As Coach and CEO at RebootHQ, Jerry Colonna talks about just because you feel like s**t doesn’t mean you are s**t, that there’s a very tight correlation between high achievers and impostor syndrome, and that cringe-worthy moments are great moments of learning. Have you been enjoying these Heartbeat episodes, lately? If so, it’d mean the world to me if you wrote us a review in iTunes. The more reviews we have, the more we’re able to share all our lessons from leaders. Thank you! CLAIRE: Hi everyone. I’m Claire Lew, and I’m the CEO of Know Your Team. We make software that helps leaders avoid becoming a bad boss. And on today’s episode of The Heartbeat, I have a guest who I have literally been looking forward to having on this show all year. I have Jerry Colonna, who is an — what’s the right word? Famed, notorious. I don’t know. JERRY: The Notorious RBG. [Chuckles] CLAIRE: I think so. Something like that. But as an executive coach. And you run your own executive coaching practice called Reboot. Most recently, you published a book by the same name, Reboot, and it’s on leadership and the art of growing up. And I couldn’t put this book down. There’s so much to get into on this. And then it’s so funny, I have so many folks who’ve actually either been on the podcast, CEOs, and executives, who’ve talked about this book with me or the audiobook. There’s so much to respond to and to get into with you there. But prior to you being a “CEO whisperer”, you were at one point an executive yourself, but has spent most of your career as a venture capitalist. So you founded Flatiron Partners, which for anyone who’s in the tech industry obviously knows Flatiron. And then also you are a partner at JPMorgan’s private equity branch. They’re PE part of JPMorgan Chase. But I’m honored to have you here, Jerry. And to kick things off with this question that I’ve been asking leaders. JERRY: Before that question, can I just say thank you for having me on? CLAIRE: You bet. JERRY: It’s really an honor and I appreciate the work that you’re doing in the world. It’s important. CLAIRE: Thank you. That means a lot to me. Thank you. All right, drum roll to the question. So you don’t know what the question is, but this is a question that I’ve been asking for the past two and a half years to leaders who I respect. And it’s what’s one thing, or it could be a few things, that you wish you would’ve learned earlier as a leader. JERRY: It’s a beautiful question and it’s one that I have an answer to right away. And that is that you’re not alone. One of the hardest things about being a leader really stems from the sense of isolation and the fact that — I’m going to badly quote Shakespeare, okay? CLAIRE: I won’t know the difference. [Chuckles] JERRY: In one of the histories, Henry V, Prince Hal, who in Henry IV is kind of a ne’er-do-well character who’s just like totally irresponsible. In Henry V, his father dies suddenly and he’s thrust into a leadership position. He’s King and he’s immediately challenged by the Prince, the dauphin of France. And France moves troops into Calais, which is on the other side of the channel. And Henry has to raise an army and go defend English territory. And the night before the battle of Agincourt where it’s very clear that the English soldiers are outnumbered, 10,000 to one, they’re always outnumbered. Henry is walking through the camp and in a soliloquy, he says among other things, “Upon the King! Let us our lives, our debts, our souls lay upon the King! Oh, hard condition, we must bear all.” I think one of the hardest things is the sense that it’s all on our shoulders. And when we believe that we are alone, we wake u