The Perils of Being a Planner


As I prepare for my trip, the one piece of advice I keep hearing over and over again is that I should not plan too much.

This is a major problem for me because I am a planner with a capital P.

When I traveled in the past (usually for about 2 weeks at the most), I planned every day out in advance.  My theory was that I had such limited time; I needed to make sure I squeezed in everything I wanted to see.  I didn’t want to waste time trying to figure things out on the fly.

Likewise, if it was up to me, I would have my entire trip planned out with a day-by-day itinerary for the entire 10 months or a year or however long I’ll be gone.  See, right there I have a problem.  If it was up to me, I would know exactly how long this trip will last.

And actually, I do have an idea and I do have an itinerary.

I created the itinerary with a goal of coming up with a budget.  I needed to have an idea of how much this whole adventure was going to cost me so I would know how much I needed to save and, thus, when I would be ready to begin.  So I spent countless hours poring through guidebooks and web sites coming up with an estimate of how much time I might want to spend in each country, which cities I might like to visit and what sites I’d like to see, how much a typical hostel or guesthouse will cost and what the average meal might run.  All of this information got thrown into a massive spreadsheet (thanks to Shannon of A Little Adrift for her awesome template) and according to this spreadsheet at this moment (it has changed often), this trip will last exactly 319 days.

But I am going to force myself not to follow it.

Believe me when I say that will be a challenge.

In fact, most aspects of trying to plan for this trip have been a challenge.  Early on, I hated not knowing if or when my condo would sell, which would have a huge impact on my ability to travel long-term in the first place. Then, I hated not knowing yet whether the wonderful country of Russia would decide to grant me a 3-month business visa (they did!).  I also hated not being able to apply for worldwide medical insurance until 30 days before I leave (seriously, what is the reasoning behind that??).  And I hate that with less than a month until my departure, I still don’t know the identities of the families with whom I will be living in Russia.

I like to have a plan and I don’t deal well with uncertainty.

I know people are right.  I don’t want to force myself to stick to an itinerary just because it’s there.  I want to feel free to stay in Latvia a while longer if I absolutely love it or leave Ukraine after 3 days if I hate it (I don’t think I will, but who knows?). If I learn anything on this trip, I hope I will learn to be more flexible and spontaneous.  I hope I will allow myself to throw the itinerary out the window once in a while and even if I have Plan A in my head, I hope I will be happy resorting to Plan B or C or even D. Even better, I hope I can learn to be content sometimes going without a plan altogether.

But then again, is having a plan really all that bad?


15 thoughts on “The Perils of Being a Planner”

  1. Pingback: Why I Quit My Job to Travel – and What’s Next «

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  3. i know how you feel! I am the ultimate planner, but its true that you need to be able to leave the plan behind sometimes when travelling. sometimes you meet awesome people who convince you to go somewhere you were not originally planning to – and you need to be able to deviate from the plan without feeling bad. Its a skill im still learning…. luckily (or unluckily) my boyfriend is less of the planning type….

  4. I’m with you–I’m a planner too. The idea of traveling without an itinerary would be nerve-wracking. But…traveling long-term is much different than only having a week or two. You don’t schedule out every minute of your day 6 months from now if you’re going to be at home, right (right???)? “On the road” IS your new home, so it makes sense that you wouldn’t need to schedule everything out in advance.

  5. I’m a planner myself, and even on short trips, I find myself planning where and what I’m going to do sometimes to the hour. Hopefully, you’ll learn to balance between necessary planning and being overly controlling on your RTW trip. Best of luck!

  6. I love the planning part of traveling. I don’t plan every detail of every day, but I like to research the places I want to visit so I don’t miss things. I’ve only ever taken short trips, and I think if I didn’t plan those out, I would’ve missed the things that were important to me. But on my upcoming RTW I’m also trying to be more flexible and spontaneous. Although I still have a pretty rigid plan by most travelers’ standards. Here’s to becoming more spontaneous! 🙂

  7. Yeah, I have always planned my trips to Europe down to the day. The only exception was one two week stretch on a 7-week trip in ’07. I don’t think there is anything wrong with planning as long as they are flexible plans. And you know what? Half the fun of preparing for a trip is planning. If I had a dollar for every time I stared at my blank calender at work with a big smile on my face I wouldn’t need to save for my RTW.

  8. Katie, this is great. I am a planner as well and I hope that on our trip I learn to relax and let things happen without being such a control freak. I can’t wait to see how it goes for you… I think like someone else said you’ve got all the big things planned and you can leave the little things up to chance.

  9. I am a Type A, obsessive-compulsive, anal retentive personality. I like to PLAN everything. Seriously. But I just took my first backpacking trip abroad and spent two months wandering through Thailand, Cambodia and Laos. I had NO plan. I bought the plane ticket on a whim. I barely had time to pick up my copy of Lonely Planet before I left (and to be honest, I only had a guide book for Thailand, as I didn’t anticipate going to Cambodia or Laos). And you know what? It was AMAZING. You will love it. You will let go of planning more than you imagine. Yes, when I do it again, I will probably plan just a little more. But not much. The spontaneity was half the fun!

    Have a wonderful time on your adventures!

  10. wow! i could relate to this. i was always the planner. i never want to leave anything to chance. i have that fear of running out of money in the middle of nowhere. lol. but i guess, like you, that is one of the things i want to learn (or unlearn?) when i do my big trip. learn to leave some things to chance and spontaneity. people say you discover a lot of unexpected travel joys when you do. safe travels and more power, katie!

  11. I am 100% a planner as well. The problem is that things happen in your travels that are totally beyond your control. I was in San Diego a few years ago with a hiking trip planned to Joshua Tree. Due to wild fires, I couldn’t leave the county and had to change my plans. My hotel turned into a refugee camp for those displaced by the fires and the whole trip was ruined for me. I couldn’t afford to change my flight home so I just went with the flow for the next 5 days. Of course, this was in the US and I didn’t have the language barrier but I think you need to adapt any “anything can happen” attitude when you travel for a year!! Good luck.

  12. I think you are doing a good job of balancing that very fine line between too much planning and not enough.

    Just like stretchy waistband pants…there’s gotta be room for a little give.

    (Oh my, did I just compare traveling to jogging pants?! I clearly need to work on my analogies…)

  13. Congratulations, Katie…

    You are going to have a fabulous time. Please don’t confuse planning (having enough money, the correct documents for travel, and a modest concern for a place to sleep) with a compelling need to be on an on-time, all-the-time quick-step march to get from Point A to Point B.

    While you are on this adventure, you will get to put Curiosity into High Gear, to look around you, smell new things, eat (carefully) new things, observe and inquire.

    It is the height of maturity and good judgement to be able to do all that and know that you have a place to sleep.

    Bravo, you!

  14. I am a planner too and currently a month into my RTW trip… I really struggled with not making fixed plans, and freaked out that everything would go wrong – that I would mess up if I wasn’t completely organised…

    But now I LOVE it! For the first week it was tough, but now I’m really enjoying being able to change my plans and go to places at the last minute – places that I never considered going to before!

    1. Thanks for commenting Lauren – good to hear from someone going through the same thing! 🙂 Sounds like you’re having a blast on your trip!

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