“I was surprised, as always, by how easy the act of leaving was, and how good it felt. The world was suddenly rich with possibility.”
Not a Kerouac quote, but by Jon Krakauer, from his nonfiction book Into the Wild (1996).
Misattributed
Source: On the Road
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Jack Kerouac 266
American writer 1922–1969Related quotes

“And after reading Thoreau I felt how much I have lost by leaving nature out of my life.”
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Context: Then of course I recall the incident which I think had some form of deep, psychological impact on me. The time where I was compelled to read out the most insincere, hypocritical ‘apology’ out loud to my fellow peers, that was written by teachers, for a video that should be more abhorred for its stupidity than for its supposed racism, that was absolutely non-existent. I witnessed firsthand, things that were completely beyond my level of comprehension at that time, that was completely beyond my preconceptions of how a school worked, where rules of an official institution was dictated by the unreliable stupidity of the public, and where punishment was dictated not by logic, or by an understanding of a scenario, but because, a book says so. That ‘apology’ given two years ago, and the subsequent deletion of my first Youtube account was not a sign that I knew my ‘mistakes’ and wanted to ‘change for the better’, it was a sign that other people effectively made me say so. Never have I felt so much anger, unjust, and indignation for how things are, how people are and how it affected me and probably many others too. Before that I was passive, soft-spoken and enjoyed the supposed goodness of the world. Never again would I be the same.

[Michael Pollan: Why the family meal is crucial to civilisation, Sat 25 May 2013, The Guardian, https://www.theguardian.com/lifeandstyle/2013/may/25/michael-pollan-family-meal-civilisation, 2018-05-23]

“You'd be surprised how much being a good actor pays off.”
Responding to a question from students at Shanghai's University of Fudan as to which experiences best prepared him for the presidency (30 April 1984), cited by Paul Slansky, The Clothes Have No Emperor
1980s, First term of office (1981–1985)

“Funny, how just when you think life can’t possibly get any worse it suddenly does.”

1900s, The Strenuous Life: Essays and Addresses (1900), National Duties
Context: Besides each one of us working individually, all of us have got to work together. We cannot possibly do our best work as a nation unless all of us know how to act in combination as well as how to act each individually for himself. The acting in combination can take many forms, but of course its most effective form must be when it comes in the shape of law —that is, of action by the community as a whole through the lawmaking body.

If I Should Die Tonight.
Song lyrics, Let's Get It On (1973)