I Wanted a Map. Guy Kawasaki Handed Me a Mirror.

I wanted a map. Guy Kawasaki handed me a mirror.

I was 25, my daughter Haley just born, sitting across from him at breakfast, trying to get him to help me chart my career path. I don't remember what I ordered. Probably eggs. In 1996, everything was eggs.

I don't remember exactly what I asked him. Probably some version of: how do I know if I'm on the right track? What he said back is the part I've carried for thirty years: "You could be sweeping the floor at Toys R Us right now and I wouldn't be worried about you." Not because I had a plan. I didn't. Because the fact that I was sitting there, 25 years old, trying to figure out how to be great at what I did, mattered more to him than whatever job title I happened to be holding.

I didn't fully get it at the time. I wanted an answer, not a reframe of the question.

Years later, at Dell, we'd go around the team sharing how we'd each gotten there. Mine always sounded like it hadn't fully ruled out the Toys R Us floor. Minted MBAs who'd come up through Big 5 consulting or a Fortune 100 logo before landing in the room. Then me: failed startup guy, no framework, no case study on the wall. I couldn't have told you what a SWOT analysis was if you'd handed me the template with the boxes already labeled.

I did fine anyway. Even got Employee of the Year one year (pat on my own back, I know). I still don't fully know what I did to earn it. I've decided not to ask, in case they want it back.

I still don't think I've ever had the plan before the choice. Usually I make the choice and hope the plan catches up.

What are you waiting to feel sure about before you'll let yourself start?