Every Entrepreneur Has Imposter Syndrome. Here's Why We Need to Talk About It. Everyone feels the same way, but no one will admit it. Let's break the stalemate.

Early this fall, I was having lunch with the CEO of a multibillion-­dollar company called IAC. You may not know its name, but you definitely know its brands: Match.com, Tinder, CollegeHumor, Vimeo, The Daily Beast and more. It's a digital behemoth, and Joey Levin, its CEO, is as sharp as they come.

When I first started covering business, lunches like these intimidated me. I was keenly aware of how much more knowledgeable these executives were than I was, and I felt the need to hide my deficiencies. But these days, I understand that the opposite is actually true: When you're confident in your foundation, you're able to admit shortcomings. My conversations with CEOs now tend to be about what we're learning, and what we still want to figure out. So as Levin and I talked about management, I told him about my own leadership hang-ups. "I was a writer or an editor for most of my career," I told him, "so when I became a manager, I felt like I had to make it up as I went."

"Everyone does," he replied.