Five Philosophical Rules For A Great Vacation

Some vacations overperform. Others fail to live up to our expectations no matter how much money and itinerary planning we throw at them. I’m convinced these varied outcomes are not only a matter of chance, but drastically impacted by our approach to the entire venture of getting away from it all.

Of course, some limiting factors are obvious: maybe a thunderstorm parade nixes your entire week at the beach, or you’re an arts and culture person dragged to a bottomless-cocktails-at-the-resort kind of getaway. Either we’re powerless against these acts of fate, or the problems are so obviously problematic that they don’t warrant mention.

I could take the philosophical line and tell you that your dissatisfaction with sodden beach vacations is just an opinion you could change, and blah, blah, blah. But I’ll leave that for another day.

I want to focus on “meta rules” that are up to us but don’t require enlightenment. I’ve found some that reliably nudge vacations toward the overperformance category when I’m careful about them. Not only do I have a better time when I employ them, but their use seems to lodge trips in my mind among my cherished memories.

Scrawling a vacation departure date on the calendar psychologically anchors us. If life is particularly hard, it might seem like a light at the end of the tunnel.

Indeed, studies find that people preparing for vacations spend weeks in elevated states of happiness compared to those who aren’t going1. The real trick is figuring out how to milk this for all it’s worth without setting ourselves up for delusion and disappointment.

So yes, presavor and expect good things from your trip (and see #5). But we must concurrently season those expectations in ways that ground them in reality and increase “vacation resilience.”

Because things will go wrong. Flights get canceled, photoshopped images deceive, the weather weathers, and somebody inevitably gets food poisoning from that dodgy stall in the souk.

The preventative is ancient and found across many philosophical traditions — premeditatio malorum, or the premeditation of evil/bad things. The gist is that if you consider/expect what’s likely to go wrong and how you’ll respond, you’ll shrug when they do go wrong.

I can outpremeditatio-malorum any airline blunder. The worst delays were expected. They were built into the psychological itinerary. Similarly, I assume every artwork and sight of natural beauty will be 70% as good as its promoters claim.

Because my expectations are low, they’re frequently exceeded. I’m often blown away by how great things are. I was expecting mediocre but got good or excellent. Studies find this approach, called “defensive pessimism” in research, really works to improve happiness and performance.

Similarly, give up the idea of vacations being life-changing or you-changing. As the saying goes, wherever you go, there you are. There’s a funny Adam Sandler skit that hits this perfectly: “You’re still going to be you on vacation.”

It’s essentially a comedic take on Seneca’s Letters 28 and 104.

"What good does it do you to go overseas, to move from city to city? If you really want to escape the things that harass you, what you're needing is not to be in a different place but to be a different person." — Seneca, Letters, 104

I’ve traveled a lot on my own, and most of those trips turned out great, but my favorite memories are from vacations taken with others. There’s real power in using destinations and things as excuses to connect with people. This also buffers us against many problems. If your beach vacation with friends is rained out and you’re stuck in a rental, you’ve got an opportunity to savor time with them, get to know them on new levels, and get up to creative hijinks that will be the basis of great memories.

Apropos premeditatio malorum, you can prepare yourself by always thinking, “I’m doing this for the people, the places are just icing on the cake.” One alternative I found while traveling alone is finding cool people to spend a few hours or days with. I’ve met fellow partner acrobatic hobbyists in Mexico via the internet before one trip, and joined another guy hunting rare fruit cultivars in Bali on another. I’m still in contact with some of these people years later.

Finding awe has probably gotten harder in our modern world. It’s often something we must seek and cultivate rather than having it hit us over the head out of the blue. Yet for all the work, it’s worth it. Awe is a powerful lever that pries us free from doldrums and life’s dead ends. It’s a charm against life weariness and despair.

Luckily, it’s usually easier to find awe on vacation than at home, since we’ve stepped outside our usual routines and habituated environments. To make awe more likely, seek out places that slap you.

Christians can walk the Camino de Santiago, spiritual seekers can take week-long meditation retreats or visit distant monasteries, and communing with nature at national parks is another kind of awe-inducer.

I suspect secular and spiritual pilgrimages based around experiencing awe are among the most underrated and least chosen types of vacations. In the Middle Ages, they were one of the few reasons ordinary people left their shires. Now, most people can’t be bothered to seek such things, not when there’s so much glam to bask in.

When we look around and make space for it, we find opportunities for bite-sized awe moments in unlikely places, even in the midst of secular experiences. I’m not a Christian, but found awe and a moving experience meditating in the tomb of St. Francis at Assisi. Awe found me staring up at towering redwoods. I’ve caught a glimpse of it among the stars on a clear night in the desert. But in order to experience it, we do need to seek it and allow room for it.

I once vacationed with someone with a daunting itinerary; she wanted to see so many places and things that I had to push back to prevent a grind. Upon reaching these destinations, she stayed behind her phone, snapping pictures. As soon as she finished taking photos, she wanted to move on. The photos were edited with filters and uploaded to social media platforms.

Later, when I mentioned things that I’d observed about the sites and artworks, she’d almost never noticed what I’d noticed, or seemingly much of anything. Why was she even going to these places if not to experience them when she was there? I eventually concluded that she didn’t particularly care about the sites, but enjoyed curating a perception of worldliness.

This might be an extreme few embody, but the traits are common:

• Living through a lens, capturing for tomorrow’s remembrances and missing what’s there today.

• Traveling not for yourself, but to project an image or induce envy.

I would never tell Erik Hogan to stop taking pictures during his travels. He approaches subjects with an artistry and reverence that focuses his attention and helps him see and think. His photo-essays are a testament to this process. But most of us aren’t taking that approach.

Just as a ruminating mind keeps us from living because we’re never here now, phones add a layer of abstraction and distraction from our moments. Are you even vacationing if your mind is cataloguing for later review?

And indeed, studies find that taking photos during enjoyable experiences reduces our enjoyment of them. A decrease of enjoyment from 72.6 to 63.8 on a 100-point scale was noted in one experiment2. Similarly, taking selfies and other photos specifically for upload to social media increases anxiety and reduces the happiness produced by experiences3.

The optimal number of photos is probably not zero, but it’s not much higher either. Most people should take few or no photos, and never post vacation shots to social media. You’re not traveling for likes, so don’t spend your moments orchestrating them.

Context is often the difference between a blah vacation and one filled with meaning and interest. Places and things have pasts, and historical events — large and small — hinged around them. The future will hinge on them too. Learning about them through media makes everything you see on a trip more resonant and interesting.

I’ve taken to “pregaming” every trip with fiction and nonfiction books about the places, things, and people associated with the destination. I continue to read during the trip. This not only puts curiosity colonization on steroids, but helps develop life-long passions.

• On my last trip to NYC, I was reading Wolfe’s Bonfire of the Vanities, and walking past Park Avenue and Wall Street, struck by how the old-money isolation, luxury, and social status of these places hadn’t changed very much.

• I did a summer semester in Oxford in college, and prepped for a trip to the Royal Shakespeare Company by reading about Elizabethan England and the script of the play I was going to see, which really enriched the experience.

• I’m eagerly anticipating a September trip to Sicily, and have The Italians and The Leopard queued up. Got any other suggestions for the crazy Sicilian cross-pollination of Greek, Roman, Norman, and Arabic cultures that took place there?

If you’re traveling to a small town/city you assume left no literary or historical mark, you’re probably not out of luck completely. In the US, Arcadia Publishing has put out thousands of books about obscure towns and cities and their histories, written by local historians. Many small European cities have similar treatments.

But don’t limit yourself to books. Prep for art galleries, architecture, and concerts with your eyes and ears too. For instance, while prepping for a Beethoven concert, I listened to and read about Beethoven’s efforts to metaphorically heal and raise money for soldiers wounded fighting Napoleon’s seemingly invincible army at the Battle of Hanau. Beethoven created the famous 2nd movement of his 7th symphony, Allegretto, with them in mind.

Beethoven was deaf at this point, but insisted on conducting the symphony personally during a fundraising concert for the veterans in 1813. His conducting style was spirited with personal conviction. He crouched low for soft passages and leapt into the air during crescendoes. The 2nd movement’s haunting, thymic pulses struck a nerve with the audience, and when it ended they virtually rioted. The shouting and demands for a repeat were so loud and insistent that the orchestra couldn’t move on to the 3rd movement. Beethoven gave in and repeated it, a virtually unheard-of thing.

In concert, I heard it with all this in mind, and it struck a nerve with me too. It will always be a song of healing and restoration for me. It would have been a great movement without context, but with it it became something epic and emotionally charged.

As you experience what you’ve learned about through anticipatory context, it enhances your ability to understand and absorb it and place it into a lattice of ideas. If I hadn’t read about Angkor Wat, it would have been an impressive pile of rocks in the forest. Because I had, it became intellectually and emotionally salient and embedded in a people’s history.

Similarly, I’ve sometimes found regional histories dry or confusing. Why did that movement start then? Why were those guys always getting invaded? But once you’ve been there, you see how places, regions, and movements “fit together on the game board,” and suddenly the fog lifts and things snap into place.

Thanks for reading Socratic State of Mind.

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