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.

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.