More than seven years ago, I got an invitation for a retreat in Big Sur, California. It was organized by the venture capitalist Bo Shao, then a newfound friend whom I’ve grown to admire. Retreats had not crossed my mind, but I knew that Bo had undergone a significant personal journey and wanted to share some lessons and introduce his mentors. It was expensive—for me, at least—but I trusted Bo, and I was curious. Our week-long stay brimmed with practical insights and had a lasting impact on me. When we were sharing reflections on the final day, I admitted that the retreat had made me realize I wasn’t the husband, father, son, or friend I thought I was. Which is to say, I wasn't the person I aspired to be. And yet, here were some tools for bridging this gap. Gratitude sat heavily in my chest. We largely assume we know who we are and how we’re doing. But stepping out of our comfort zones and surrounding ourselves with wise mentors feel like necessities. Confronting the truth of our identities without these components is a longshot.