Do You Know What You are Doing??

I got this question from a friend this week as I launched what could be a fairly major initiative on my “healthy eating” blog. Done correctly, this initiative will require recipe creation, budget analysis, financial support, PR/media outreach, blogger engagement, the launch of an email tool, and I’m sure plenty of other things I haven’t thought of yet.

Thinking for a second, I realized … no, I don’t know exactly what I’m doing. Which is part of why I’m doing it, and most of what makes it fun.

What followed was a great exploration around what degree of “knowing what you’re doing” makes for the best experience. It’s probably different for every person and every situation, but I saw a few principles:

1. The biggest and best adventures have been those where I started at 0%, and even with years of experience, never got above 20% or so: Becoming a parent. Falling in love. Starting a business. Being born :-).

2. In my consulting work, I seem to like to live at about 60% knowing what I’m doing (clients, please keep reading … :-)). This is where experience lets me do a solid job of framing the problem and the possible solution(s), but success requires reaching past the known, well into the unknown and untested – preferably by anyone. In venture roles, I tend to start far lower. I’d guess that experts like to drive their number closer to 90%, and inventors/entrepreneurs like to keep pushing it lower. Seems good to understand your preferred set point, and make career/life decisions accordingly.

3. The more I do things I don’t know how to do, the better I am at other new things the next time around. This is true even if I fail. Which means that in this way, failure isn’t exactly even failure, just practice.

I’m curious … what is your “know what you’re doing” sweet spot? What career decisions have you made to get/keep you in that zone?