Getting in over your head

I was out last night with some of the little league coach dads, and we got to talking about whether it's better for our kids to be bumped up a level (but be at the lower end of skills/experience) or stay back a level and have a chance to really excel.  The consensus was that you want the kids to stretch, and learn from people who are better than them, but not to take it so far that they feel demoralized and tiny. It got me thinking back to the time in first grade where I got bumped up to the higher math group, but then couldn't hack it and got bumped back down.  I can still see the workbook where I doodled all over the pages because it was easier to do that than to engage in the work. And then I thought about the time I took intro to computer science my freshman year at Stanford (never having done any coding before) and feeling so left behind by the rockstar kids in the class, who seemed as though they'd been coding since they were six. I dropped the class.  That one really stuck with me -- I really enjoyed coding, but didn't stick with it (at that moment in time -- I came back to it later). But for years, I regretted not giving it a better shot. Then, 5-1/2 years ago, I was out to lunch with Brad Burnham from USV, intending to pitch him on funding one of our spin-out projects at OpenPlans, and he asked if I wanted to come and do some work with them.  The area of work that Brad wanted to focus on at that time (tech policy) was something I had touched on during my time at OpenPlans, but I was by no means an expert.  And stepping up into a big name VC firm was exciting but intimidating. I remember going home and weighing a bunch of options -- at that time, things were changing at OpenPlans, and there was one opportunity there, another opportunity at another tech company, and then a very unformed (and kind of terrifying) opportunity with USV.  As I thought about all of that, I remember thinking that going in the USV direction was definitely the most interesting, but it would mean getting in way over my head. I obviously decided to go that route, and it has been a steep and amazing learning curve ever since (starting with the policy work, then getting into everything we do at USV).  And I think I have learned a whole lot from people who have been doing this for decades.  I'm glad I made that decision -- and more importantly that I stuck with it, even though there have been plenty of times when I doubted whether I could do it. I think this is particularly relevant in the startup world, where things are changing constantly, and there's plenty of opportunity to step up into bigger roles as things change.  My colleague Bethany wrote about this last week -- how a startup is almost like a completely different organism every six months, with different holes to fill and different ways to contribute.  It can be scary.  I remember back at OpenPlans, when I went from managing a small product basically by myself, to inheriting a 20-person engineering team, and then 2 years later running a diverse division of the company.  The first time I had to decide someone's salary I was like, oh shit, and the first time we did a restructuring, I was like really oh shit. Going through all of this, the earlier failures that continue to haunt me (and believe me, there are others) have continued to serve a pretty good purpose: reminding me, when things get hard or intimidating, or when doubt creeps in, that I want to stand up though it and learn from the situation, rather than shrink from it. I hope we can teach our boys (and girls) to do the same.