Is Planning a Trip the Best Part of Travel?

Our honeymoon is an exercise in pure fantasy. We imagine ourselves in water-top bungalows in Fiji, in Swiss Alpine chalets with fireplaces and bearskin rugs and private cheese cellars, and in penthouse suites at resorts on the Mayan Riviera with swim-up bars and infinity pools. We imagine that, after our wedding, we’ll suddenly have money and will be able to afford private seaplanes to private atolls called “Hammock Island.”

None of this is particularly likely. Don’t get me wrong — we’re going to have a great time no matter what we do, but we’ve got nine weddings including our own next year, and my career is in blogging. We’re not flush with cash we can spend on two-week-long romantic luxury trips. But that’s not what matters. What matters is the planning.

Planning is a lifelong affliction.

This has been an eternal problem for me. I love planning trips. I have an old chest back at my parents’ house covered in stickers and full of books and maps. Half of the books — usually Lonely Planet, sometimes Rick Steves — are to places I’ve never been, and will never go. The maps all trace elaborate, unlikely routes I’ve never even started. No, I’ve never crossed the Darien Gap from Colombia into Panama as part of a six-month-long Pan-American ramble. No, I’ve never bought a motorbike for meandering across Asia. No, I’ve never kayaked the Nile from source to sea.

And thank god I haven’t. My Pan-American trip would almost certainly have involved malaria, my motorbike across Asia would have resulted in a stolen or broken motorbike, and my Nile kayaking would have ended in death-by-hippo. I’m an adventurous person, but only in the sense that I will try literally any beer you put in front of me. I don’t like bumpy travel, I like travel on smooth trains with legroom and a viewing car.

The crux: I like planning better than actual travel.

I’ve come to realize, over time, that I enjoy planning my trips more than I actually enjoy taking them. I like clearing off my desk to lay down a full world map. “Why is it full world?” you ask, “You’re just going to Europe.” Yeah, well, I also have literally no reason to have this old-timey compass out as I plan, except maybe to use as a paperweight, but it makes me feel exotic. It makes me feel adventurous.

My plans are always far better than my travels anyway. In my plans, I have an unlimited budget and an endless amount of time. In my plans, I have all the correct gear, and every hostel I stay at has a brilliant book I’ve never read before and not just 10 copies of fucking Shantaram. In my plans, I’m no longer an introvert and I make interesting friends I stay in touch with for the rest of my life. In my plans, trains and planes are never missed. In my plans, I never get a single bug bite, and I never get swamp ass.

“Want to make God laugh?” the old saying goes. “Tell Him your plans.” Well, hey God, I’m not even considering following through on my plans. Who’s laughing now, big guy?

But it’s more than just lacking follow-through (or as my mother calls it, “stick-to-itiveness”). I genuinely enjoy the reading and the researching that goes into planning. I may actually learn more about a country in researching it than I do by visiting it. And an education at home is more affordable than an education abroad.

Of course, when you travel, you’re putting yourself in a state of constant discomfort and distress. You’re entering a world you don’t have experience dealing with, and then when you’re confronted with a situation, you have to discover who you really are by seeing how you respond in the moment. You learn about yourself and then you grow. But learning hard truths about yourself sucks. Growing hurts. As Thomas Jefferson said, “Travel makes men wiser, but less happy.”

Does travel make you a better person? Yeah. Does it challenge you in ways you never thought possible? Yeah. But it’s way more fun to imagine growth and fulfillment with a tall mug of coffee and a book in your easy chair than it is to actually experience it.