18 Real and Fictional Leaders to Learn from

Philip Skogsberg
4 min readAug 29, 2021

Lessons, insights, or perspectives learned from both real and fictional people I admire

From Arnold Schwarzenegger I learned the virtue of hard work and positive self-belief; that you can achieve your goals as long as you can visualize the path towards them clearly enough and apply consistent and intelligent effort in that direction.

From Richard Feynman: Intellectual humility, the joy of finding things out, to try to understand the truth about a thing and not to settle merely for its surface attributes.

From Carl Sagan: to look to the stars and from that vantage point, to look back at us on this pale blue dot; to be humbled in the face of our insignificance, yet inspired by the fact that we can give meaning to the universe.

From Warren Buffet: that you shouldn’t invest in things you don’t understand.

From Steven Pinker: that human progress is real, that the world is a better place than most people presume, and that we can learn what drives that progress.

From Sam Harris: what it means to be rational, the evils of dogma whether ideological or religious. That you can meditate and contemplate your existence without believing in anything supernatural. That we don’t have free will, and that this insight should make us more ethical, not less.

From Benjamin Franklin: what it means to be a true polymath, how to be serious in your pursuits but retain your curiosity, childishness, and quirkiness.

From Elon Musk: to reason from first principles and to think big; that fun is a good enough reason to do something, and that you can accomplish very hard things as long as it excites you.

From Jean Luc Picard (Star Trek): what it means to be a good leader; that you can be humble yet steadfast, flexible yet principled, visionary yet practical.

From Steve Jobs: the power of a clear vision of what you want to create, and the transcendent impact of stories. That you can stretch the definition of what is possible if you push yourself and your teammates and set a high bar of achievement.

From Christopher Hitchens: the virtue of thinking and writing clearly, to call out bullshit when you see it, and that the grave holds plenty time for silence.

From Peter Thiel: that if you want to build something valuable you need to discover a secret about the world that few people believe in right now; that there’s often something insightful to gathered from an unconventional narrative, but that it’s not enough to be contrarian, you must also be contrarian and right.

From Spiderman (Marvel): that it’s always possible to do the right thing, that you can make a difference just helping one person at a time.

From Jocko Willink: to take (extreme) ownership of your mistakes, that every good leadership trait is dichotomous. The virtues of getting up early, and that when you think you can’t take it anymore you always have a little left in the tank.

From Tyrion Lannister (Game of Thrones): that small people can have a big impact on the world, the power of humor and wits, the pleasures of good wine and good conversation.

From Paul Graham: how to write simply, how to work hard, how to choose the right ideas and work on the right things.

From Tyler Cowen: what it means to be truly well-read on a wide range of topics.

From Marcus Aurelius: to worry about what you can control and let go of the things that you can’t. To keep your ego in check given that in the large scheme of things, no one will probably remember who you are a few decades or centuries from now. But that this is also a cause for relief since it should lead you to take your problems less seriously, and enjoy the things that you can.

Originally published in Sképsis.

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Philip Skogsberg

Co-founder & COO @Challengermode. Trying to think better thoughts, some of which appear on my newsletter: philipskogsberg.substack.com