My 2017 Self Improvement Questions

I ask myself questions. These then get refined to better questions. It implicitly steers my thinking.


  • Am I heading toward a few of my goals as fast as possible? How do increase the “gain” on feedback mechanisms to increase the accuracy of this answer?
  • Time is a constraint but more specifically time w/ high mental clarity is a larger constraint. What are the 80/20 inputs to increase this for me personally? What is a realistic # of hours per day? [this is highest leverage item to improve?]
  • Where are you experiencing a high noise to signal ratio in your life? What is your plan to resolve this?
  • By and large, I have less intimacy of friendship after 1 year in SF vs what I had in DC. What is the most effective way to resolve this?
  • I notice that physical environment often affects my ability to think clearly as a function of mental and emotional state. What are the inputs I can control in an 80/20 manner?
  • What am I likely to regret by the time I am 40? Of this, what has the highest negative expected value? What are the most effective ways to mitigate this? Does this seem like a high ROI endeavor? Of this, what can I outsource?
  • I am often displeased with my performance in interacting with others. Of this, what do I want to improve and what is not worth improving? What is the 80/20 way to do so?
  • Which decisions have low expected value delta (delta from “right” vs “wrong”) however are carrying high background cognitive load? What steps will you take to speed decision making here and accept a higher miss rate?
  • What are the largest inputs to your emotional/mental wellbeing? (Sleep, food, people, etc.). What are 3 hypotheses related to improvement? What is the MV way to quick assess efficacy?
  • What are your learning goals and plan for 2018? How much of this can be driven by spontaneous curiosity vs advanced planning?
  • What is the stack ranking of habits that would create 80/20 results on your goals and values for 2018? What experiments do you want to run?
  • What are experiements I want to run on diet this year? How do I make this as effortless as possible?


  • What are populism tipping points based on past? How likely are these to apply today?
  • What are the largest inconvenient truths each party fails to deal with? Are there any leaders in either party that are taking these on?
  • Who are the democratic candidates that understand and have credibility with running a business? Which ones understand probability and resource limits deeply?
  • How likely is it the Democrats are able to self disrupt and clean house for real? What are the 80/20 inputs to this?
  • What does the outcome probability tree with North Korea look like? What are the two most most probable outcomes? Are there any low effort actions you want to take regarding this?


  • Why are companies not successfully targeting the main issues I see? Is it a value capture issue? How can this be remedied?
  • Who can help me speed my rate of learning? What are the major gaps in my knowledge?


  • How much will machine learning add to productivity improvements? Where will it add the most? Is this priced in? Am I positioned to benefit from this?
  • How will I improve on my understanding of CRISPR this year?
  • What are the largest threats that may play out this year? Is this probability adjusted? Do you want to alter your positions?
  • Where are we in the LT debt cycle? Does this alter your position?
  • Are you too concentrated in technology that could drop w/ fund flows out of public tech? Will the tech that you are invested in sustain this kind of outflow? What is the probability of this during the next year?