"To a young person, just entering on adult life, the world seems full of “insides,” full of delightful intimacies and confidentialities, and he desires to enter them. But if he follows that desire he will reach no “inside” that is worth reaching." —C.S. Lewis, The Inner Ring

“Mother wanted me to be independent, and not to run with the herd. I was to be original, individual, I was to have a definite character and ideals of my own. I was not to be an article thrown together, on the common bourgeois pattern, on everybody else's assembly line.”

Comfort the afflicted and afflict the comfortable.

Have the humility to care nothing about what other people think.

You don’t have to outlaw ambition to suppress it. You just have to schedule it to death.

New media lowers the cost of coordination; bureaucracies raise the cost of permission. When those curves cross, suppression shows up dressed as policy.

“The trouble with market research is that people don't think what they feel, they don't say what they think and they don't do what they say.” ― David Ogilvy

Eternal neophyte.

Go like you will never stop. Burn the ships like you will never return. Give like you will never receive.

Drifting is a synonym for optionality.

"Every business and profession has its network, through which referrals and favors are exchanged."

Celebrate the awe of being alive.

"As a general rule, it is foolish to do just what other people are doing, because there are almost sure to be too many people doing the same thing."

Become both the prophet and engineer of change.

The joy of meeting new people who feel like they’ve always been part of your life. The fleeting nature of connection and those moments made eternal by the act of retelling. Many such cases: friendships, romances, and so many other types of relationships with the world.

Treat knowledge like a public good, not a gated vendor contract

You don’t win by out-arguing. You win by out-narrating. “You can’t change the world. All you can do is make your own world and invite other people into it.” – George Lucas The job of the university is to help students build worlds worth inviting others into.

"Beauty is the first test: there is no permanent place in the world for ugly mathematics." G. H. Hardy

To avoid procrastination, Victor Hugo would write naked and have his helper hide his clothes so he couldn’t go anywhere until he finished.

Jailbreak Rule #9: If we can’t explain a fee in one sentence, we don’t charge it.