How to Leave the Plan Clan and Save Space for Serendipity

Written by on 20 May 2014

Just weeks into my trip around the world in 2013, there quickly emerged two distinctly different Commitment Clans within our bigger Travel Tribe.




There were those who planned.


And, there were those who did not.


Those who planned would spend days before our arrivals pouring over travel books in our tiny library. They would memorize the maps and major cities of every country we visited before we got there. They would know which sights they would visit, how they would get there, how long it would take, and every other detail you could possibly imagine.


One kid even taught himself key phrases in all the native languages.


These people were living, breathing travel guides.


Those who did not plan… well… they did things a little differently.


For starters, they didn’t even know where the library was. They were too busy talking to their professor about his year spent in Antarctica to worry much about what Lonely Planet had to say about Beijing.


They might have had a vague idea of where we were headed (Mauritius is somewhere in Africa, right?), but they didn’t concern themselves with any particulars.


I remember the phrase “wing it” being used a lot.


But most importantly, they had no idea where they were going, how they would get there, how long it would take, or basically any other detail associated with travel that would normally occur to any ordinary person abroad.


Not only did they not have a plan, they were dead set on keeping it that way.


It was though having a plan was akin to looking Divine Guidance in the face and saying, “I can definitely do this better than you.”


And who would do such a thing?




I would.


You see, I used the words “normal” and “ordinary” before purely to make myself feel better.


Because, (not shockingly) I happened to fall into the former category of planners, or what I like to call--


The Plan Clan.


Except for that whole “days in the library” thing… that was definitely not for me. But, boy, did I flex the hell out of Wikitravel!


I just couldn’t get that old adage out of my head:


A failure to plan is a plan for failure.


Looking back now, I don’t believe one could possibly fail at experiencing the world through a four-month voyage around the world…


But that’s not the point…


I held on to the notion that without a plan I would somehow miss something I was meant to experience or see and this whole endeavor of traveling around the world would be for nothing.


Now, to be clear, I’m not saying that I had a plan and always stuck to it.


I actually did the opposite.


I was one of the lucky ones who learned the ability to release the plan if an unforeseen and way more awesome opportunity presented itself.


In fact, now that I think about it, I did that a lot.


But nevertheless, I needed that damn plan to start.


Call it FOMO.


Call it anal.


Call it perfectionism.


Whatever you call it, I had to have it.


There were times when my plan worked out and times that it didn’t. There were times when my praises could not be sung any higher (how did you find this place?!) and times when I wished critical voices would be lowered (is this seriously what we drove 700 miles for?!). Through the good and the bad, the success and the failure, the planning mindset remained ever-present, even when the plans themselves were abandoned.


And I managed to learn a lot that way.


But surprisingly enough, or maybe not surprisingly enough, my concept of reality and my belief in possibility were turned on their heads the moment when I was forced to plan…


To have no plan.


Here’s what happened.


In January of 2013, my Semester at Sea voyage set sail from Ensenada, Mexico en route to Hilo, Hawaii. We had exactly 106 days, 16 cities, and 12 countries to go before we ended the voyage in Barcelona, Spain at the end of April.


Then that was it.


The trip was over.


And we would all be in Spain, each on the hook for finding his/her own way home.


Now, I was very aware of this fact at the beginning of the trip, but I started to get a little overwhelmed. As you can imagine, the expense of getting around the world in the first place was pretty great. And all those little “plans” in between weren’t exactly free either.


So when push came to shove, and I saw that flights from Barcelona to Dallas (or anywhere in the United States for that matter) were upwards of $1,500-2000…


I felt as though I had no choice.


The only plan I could choose was one I couldn’t afford, so as you might guess, I chose no plan.


And I hated it!


I rationalized this otherwise out-of-character decision by saying that I was simply leaving room in my schedule to backpack around Europe or do some other traveling when Semester at Sea was over. I simply didn’t know when I would be flying home, so therefore, I couldn’t book a flight.




Plan problem, solved.




I put the no-plan nerves off for a while, and it wasn’t until we got to India in March that the itch to plan began to hit me with renewed force.


People were starting to talk about their trips after the voyage. Who would travel with who, where they would go, whose parents would be there to celebrate, and inevitably, the elephant in the room…


How on Earth would we all be getting home?


Now, in between Mexico and India, I certainly hadn’t made any money.


So, to me, my options hadn’t really changed.


In this corner: Spend an exorbitant amount of money with the Plan Clan.


In that corner: Continue to leave space for serendipity, hope for the best, yet remain living in uncertainty.


Thankfully for me, serendipity swooped into the space I’d left in the absence of a plan, and gave me something more than I could have ever imagined.


On our second to last night in India, I was in a hotel that miraculously had wireless internet. Before going out for the night, a few of us were drinking wine and catching up with our friends stateside. During this hour or so of connectivity, I received a message from one of my best friends, Matt.


Matt wanted to know what my plans were for Memorial Day Weekend.


Having no set plans post April 25th, 2013 because, for all I knew, I'd still be in Barcelona, I wasn’t really sure how to answer that question.


So I said


Nothing… why…?


Turns out, Matt’s private equity firm planned an annual associate’s retreat that fell on Memorial Day Weekend every year. That year’s retreat was in Costa Rica. Every associate was invited and was allowed to bring one guest, all expenses paid, all plans taken care of, all by the company.


His only question was,


Did I want to join?


Did I, ever!


Once I said yes, the planner in me quickly launched into logistics and started wondering about what a flight to Costa Rica might cost. I asked him what he needed from me and what we should do to plan this puppy out.


All he wanted to know was where in the world I’d be by then so his company could book my flight.


I’m sorry…




Did you catch that?


‘Cause I sure didn’t.


Unbeknownst to me, I had agreed to a trip for which the company would pay not only for the event itself but also my travel both to and from.


Talk about a serendipitous jackpot!


Memorial Day was almost one full month after my arrival in Spain. That gave me nearly 30 days to travel around Europe on a Eurail pass that I could then afford, thanks to not having to purchase a flight from Barcelona. Not only that, but after the company flew me to Costa Rica for the retreat, they flew me to New Jersey so I could see a dear friend and former teammate get married and successfully reenter the United States.




And had I over planned... or ever planned at all... I would have completely missed out on this opportunity.


Not having a plan might sometimes sound scary.


But leaving space for serendipity will always sound amazing.


I’ve always been jealous of people who would live without a plan—people who were perfectly content letting life just happen. It takes an amount of surrender and trust that I often only embrace when forced to.


I still struggle to live out this maxim to its fullest, but whenever I get scared, I remember the possibilities that live on the other side of that fear.


And I choose serendipity.




Are you a member of the Plan Clan or do you already save space for serendipity? Can you remember a time when you let the cards fall where they may and fate dealt you an unbelievable hand?


I believe that every greatness we enjoy right now can be traced back to one person, conversation, or observation that provided a turning point in our lives. I’d love to hear if you believe this, too.


Did this story resonate with you? Or did it make you think of a story of your own? Share your story or your reaction in the comments below.


Because sharing stories an instinctual, powerful way to touch the hearts of others and change the world around us.

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