It’s not how many times they knock you down that counts, it’s how many times you get back up.

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Want to live like an Instagram star and travel the world shooting sexy videos with your amazing partner?

I can’t help you, sorry.

On the other hand, if you are looking for knowledge, meaning, and fulfillment in the real world, you’ve come to the right place. For the next ten minutes, I will present 28 nasty traps and 14 smart things you can do to improve your life.

Hang on — this may be bumpy.

28 Nasty Traps that are Holding you Back

  1. Pretty much everything we do is about signaling to others rather than creating, adding, or obtaining real value. Signaling means brand names, credentials, certificates, clothes, height, looks, money, points, social media, likes, followers, etc. It’s not clear what “real value” is, anyway.
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Now for the good news: there are two ways out of all these traps:

Blue Pill: How to Win Without Understanding the World

This is actually fairly easy. If you only learn one skill in life, forget everything I’ve just written and learn how to sell. If you can sell, you’ll probably be fairly happy and fairly comfortable you entire life long. You may sell a lot of things no one needs, you may not come to understand the world, but you may not regret anything when you’re at Disneyland with your happy kids.

Red Pill: How to Actually Change Your Mind

On the other hand, you can put in the hours it takes to become a different person from the one who started reading this just a few minutes ago. It comes down to one thing: question your assumptions. Work hard to reshape your approach to understanding the world. Get rid of bad habits and form new ones. This is going to take 1–4 hours a day for 2–5 years, and then you’ll probably want to continue rebuilding and resharpening your tool kit for the rest of your life. I didn’t say it would be easy. You won’t get a certificate. But you will understand the world better, and you might be a better person because of it. At the very least, you’ll say “I think there are two sides to every story” and “I think you’ll find it’s a little more complicated than that” more often.

  1. Be willing to question everything. Question all your assumptions. You live in several interlocking complex adaptive systems — don’t assume you understand how anything actually works. Don’t assume you know why people behave the way they do. Always go down to the assumption level and assume something is wrong there. This will pay off immediately in your relationships with others — ask questions rather than make assumptions.

11. Find and spend time with those who are already doing these things. Join a community of like-minded people. Make it a point to meet others whose opinions you value and want to learn from. Reach out to people and see who will have lunch with you or take a phone call. Ask questions by email. Just telling people you want to learn is often enough to get them to want to spend time with you. If you don’t have a local meetup, create one. Put together a group to work on these things and share meals and knowledge.

12. Write or speak or communicate what you have learned. Join the heretics and look foolish. Get up in front of your local group and report on a book you’ve read. Question authority (even 16-year-olds who speak at the United Nations). Start a blog. Start teaching a short course somewhere, or teach a workshop, or get involved with someone else who is. Or go to your kids’ school and try to figure out how to help them stop filling kids’ heads with nonsense (let me know how that goes). If you’re not a natural creator, start helping someone who has the right message but needs more resources and amplification.

13. Acknowledge your mistakes. People say about me: “David is opinionated, yes, but I’ve seen him many times get rid of an opinion and pick up a new one when he sees that his previous one was wrong. He’s weirdly flexible in that way.” I have a habit of getting back to people to tell them I was wrong about something, even if it was a conversation we had months ago.

14. Be the change. Most of the big stuff is broken. Start caring about the big stuff and forget the small stuff. Show people that you have abandoned your platform belief system and are now looking at the world on a case-by-case basis. If enough people did that, everything would change for the better. If political candidates could get elected by saying “Hmm, that’s a good question, I don’t have a snappy answer, have there been any meta-studies or randomly controlled trials?” — that might change our entire political system.

I didn’t say this would be easy, but after twenty years of mistakes and ten years of learning, I do say it will be fulfilling.

Surprise: If you want to watch the videos, they are all waiting for you at my YouTube channel, so get started!

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David Siegel is a serial entrepreneur in Washington, DC. He is the founder of the Pillar Project and 2030. He is the author of The Token Handbook, Open Stanford, The Culture Deck, Climate Curious, and The Nine Act Structure. His newsletter is at CuttingThroughTheNoise.net. He gives speeches to audiences around the world — see his speaker page if you would like him to speak at your next event. His full body of work is at dsiegel.com.

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Provocateur, professional heretic, slayer of myths, speaker of truthiness to powerfulness, and defender of the Oxford comma.

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