To Plan or Not to Plan: How Much Should One Prepare for a Visit to Another Country When We Value Spontaneity?

Besides acquiring a passport, booking flights, and reserving lodgings, how much should go into preparing to visit another country if we still desire to retain some freedom to wander while traveling?

Photo by Dariusz Sankowski on Unsplash

There was a lust of wandering in his feet that burned to set out for the ends of the earth. On! On! his heart seemed to cry. Evening would deepen above the sea, night fall upon the plains, dawn glimmer before the wanderer and show him strange fields and hills and faces. Where?

–James Joyce, A Portrait of the Artist as a Young Man

There’s something that almost always happens to me when I travel somewhere. At some point, I wonder if I truly got the most out of my time in a place. What did I miss? Should I have prepared more? After all, it is more than probable that this will be the last time I step foot in a new country. Did I truly make the most of my time here? How do we not only physically plan for an upcoming trip, but mentally prepare as well?

In two months, I’ll be taking a solo trip to Ireland. My flight and hotel have been booked for months, and yes, I’ve since renewed my passport this time and don’t plan on f***ing up my travel plans like last year. Before I arrive, I’ll have plenty of Euros in hand, a tour booked to some archaeology sites that require reservations, and a distillery or two added to the itinerary. Other than that, I sincerely do not want to plan for much more. I want my trip to be as spontaneous and flexible as possible. But is that wise? Will I be repeating history soon enough and wondering if I should have planned more? This is the paradox I, and many other travelers I presume, often wrestle with—how much to plan or not plan, that is the question.

Though we all fall on a spectrum when it comes to planning, to my mind, we lean toward one of two opposite poles with there being essentially two kinds of travelers: the ultra-planners and the carefree serendipitous ones. Where we are going and for how long are typically the biggest factors that will dictate which of the two we will be. I, like many other travelers, have inhabited both of these mindsets. For instance, I spent months researching, planning, and physically preparing for a 2014 backpacking trek on the Appalachian Trail. When it comes to extensive adventures, one can’t help but become obsessed with planning given how high the stakes are.

By contrast, on many of the solo road trips I’ve taken over the years, I’ve often done little more than pack some bags and camping gear, hop in the car, glance at the map from time to time, and let the open road determine where I go and what I see. I love the thrill of not knowing where I will end up at the day’s end. When I get tired, I find a campsite, typically near a national forest or state park, and rest my weary head waiting for the next day to repeat the same pursuit of serendipity.

My wife Hilary is much more the planner and exquisite at it (although she too loves being spontaneous). I admire this ultra-planner in her and I also benefit from her efforts because a lot of the time I get to be the clueless serendipitous one being surprised by her meticulously crafted itineraries. However, with Ireland, I will be on my own and I’ve been dwelling on just how much mental effort should go into trying to predict the future. But I don’t want to be a soothsayer trying to anxiously predict all future moments of my trip. As I wrote in a previous post on applying the adventurous mindset, I want the world to pull me along for the ride and allow my travels to unfold however they will.

I agonize—perhaps too much—over the fact that we live in a world where more and more of us are expected to plan everything ahead of time. Weddings are no longer the only RSVP-mandated event these days. Dinners, movies, oil changes for the car, children’s two-year-old birthday parties. By the time I reach 40, I’m guessing someone will come along pressuring me that I need to soon reserve my 450-square-foot room in a senior living community along with my burial plot. I presume there will be a package discount of 20% off my funeral expenses, and you must act now! Besides, all the 40-year-olds are doing it and the deal is simply to die for.

I get the reasons to plan. But I still hate it most of the time. It eradicates any hope for spontaneity and tamps down the chance for serendipity. When it comes to many national parks, time entry tickets are now required for certain dates and times just to enter the parks. While I understand the need for places to better organize and control the massive crowds that flock to these wonderful places, at the same time, one can’t help but feel a bit of coercion and a sense of loss in our ability to travel unencumbered without having to plan and control everything ahead of time. In my forthcoming book, I lament this style of traveling we may unwittingly fall victim to by saying,

Those of us who do make the effort to venture out tend to bog down a lot of the thrill a new place offers us by overly obsessing over the costs of bus fares, plane tickets, hotel accommodations, weighing the restaurant options, and placing reservations here and there. We become all too consumed by this ordeal of planning. We plan out which beaches and monuments and historical places we’ll check out and for how long, snap a few quick photos of us being there to make sure we earn our social status for social media postings, then quickly rush to the next hotspot to repeat the whole process as if we’re in some frantic race to get the experience over with. What’s the point of this?

We let go of all sense of spontaneity and uncertainty, which are important parts of what adventure is all about. Rather than simply packing up a few reasonable essentials, booking the plane ticket, and letting our tale unfold and allowing whatever happens to happen, we systematically attempt to plan every detail out in a work-schedule fashion. By the end, the mystery and suspense of our experience are all predetermined and there’s a part of us that may feel a bit cheated, though we know not why. We know exactly where we will be and when we will be; what things to expect; for how long we can enjoy our time always peering down at the wristwatch; and what we’ll be wearing to dinner on this or that night.

The experience is completely predictable and no time is set aside to just simply explore and wander and let yourself become lost and enchanted by the unexpected with what a new place has to offer us. We try our hardest to control every detail. Instead of letting the experience mold and shape us, we try to mold and shape the experience. 

While I recognize that some planning and concern over safety are paramount when traveling (as I certainly wouldn’t advocate being completely mindless while in unfamiliar territory) I still worry about how many of us compromise our experiences with this style of OCD traveling—our minds being locked in a loop of constantly planning for the imminent future rather than taking a breath to appreciate what is before us in the present.

I continue to mull over the cultural origins of this in the book,

This overall style of experiencing a place feels anxiety-ridden and depressing. All this worrying is likely because we’ve allowed our time to be constrained by all of modernity’s endless expectations, demands, and fears; the overwhelming commitments, responsibilities, and anxieties we’ve become absorbed by; insurmountable debt, bills, rent, mortgages, schooling, jobs, house chores, another appliance to replace or add to the household, car maintenance and repairs, pets and children to care for, tomorrow’s impending storm, terrorist threats, this week’s theme in the neverending culture wars. All of this cultural neuroticism weighs heavy on us and pours into our psyches all at once, shaping our behaviors and how we see the world and each other.

This constant need to control every circumstance we find ourselves in is, I suspect, a bad habit instilled in us over a lifetime by a culture and society obsessed with time, and efficiency, and that prescribes a cookie-cutter list of things to do to obtain the wealth and status we all desire. At some point, we must learn to unconstrain ourselves—if only for a while—to let go of some of our worries, and more consciously minimize and declutter our lives a little, so that we may once again learn the art and peace of wandering in this world—the only one we’ll ever know.

I try my best to keep the place I am visiting somewhat mysterious. I’ll look at the map to familiarize myself with a place, read some history and literature of the country, and maybe gander at a few blogs and photos to try and anticipate cultural customs and social norms. And I’ll keep abreast of the U.S. State Department’s travel map and pay some attention to the local news of the place I’ll soon be. But like a good meal, I don’t want to spoil my appetite. I want some suspense about what I’m going to experience. Our world has created the means to neurotically attempt to foresee experiences before they happen as if we’re under a spell too enchanted by oracles desperately trying to prophesy our future.

Dublin has been dubbed a “walker’s city” and so I feel compelled to treat it as such and will aim to experiment in my pursuit of spontaneity as much as I can in my upcoming trip to Ireland. I look forward to putting theory into practice and seeing how much spontaneity I can ultimately get away with before I regret not planning more. To be continued…

For consideration:

●      How much do you typically plan for an upcoming trip?

●      In what ways do you prepare to visit another country?

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Cheers!

-JSB