Critical Thinking

30 Questions That Will Give You Clarity

And help you do more meaningful work.

Photo by    Cameron Clark

Photo by Cameron Clark


I am a firm believer that asking more questions is essential to living a joy-filled, whole-hearted life. Asking ourselves ambitious questions leads to better, bigger, braver living. Asking smart questions leads to more creativity. Asking meaningful questions is a sign of respect and leads to stronger relationships.

Many people don't ask questions because of ego or fear of being seen as less intelligent and thereby less likeable. These fears rob you of deeper relationships as well as lucrative opportunities. 

Until you question something, you can't improve it, which is why being curious is one of the hallmarks of a great leader. Here are 30 questions to help you think more deeply and more clearly about different areas in your life:

1. On whether or not ego is driving a decision:
Would I do this even if nobody ever found out?

2. On creating stretch goals:
How can I play a bigger game?

3. On whether or not we achieved something solely through hard work:
Could a woman living in a developing nation on $2 a day also achieve this solely through hard work?

4. On being overly critical of ourselves:
What would I say to my child if they had made the same mistake?

5. When we get scared of our own ambition:
What if things work out?

6. On the amount of time something will take:
How old will I be by that time if I don’t pursue this?

7. On whether or not our values align with our actions:
Do my calendar and bank account reflect this?

8. On whether or not we’ve created a bubble/echo chamber for ourselves:
Do I listen to/follow/read people I respect yet disagree with?

9. On whether or not we’re addicted to something:
Could I give this up for 30 days?

10. On evaluating the motivation behind an over-packed schedule:
Would I stay involved in this if my friends weren’t interested in it?

11. On anxiety:
When/on what do I procrastinate the most?

12. On whether a belief we hold is fact-based or simply comforting:
If I was given solid evidence to the contrary, would I be willing to change my mind on this?

13. On being open to new ideas:
When was the last time I changed my mind on a profound topic?

14. On our ability to think for ourselves:
What do a lot of people believe that I disagree with?

15. On selflessness:
When was the last time I did something I had no interest in (without complaining) purely because my spouse/kids/friends wanted to do it?

16. On clarifying whether or not doing something fits our priorities:
What do I hope will happen as a result of this?

17. On whether or not others feel safe being honest with us:
How often do I punish, gossip about, or withhold opportunities from people who gave me "negative" feedback, told me "no," or voiced an opposing opinion?

18. On whether or not a potential collaboration will be healthy:
How often does the person I'll be collaborating with punish, gossip about, or withhold opportunities from people who gave them "negative" feedback, told them "no," or voiced an opposing opinion?

19. On whether or not to speak up:
Who or what benefits if I bite my tongue on this issue?

20. On critical thinking vs contrarianism:
Do I disagree with/dislike this for specific, merit-based reasons or simply because everyone else agrees with/likes it?

21. On identifying a gap in the market:
Is this truly a gap or have I just not done enough research?

22. On letting go:
Am I holding on to this because it’s beneficial or simply because it’s familiar?

23. On contentment:
Am I truly content or am I making excuses for not changing something that would benefit from improvement?

24. On the trap of conventional wisdom:
What do I believe is wrong but sounds right?

25. On preconceived notions:
Have I allowed one bad experience with something to color my perspective of everything or everyone connected to it?

26. On fearing change:
Do I keep looking for potential solutions to an issue while refusing to try the ones I’ve already come across?

27. On whether or not we’re limiting or disempowering others:
For my belief to be true, does it require that another person’s experience be erased, dismissed, or untrue?

28. On making a bigger impact in our daily lives:
What can I do this week to add good to others’ lives?

29. On pricing or negotiations:
Where am I allowing fear to dictate my ask?

30. On allowing false humility to take root:
Where am I downplaying my talents or gifts?


Originally published April 2018

30 Questions That Will Help You Think More Clearly

Photo by    Cameron Clark

Photo by Cameron Clark


I am a firm believer that asking more questions is essential to living a joy-filled, whole-hearted life. Asking ourselves ambitious questions leads to better, bigger, braver living. Asking smart questions leads to more creativity. Asking meaningful questions is a sign of respect and leads to stronger relationships.

Many people don't ask questions because of ego or fear of being seen as less intelligent and thereby less likeable. These fears rob you of deeper relationships as well as lucrative opportunities. 

Until you question something, you can't improve it, which is why being curious is one of the hallmarks of a great leader. Here are 30 questions to help you think more deeply and more clearly about different areas in your life:

1. On whether or not ego is driving a decision:
Would I do this even if nobody ever found out?

2. On creating stretch goals:
How can I play a bigger game?

3. On whether or not we achieved something solely through hard work:
Could a woman living in a developing nation on $2 a day also achieve this solely through hard work?

4. On being overly critical of ourselves:
What would I say to my child if they had made the same mistake?

5. When we get scared of our own ambition:
What if things work out?

6. On the amount of time something will take:
How old will I be by that time if I don’t pursue this?

7. On whether or not our values align with our actions:
Do my calendar and bank account reflect this?

8. On whether or not we’ve created a bubble/echo chamber for ourselves:
Do I listen to/follow/read people I respect yet disagree with?

9. On whether or not we’re addicted to something:
Could I give this up for 30 days?

10. On evaluating the motivation behind an over-packed schedule:
Would I stay involved in this if my friends weren’t interested in it?

11. On anxiety:
When/on what do I procrastinate the most?

12. On whether a belief we hold is fact-based or simply comforting:
If I was given solid evidence to the contrary, would I be willing to change my mind on this?

13. On being open to new ideas:
When was the last time I changed my mind on a profound topic?

14. On our ability to think for ourselves:
What do a lot of people believe that I disagree with?

15. On selflessness:
When was the last time I did something I had no interest in (without complaining) purely because my spouse/kids/friends wanted to do it?

16. On clarifying whether or not doing something fits our priorities:
What do I hope will happen as a result of this?

17. On whether or not others feel safe being honest with us:
How often do I punish, gossip about, or withhold opportunities from people who gave me "negative" feedback, told me "no," or voiced an opposing opinion?

18. On whether or not a potential collaboration will be healthy:
How often does the person I'll be collaborating with punish, gossip about, or withhold opportunities from people who gave them "negative" feedback, told them "no," or voiced an opposing opinion?

19. On whether or not to speak up:
Who or what benefits if I bite my tongue on this issue?

20. On critical thinking vs contrarianism:
Do I disagree with/dislike this for specific, merit-based reasons or simply because everyone else agrees with/likes it?

21. On identifying a gap in the market:
Is this truly a gap or have I just not done enough research?

22. On letting go:
Am I holding on to this because it’s beneficial or simply because it’s familiar?

23. On contentment:
Am I truly content or am I making excuses for not changing something that would benefit from improvement?

24. On the trap of conventional wisdom:
What do I believe is wrong but sounds right?

25. On preconceived notions:
Have I allowed one bad experience with something to color my perspective of everything or everyone connected to it?

26. On fearing change:
Do I keep looking for potential solutions to an issue while refusing to try the ones I’ve already come across?

27. On whether or not we’re limiting or disempowering others:
For my belief to be true, does it require that another person’s experience be erased, dismissed, or untrue?

28. On making a bigger impact in our daily lives:
What can I do this week to add good to others’ lives?

29. On pricing or negotiations:
Where am I allowing fear to dictate my ask?

30. On allowing false humility to take root:
Where am I downplaying my talents or gifts?


Originally published April 2018

The One Trait the Best Leaders + the Most Creative Pros Share

If you're the first to always throw cold water on ideas — either yours or those belonging to others — it's time to stop and ask yourself why.

I don't advocate giving false praise or telling everyone their idea is fantastic when it's not. There is, however, a serious difference between giving warranted, beneficial feedback that someone may not want to hear and shutting down an idea before it even has a chance to start.

Being a critical thinker and having a critical spirit are two different things. The first requires an open mind, the second refuses one. Getting into a pattern of throwing ideas out before listening to or examining them is toxic. Keeping an open mind is something that the best leaders and the most creative artists have in common.


Originally published June 2012