A Not-So-Secret Secret

A few years ago I spoke at a conference and afterwards a young wedding professional came up to meet me. They rattled off a list of about a dozen "big industry names" they had met and then said, "After meeting you, I now only need to meet one other person and I'll have met all the people I need to learn from in the industry."

Um, what?

Here's a not-so-secret secret: Some of the "biggest names" in the industry are majorly in debt and barely holding it together, regardless of the life their Instagram depicts. Some of the people you've "never heard of" in the industry make high six or seven figures annually and are quite content to fly under the radar.

Everyone you meet has something you can learn from: success, failure, a different angle of thinking, an opinion that challenges yours and prompts you to articulate and define your stance better.

The people who commit to constantly learning, unlearning, and who check their bias and ego at the door are the ones who will succeed over the long haul.

(By the way, the person I met is unfortunately – but not surprisingly – no longer in business.)

Originally published May 2014

30 Questions That Will Help You Think More Clearly

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?

Cultivating the Leaders On Your Team

One of the best gifts I’ve ever received was being given way too much high-stakes responsibility at my first "real job" when I had little experience.

When sink or swim is your only option, you learn how to swim — fast.

Being a control freak only ensures that your company never gets to the next level. If you’re interested in cultivating your employees into leaders, they don’t need more busy work. They need more of the important stuff you’re hesitant to take off your own plate.

Originally published February 2015