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You often don't know what you don't know until you ask a question you never knew to or how to ask.
Questions, in that way, can be moments of seemingly divine intervention, unlocking what's there beneath the surface, but not yet identified or recognized.
What follows are angles I've used to generate new questions, as well as actual questions derived from those angles, that I hope you can use to generate insights that actually improve your life.
And really, even one insight can make a question worth it. One insight is enough to help a problem melt away.
As time goes on, and I stumble into more questions that helped me, I'll add them here. But let's get into what's there presently:
How To Design Your Own Questions For Generating Insights
The following are the angles used to generate the questions in this piece. These are the starting points you can riff off to create your own questions.
- Polarities/Extremes/Opposites
- Dissociative Questions/Seeing From Others' Perspectives
- Directing Attention To Little Noticed Places
- Constraints and Benefits
- Foreign/Unfamiliar Ideas/Actions
- Looking At Your Own/Others' Behaviors/Thoughts
- Looking At Your/Other's Past Experiences
- Following The Breadcrumbs/Thread (If That's True, Then ...)
- How Would I/This Be Different With x
- Imagining The Best
- Imagining The Worst
- Where Is The Most/Least Resistance
- Questioning What's Possible/Generating New Possibilities
- Questioning Assumptions
- Looking For What Distinguishes Something From Something Else
- What Would Need To Be True For x
Now, to the questions derived from those angles:
Polarities/Extremes/Opposites
- What is your favorite exercise/album/tool/place/x? Why?
- What is your least favorite exercise/album/tool/place/x? Why?
- What is the most extreme argument/idea/tool/action/x?
- What is the least extreme argument/idea/tool/action/x?
- What if you had too much x?
- What if you had too little x?
- What has been most helpful with x?
- What has been the least helpful with x?
- What is most valuable with x?
- What is least valuable with x?
- What is the most common problem with x?
- What is the most common solution with x?
- What opposites of this are valuable?
- What opposites of this are worthless?
- What would my life look like if I had 10x more patience/time/x?
- What would my life look like if I had 10x less patience/time/x?
Dissociative Questions/Seeing From Others' Perspectives
- Who are the biggest critics of this? What's their argument?
- Who are the biggest advocates of this? What's their argument?
- What is my competition seeing?
- What trends are they hopping on? Are they signs of bigger shifts?
- How can you meet the needs they're meeting in a distinctive way?
- (via Roger Martin, but slightly altered)
- What would you tell someone with this ____ (disease, problem, circumstance, income situation, relationship, etc.)
- What is one opinion of my enemies that I agree with?
- What is one opinion of my allies that I disagree with?
- What's the most controversial opinion that you agree with the most?
- What's the most controversial opinion that you agree with the least?
Directing Attention To Little Noticed Places
- What is the most overlooked argument/person/subject/location/tool/x?
- What is around you and in front of you right now?
- What do you pay the least attention to out of all of those things?
Constraints And Benefits
- What would you do with 10/20/x less hours a week?
- What would you do with 10/20/x more hours a week?
- What would you do with 1000 more dollars a week?
- What would you do with 1000 less dollars a week?
Foreign/Unfamiliar Ideas/Actions
- How is this done in x/company/country/city/culture/religion?
- What are the taboos in x?
- What are the values in x?
Looking At/Questioning Your Own/Others' Behaviors/Thoughts/Assumptions
- What are my assumptions with x?
- How do I usually approach x?
- What would happen if I approached x like x?
- What makes me angry?
- What makes me happy?
- What makes me sad?
- What do you envy?
- How much time do you spend consuming over creating? What makes you feel better?
- What do you feel like you need? If you changed "need" to "would die without," what would change about the answers to the first question?
- What do you admire most in others?
- What do you dislike the most in others?
- What do I always assume about x?
- What do I never assume about x?
Looking At/Questioning Your/Other's Past Experiences
- What food(s)/exercise/activity/x make you feel the best?
- What food(s)/exercise/activity/x make you feel the worst?
- What are the worst surprises you've ever had?
- What is the biggest commonality between all of your worst surprises?
- What are your codes? (Think Louis Vuitton's signature)
- What is the promise, story, and experience, you repeatedly give the rest of the world (your brand)?
- What are the charlatans (or at least, money-making focused) doing in this space/field?
- What Traits/Conventions/Cliches Are Valuable In This Field/Industry?
- When was I wrong about something similar?
- When was I right about something similar?
- What would need to be true about what they're seeing/thinking/feeling for them to be acting this way?
- What is the common thread connecting all of your worst moments?
- What is the common thread connecting all of your best moments?
- What puts you in flow states the most?
- How can you do more of that?
- What am I pushing out of my life by not having patience?
- What are you most averse to?
- What is your worst fear?
Following The Breadcrumbs/Thread (If That's True, Then ...)
- How would my life play out if I continued doing all of this for the next six months, year, three years, five years, etc.
- If it's true that x, then what would that mean about x?
- If it's true that global warming is real, what would that mean about living here for the next 5, 10, 15 years?
- If divination is true, what would that mean about free will?
- If x played out like that, then what does that mean for x?
- What if this was actually a good thing? Then what ...
- What if this was actually a bad thing? Then what ...
How Would I/This Be Different With x
- How would x be different if I replaced it with x?
- How would my day be different if I replaced scrolling/reading/relaxing with x?
- What if x took the place of x?
- How would my life change if I had x?
- If you could start life over from the beginning, what skill would you prioritize learning first?
Imagining The Best
- What would success look like with x?
- What would be your favorite outcome?
Imagining The Worst
- What would disaster look like with x?
- What would be your least favorite outcome?
Where Is The Most/Least Resistance
- What is the hardest way of going about this/achieving this/x?
- What is the easiest way of going about this/achieving this/x?
Questioning What's Possible/Generating New Possibilities
- What would I do/think/have if I had no chance of failing?
- What would a dream version of x be like?
- What would a world/country/business/relationship look like if x?
Looking For What Distinguishes Something From Something Else
- What makes x different from x?
- What makes x the same as x?
- What makex x better than x?
- What makes x worse than x?
- What makes x easier than x?
- What makes x harder than x?
What Would Need To Be True
I have to thank the business strategist, Roger Martin for this way of questioning. It's always immensely helpful, and I recommend reading his work, even if you're not involved in business strategy, because it's applicable to life.
- What would need to be true for this to be good?
- What would need to be true for this to be bad?
- What would need to be true to have a good rest of the year?
- What would need to be true to have a bad rest of the year?
- What would need to be true for this to be successful?
- What would need to be true for this to be a failure?
- What would need to be true for this to be easy?
- What would need to be true for this to be hard?
- What would need to be true for this to be the best x?
- What would need to be true for this to be the worst x?
- What would need to be true for us to accomplish ____ if (constraint)?
- What would need to be true for this to be the problem to solve?
- What would need to be true to have the worst hour?
- What would need to be true to not walk away from this wiser?
- What would need to be true for this to completely fail?
- What would need to be true for this to completely succeed?
- What would need to be true for this to be easy/hard?
- What would need to be true for this to have extreme outcomes?
- What would need to be true for this to be perfect for my audience/customer?
- What would need to be true for this to be extremely profitable?
- What would need to be true for me to succeed by working only 2 hours a day at this?
- What would need to be true for me to have no competition?
- What would need to be true for me to succeed without adding anything new?
- What would need to be true for my current life to be perfect, and require nothing else?
- What would need to be true for this moment to be perfect/terrible?
- What would need to be true for this business idea to be perfect/the worst?
- What would need to be true to have the worst possible customer or audience/best possible?
- What would need to be true for this disadvantage to be an advantage?
- What would need to be true for this advantage to be a disadvantage?
- What would need to be true for the status quo to be a good idea?
- What would need to be true to fail to be at peace right now?
The Questions of Others
Tim Ferriss
The following are questions I've gathered from Tim Ferriss, and I hope you find them as helpful as I have.
- What if I could only subtract to solve problems?
- If I could only work 2 hours per week on my business, what would I do?
- What if I did the opposite for 48 hours?
- What are people saying always, never, and should to about with this?
- What are the technical nerds doing at night or on the weekends after a work week?
- What are rich people doing now that other people might be doing ten years from now?
- Where are people cobbling together awkward solutions and is there room for innovation?
- Who are two close friends/two people at the bleeding edge of something?
- What do practitioners of this say about its future?
- What in this field is new, very old, or abandoned?
- What would you do if you still knew you were going to fail (and were only doing for the process/experience)?
- Who and what do I surround myself with the most? If I will become like those people and things, is that an outcome I want?
James Clear
James Clear's newsletter is the source of these questions, and seeing as he sends a new email out every week, I'd recommend subscribing to get any new questions he might be advocating for.
- If someone took control of your life tomorrow, what’s the first thing they would change?
- If you met someone exactly like yourself …
– same experience
– same resources
– same problems
- what advice would you give them?
- What are the most likely sources of pain in my life over the next year? How can I prepare for or prevent them?
- What should you do more of this decade? What should you do less of?
- What is the biggest opportunity I could pursue in the next 5 minutes?
- If you were forced to work for just one hour per day, what would you work on during that hour to be most effective?
- What is the most neglected important area in my life right now?
- What are you avoiding just because you know the answer is painful?
- Over the last 10 years, what has become more important to you? What has become less important?
- Think of the ultimate outcome you are hoping to achieve. Is there a path to accomplishing this where you would encounter less resistance?
- What would 10-year-old me say? What would 80-year-old me say?
- Who is your biggest fan? How can you thank them today?
- Simple question to find work you love: What do you enjoy refining? (It’s the areas you can’t help yourself from editing and optimizing where you have a long-term advantage.)
- If someone could only see my actions and not hear my words, what would they say are my priorities?
- Imagine each day is only 12 hours long. What would you cut out?
- What is one repeating problem you can automate or eliminate today?
- Some questions to consider before you speak:
- Does this need to be said?
- Does this need to be said by me?
- Does this need to be said by me right now?
- via Jerry Colonna: "How are you complicit in creating the conditions you say you don’t want?"
Other Resources For Questions
- My 'Socrates In Your Head' post is full of the questions and angles I use to change my mind quickly, and reduce cognitive dissonance
- This collection of questions from New York Magazine is pretty entertaining
- For relationships, the Gottman Deck can be helpful
- A helpful post for questions that can be applicable to business
- A collection of questions from Morgan Housel that I've found helpful in thinking differently
Final Thoughts
People don't like to question themselves for many reasons, including the time it takes to do so.
But insights often drive the progress we make in life, and even if it takes an hour out of your day (like using my Socratic question guide does for me), the results of questioning yourself can be worth it.
Hopefully you also find a similar magic to me when you meet the right question.