I've Spent My Whole Career Winging It

I've spent my whole career winging it. My first executive title just made it official.

Ray Kaupp paid me $500 to design a flyer for his team at Apple. I had no idea that was a lot for a flyer. I just knew it covered rent. Six months later he asked me to join the startup he was spinning out of Apple. Six months after that, the woman I reported to got fired. Nobody else was in line for her job, so at 23, with zero executive experience, I got handed it.

I had no idea what I was doing. I just showed up every day and figured it out as I went, one meeting at a time, hoping nobody noticed how much I was making up on the spot.

Years later, at a YPO forum, someone offered up a phrase that stuck with me: life is choice. It made me look back at my own path and put words to something I'd never said out loud before: everything I had done, I hadn't done before.

It kept happening after that too. Startups, then Dell, moving through product, sales, biz dev, marketing, operations... I don't think I ever once walked into a role feeling ready for it. I just kept saying yes before I could talk myself out of it.

I still don't know if that's confidence or just stubbornness. Probably some of both.

What's the role you're still waiting to feel ready for, instead of just walking into?