A philosophy of long-term travel

I like “loops”. I dislike “going there and back”.

In the past, this predilection only reared its head when I went day hiking. I prefer a trail or combination of trails that brings me back to the starting point without taking the same trail twice—even if it means a significantly longer hike.

It’s one of the many aspects I find so compelling about this adventure. Circumnavigating the globe is the ultimate loop.

But it turns out that my “loop complex” goes a little deeper. Not everything in life has a destination that is the same as the origin. Take our trip through India for example. We knew two things: we were flying into Kolkata on April 4th and we were flying out of Mumbai on May 5th. From East to West. Everything else in between was to be decided en route.

But as I’ve written before, one of the most paralyzing things about this trip is being faced with the decision “where next” and having EVERY CITY IN INDIA as the possible solution set. It makes travel exhausting and NO FUN.


This is where my “loop theory of travel” becomes the “linear theory”. The rules are similar: No there and backs. No crossing a trail we’ve already blazed. Every step forward must bring us one step closer to our end point. The only exception would be for a must-see-cannot-miss destination. Because there’s no sense in adhering to rules blindly.

india map all cities
In my head, India stopped looking like this

india map central route
And India started looking like this
india map coastal route
Or this

Both being much more manageable. The only decision we had to make was between the two trajectories, and once we’d done that (we implicitly chose the first in heading to Varanasi) at each step of the way, I saw a relatively limited array of possible next stops that would bring us closer to our destination, without breaking any of the rules.

What I’m describing is really just another form of “embracing constraints”. By eliminating options we simplify decision-making, by limiting resources we encourage creativity in solving problems, and most importantly, by shaping the constraints, we make more personalized decisions (some would say “quirky”) rather than following the herd.

No Planes

Before continuing, let me add one more quasi-rule: no planes. Or perhaps better-stated: avoid plane-like travel.

Practically every book on long term travel advises against taking planes, wherever possible. The reasons given are usually two-fold: you don’t get the secondary benefit of seeing life on the ground pass by, and you have less opportunity to strike up conversations with your fellow, often local, passengers. This of course depends on how inquisitive/chatty the passengers are and how much you’re looking out the window on that five hour bus ride or overnight train. I don’t disagree that those are worthy, if not overly-romanticized, reasons for avoiding planes, but I think they fall secondary to the following.

This is why planes should be avoided: they break all the rules that governed how travel has always worked in the past. With planes you can go from any point A to any point B ANYWHERE IN THE WORLD. It’s practically teleportation. Which is great in 99% of cases where the destination is the point and the journey is a pesky implementation detail. But for us, the journey is the point. Not only do planes open up a can of worms with their tantalizing (but paralyzing) wealth of destinations, but they also kill that visceral sense of change one feels when moving from one region to the next, experiencing firsthand where culture, cuisine, and genetics overlap.

Sticking to the ground also means visiting some places simply because they are “on the way” rather than convenient or recommended or in the guidebook. On-the-way cities hold the most surprises.

Of course, sometimes there is little choice. Had trains or buses (that took less than 3 days) been available in Southeast Asia we would have jumped on them. Instead we took planes that we pretended were trains: nonstop one-hour flights between cities in adjacent countries. This is one of the most satisfying aspects of traveling in India. Trains and buses are almost always an option. The terrain is almost always passable.


It isn’t always an easy path. Somewhere between Kolkata and Agra, Stephanie said (in moment of frustration) that she was fed up with “my linear mode of travel”. I didn’t even realize it had a name. Or was “mine”. In fact if she hadn’t said that, I probably wouldn’t be writing this post. I didn’t think I was being overbearing, but India is a big place, and we both were constantly struggling with the where-next problem. Without us having explicitly agreed to any of what I wrote above, I realized I was subconsciously ruling out cities that fell outside the bounds of my East-West swath of destinations from Kolkata to Mumbai.

Meanwhile Stephanie had become enamored with the desert. I think she liked its lack of density and wide-open spaces. She wanted to get to Rajasthan as quickly as possible. From Agra we caught a bus to Jaipur. We treated ourselves to a nice hotel for a few days, and discussed plans to go to Jaisalmer (West, there-and-back) and/or Amritsar and Simla (North, there-and-back) but nothing seemed to be sticking. She wasn’t happy with either because they both had us going out of our way only to come all the way back to Mumbai in the end. And though plane tickets were ten times as expensive as similar train tickets, we certainly could have flown to solve the problem.

But there was a bigger issue. We knew we could go to either of those places. We could go to both. It’s not that our bodies couldn’t handle the long train rides there and back. It’s just that after traveling for so long and seeing so many places, we’ve both come to realize that the destination is actually kind of inconsequential. It’s not that we’re numb to where we go, in fact it’s exactly the opposite. Every place is new to us, every place holds amazing treasures to be discovered. And in that sense, it doesn’t really matter where we go. Wherever it is will be awesome. Some places just more than others. But inadvertently we realized that Jaisalmer and Amritsar didn’t pass the must-see-cannot-miss test to make them worth going “out of the way” (on this trip).

Where Next?

It was a weird moment. We’d come full circle. Stephanie admitted having a similar faith in the linear approach. It gave us a reason for being, a purpose, however tenuous. It won out against the dozens of amazing places in India that were not “on the way”. Whatever destination we chose had to bring us one step closer to Mumbai. We chose Udaipur. I’m so glad we did.



Excellent post. Good to see the “deeper” feelings and concerns that you have as you are both working through the day-to-day details.

The choice can be paralyzing – and your identification as a “linear traveler” is intriguing. I think I fall somewhere closer to Stephanie where that is concerned, that my destinations are more gut instincts about what compels me, then I cross my fingers and hope it get’s me closer to my next flight :) That being said, Udaipur=lovely!

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