🏴 33 Questions to Find Your Obsession.


​zach.blog​

10.1.23

To the obsessed,

Finding your obsession is like a maze.

In it, questions are keys. They unlock new doors, that you never knew existed.

β€œOur job in this lifetime is not to shape ourselves into some ideal we imagine we ought to be, but to find out who we already are and become it.” - Steven Pressfield

Warning: I don't think you can sit down at a desk, and journal your way to your life's purpose. When you find it, it's obvious. And you only find it through output.

Use these 33 prompts to make the maze clearer, but don't expect to instantly find your way to the center.

Besides, the path of finding your obsession, is as important as obsession itself.


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33 Questions to Find Your Obsession:

  1. What activity makes you forget time exists?
  2. What part of you do most people don't understand?​
    ​When you're told you 'shouldn't' be a certain way, because it's 'not normal,' what would happen if you turned that knob to 1000%?
  3. What is the thing you can't not do?
    ​
    "The best reason to start a company is because you cannot tolerate not starting it." - Marc Andreessen
  4. What have you created without planning to?​
    ​
    No one told you to do it. No one told you how to do it. It's as if something pulled you into action.
  5. When do you forget to eat, pee, and sleep?
  6. What memories or stories do you have from childhood, that represent an extreme or unique behavior?​
    ​One for me: In summer after 6th grade, I read every book (7+?) by an author named Walter Dean Meyers, about life in Harlem. I have zero interest in those books now, but that obsessive desire to read hasn't changed.
  7. What do you work on when you're procrastinating?
  8. How do friends brag about you? This is ___, they're the best ___ I know.
    ​When our minds get busy, our gifts become invisible.
  9. What is no one is able to do (because they don't have your DNA), and no one willing to do (because they don't have your desire)?
  10. What is your deferred life plan?
    ​"Don't do the deferred life plan. I've watched so many people say 'I'll do what i really care about later', but it never seems to happen. The people who say (and do) 'either right now or probably never' all seem pretty content. As my grandma loves to say, 'It's later than you think.'" - Sam Altman
  11. What experiment would you be most excited to try?
  12. When you go in a bookstore, what section do you gravitate towards?
  13. What mediums do you have a love affair with? What details do you obsess over? The trimming of a hardcover novel. The notes of your favorite song. What lines do you read between?
  14. Who do you idolize? What is the throughline of what they do, or create?
  15. What would you make for an audience of 10,000 of you?
    ​"Obsess over figuring out the funnest, most exciting, most natural shape of yourself as a writer and start doing that. There are a LOT of people on the internet … so even if only one in every thousand of them happens to match that, that amounts to over a million people who will absolutely love what you’re doing.” - Tim Urban
  16. What is the most exciting thing you could starting working on tomorrow?
  17. What could you create every day forever?
  18. What do you think about when you don't try to think of anything?
  19. With who do you get the most energy? What do these people have in common?
  20. What do you do without discipline required?
  21. "What could you not be paid a billion dollars to stop doing?" - David Senra
  22. "What is the torture that you're comfortable with?" - Jerry Seinfeld
  23. "What feels like play to you, but looks like work to others?" - Naval Ravikant
  24. What is the hardest question you'd be excited to solve?
  25. "What are the behaviours you could bet dollars on yourself not doing and still be sure to lose?" - Jeremy Giffon
  26. "Where do you feel great resistance or fear?"- Steven Pressfield
  27. "What do you do that looks hard to others but feels easy to you?"- Paul Graham
  28. ​Write a letter from 80-year old you to present-you. Looking back on your life, what is the one major accomplishment you'd want to have achieved?
  29. "What are you excessively curious about- curious to a degree that would bore most other people?" - Paul Graham
  30. "What's the weirdest thing you spend a lot of time on? What's a passion you'd be embarrassed to admit publicly?" - Patrick O'Shaughnessy
  31. "What is the thing you want to do the most on your own?" - Robert Greene
  32. "If you were the last person on earth, would you still do it?” - Steven Pressfield
  33. What do you do that feels selfish, but serves others?
    ​When you unlock this, you unlock the world.
    ​

Lastly, remember: Output is the path to obsession.

"The way to figure out what to work on is by working."
​
"I think for most people who want to do great work, the right strategy is not to plan too much. At each stage do whatever seems most interesting and gives you the best options for the future. I call this approach 'staying upwind.' This is how most people who've done great work seem to have done it.
​
- Paul Graham, How to Do Great Work​

Let me know what you thought of this edition!


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Stay obsessed,

Zach 🏴

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Ten Bullets - For The Obsessed 🏴

Every Saturday, I send out 10 ideas I can't stop thinking about. To help you build companies, make content, and follow your obsession.

Read more from Ten Bullets - For The Obsessed 🏴

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