What Really Drives a CEO?

“If we wanna know how our inner world is… look around us.” -Taylor Conroy

Self-awareness is a constant theme in my podcast conversations with leaders. It’s why they read, journal, ask for 360 evaluations, and meditate. Taylor Conroy takes his commitment to self-awareness a step further.

Taylor is an extremely popular TEDx speaker, social entrepreneur, and now CEO of The Idea Collective. In our recent conversation Taylor shared how he’s learned about his deepest wound that is, “Directing the course of my life.” He tells stories of how this wound has shaped his decisions and thoughts, both personal and political. And he gives examples of how to leverage this awareness to make sure you spend your time on things that matter. To see the full interview, check out the video below.

For years, Taylor Conroy used his charisma and a cutting-edge fundraising system to rally people to build houses in third world countries. His company brought hundreds of houses to people in need. Taylor gave popular talks and spread the word. Fundraisers had life-changing experiences while building the houses. Everything looked perfect. Then, Taylor went bankrupt.

“When stuff gets good, Taylor f***s it up.”

Taylor’s out of bankruptcy now and living by the ocean in California, but he’s still eager to grow and help others. He told me that plant medicine ceremonies, like taking ayahuasca, have been invaluable to him, “Like seven years of therapy in one night.” A few weeks ago, Taylor took ayahuasca and recalled a painful memory, “A gaping, bleeding wound.” This wound is the source of his belief that, “When stuff gets good, Taylor f***s it up.” It’s also the reason he’s been a skilled lifeguard, firefighter, businessman, and speaker.

Take a plant-medicine-fueled trip 21 years back in time and Taylor is 6 years old, acting out at a friend’s birthday party. He’s confused, upset, and eventually taken out of the party and put alone in the back of the family car. Embarrassed, he struggles to make sense of the situation, “No one’s like going through some process with me. I’m just in s**t.” In that moment, he internalizes a new story about himself, “Taylor ruins things.”

Recognizing this story has massively changed Taylor’s professional direction. He just dropped plans to write a book and turned down an advance of about $100,000. He says he’s more in touch with the things that he actually cares about, instead of the proving that he doesn’t ruin things.

This new outlook is hard to paint in black and white. Taylor has made major life decisions to try to cover his wounds. He’s committed years to saving the day through building houses, inspiring audiences, and literally saving people, animals, and property as a firefighter. This sounds noble, but Taylor calls it a, “Band-Aid on a gaping, bleeding wound.” Now, he’s feeling secure and turned down book deal. Would the book help a lot of people? I bet it would.

I asked Taylor how he’s using his self-knowledge. He said that simply knowing is 99% of the solution, like casting a bright light on a shadow. He also laughs at it, and we laughed a lot. If you check out the episode, I completely crack up when Taylor hits the punch line of his dog saving story.

A man with an urge to save the day makes a tough partner, personally and professionally. Taylor’s feeling more free to enjoy relationships and let go of toxic stuff.

He’s not even out to save himself anymore.

We talked about what he would say to his younger self and he was happy to let everything pass. He said it’s all been valuable and made him better.

How does all this talk of feelings and self-awareness help the bottom line for Taylor’s company? He said that work is accepted from a place of, “That sounds like fun.” Lately, new deals have been coming through easier than ever.

To hear directly from Taylor Conroy, click this link to the complete video interview.