The question bank

When I tell myself to do something again and again and again, but don’t, it’s an indication that it’s important. I mean, why would I repeatedly avoid something I’ve decided many times is good and necessary for me? Only because I’m scared and it’s hard and it might actually help.

The weekly review is one such thing. Countless times I’ve said, “I’m gonna do it.” And finally, I think I’m getting somewhere. Each Sunday—for the last two months or so—I’ve completed what I’ve termed “RPR”—review, plan, reflect. 

  1. I review the previous week, my priority, my projects, my processes and what’s on the periphery.
  2. I plan the upcoming week, making sure everything is in its place and that there’s a place for everything. 
  3. Finally, I reflect.

“Reflect” is the hardest. I’ve tried disconnecting and writing in my notebook. I’ve tried answering the same questions every week. Nothing. So last week I tried a different approach and slapped together a list of questions from various sources. The idea: I choose two or three that grab my attention, then meditate on them. I can sit and think about the answers, or write them out on my laptop or in my notebook, or I can just jot down points which help me craft or explore a response. 

So far, it’s working. For example, this week, I chose the following questions: “How am I complicit in creating the conditions I don’t want?” “What are the craziest things I could do, and what are the consequences?” and “What do I not do because I’m scared?” The answers yielded were interesting and I obtained them by asking myself the questions repeatedly through the day. 

So, because this procedure and bank of questions has released some value for me, I thought I’d share them with you.



From Ryan Holiday:
– What do I spend my time/attention/energy on?
– Is this in my control?
– What does my ideal day look like?
– To be or to do?
– If I am not for me, who is? If I am only for me, who am I? 
– What am I missing by choosing to worry or be afraid?
– Am I doing my job?
– What is the most important thing?
– Who is this for?
– Does this actually matter?
– Will this be alive time or dead time?
– Is this who I want to be?
– Life is a question; am I answering with my words, deeds and thoughts?

From Peter Thiel:
– What’s my 10 year plan? Why can’t I do it in six months?
– How do I become less competitive in order to become more successful?

From Robert Greene:
– What are my weaknesses? How can I turn them to strengths?

From Taylor Pearson:
– Can I create more demand without creating more supply?
– How can I leverage technology to gain more control and/or autonomy?
– Define life as a collection of systems; where are the limits in my respective systems? What’s the obvious and/or non-obvious way to improve the limit?
– Am I working on something that is unconventional, which will multiply, not add, results?
– What do I find interesting and easy that others find difficult?

From Tim Ferriss:
– How am I complicit in creating the conditions I don’t want?
– What are the craziest things I could do? What are the consequences? How would my life be re-shaped?
– What do I spend a silly amount of money on? How might I scratch my own itch?
– What are the worst things that can happen? How could I get back here?
– If I could only work for 2 hours per week on my business, what would I do? 
– What’s the least crowded channel?
– What if I couldn’t pitch my product directly?
– What if I created my own real-world MBA?
– Do I need to make it back the way I lost it?
– What if I could only subtract to solve problems?
– What might I put in place to allow me to go off the grid for 4 to 8 weeks, with no phone or email?
– Am I hunting antelope or field mice?
– Could it be that everything is fine and complete as it is?
– What would this look like if it were easy?
– Define, Eliminate, Automate, Liberate: can I unlock progress with any of these concepts?

From Naval Ravikant:
– Naval said, “Earn with your mind, not your time.” Am I doing that? If yes, can I do it better? If no, why not?

My Own:
– What narrative(s) am I selecting? Should I choose differently?
– What am I filtering for?
– Where are my blindspots?
– What excites me?
– What don’t I want others to ask me? Why?
– When was the last time I changed my mind?
– If resources (time, attention, energy, money) weren’t scarce, what would I do?
– Two circles: my skills and what the world needs. Where’s the overlap?
– What do I not do because I’m scared? 
– What would I do if I was completely free of obligation–no friends, family etc.?
– Do I have skin in the game in everything I do?
– Who do I admire, and why?
– What small change could I make that would have a disproportionately large impact on my life?
– What do I most criticise others for? Why? Do I make the same mistake?
– What secrets do I have, but refuse to share?
– What am I risking? Am I too risk averse? Do I need to take more chances, or less?
– What do I know to be wrong, and what does that reveal that I think to be right?
– What if my strengths are actually weaknesses? What if what I think is my best asset is actually my worst?
– I have six monhs to live and a billion pounds to hand: what do I do?
– What do I want? Why do I want it? And do I want what I think I want?
– What’s my A? What’s my B? How do I bridge the gap?
– What’s the one thing?
– Do I have the full complement of PACE plans (primary, alternative, contingency, emergency)?
– Am I seeing complexity where this isn’t any? Is it simpler than it appears? Or more complex than I’ve come to believe?
– Do the possible joys of life outweigh the inevitable suffering?
– Which domain(s) in my life do I have a fixed mindset and a growth mindset? Could I be mistaken about them?

Oh, if you have any questions that help you reflect and explore, send them over. You might receive a GIF expressing my gratitude.