Almost Fearless

The Art of Unplanning: Day 24 of 30w30d

This post is part of 30 Ways in 30 days to Redesign Your Life and Travel the World. This series seeks to give you the practical, real world steps you need to take to get from wherever you are, to exactly where you want to be– traveling the world and living the lifestyle you want.


30 ways in 30 days, unplanning, planning, against the grain, travel

The world is massive.  Travel is a messy, glorious thing.  We’ve been talking about planning for travel, but now it’s time for a little chaos theory.  Allowing kismet to pick your next destination.  Following your instincts when picking where to stay.  Giving chance complete control over that evening’s dinner.  Blindly heading into the night to see what finds you.

Planning is a wonderful thing.  It makes taking the leap possible.  It makes you feel more comfortable.  It’s also a great for a backup plan.  But we don’t quit our jobs or become digital nomads to follow a schedule.  We want something more than rigid itineraries and daily activity lists.  That’s for vacationers.  We’re travelers.

A Vague Notion is Enough

A good travel plan knows where you start and generally the direction you’re going in.  No more and sometimes less.  Until you get there, you’ll always be handicapped in your understanding.  How long to stay in Paris?  Well,  that depends, will you end up loving it or wanting to leave as soon as possible?  Did you meet someone?  Did they share their plans to bike southern France and invite you along?  Is it hotter than you thought and you want to head north now and finish the southern route when it’s cooler?  Are you running out of money and want to skip over to SE Asia ahead of schedule? Here you are, two months before you leave, knowing none of this and you wonder: should you book two days, one week, a month?  Even if you read every travel guide, you’ll never be able to predict how you’ll feel, who’ll you’ll meet or the chance encounters you’ll have.  If you plan too tightly and can’t ditch everything for the unexpected adventure, you’ll be traveling but stuck.  You will have traded your hard earned freedom for an arbitrary schedule you created.  Be careful.

You Are Not Looking for Sites, You’re Searching for Experiences

If you don’t plan, show up somewhere and wait for something to happen… probably nothing will.  As a former-vacationer, you might be used to the kind of travel that involved checking monuments and museums off a list.  Your mindset needs to change.  The most memorable times of your travels won’t be at the foot of some attraction, snapping the same picture as a million other tourists.  No, it’ll be the seaside fish stew you made with the local who rented you a bike that morning.  It’ll be the family you stayed with because of a chance encounter and helping the kids set the table and practicing their language.  Or it’ll be a sun-drenched day, where ever, in a spot you only found because you got incurably lost, but discovered something more beautiful and rare than your intended destination.  How do these things happen?  You seek them.  Like a tourist seeks items on their list you seek experiences.  You smile at people and make eye contact.  You start a conversation and let it naturally unfold.  Say yes, even if you’re not sure.  Get lost.  Do something on a whim.  You’re open to anything.

Plan, But Don’t Commit

A plan is what you follow when nothing else interesting happens.  You might pick out a hotel for the first night, so you can collapse after a long day of travel, but the next day you might walk around town to see if there’s somewhere better.  You might make plans to take a certain train or bus to the next town, but only if something better doesn’t occur to you.  If you’re not feeling a place, you leave.  You don’t feel bad that you didn’t spend enough time somewhere.  You don’t compare yourself to other travelers.  Maybe you may have countries on your list that you skip altogether in order to spend another month where you are.  A plan is just a plan.  It’s not what happens.

Let Go of Expectations

As you travel, you might find old expectations haunting you.  You imagined this big trip for so long and now the phantom memories of those days cloud what you’re really doing.  You might have had big ideas about how many pictures you would take or how fluent you’d become or how you’d actually end up spending your day.  More than likely you imagined squeezing every glorious drop out of this experience and that meant – at the time – doing as much as possible.  Now on the road, things are slower.  You’re perfectly happy skipping the 100th old church in order to play chess in the street.  But still, you feel a little bad.  Are you wasting it?  No!

It’s okay to be disappointed.  In fact you’ll likely feel all kinds of negative emotions at some point in your trip.  It’s not about not feeling those things.  It’s about feeling it, then letting it go.  Why?  Because this isn’t about what other people think, and especially not what a pre-trip you thought your travels would be.  So be lazy one day and skip the big important thing.  You won’t die.  You should do whatever you want.  And in the end, it’ll be there for you later.

The New You

You walk out the door in search of breakfast, with no idea of where a place might be, what the menu actually says or what kind of food you’ll be eating.  When people ask where you’re going next, you offer an annoyingly vague (to the asker) response, like, “I don’t know, I was thinking south”.  You sign into your hostel, but you don’t give an end date.  You might leave that night or in a month.  You always seem to be meeting people, making friends and bringing unlikely groups together.  Someone asks you offhandedly if you want to hike the volcano tomorrow morning and you say yes, even though morning is only 4 hours away.  You spend the first day in any new place, just walking around.  You have that story…  or a few of them:  the month on a strangers yacht in the south pacific, or living in a monastery with the sisters in perfect silence or working at a vineyard just because.  It’s those things you remember, what you’ll consider the best times.  It’s the adventure you never planned.

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



  • Even thought we no planning is important, it can become a bit too robot-like to have everything planned out. I like life to be spontaneous sometimes. So, once a month I try to just go for a walk into town, sit in a cafe, read, window shop. In this time I’ll make the effort to talk to a stranger or two. Sometimes, I end up going out for a drink with them and hear some cool stories of their travels in China. I don’t how this would work in ones own country, but when you’re an expat it seems to work.

  • This article really resonates with me. During my travels throughout college this is how I tried to do it. It doesn’t work all the time but you certainly get a better experience.

    Traveling without a plan also reduces the stress (as does not having great expectations) of feeling the need to see something or be somewhere. I can’t tell you how many times I was experiencing something amazing but had that voice in my head telling me I had to move on to experience the next stop. When you don’t plan you don’t worry about that next stop, it’s a lot easier to focus on the moment and live every bit of it.
    .-= Mark Lewis´s last blog ..Interview with Neil Wood =-.

  • Reading this one we have to laugh (and maybe cringe?). We are currently 3 days into the UK, riding out our Schengen Zone visa restrictions, and driving letting agents crazy with our vague answers to their questions “How long will you be staying?” and “What area would you like to be in?” Our answers are maddening to these wonderfully well-meaning people. “We’ll be here three to six months. Probably.” and “We can be anywhere really – we’re open.” THEN when they hear that we don’t have jobs, or local bank accounts… I wonder what they say when we walk out of the office?
    We just left Venice, where we booked a wonderful little apartment in a non-tourist part of town 3 days before we got there (for a terrific weekly rate). We then raced across the continent, took a ferry from Amsterdam to Newcastle, and headed to Edinburgh. We confirmed the first few day’s cottage only 3 hours before we landed. That one we sweated!
    We had planned on being near Edinburgh. Today we met a charming woman who has a place in Perth to rent, and we may end up there instead.
    Sometimes this on-the-fly living is unnerving, because we are traveling with our kids, and even though they’re terrifically flexible, still – needs must be met.
    The other day Bob said to me “After this – what are we going to do?” He meant for a living. Nevertheless, my answer felt true: “We’re going to do anything we want to!” Bravery is a muscle, and we’re building it! AND having a terrific time.
    .-= Brenna Gibson Redpath´s last blog ..Happy Cows Come From Austria =-.

  • Brenna–

    I love it. We had a similar thing happen on our way into Canada last month– we were flagged for a random inspection, because I think, we were so vague about what we were doing! We made note for next time to get our story straight before doing a border crossing. We were like, yeah, we’re going to drive up and we don’t know where we’re staying, but then I think we’ll go to Alaska and we want to travel for what, two weeks, no make that a month. They just looked at us and waved us over to the inspection site. Oops.

    Build that muscle!


  • We had that happen in Australia. We were so tired from the flight that they asked us if we were carrying any food and my husband said yes. They totally flagged us over to the inspection line and we had to throw away the food we brought for the plane ride.
    I don’t know if this has happened to y’all. But I’ve learned, the more I travel with the hubby, the better I become. Our honeymoon was kind of disastrous because we hadn’t traveled that much together and we went to france. We didn’t speak french, we had the pressure of what a honeymoon should be (romantic 100% of the time), and we had just left a reception where two families hated each other, and hated the fact that we were getting married. So we get to france and we get lost, we loose our tour book, people don’t understand us, and it was just a tad frustrating.
    Even though Australia and France are TOTALLY different, this past trip that we took was amazing. The hubby and I are totally more relaxed, prepared for mishaps and have taken a more relaxed approach to traveling.
    .-= Carolina´s last blog ..Get Healthy and Fit, Part 1 – Habit Edition =-.

  • ah…keep talking my traveling friends…I am homebound, job bound and dreaming. it is almost dangerous (?) for me to read these posts. I just read Brenna’s post then some of their blog. I act like I haven’t done this before. I’ve backpacked for 6 months on the AT, trekked in Nepal and spent a month in England in college. I think those trips are so ingrained in me and I’m reminded of the magic travel creates by reading these posts. Thank you for making this all seem like reality. Winter’s coming and I’m hunkering down to plan the next phase of my life. You all have given my new energy and vision. best, robyn
    .-= Robyn´s last blog ..Trash Talk =-.

  • These are great ideas, Christine. It’s like we have “permission” to not to have everything so planned out.

    Question: how do you travel like this and still deal with plane tickets?
    .-= Lisa Sonora Beam´s last blog ..RE: The Gift in Your Freakiness =-.

  • Really enjoy reading your great ideas on travel. I have to admit I’m a conventional vacationer with hopes to become a true traveler to travel the world without any plan, any timing. The most ‘unplanning’ experience I had was to decide on where to go, what to see and what to eat only when we arrived to that country but we still have had planned duration of that travel… not open as I wish.
    .-= Cecil Lee´s last blog ..Travel Snapshot – Portrait Of A Long-Tailed Macaque =-.

  • I totally don’t agree with Plan but don’t commit point. How can one be like that without taking any commitments. But I agree with point of looking for experiences. Tat was a cool one.

E-Commerce powered by UltraCart