According to Plan

Why Your Travels (And Life) Should Never Go According To Plan

Derek Perspectives, Travel Tips & Advice 85 Comments

This post is brought to you by Bupa Travel Insurance.

According to Plan

During my senior year of high school, and after a great deal of debate, I eventually chose the university that I would attend for the next stage of my studies. I chose a university in Atlanta, Georgia. However, when I graduated with a Bachelor’s Degree some four years later, I had not only attended that university in Atlanta, but I had also attended a university in Melbourne, Australia and a university in my home state of Massachusetts as well.


When I first started traveling back in 1999, my plan was to travel for three months. I even had a return flight back to the USA, for exactly ninety days after I touched down in Bangkok. Go figure. I ended up traveling for 14 years…so far. I’ve visited countries I never imagined I would ever visit, I’ve had experiences that I never even knew were possible and I’ve met people whose existence and culture I had been completely unaware of.


Furthermore, when I decided to try and travel indefinitely, I quickly reached the conclusion that the only way to make this happen, to fund my travels, would be to teach English around the world. Fast forward to now and I’ve used a combination of English teaching, working on cruise ships and working online to help keep this traveling lifestyle going.


In about two weeks or so from today, I’ll be launching a new website project that I’ve been working on with a friend of mine. And I’m extremely excited about this project, even though the project that will be launched looks absolutely nothing like the original idea we had started with a few months ago. There’s almost zero resemblance.


The point of all this is that every stage of my travels, every stage of my life actually, never ends up being what I thought it would be. I go in thinking I’ll attend one university, I come out having attended three. I go in thinking I’ll travel for three months, and now I feel as if I could travel forever.

And you know what? I wouldn’t have wanted it any other way.

In fact, I’m a firm believer that nothing should ever go according to plan. Nothing. If something does go exactly according to plan, the chance is high that something is wrong. How can things go exactly as planned when there is no way for us to know exactly what will happen once we start to put that plan into action?

If we’re open to new ideas, and we welcome the chance for our ideas and goals to constantly evolve based upon new experiences we have in life and new information we receive or learn, it would only be natural that our plans should change often as well.

That Includes Travel Plans!

If it’s travel we’re talking about, it doesn’t matter if you’re going on a two week holiday to the beach, a three month trip around Asia or South America or a one year round-the-world adventure. It should never go according to plan in my opinion.

Of course, that’s up to each of us. The opportunities to disable our original plan and head off in a direction we once would never have conceived of instead, will always be there. Such opportunities will appear all the time. It all comes down to whether or not we embrace those opportunities and see where it takes us, even if it takes us far away from our original plan, or if we choose to ignore them instead.

When I traveled to Romania for the first time back in 2011, I was on the tail end of a two month Eurail train journey around Europe. And my plan for Romania was simple, to get a quick glimpse of the country over the course of one week and then hop on the train to Istanbul where my European adventure would come to an end. Well, that didn’t happen. Before I knew it, I was enjoying Romania so much that I made a sudden decision to abandon my original plan and change course completely. Soon after, I had set up a ‘base’ in Bucharest, I had started traveling all over this country and I began spending more time here than I would have ever guessed I would spend in this land over the course of five lifetimes.

And I’m so very happy I made that sudden change of plans. In fact, I’m so very happy that I made all of the above changes in plans over the years and that as far as I can remember, I’ve never completed anything major in my life according to the original plan. For me, the result of being open to spontaneous, unexpected change is a life more in tune with what I truly want to gain from each day I spend on this planet. And that certainly seems worth it to me.

So here’s to change. Here’s to a fuller life. Here’s to welcoming the notion that what might be our plan today, could very well be crumbled up, tossed away and replaced by an even better plan tomorrow.

Are you open to change? Do your travels/life situations usually go according to plan or do they end up being different than what you originally expected?


Sign up to receive my best travel advice, deals, news, stories and inspiration from every corner of the globe. Sent once per week.

Are you ready to earn money and travel?

How to Work on a Cruise Ship and Travel eBooksClick above and get started!

Comments 85

  1. Pingback: Travel Blog Love: January 2014

  2. Great post Earl. So true. I believe you should never plan a trip, just go with it. I have planned in the past and nothing goes to plan or I enjoy a place too much and want to stay longer, like you in Romania. I love talking to other travellers and finding out things that those guide books don’t have in them. Then our route changes once again.

  3. Pingback: Wandering Earl | Lightning Frog

  4. Great post Earl! I totally agree with you.
    Last year I was heading to the little town Tuticorin in the south of India to teach English in the orphanage, but I ended up in Indore teaching Russian culture to the college students. Changes can be for the best)

  5. Hi!

    I’m finding myselg enjoying tremendously your posts and being sucked into your wonderful crazy adventure world. I myself want to break free from my current life plan, since it doesn’t agree with my soul. I do however have a question for you.

    How did you teach English overseas? Did you need TEFL certificate or other certificate?

    Your life is a dream to me. I so wish I could fulfil it too.

  6. Hi Earl!

    This is all so true. I agree things can change in an instant and nothing should go according to plan. I’d like to think I know what is in my future, but I remain open to any and all changes, whether travel plans or life plans. You never know what experiences and opportunities these changes could lead to. However, I do want to travel more in the future – that’s one thing I hope doesn’t change. I really enjoy reading your blog and following you on your endless journeys. It must be an amazing experience and I enjoy reading your stories and reflections. Happy travels!


  7. Pingback: How I Stay Organized While Traveling, Working & Being A Fool - Wandering Earl

  8. Excellent post. I identified with the last bit of being open, as plans can change in a moment. I’m currently HelpXing in Ireland, heading up to Nortern Ireland next month to WWOOF as my visa is nearly up here….or so I’ve planned 🙂 thanks for the inspiration and reminders. Cheers, Earl!

  9. Hey Earl,
    That’s all so true, I remember in my teens I was always fairly certain I wanted to be a journalist. But as we grow our perspective changes, and nothing changes perspective faster than travel. So just like you, here I am after my first trip yet to set foot back on home soil.

    Here’s to dreaming but not inflexibility.

    Happy travels,

  10. Scooby-Doo and the mystery gang’s attempt to capture the monster, ghosts, ‘bad guys’ never went according to plan, but it always worked out in the end.

    We should all just trust that we don’t know where the story ends but we can hope to make it a great one.

    Great post, Earl!

  11. I never plan! I stopped doing that a long time ago. There is simply no point, and like you said, there is no other way I would rather have it. It’s so much fun to be spontaneous and then there is no let down when something doesn’t follow through 🙂

  12. I’m a firm believer in setting realistic goals and a plan to achieve them. As you said, the plans will change but at the end of the day, as long as it still ladders up to achieving your goal then we should let the universe decide for us. Being too strict on plans i.e schedules, rules etc limits the opportunities to what we can experience.

  13. Preaching to the choir, my friend! I’ve long been a proponent of “life happens while you’re busy making plans” and in my own full-time travels for the last 7 years – as well as in my “former life” before selling everything to travel, I’ve reinforced that lesson many (MANY!) times over.
    I’m now at the point when people ask me (as they often do) what my travel plans are – for example for 2014….I don’t even make plans any more. I might have an idea of what I’d like to do, but more often than not opportunities come to me in a serendipitous way, and it’s simply up to me to roll with it and be open to change.

  14. Fantastic post Earl.
    Am I open to change? Always.
    Do things always go to plan? Well that depends!
    Do my plans end up being different to what I thought? Well, that is what travel is about. Adventure.

    I don’t think one should be entirely clueness, neither is it a crime to have some sort of, albeit, rough plan. I think what is important is to be open to opportunities and as a result, a change in plan.

    I am sure that when I agreed to go to Czechoslovakia 20 years ago, I never for a moment thought that that would be the beginning of never going back to my hometown – Manchester in the UK. I never thought that I would live in Eastern Europe, marry a German, open two schools, sleep in a casino, get mugged by a bunch of kids in Egypt, have my Bed & Breakfast disappear, literally. Or party with expats in Hong Kong.

    I say yay for openness, flexibility, believing in others, and absolutely going with the flow when it all looks like things are about to fall apart!

  15. I plan other people’s holidays for a living, but my own travel plans are always in disarray. It’s almost embarrassing … and probably why my friends and family have not yet taken own of my trips 😉 But I always want to be open for whatever opportunity comes up so making plans, advance bookings, even return tickets for some period of my life, just feels too restrictive. I remember when I first went travelling and a travel agent was trying to sell me a Contiki tour in Europe. Even though I had NO idea of what this travelling thing would look like, I knew I did not want to be stuck on a bus on someone else’s itinerary! Poring over a map asking a friend “where are you going to go next?” and he replies “I don’t know, you?”, “I don’t know either”. Wow! What freedom!

  16. Awesome writing, I love this idea of things not going as planned being preferred. I wouldn’t travel any other way, too much planning gets in the way. I am just starting out, after working maddening hours starting-up my own restaurant, I sold it and am heading out. I will try to blog, thanks for the inspiration!

  17. Great post, as usual Earl. While I do look back on my life and think, “Wow, I never thought I’d ever be doing this right now, or be with this person, or be in this situation. Funny how things turn out!” I have to say that I don’t agree 100% with the statement that things should NEVER go according to plan. I realize that I am picking apart the semantics right now, but I happen to have a group a friends that rarely stick to their plan — and not in a good way. They have a habit of saying things such as “We should go to this city for New Year’s!” or “Let’s do this on Friday night!” or “I’m totally doing this for your birthday!” and then it never happens because they never plan it out or put any effort in. In those cases, the plans simply get cancelled. Not replaced with something better by a last minute spontaneous decision, they simply never happen because of laziness. In that case, it is so refreshing to meet someone who actually makes a plan and sticks to it. That is called reliability. And I find it frustrating when people put down those people by calling them “boring” or “unspontaneous” or “uptight”, when in reality they are just the people who like to actually DO something, instead of be lazy and at the last minute resort to a default plan that isn’t actually any fun.

    So appreciate the planners in your life, while at the same time being open for POSITIVE and PRODUCTIVE change.

  18. I love this! I plan the big stuff but leave the details for later. I used to want to get everything perfectly laid out, but life is not that neat. I’ve come to realize that wanting to get everything right on the first try just kept me from doing anything, so it’s better to just roll with the punches.

  19. Pingback: 1 Minute to Immediate Fulfillment and Success

  20. My best travel experience: the day before we went to Munich we were in Austria and met an older couple from Munich. They invited us to stay with them while in town and we spent 4 days with them. It was a blast. They got us drunk and fed us every night. Stay open to possibilities is the best advice I could give anyone.

  21. lol The past two years I keep saying I’ll make it. I’m saying it again this year! I may have a travel buddy this time so that will help. I have no idea where I’ll go this year. lol

  22. Great post, and as always, beautifully and eloquently written. I’m a super planner… I even have a 5 year life plan. I’m afraid that if I don’t plan, I’ll never accomplish my goals. The unfortunate thing about planning is that it doesn’t allow for much flexibility. Lately, I’ve prayed for the Lord to step in and disarray my plans if He deems fit to do so. His ways are better, anyway.

    Great post, Earl.

  23. So true! While I do like having a big overall plan for my travels aka what countries I’ll go to, the smaller details are better left up to the moment. You never know who you might meet along the way that might change the course of your travels. I’ve been fortunate to meet some amazing people along my travels and then alter my plans accordingly so we could travel together for a bit. Sometimes it’s not where you are but who you’re with that makes all the difference. After a year in Australia I felt the same way, sometimes not having a plan, is the best plan you can make! My post: Who says you have to grow up?

  24. The longer we travel the more adventurous we have become. I used to plan absolutely everything before we set off. Now that we’re nomadic, we often don’t even know where we’ll be sleeping one day to the next but it always works out well in the end and we have an amazing time. Spontaneity is brilliant.

  25. Sometimes when I travel and stay somewhere for while, I slip into a routine. Then, when I have to relocate, I feel myself becoming nervous. Change is inevitable. I feel nervous because I don’t know what to expect. However, when I arrive at the new locations everything is so different then I could ever imagine it would be. My nerves slowly calm down and I quickly start to enjoy the ride again. This is why I embrace change. It challenges me to step out of my comfort zone and pushes me into new adventures, which I would otherwise never would have experienced.

    Thanks for the great post again.

    1. Hey Jesse – That’s a great way to explain it and I am of course familiar with that up and down process. Luckily, the more it happens, the more we realize that the fear isn’t necessary and the more we are willing to push ourselves even farther away from our comfort zones.

  26. I completely agree! Even though I’m a scrupulous planner (mainly due to my tendency of becoming over-excited) I never think twice about going ‘off-piste’ so to speak. Plans are great and help me imagine trips but I find that once you’re you get there, other things arise and it’s best to just go with it. A lot of my favourite memories have been completely spontaneous.

  27. Definitely agree! If a great opportunity comes up, grab it with both hands.

    (Though having said that, it’s good to make sure you’re not throwing the baby out with the bathwater – no point in giving up a great planned opportunity for a mediocre spontaneous one.)

    But some of the most memorable moments are the ones that you don’t expect – I remember paragliding in New Zealand as a totally impulse decision because it was too windy for a second skydive. And you know what? I loved it! Carpe diem!

    1. Hey Katie – I agree with that and I think we should be open to the changes that ‘feel right’, those moments when we suddenly have an urge to follow a new opportunity, when our guy tells us we should make a change. Those are the changes we should follow!

  28. Completely agree Earl. Life’s more exciting this way. Even though I understand why some people can live their lives by a certain set of plans and rigid rules, I know for sure that I want mine to go in any way at any given moment if I choose to. Why? Because I’m the author, and I write as I go, that way I can give myself a nice striking and unexpected ending! Cheers bro, great thoughts as always.

  29. I agree, life seems to go in odd directions if you just let it flow a little more. Of course I like plans so have to deal a little with the internal stress of my plans not working out but usually it’s for the better!

  30. Earl, great post. We regularly chat about this theme and have adopted a “follow the omens” mentality that has taken us to amazing places (and kiss-worthy locations!) and beyond. In fact, we practiced it to the point of exiting our six-figure jobs, giving away all of our possessions and putting just 100 items each in our bags just this past September. At 46, Mike (retired Las Vegas fire chief) and 36, me (former national brand director), we lived in rural Ireland for a few months, and jumped at the opportunity to make our way through Italy, Sweden and England when we allowed our plans to veer from the plan. It was exceptional. We now use Chicago as a home base to live big and kiss often…with just a handful of items and from a tiny studio. A year ago, we could have never predicted the fulfilling, simple life we’re living today. Eliminate distractions, follow your heart, take a risk. This is no dress rehearsal, as we like to say. Keep up the great work.

  31. I have to agree with you, even though I am a natural planner. Some of the best travel moments I’ve had weren’t planned and some of the best memories were the result of spontaneity. So, here’s to changed plans!

  32. I agree with that. I kind of did that with Ghana this year. I really knew nothing other than we’d be in a village with no running water and that fruits and veggies may be hard to find. I had such a stressful time. I didn’t realize what the transportation situation was going to be like, or that there really weren’t many fruits around, or how overwhelming the whole darn thing would be. But now I know for next time. That whole trip was pretty spontaneous. I had no plans to be in Africa this year. lol I thought I’d be going to India, and that didn’t happen. Anyway, from that experience and others, I’m learning that a bit of a plan is a good thing, unless the whole idea is to just see what happens and where you end up.

    I guess though, no matter what plan you have, it can change and you have to be quick on your feet to take what you get and run with it.

    1. Hey Kendal – That’s the idea…regardless of how much planning you do (and everyone feels the need to do a certain amount of planning for the most part), as long as you are open to those plans changing at some point, our travels and our lives in general will typically benefit. Let me know if you do make it to India at some point!

  33. My life is exactly the opposite of what I had planned for myself. While this is alarming at times, it is far better than anything I could have ever planned.

    1. Hey Kaylin – Usually the end result when we are open to such change is a plan that is better than anything we could have originally come up with 🙂

  34. I’ve taken a couple of trips in which I would have gotten more out of the experience if I’d done more than just show up. A bit of research helps – but I’ve also tried to deliberately limit my Google Image/You Tube exposure to a place before I go. It’s wonderful to be (pleasantly) surprised.

    So I’d say have a plan, but be willing to improvise.

    1. Hey Ed – Indeed. Having full expectations of a destination before you even arrive can sometimes lead to disappointment. I’m the same way as I rarely do much research at all, preferring to be surprised or at least unaware of what I will fully experience in any country I visit.

  35. In theory, I like spontaneity. But the thought of things not going according to plan actually terrifies me. I am going to Italy for the next six months. This will be my first time on a plane, my first time out of the country, and my thoughts are overwhelmed by crazy paranoid panic. My mind sounds like this: “what if my flight from Zurich is canceled? Do I get stuck there? What the hell is an electronic flight ticket anyway? Do they just KNOW I’m coming? My baggages follow me right? I don’t need to track them down at BOTH layovers…right?” And, technically, I know the answer to each question, but Panic (that’s what I call my brain now) just won’t hear of it.

    There had to be a time where the same panic flowed through you. How did you calm down, to let yourself live the experience?

    1. Hey Marie – That’s an interesting point and I don’t think I can really remember panicking too much. But I think it’s normal to be terrified and in the end, all it takes is one trip – your trip to Italy – for all of that fear to disappear. As soon as you arrive in Italy and the trip was easy and without any issues, you definitely won’t go through the same thing the next time around. So I guess the point is that you just need to force yourself to travel and once you do, the fear disappears!

  36. Great read once again,

    By deciding to take our home with us via a boat we have allowed for some planning but mostly follow our noses on our travel plans. I for one like to get to a spot and take a bit of time to take in the experience and once I caught my breath then make some plans. trip adviser and sites such as these help me define some of my must have travel experiences.

    Sites like yours inspire so thanks

    the Miss

  37. I totally agree, travel plans and life plans should never be set in stone. Things can change at any moment so there’s really no way of knowing what next week or even tomorrow will be like.

  38. Being flexible is good. 🙂 I think I’ve got that part down pretty well, it’s just the accepting where it leads me part I need to work on still. I’m not always happy with the changes in plans, but hey, the journey isn’t over yet! I can’t wait to see where 2014 takes me….

    1. Hey Kendal – I think the more open you are to potential changes, the more accepting you become of where it all leads. In the end, if you don’t go into a change with a positive attitude, it will be hard to find the positive side of things.

    1. Hey Brian – Ha, yes they do but if you read any of the documentation I send to those who sign up for a tour, there is a big paragraph explaining that things rarely go according to plan and that unexpected should be expected, even on one of my tours!

  39. You’ve nailed it again, Earl! God…if my life went according to my original plan, I’d be working who-knows-how-many-hours-a-week in some huge law firm somewhere, probably while slamming my head into my desk every change I could find. Because I was open to change, I’m where I am now…and I think I’m far happier because of it. Life is all about surfing the waves of entropy!

    1. Hey Megan – That’s how it works…being open to change leads us to places we would never have imagined. I certainly wouldn’t be where I am at all right now had I stuck to my original plan and ignored the opportunities for change.

  40. Great post! I find things more to my liking if I just go with the flow. These days rather doing a lot of planning, I do a lot of researching. Having a general knowledge base about an area helps to me adapt once I’m on the ground. That being said, I realized as I just finished typing that sentence that it’s not even true anymore. Nowadays I do enough planning and research to get the broad strokes and let the details fill themselves in. The little things are what make life fun anyway!

  41. SO TRUE! I never thought I’d actually live in Thailand (and possibly Saudi next) but I’m so glad I’ve kept an open mind. You never know where travel will take you!

    1. Hey Mitch – And a mighty good poem that is…thanks for sharing the link so that I could read it again…it had been a while.

  42. Excellent post! “How can things go exactly as planned when there is no way for us to know exactly what will happen once we start to put that plan into action?” That really is the crux of the matter. It’s okay to plan, but how gracefully can you change them, then becomes the question. John Lennon said : ” Life is what happens when you making other plans.” It’s our ability to change plans that stretches our brain and soul. Travel Zen is pure bliss.

  43. In true Gemini style the love or hate of change is like everything else about me…changeable. On the one hand I love big change and I thrive on it as I tend to get bored easily but on the other hand I have a hard time with small spur of the moment changes. Coincidentally just this morning my boyfriend declared that we were going down to the local track here in Puerto Vallarta rather than to the gym as I had thought we were doing. It threw me into a complete tailspin! But when it comes to travel we never know more than a month in advance where we are going. For example we know we are leaving PV next week to travel through Guatemala and we think we’ll head to the Yucatan in March but that is open to change. We also think we may go home to Seattle/Vancouver in the summer but come Sept we’ll be hitting the road again to destinations as yet unknown. Maybe Europe…maybe SEA…maybe South America!
    As the great writers of The Peoples Guide say “Wherever You Go…There You Are!”

    1. Hey Sarah – I guess no matter what happens, your adventure shall continue and you just might end up doing something that isn’t even on your list of options right now…we shall see.

  44. I literally loooove making plans, espacially travel plans! But most of the time I end up throwing my plans away and do whatever I feel like in that particular moment. And this was always the best decision so far.

  45. Right-on Earl! I’m a big planner, but my plan is to open up and let things happen that you can’t know about before you start. I like to say that I find security in insecurity. The best experiences I’ve had traveling were never part of the plan before I left. So, the “Plan” is to allow the unknown to take over once the plane lands, or the train comes to a halt.

    1. Hey Steve – And the best experiences I’ve had came about in the same way as well…created from experiences that I had never thought about or planned to do in the first place. Planning is definitely reasonable…always sticking to it and ignoring opportunities for positive change is what holds us back.

  46. I couldn’t agree more.That is how I wound up in Romainia and Moldova in ’09.Heck,until two days prior to going,I had never heard of Moldova! My motto for life and travel( since they are one in the same now) The plan is…there is no plan!
    Look forward to your new site!

  47. That’s so true. I actually hate making plans. All of my travel I started with not a single plan at all and it all worked out so far. And all these twists and turns make the traveling so much fun! You’ll never know what’s coming tomorrow 🙂

  48. Awesome post Earl! I agree mate, it is always good to have some loose plans to start with as they are what get us going and motivated but you have to be open to change and the other possibilities that can bring. Good job travelling for 14 years straight too!

    1. Thanks for that Ardun and yes, some basic planning always comes in handy…even detailed planning works too, as long as you are open to having those plans change at some point.

  49. Perfect blog! I agree, the best things happen when you’re open to changing your plans. The last trip to South-America I didn’t plan anything accept for my flight to Buenos Aires (partly because i’m a lazy) and it was a pefect trip.

    Curious about your new project!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.