Leadership + Influence

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

You Are Not A Brand

Photo by    Cameron Clark

Photo by Cameron Clark

You are not a brand. You may be the face of your brand, and it may even bear your name, but the fact of the matter is that you yourself are not a brand. You are a multi-faceted human being and, in the words of Walt Whitman, you "contain multitudes."

You can build a brand that reflects your values and is infused with your personality and worldview, without allowing it to dictate how you behave, limit what you say, or define how you look at every second of every day. Being authentic doesn’t mean laying all your cards face up on the table. It also doesn’t require you throw “pearls to swine” and allow anyone and everyone access to every part of your life. Plus, if you want to scale or build a brand that will exist long after you’re gone, it will need to represent something bigger than yourself.

You can create multiple brands – completely separate from one another – with different target markets, different business strategies, different visual identities, different product categories, and set up specific branding for each of them that may not reflect your personality at all. There are zillions of companies like this that are very successful.

Others don’t get to define you, you get to define yourself. People may label you or assign motives, but at the end of the day, your actions and thoughts are your responsibility. This is why you are not a brand, no matter how popular or mainstream the term “personal branding” continues to be.

Brands can be shaped by us, but are ultimately defined by others. We, as humans, can be shaped by others, but ultimately we are defined by ourselves.


The original version of this post was published January 2014

Birthday Reflections + 63 Life Lessons Learned

artist: Anthony Burrill

artist: Anthony Burrill

Today's my birthday, and every year around this time I update a list on lessons I've learned – some while growing up and reinforced as time goes on, and some new. We all have stories and lessons learned from personal experience and I feel very strongly that we should not take them for granted nor forget. Here are 63 lessons I've learned, in no particular order:

1. If you're lucky enough to choose who you work with, opt for people who are intentionally kind rather than superficially nice.

2. There's always a deeper story. Ask better questions.

3. What people don't tell you about dreaming big is that dreams take time to fully articulate themselves. Keep pressing in. Clarity will come.

4. Being a critical thinker and having a critical spirit are two different things. The first requires an open mind, the second refuses one.

5. Bad things happen to good people. It's not always because of some moral failing or attracting it into your life because of emitting negative energy into the universe. Believing that you can control everything that happens to you is a philosophy of bondage, not freedom.

6. If people are really concerned about you, they will pick up the phone to call. The ones who don't call aren't really concerned. 

7. Your mental health is important. We all have issues, some that we don't even know exist. See a licensed therapist if necessary.

8. Life is not so much about being fearless, it's about moving forward despite our fears.

9. Good shoes make a huge difference and the money spent on quality is an investment, not a splurge.

10. You can't be responsible for other people's demons. 

11. When making purchases, support the original artists whenever possible.

12. Asking, "why me?" is the same as asking, "why not someone else?"

13. Rocking the boat is not the same as throwing someone under the bus.

14. Jaded is not a healthy lifestyle.

15. Learning how to take a compliment and accept forgiveness are just as important as giving both generously.

16. Comparing everything in your life to your "glory days" or a previous season will get you nowhere.

17. If you've "arrived," you've settled.  There's always more to learn, more to explore.

18. Being "too busy" is a myth. We make time for the people and things that are important to us.

19. Trials make you bitter or better. How you respond is up to you.

20. Being authentic doesn't mean laying all your cards face up on the table.

21. The healthiest people have more boundaries, not less.

22. True humility doesn't hide its gifts.

23. Choose the option with the story.

24. Your children and grandchildren will care more about your jewelry than you do. Buy less, choose well.

25. If you can't give up something for 30 days, you're addicted.

26. The right words at the wrong time are the wrong words.

27. The books you read as a child can spark lifelong passions. Encourage the children in your life to read.

28. People have a right to live fully, not just merely.

29. Don't expect people to fight fair. More importantly, don't allow that to make you cynical.

30. The quickest way to turn a good habit into legalism is to insist that everyone else do it as well.

31. Consistent acts of kindness trump random acts of kindness. Habits always win.

32. "Buy all this stuff to simplify your life!" is the new face of materialism.

33. Erase the phrase "Oh, they would never do that" from your vocabulary. People will surprise you – for better and for worse.

34. Your values aren't really your values until they impact your wallet and your time.

35. When in doubt, give people the opportunity to save face. When not in doubt, give people the opportunity to save face. Dignity transforms.

36. Expecting people to be perfect is an exhausting way to live. The people you love and respect will disappoint you. Love them anyway.

37. Blind spots are called that for a reason: YOU can't see them.

38. Social media doesn't make a person better or worse, it amplifies who they already are.

39. If design didn't matter in the grand scheme of things, snowflakes would be ugly.

40. Fresh flowers bring a room to life and are worth including in your weekly budget.

41. Surrounding yourself with passionate people means having to work harder on your relationships. This requires less assuming and deeper listening. It is worth it.

42. People are not projects.

43. Mondays represent a clean slate and fresh start. Going through life hating them is a waste. TGIM.

44. God doesn't need a consultant.

45. Looking for the good doesn't erase the bad. Looking for the good simply allows the bad to be viewed in the appropriate context: as a part, not the whole, and often as something that can be restored or given a second chance.

46. Generous people change the world, not because of what or how much they give, but because they are doers and see possibility where others don't.

47. "It's okay to be average" is one of the most poisonous and destructive lies you can choose to believe. You have untapped potential and the only person who can use it is you. What an endless, amazing gift.

48. If your dreams do not add good to the lives of others, you are dreaming too small.

49. There is power in creating something of your own, even if no one else ever sees it.

50. If you catch yourself randomly thinking something nice about someone you haven't spoken to in a while, send a quick note to tell them so. It will make both of you feel good.

51. Love without hope is sentimental, powerless mush. Transformation can only truly occur when hope is present and encouraged.

52. Gifts celebrate a spirit of generosity. The very nature of giving a gift requires thinking of other people before ourselves.

53. Happiness and joy are not the same thing. Happiness is circumstantial. Joy can sustain you through every curveball life throws your way.

54. The true legacy of books is in the ideas they nurture and spread, not in the packaging.

55. Optimism is a muscle. The more you use it, the stronger it gets.

56. It is impossible to have an open mind and a closed fist.

57. If a woman living on $2 a day in a developing country could not accomplish what you have through her hard work alone, there is some amount of privilege in your life.

58. Open doors for people who will open doors for people.

59. People can change. If we couldn’t, then the concepts of growth and redemption are fraudulent.

60. People who won’t show up for the tough days aren’t people you need in your inner circle, no matter how “positive” they or their brand may be.

61. Authentic always means "real." It does not always mean "good."

62. It's okay to question everything: your faith, your career path, your political views, your choice of friends. In fact, it's dangerous if you don't.

63. Giving a damn brings true joy, apathy kills the soul.


The original version of this post was published October 2009