Two men stand on a city sidewalk, looking at a smartphone and discussing time management. Both wear jackets; one pairs blue jeans with sneakers, the other with brown shoes. Pedestrians bustle in the background near buildings and bollards, epitomizing efficient planning in their daily lives.

Why I Never Plan Ahead of Time

Planning ahead is a sure-fire way to ensure things go wrong.

Rarely does one formulate a plan and then flawlessly execute it (especially in the world of travel).

My philosophy is simple: if you don’t have a plan, then nothing can ever “not go according to plan” (for those who struggle with double negatives: if you don’t have a plan, everything goes according to plan).

My travel nightmare (well, not my nightmare (that would involve bears and robots), but let’s call it a “least desirable scenario”) would be to have all my plane tickets, lodging, tours, transportation, and visits planned before walking out my front door. One of the aspects of travel that I enjoy most is the freedom to do as I please. To move about freely from place to place, to try out different hostels and hotels, to get local feedback on attractions and tours, to decide spur of the moment to hop on a train to a neighboring country – because that’s what travel is all about.

Before you get upset, I am not saying that I foolishly ventured out into the world without having done my research beforehand – research and education are the keys to successfully traveling in this fashion.

Warning - SHARKS
Shit, sharks? Better adapt to this.

The Art of Adaptation

In order for this strategy to work, you need to be adaptable.

Adaptation is an inherent part of travel. The same food, services, and luxuries you are used to back home, are not going to be readily available to you. However, adaptable does not simply mean that 400 instead of 800 thread count sheets are okay with you.

Instead it means that you can go to sleep after a night of exploration (read: heavy drinking with the locals), wake up before checkout, pack your things, move to a new place, enjoy a full day of activities, and then repeat. It means that you are able to make spontaneous decisions without having to rearrange your itinerary as a result, and that if your new friend wants to take you to their home tomorrow for a home-cooked meal, then you are ready, willing, and most of all able to do so.

It may sound appealing to book a hotel for six nights ahead of time and know where you will be staying, but what if circumstances change? What if the hotel’s toilets have no seats? What if the included continental breakfast was a sham!? If you’ve only committed to one night at the hotel, you can easily move on in the morning without worrying about cancellation fees or losing deposits.

Germany Train View
Feel the freedom in your hair.

No Plan Benefits

Not having a concrete itinerary only adds to the adventure that is traveling.

I love the freedom of meeting new people, finding out what they are up to, and then joining in should it fit my agenda. Trying to plan a trip ahead of time can (and will) result in you doing everything you “planned” to do, but not everything you ended up wanting to do.

When you have a “plan,” it can seem as if you are touring a place like a museum exhibit instead of experiencing it as a local. Spending your days surrounded by other tourists and chaperoned around by your “guide” is a travel sin. It will result in you fabricating and embellishing tales for friends and family since you have failed to experience anything genuine on your trip. By guessing and booking everything ahead of time, you are going to miss out on the true offerings of your destination.

Weather is a perfect example. If the anticipated weather decides to turn, you may lose out even more. Rain today? Looks like you can’t go hang gliding. What’s that? No unplanned days to fit it back into your schedule? AND you lost your deposit? Wow, sucks to be you. Next time, don’t plan so hard.

Top Reasons Not to Plan

Gonna Have A Bad Time
Possible outcome of planning.
  • No need to worry about cancellation fees
  • You’re not tied to some guesswork you did ahead of time
  • You have the freedom to be spontaneous
  • You’ll end up seeing more of what you want to see
  • You’ll learn to rely on your instincts, and you’ll learn to adapt

Granted, sometimes you will need to obtain visas, permissions, clearances, or some sort of confirmation prior to either arriving at your destination or participating in some activity (elections). But when it comes to “planning your trip”, you are better off letting it develop organically. Again, that does not mean you do no research ahead of time; research is your most valuable asset while traveling, and your being educated it what allows you to be so flexible in your travel plans.

Don’t be a slave to your itinerary.

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One Comment

  1. Hello Tyler; this is the first post of yours that i have read. I followed you here from the bhb group on linked in. I find your approach to travel completely unique. However, I can see the merits in your suggestions. as a blind person I’m not sure it would work best for me personally unless i really trusted the person i was going to be traveling with. And there is the question of what do you do if something happens to that person you are depending upon. but i do like your approach. Its kind of like running a basketball or football play. You know what you want to run because you have studied and trained but at the moment when the game is on the line you will have to improvise. we can all learn to be a little more flexible and adaptable. thanks again and take care, max

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