Leadership

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

Why New Year's Resolutions Are Worth Setting


I love it when a year changes over to the next. I especially love New Year's Eve and New Year's Day because people all over the world embrace the concept of a clean slate and a fresh start. They are international days of optimism and the energy is contagious.

New year's resolutions get a bad rap. Some people claim that they never keep them so they just give up on setting them. Other people claim that resolutions are an example of not being content with who we are or failing to embrace our flaws. I find, though, that wanting to change and be better stems not from a lack of self-esteem, but rather a desire to use some of the untapped potential that we know exists in us.

This is healthy. If I am the same exact person I was a year ago it means that I've gone twelve months without learning anything:

  • Nothing from books.

  • Nothing from conversations with friends and colleagues.

  • Nothing from a thoughtfully made TV program or movie.

  • Nothing from a joyful (or difficult) experience.

This results in a boring life. Our one over-arching resolution should always be to be a better person by this time next year.

You can't outsource potential and the thing about your potential is that you're the only one who can reach it. Success changes the dynamics of relationships more often than failure does and I'm convinced that we usually self-sabotage out of a fear of success rather than a fear of failure.

As the old saying goes, "People stay in hell because the street signs are familiar." Don't waste your potential just because the people around you may be wasting theirs. Change and growth are hard work, but worth it.


Originally published January 2012