Do you have the courage to lead?

"I define a leader as anyone who takes responsibility for finding the potential in people and processes, and who has the courage to develop that potential." — Brené Brown

“Charlene, we don’t feel that you trust us. We are constantly playing catch-up. We do not realize our team’s full potential. To scale, we need you to trust us.” 

I received this candor feedback from my team last week. It was authentic and direct—the kind of feedback I appreciate and love. But it was also tough—the kind of feedback that made me doubt myself. I have coached many leaders to empower their teams, yet I have failed to empower my very own. How long have we been operating in such a dysfunctional way? How can I build trust? How can I empower my team? 

As much as I wanted to protect my ego, my goal was to create the best team possible. Quoting Brené Brown, If we want people to fully show up, to bring their whole selves including their whole hearts—so that we can innovate, solve problems, and serve people—we have to be vigilant about creating a culture in which people feel safe, seen, heard, and respected.”

My team took the courage to share this feedback because they cared and believed I would change. The last thing I wanted was to get defensive, so I took a deep breath and asked my team for more context.

Me: Could you tell me how I could get better?

Team: We want you to share every project and decision with us.

I was so eager to run with my conviction that I’ve overlooked the importance of sharing context, articulating the vision, and getting my team’s buy-in. I loved to share the result and move on to the next things. While this habit may have expedited a few projects, it was very demoralizing. What’s worse is that I have missed the opportunity to empower my team and delegate effectively. It’s time to change. 

Me: You got it. I will share everything as soon as I can. I also started a private Substack to share my top of mind with the team. 

Team: We want you to share the detailed curriculum design for LivingOS Bootcamp with us.  

This ask is challenging because it fundamentally changes the way I work. I love to improvise and work under tight deadlines. I like to finalize my curriculum during the T-1 hour. While the deadlines energized me with the adrenaline rush, they sent my team panic attacks and took away their opportunities to review and give feedback. To keep my excitement and make my team stay sane, I promised to give myself an earlier deadline so that everyone could have time to review and make it better. 

Me: You got it. I will create artificial deadlines so that I can enjoy the magic of improvisation and you can review and give feedback. 

Vulnerability doesn’t come naturally to me. I had a few betrayals earlier in my career, so I had to actively remind myself that it was safe to trust people, starting from my team.

Plus, my team at LivingOS is different from all the other teams I’ve ever worked with. We have known each other for a very long time: Eva since elementary school, Ju-Han since my first year in high school, Lynn since my last year in high school, and Chris since my first year in college. Most importantly, they have all become my best friends.1 They chose to believe in me, so it’s my turn to believe in them. 

And I believe in you, dear readers. That’s why I decided to share this journey before I knew the outcome. Specifically, here are the open questions I’m working with my team and coach to address: 

  1. What kind of leader do I want to become?2

  2. How can we cultivate collective courage for the team? 

  3. How can I share a vulnerable emotion every day? 

To the growing pain that makes us stronger together,


PS - Special thanks to the 19 wonderful humans who shared their theme song with me! It’s so great to know people through music. You can check out the playlist here.


 “Hire your best friend,” as Rebecca told Keeley in the Ted Lasso Finale.


My working definition is “believe in my team and give them the resources and freedom to do great things.”