This post is a little more personal and not at all technical. I realized I’ve been wanting to write about this for awhile.

On the latest episode of Hanselminutes two of my favorite internet friends had a discussion on age as they are nearing their 40th and 45th birthdays. I happened to come up a couple times as a reference point for The Young’uns.

Age has always been a sensitive issue for me. When I was 5 my mom homeschooled me and when she couldn’t do it anymore and it was time to go to public school I was effectively done with first grade so she bumped me ahead to second grade. The rest of my primary and secondary school years I trailed all my classmates in age by a year. I got my license my junior year, graduated at 17, etc. I played sports on teams consisting of all older players. I was always very determined to prove that my age didn’t matter.

When I started running companies when I was 15 my age was an advantage. It got me attention and customers. When I started working real jobs at 19 it was also an advantage because people couldn’t believe how mature and experienced I was “for his age.” At about 25 when all my peers had experience too (with degrees to boot) it wasn’t as advantageous.

Now I’m 31. In the SF tech scene I frequently feel old. My experience frequently gets deferred to (which often makes me slightly uncomfortable). Some of the younger engineers I’ve worked with lately have made me feel really old. They’re insanely smart but make me realize how much experience I actually have now (going on 16 years of doing computer stuff for money). 30 under 30 lists drive me crazy not because that’s my goal in life, but just because it’s impossible nonetheless. My wife consoles me by saying there’s plenty of time for 81 under 81.

Back to the Hanselminutes episode. Rob talks about a recent dinner we had together where he was giving me some advice (that I appreciated) and my reaction. I (not surprisingly) reacted by giving him a look that said I have it all under control. Almost certainly I was overcompensating for my age insecurities. I rarely feel like I do have everything under control and I crave insight from people more experienced than me.

At the same time, I do know some things now. More importantly I know what I don’t know. All of that experience has lead me to a position where I can be a founder of a startup. I’m not doing this because I’m young and impetuous and want to ride the wave of the current ‘bubble.’ I’m doing this because I know what it will take for me to be happy in my work and I’m not going to spend any more time not pursuing it. I’ve known that for a long time, but I’m at a point where my age is an asset in making this happen. So I’m going to.