  • Memorize the public transportation system
  • Attain basic proficiency in Russian
  • Figure out how to buy a car and sell it in three months
  • Find a company that sells gas canisters for my stove (threaded for imperial, not metric)

I tell myself this is all part of good planning. You know what it really is? Procrastination.

If I can stretch my preparation phase out to infinity, I never have to face the anxieties and icky decisions that are on the other side. I don’t have to deal with resistance from work or my fear of being alone in a strange city or even what I’m going to do with my cat.

Yeah, at this rate, I’ll be leaving for Almaty in about 17 years.

How to Stop Overthinking It: Fail Fast

Rather than trying to learn everything about the ocean — from wave mechanics to shark biology — before you risk dipping a toe in the water, take a lesson from the world of Agile.

Agile is a philosophy used in fields that have a lot of complexity and uncertainty, like software development and marketing. (So yeah, perfect for travel.)

Know how you learn stuff in Agile? You try it before you’re ready.

Usually, this means you fail.

In fact, your goal is to fail as fast as possible. Because the sooner you fail, the sooner you learn.

It’s just like that with travel. There’s no way you can map out every possible contingency from your living room half a world away. No matter how well you prepare, you’re going to have to learn a lot of things in the moment.

And you know what? Sometimes underplanning can be freeing. You never know when you’ll find a lovely oasis you want to linger in.

And if you’re in Uzbekistan, you might learn that mailing a package is a three-day process, complete with sewing.

Yeah, it took us awhile to sew that cover. And buy the fabric. And find the right size box. Good thing we didn’t pre-book a hotel halfway across the country.

No amount of overthinking could have prepared us for this one. And honestly, a lot of travel is like that.

How to Stop Overthinking Travel to Death

2. Waiting for the Right Time

Sometimes when we’re nervous or ambivalent about doing something, we’d love some help from the universe.

And it can’t just be a subtle sign. When we look down the Sixth Avenue of life, we want to see a string of green lights beckoning us forward.

For travelers, that might look like:

  • Blessings and enthusiasm from our boss, partner, and loved ones
  • A quiet time at work with no big projects looming
  • All the folks back home enjoying perfect health
  • A peaceful world with no terrorist threats or civil unrest
  • A promotion that eases our money worries

Uh, yeah. When’s the last time that all happened at once?

How to Stop Overthinking It: Make Now the Right Time

A girl I know decided to conceive her first child when she and her husband were living in her parents’ basement.

Her rationale: there’s no right time to have kids.

They’d actually put it off for a while. They wanted to buy a house in the suburbs first.

But then they realized the truth. When you have a big life goal, now is usually the best time to go for it. You never know what’s going to happen in the future. And to a large extent, you can’t control it.

There’s a great story in one of the early Chicken Soup for the Soul books about a teenager who toured all over North America on a motorcycle. People said he was irresponsible and that he should be in school getting serious about life.

Then, when he was in his early twenties, he was paralyzed in an accident (non-motorcycle-related).

Bet he was glad he didn’t listen and took that trip when he had the chance. He’s a great example of why we all need to learn how to stop overthinking this life stuff and just … live.

How to Stop Overthinking Travel to Death

3. Catastrophizing

As awesome as it is, being on a trip creates opportunities for life to go awry. Much more so than, say, watching Dance Moms on your couch.

So naturally, you start to worry. What if you make a terrible mistake with disastrous consequences?

Some terrible travel-related mistakes I worry about:

  • Getting robbed and losing my camera, wallet, passport, and car keys
  • Buying plane/train tickets to the wrong city
  • Cutting it too close with airline connections
  • Sleeping through the alarm and missing a flight
  • Suffering an injury in the wilderness
  • Not being able to get a visa I need on the road
  • Airlines losing my bags
  • Breaking my cell phone

Granted, these are all pretty crappy things. Let yourself go down that particular rabbit hole, and the couch and Abby Lee Miller start looking better and better.

How to Stop Overthinking It: (Almost) Nothing Is Permanent

When we worry about something, we tend to overestimate its impact and staying power.

What if I’d told you that every single one of mishaps in the list above has happened to me? (No, not all on one trip, thank god.)

Yet somehow, I’m still here. I made it home. I didn’t die alone. Some of these traumas were so life-altering that I totally forgot about them until I wrote the above list.

When you feel anxious about doing something, Tim Feriss, author of The Four-Hour Work Week, recommends purposefully overthinking your worst-case scenario.

Really wallow in it. Like this:

I just know that while I’m gone, my boyfriend is going to leave me for that Polish model he follows on Instagram. He won’t be around to watch my car, which will get vandalized and towed to the junkyard and crushed with my skis in the trunk. Meanwhile over in Moscow, I’ll be robbed by a gang of street kids and lose my passport and wallet. The embassy will be closed for some obscure Russian saints’ day. When it opens, I’ll have no way to prove I’m Sarah Maurer from Denver. So I’ll end up living under the bridge with the street kids, robbing tourists to survive until the immigration police arrest me and deport me to the wrong country.

This exercise is great, because it shows you just how ridiculous you can be.

Yeah, indulging in ridiculous overthinking can show you how to stop overthinking. (And by the way, if you talk to frequent travelers, you start realizing that losing your passport abroad is the common cold of travel afflictions. Consulates see it 20 times a day.)

So stop thinking of mistakes and mishaps as permanent. They almost never are. Believe that if something goes wrong, you’ll figure it out.

How to Stop Overthinking Travel to Death

Yeah, broke it in Italy

4. Waiting for Someone to Go With You 

This is a hard one, because traveling with friends and sig others is really special. It’s nice to have someone to share your memories with. Years later, the two of you can look back and talk about the crazy things that happened, and it’s like living it all over again.

But I think sometimes we get in this rut where we make finding a co-traveler into an absolute condition. Or worse, put off traveling until we can go with the romantic partner of our dreams.

I recently saw a dating site profile that depressed me. All the pictures were of this guy in fabulous places like Jordan and Zimbabwe.

Then I read the profile. He’d quit traveling, he said, because he wanted to dedicate his energy to finding the perfect girl.

Can you hear my head exploding from there? It was like the law of attraction moving at warp speed in reverse.

Making your dreams dependent on someone else tends to delay them. Because truth be told, finding a wingman for your adventures can be a real pain.

  • You’ve got to find someone who likes your dream enough to throw time and money at it.
  • There are the logistical issues of getting schedules to match.
  • Not to mention, all of the dream-killing thought habits above. Chances are your wannabe travel buddies have them, too.

Yeah, the odds of actually finding a traveling companion before the second coming are kinda stacked against you. So ask yourself, is it really worth the wait?

How to Stop Overthinking It: Risk Going Solo

The first time I spent a week traveling by myself, I was really nervous about it.

But do you know what? I had a blast.

Sure, some days were lonely. I was in China where meals are served family style, so restaurants were really awkward.

But I also talked to about five times as many strangers as I normally would have. Some were locals. (It’s a lot less awkward speaking bad Chinese when only strangers are watching.)

And some were fellow travelers. Many were actually solo travelers. We just looked at each other in the hostel bar and started talking. I haven’t made friends that easily since grade school.

For more great travel alone trip tips, check out my solo travel Pinterest board.

Travel tends to unite people. Often, these friendships last.

One of my best friends from college invited her favorite road buddy to her wedding. (And road buddy came.)

It’s also possible to meet that special someone. You’re on vacation. You’re relaxed and doing something you love. A backpacker’s café has got to be one of the easiest places in the world to strike up a conversation with attractive strangers.

So if you can’t find someone to share the adventure with, resolve to go solo and plan accordingly. And hey, if someone hops on board your bandwagon, consider it a happy surprise.

How to Stop Overthinking Travel to Death

First solo trip, 2004

And Finally, Have Faith

When you’re learning how to stop overthinking travel (and life in general), a lot of it comes down to faith.

You can’t know everything ahead of time, and you can’t change the future. You just have to believe that you are smart enough, capable enough, and tough enough to deal with whatever comes your way.

I think this Strumbellas song says it pretty damn well:

So have faith. George Michael would be proud.

And there you have it. In Dante’s Inferno, the lobby of hell was reserved for the uncommitted. Don’t linger in limbo forever. Figure out how to stop overthinking every damn thing.  Make 2017 the year your travel dreams come true.

Got any tips on how to stop overthinking your travel plans to death? Please share below, because believe me I could use them.

How to stop overthinking your travel plans to death

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