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Debugging questions for entrepreneurs, creators and high performers

Do solo or with someone.

When you’re going through these prompts, ask people at the beginning to write down anything that’s currently on their mind and might distract them and put it aside mentally. Between every prompt, shake out or get up briefly.

Hamming Prompts

  • What's your top 3 most harmful habits? When your monkey brain takes over your rational brain?
  • What keep you stuck in this local maxima ?
  • What’s your biggest bottleneck?
  • What would a "force multiplier" be for your life?
  • If you were the protagonist in a book, what should be the protagonist’s next step?
  • What would a rational version of me do?
  • Think “everything in my life is going fine”. What comes up in protest?
  • What haven't you solved yet that you really should?
  • Imagine you’re your future self (in a month, year, decade). Looking back, what would you tell your younger self to do differently?
  • What’s a thing you keep doing wrong though you should know better?
  • What are you doing regularly without even knowing why you do it?
  • What makes you sad/upset/worried/bored frequently?
  • Which process, if any, are you using to solve problems in your life? What would help you recognize problems, solve them earlier? What could be better about this process?
  • If you had 20 minutes to work on something to improve the rest of your life as much as possible, what would it be? What if it's 5 minutes?
  • What are your major resources in life? What drains them?
  • What’s a Pica for you (i.e. what are you doing that is a placeholder for something you crave)?
  • What are your “spinning plates”? What is fun and motivating for you and attracts your focused attention?
  • Bonus question: What do birds do that you can learn from?
  • What do you need to focus on today to make sure you don’t fall behind tomorrow?
  • what do you think of my recent performance?
  • what do you think hold me back?

Regular Debugging Prompts

  • Are you becoming who you wanted to be?
  • What would make this week great?
  • If you were the protagonist in a book, what things that you spent the last week doing were wasted/going in the wrong direction?
  • Which process, if any, are you using to solve problems in your life? What would help you recognize problems, solve them earlier? What could be better about this process?
  • What do you feel helpless/hopeless/resigned about?
  • Where do you constantly fail to meet your expectation of yourself?
  • Looking at the last [span of time], do you remember any of the following, that can hint at bugs?
  • You feel a brief flash of annoyance or frustration
  • You feel conflicted, as if one part of you wants to do one thing and another part of you wants to do something else
  • You need to exert willpower in order to do something
  • Things go differently from how you planned
  • You feel distracted rather than being engaged in what you are doing
  • It takes you a while to decide what to do
  • Anything else that feels non-ideal, or like something that you might be interested in shifting but don’t know how
  • Things are going fine, but somehow you feel vaguely unsatisfied
  • What would I do if money was not an issue?
  • Make a list of people you found consistently valuable (or fun) to be around. Why aren't you spending more time around them?
  • What would you immediately stop doing if others didn't expect it of you? Do you really need to do these things?
  • What are you doing regularly without even knowing why you do it?
  • Which habit would save you a lot of time, or make you much happier?
  • What are things that energise you, give you motivation?
  • What are your strengths? Are you using them regularly?
  • What triggers feelings of fear or anxiety?
  • What would you do differently if you knew you had unlimited time?
  • What's one thing you're avoiding because it's uncomfortable or unpleasant?
  • What have you been procrastinating?
  • What makes you feel uncertain?
  • What's something you wish you had more time for?
  • What would you do if the risk of failure wasn't a factor?
  • What would make your life easier?
  • What do you want to achieve in the next week?
  • What would make you feel more in control of your life?
  • What would make you feel more content?
  • What's your most important bug?
  • What is broken in your mind?
  • Is your current trajectory the shortest path to long term success?
  • Are you procrastinating?
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