Leisure / Literature / Psychology

Lessons Learned from On the Road and The Art of Thinking Clearly

Generally I have about two books on the go at any given time. I find that one fiction and one non-fiction pick are a good way to allocate space on the nightstand, as this covers most reading moods that might come up during a typical week. Recently I finished reading On the Road by Jack Kerouac and The Art of Thinking Clearly by Rolf Dobelli. On a particular day, when I was about halfway done each and I had happened to have them placed right next to each other, it hit me that this was both the most appropriate and the most inappropriate combination of books to be reading together. Essentially, in On the Road there are road trips, money issues, a lack of planning, spontaneity, spirituality, and a great big adventure, but absolutely nothing that we can call Thinking Clearly – not in the orthodox meaning of the phrase.

As I read on, aware of this hilarious fact, I began to think that this coincidence might have really brought out the flavor of the two books and the different lessons that they had to teach. There is a time for recklessness (“the only ones for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved…”). There is a time for rational thought, as well (if you would walk 10 minutes to save $10 on food, why wouldn’t you walk 10 minutes to save $10 on a thousand dollar suit?).

However, even more striking was the fact that these two books, ones I thought would always run parallel and never overlap, had similarities as well. These lessons were surprising and are worth mentioning.  Maybe they come from the wisdom of all humans experienced in living to the fullest – whether they gain it by mastering the rational principles of decision making, or by uninhibitedly conquering the road.

(1) Looking forward.  Dobelli discusses the classic sunk cost fallacy: just because you spent a lot of money on an advertising campaign that is failing to be effective does not mean you should continue it only to justify the investment. If you spent an hour trying to become interested in a movie you’re watching and you know that it is simply not working out, the amount of time already invested shouldn’t justify watching the rest. Kerouac doesn’t explicitly mention this, but the novel is an embodiment of the principle. Every adventure is new, and every day looks exclusively forward.

(2) Expectation management. In the financial realm, analysts predict corporate earnings on a regular basis. Stock prices incorporate these predictions into their value; if the company makes less money than predicted, stock prices fall. The catch is that earnings can be good, but if they miss expectations they still mean bad news. Some people realize this and go into life with low expectations. I think this is also harmful, because by actively expecting sub-standard events you’re inviting self-fulfilling prophecy to take over. The characters in On the Road, however, go into the entirety of life with no expectations at all. When greeting a new experience with little expectation, you’re more likely to make the absolute best of it (even if it means you’re earning a living by picking cotton, renting a tent as shelter, and getting groceries once a day with trips on an old bike; I believe this was one of the happiest parts of the novel).

(3) Illusion of skill. What matters more: the rower, or the boat? Dobelli argues that we overestimate the role of the rower and underestimate the quality of the boat. He says, aptly, that perhaps the CEOs that really know what they’re doing choose to lead companies that are performing well.  In On the Road, Neal and Jack take a number of insanely ambitious road trips across America and they do a pretty good job of having a fantastic time (and making it back home in one piece). But maybe they were victims of circumstance, in the best way possible. They met the right people, came across the right amount of money, and had the right timing to have the experiences that they did. Perhaps we can learn from them. If Jack and Neal can be skilled travellers (and they truly are), we can also learn to trust our circumstances enough and let go of the illusion that our inherent skill is the only thing that gets us through our doings.

(4) Don’t cling to things. If you bought a car that you wanted for a long time, and somebody immediately offered to buy it from you at a healthy premium – would you say yes? Most of us would say no, because we are clingers. Rationally we should say yes: we would be better off if we did. We get attached to things that we own and burden ourselves down with stuff. This isn’t healthy because material belongings can be lost, stolen, destroyed, or otherwise taken away. This is evident in On the Road as well. Do you think they packed anything for their road trips? No, definitely not. To a (significantly) lesser extent, I experienced this when I went on a 6-week trip to Europe with only one carry on. It was liberating and I was not missing anything at all, even though nearly all of my “stuff” was left at home.

(5) Optimism, always. In both books: live life using your fullest potential, and create opportunities where there are none. Nothing is stopping us from exploring our limits in the geographical world and within our own minds. Think, feel, and move with freedom and energy. Write about what you find. Reflect on every experience and be open to more.

Didn’t Make the Cut: Bonus Round of Parallels (to pique your curiosity and further entice you to read both books)

(1) Both books arguably inspired by a really good friend (Neal Cassady for Kerouac, he brought out the author’s recklessness; Nassim Taleb for Dobelli, he brought out the author’s appreciation for cognitive and social science).

(2) Challenging. On the Road is a 300 page long paragraph – challenging read. Thinking Clearly is not, it is a series of incredibly readable mini-essays – but they challenge most choices you make on a daily basis.

(3) Both end abruptly, kind of.  Thinking Clearly has 99 lessons (one short of an even 100, not that this bothered the obsessive compulsive part of my brain – it really did not; I’m serious). The end of the original On the Road draft was chewed up by Lucien Carr’s dog (this is not shocking) – and the ending had to be reconstructed from a later published copy.


One thought on “Lessons Learned from On the Road and The Art of Thinking Clearly

  1. Pingback: Fallacies: Sample of Ways Our Thinking Is Not Helpful | r&p

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