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Questions for Better Thinking

"Transformation comes more from pursuing profound questions than seeking practical answers." - Peter Block
Welcome, You Curious Maverick! 👋👋
Congratulations, you've stumbled upon a treasure trove of thought-provoking questions that defy the ordinary and challenge the status quo. Here, we don't just settle for answers; we dive headfirst into the daring realm of powerful questions.

Power of Inquiry: Why Questions Matter More Than Answers

In a world where information is abundant, and answers are just a click away, why should we embark on a journey of questions? Because the art of inquiry is a portal to infinite wisdom and boundless exploration. It's the key to unlocking the doors of possibility and igniting the flames of creativity.
Questions are catalysts for growth and innovation. They break down barriers, shatter assumptions, and lead us to discover new perspectives and insights. Great thinkers and visionaries have relied on the power of questions to challenge conventions, reshape industries, and pioneer groundbreaking ideas.
As you delve into this collection, let go of the belief that answers hold all the solutions. Embrace the beauty of questions, for they are the compass that guides us through uncharted territories, where true transformation awaits.

My Quest for Questions Journey

How to Use This Collection:

Discover the art of powerful inquiry and tap into the full potential of this question collection through a series of transformative practices and rituals:
Question-Storming: Gather your thoughts, pen, and paper, and unleash a torrent of questions without judgment. Let the floodgates of curiosity open and explore uncharted territories of thought.
Thinking Time: Find yourself a cozy nook, a journal that speaks to your soul, and allow these questions to fuel your thinking. Delve into deep contemplation, unearthing treasures buried within your mind.
The 1 Thing: Zero in on the single most important question—the one that, if answered, would make everything else easier or unnecessary. Let it be the guiding star in your quest for clarity.
Amorati Daily Ritual: Adopt the daily ritual of the Amorati—a practice that sharpens your focus and keeps you aligned with your purpose and passions.
Your 12 Favorite Questions: Embark on a journey of self-discovery by exploring the questions that align with your mission, values, and vision.

Unveil Your Beautiful Question

Join the Maverick Community

But wait, there's more to this expedition! By joining the Quest for Questions community, you'll gain access to exclusive content, engaging discussions, and the chance to connect with like-minded seekers from around the world. Our newsletter is a treasure trove of insights, delivered right to your inbox. Plus, you'll be the first to know about exciting updates, new question collections, and captivating explorations.
In the age of misinformation, we reject mediocrity and embrace the thrill of uncertainty. As the legendary Richard Feynman once said, "It's much more interesting to live not knowing, than to have answers that may be wrong."
So, fellow seeker, if you're ready to embark on a quest that transcends time and space, grab your hat of inquiry, fasten your seatbelt of curiosity, and join the ranks of the trailblazing mavericks.
Ready to take the leap? Let's dive into our Maverick's Guide to Rule-Bending Questions and unlock the secrets that lie within.


Thinking Time
The 1 Thing
Amorati Daily Ritual
Your Mission Questions

By Categories:


Life-Changing Questions

What in life gets you really excited?
What could you do to bring more of what really excites you into your life?
Summarized in just a few sentences, what is your life's story?
What would you like the next chapter of this story to be?
What would you say is the greatest accomplishment of your life so far? Brag for a minute.
What do you want to make sure you do, achieve, or experience before you're gone?
In recent years, what's the biggest lesson you've learned about yourself?
Who inspires you most, and why do you find them inspiring?
What was the biggest turning point in your life, and how did that experience change you?
What are you taking for granted that you want to remember to be grateful for?
Think for a moment about the biggest problem right now in your life. If that problem was happening to a close friend instead of to you, what would you say to comfort or advise that friend?
What meaningful or important thing should you tell a particular person that you haven't said to them yet?
When are you going to tell this person this meaningful or important thing?
What's one of the best days you've had in your entire life? Describe what happened that day.
What in your life that you have the power to change is most limiting your long-term happiness?
What could you start doing now to address what you said is most limiting your happiness?
If you had to have roughly the same work day, 5 days a week, for the next 10 years, what activities would you ideally want this work day to consist of?
What can you do to make your current job closer to this ideal, or to help you get a job that is closer to this ideal?
What is the most important thing that you know you really should do but which you have trouble getting yourself to do?
What could you do now to make it more likely that you actually do this important thing?
What do you think is holding you back from achieving more in your life than you've achieved so far?
What could you start doing now that would help address what you said is holding you back in life?
In your opinion, what is the purpose or meaning of life?
How is the very best version of yourself different from the way you sometimes behave?
What has kept you hopeful in life's most challenging moments?
During what period of your life were you the happiest, and why were you so happy then?
Imagine that you received a message from a version of yourself five years in the future. What warnings would the message give you, and what advice would it offer about how best to achieve your goals?
If you knew for a fact that you were going to die exactly 10 years from now, how would you change your current behavior?
Suppose you knew that you were going to die instantly (but painlessly) in exactly 7 days. What would you spend your last week doing?
If you could plan one nearly perfect (but still actually realistic) day for yourself, what would you spend that day doing? Describe that day, from when you wake up until you go to sleep.
When is the soonest that you can treat yourself to this perfect day, or to another day that you'll really enjoy and remember?
What valuable things have you learned, or what useful takeaways have you gotten, from answering these questions?

Personal Questions

If I had a board of directors, would they give me a raise, or would they fire me?
If You Inc. was a publicly-traded company with stakeholders would the stock price be rising, falling, or threading water?
Where has the ‘job’ mentality of the comfort zone, the path of least resistance, and do the least expecting the most crept into my thinking and performance?
Where are the growth opportunities I postponed because they require extra effort or are outside my comfort zone?
What business skills do I need to learn, so that I can create the leverage required to be a successful owner? Who can I learn them from?
How important is learning this business stuff and how fast do I need to learn it?
How do I define excellence?
Why shouldn’t that be the standard I work towards regardless of my ownership %?
If I had a board of directors, where do I need to pick up my game to deserve the raise or incremental profits I’m seeking?
What should I be doing which would add more value?
What am I doing that could be done by someone else?
What can I (and only I) do?
What shortcuts am I trying to take?
What skills do I need to master to attain the success I want?
Realistically, how much additional time and practice are required for me to achieve my outcomes?
Who can I hire as a coach or mentor to help guide me and hold me accountable?
Where do I need to practice to improve my game and thus deserve the success I want?
Where do we need to pick up the level of intensity on how we are playing this game?
What are the 50 most important lessons I learned from my stupidest decisions and biggest losses and biggest mistakes?
Where am I making them again?
What do I need to change immediately to avoid dreaded dumb tax?
What are the rules I need to put in place to avoid those mistakes?
Who around me is screaming alternative solution but I’m not hearing it?

After Action Review Questions

What were the objectives of XYZ endeavor?
What actually happened?
Why was it different from the objective?
What went well?
Why did these things go well?
Why did the things go wrong?
What are we gonna do different next time, and how?
What’s the ONE Thing we’re going to do different next time ?

6 Common Questions Transformed

How do you do it? What is the refusal I’ve been postponing?
How long will it take? What is the commitment I’m willing to make?
How much does it cost? What is the value of it to me? / What price am I willing to pay to get there?
How do you get those people to change? What is my contribution to the problem?
How do you measure it? What is the judgment I need to make?
How have other people done it successfully? What is the contribution I want to make? / What do we want to create together?

The 1 Thing

What's the ONE thing I can do to help others such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to achieve my diet goals such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to ensure that I exercise such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to relieve my stress such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to improve my skill at <......> such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to find time for myself such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to improve my relationship with my partner such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to ensure that I hit my goals such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to further my career such that by doing it everything else will be easier or unnecessary?
What's the ONE Thing I can do to increase my net worth such that by doing it everything else will be easier or unnecessary?

The Mother of All Questions

What question if I had an answer to, would set me free?

Thinking Prompts — Socratic Questioning

Attributes and Tendencies
What characterizes (X) ?
What do I mean by (X) ?
If (X) could utter a single line it would be…
Other ways to describe X would be…
(X) is kind of like …
What do I already know about (X)?
Could I expand upon that point further?
An example of (X) would be...
Similarities and Differences
- *(X) reminds me of ... because …*
- *Isn't this (X) argument similar to that (Y) one?*
- *Haven't I heard this before?*
- *(X) is similar to (Y) in this respect. It differs from (Y) in this other respect.*
- *What would be an alternative? *
- *How are (X's) and (Y’s) ideas alike? Different? *
- *(X) is somehow related to…*
- *Are X and Y ideas contradictory or do they compliment each other?*

Viewpoint Questions
- *What is another way to look at (X)?*
- *Why (X) is necessary-or beneficial and who benefits?*
- *Why is (X) the best?*
- *What are the strengths and weaknesses of (X) ?*
- *What is a counter argument for (X)?*
- *Compare... and... with regard to... *
Parts & Wholes
- *Is (X) a Genus or a Species*
- *Rectangle : Square*
- *(X) is a part of…*
- *(X) is made up of the following parts…*
- *(X) is an instance of (Y). (X) is itself composed of a,b,c.*
--- ​Assumption questions
- *Why would I make this assumption?*
- *What am I assuming here?*
- *What could I assume instead?*
- *How can I verify or disapprove that assumption?*
- *What would happen if...?*
--- ​Significance and Implications
- *What does (X) mean for (Y)?*
- *Why did the aspect I wrote down catch my interest?*
- *(X) is important because…*
- *What does this all mean for my own research and the question I think about in my slip-box?*
- *How does (X) apply to everyday life?*
- *What generalizations can I make about (X)?*
- *What are the consequences of that assumption?*
- *What am I implying by that?*
- *How does ... affect ...?*
- *How does (X) tie in with what I have learned before? *
- What effect would that have?
- *Could that really happen or probably happen?*
- *What is an alternative?*
- *If that happened, what else would happen as a result?**
- *Why?*
Reason and evidence questions
- *What would be an example?*
- *Why do I think this is true?*
- *What other information do I need?*
- *By what reasoning did ___ come to that conclusion?*
- *Is there reason to doubt that evidence?*
- *What led ___ to that belief?*
- *What is .... analogous to?*
- *What do you think causes to happen...? Why:?*
- *What evidence is there to support this answer?*
Origin or source questions
- *Is this my idea or did I hear if from some place else?*
- *Have ___ always felt this way?*
- *Has ___ opinion been influenced by something or someone?*
- *Where did __ get that idea?*
- *What caused __ to feel that way?*
--- ​Questions about an initial question or issue
- *Why is this question important?*
- *Is this question easy or difficult to answer?*
- *Why do/does __ think that?*
- *What assumptions can we make based on this question?*
- *Does this question lead to other important issues and questions?*
- *What answer can I expect by asking the question in this particular way?*
- *What was the point of this question?*
- *Why do you think I asked this question?*


Questions to Uncover Different Systems Archetypes

Fixes That Fail
Have actions been taken to respond quickly to a crisis without much consideration of long-term consequences?
Have similar actions been taken in the past in response to similar crises?
Shifting the Burden
Are actions taken to alleviate problem symptoms shifting attention away from more fundamental solutions?
Are there additional consequences that systematically erode the underlying capability of the organization?
Limits to Success
Are once-successful programs experiencing diminishing returns?
Are there limits in the system that are constraining the growth?
Drifting Goals
Are there goals or standards that are eroding over time?
Are people focused on achieving the goal or on reducing the discomfort of not being at the goal?
Are some goals being met at the expense of others?
Growth and Underinvestment
Do investments tend to be made as a reaction to growth rather than in Underinvestment anticipation of growth?
Do problems created by growth, rather than long-range planning, act as the organizational signal to invest?
What would happen if investments were made earlier, in anticipation of limits to growth?
Success to the Successful
Is there a resource for which allocation decisions are in a zero-sum game?
Does the success of each party depend on receiving the same resource?
Does allocation of the fixed resource depend on success of the parties involved?
Are there two or more players whose individual actions can be perceived as a threat by the others?
Does each player have the capacity to respond to a sense of threat with actions similar to the other party’s?
Tragedy of the Commons
Is there a large number of players who have free or equal access to a common and limited resource?
Is the system set up to be self-regulated, with no overarching governing body?
Is there any regulatory or coordinating mechanism for managing the commons? If so, is it effective?

Testing-the-Impossible Questions

What if I do the opposite of what I normally do, for 48 hours?
For business ideas: what do I personally spend a lot of money on?
If I had $10 million, what would I be doing differently? Do I really need $10 million to get this lifestyle today?
What’s the worst that could happen? If it did happen, could I recover?
If I capped my working time to 2 hours per week, what would I do?
Delegation: What if I give complete freedom for decisions up to $100? $500?
What’s an underrated channel for marketing or promotion?
Marketing: What if I don’t pitch my product directly?
Education: Instead of a formal degree, what if I made my own degree?
If I lost something, do I need to make it back the same way?
How could I solve this problem by simplifying and subtracting ONLY?
How can I disappear for 4 to 8 weeks without having my business or work crash?
Am I hunting lions or mice?
Might I actually be completely content?
What would this look like if it were easy?
How can I use money to solve this problem? How can I use money to improve my quality of life?
Can I take it easy and achieve nearly as much?

Breakthrough Innovation Questions

Examine binding constraints
What is the biggest hassle of purchasing or using our product?
What are some examples of ad hoc modifications that customers have made to our product?
For which current customers is our product least suited?
For what particular usage occasions is our product least suited?
Which customers does the industry prefer not to serve, and why?
Which customers could be major users, if only we could remove one specific barrier we’ve never previously considered?
Imagine perfection
How would we do things differently if we had perfect information about our buyers, usage, distribution channels, and so on?
How would our product change if it were tailored for every customer?
Revisit the premises underlying our processes and products
Which technologies embedded in our product have changed the most since the product was last redesigned?
Which technologies underlying our production processes have changed the most since we last rebuilt our manufacturing and distribution systems?
Which customers’ needs are shifting most rapidly? What will they be in five years?
Look beyond the boundaries of our business
Who else is dealing with the same generic problem as we are but for an entirely different reason? How have they addressed it?
What major breakthroughs in efficiency or effectiveness have we made in our business that could be applied in another industry?
What information about customers and product use is created as a by-product of our business that could be the key to radically improving the economics of another business?
Explore unexpected successes
Who uses our product in ways we never expected or intended?
Who uses our product in surprisingly large quantities?
“De-average” buyers and users
Which customers use or purchase our product in the most unusual way?
Do any customers need vastly more or less sales and service attention than most?
For which customers are the support costs (order entry, tracking, customer-specific design) either unusually high or unusually low?
Could we still meet the needs of a significant subset of customers if we stripped 25% of the hard or soft costs out of our product?
Who spends at least 50% of what our product costs to adapt it to their specific needs?

8 Category Levers

Different Benefit
What is a radically different benefit we can offer the customer/end user?
Different Experience
How can we make the experience so distinct that it is worthy of a price premium?
Different Price
How can we change the way consumers perceive value that is radically different?
Different Manufacturing
What radically different way can we make what we market?
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