As most of you can likely intimate from my infrequent blogs and tweets, I'm in the process of feeling out the next iteration of my career ambitions. After four years of idiosyncratically living part-time in the woods and bootstrapping an internet consultancy, I'm relocating to San Francisco proper, and my partners and I are beginning to intentionally exploring the next level.

One of the best things about this process so far has been actively seeking out advice from older, wiser, and more experienced people in our field. One of my constant observations — verging at times on complaint — over the past few years is that I don't feel there's a really good roadmap or template for what I do with my life. I'm coming to understand that's not really the case. Certainly there are particular novelties about my experience, but it turns out there are plenty of smart people out there who have done things not unlike what I'm doing now: working in a disruptive technology space with a lot of other folks, building a business and figuring out how to make the most of it all.

In hindsight, this is unsurprising. Anytime you think you're a really unique snowflake, chances are you're at least partly flattering yourself. Even though there aren't many people from my immediate peer group that are doing comparable things, there are plenty of people on the scene here in good old Silicon Valley who are.

And, in getting to know some of these people, it's reall nice to get some external validation. Left to my own devices, I will always expect more of myself, always in some way unsatisfied with my achievements. It's easy to sit here in my office and see all the things I haven't done, all the opportunities we missed, all the work that's still left to do.

But the outside voice reminds me, in speaking of what we've built, "you know, most people can't do that."

I really dislike elitism and am constantly en guarde vs hubris, as I wrote of one of my all-time better posts, Notes from the 99th Percentile:

I find myself stuck between the egalitarian and elite. On the one hand I believe that “everyone can/should be able to live like me, do the things I do, understand the things I understand.” But people are different. Regardless of what might exist in the realm of possibility, the way I live and the things I do are not accessible to everyone, and I want to be with my own. There’s an in-built drive to seek this, and there’s an undeniable allure to the notion that you’re a part of something special, discriminating, un-common.

People start using terms like “level” and “league” when they talk about this sort of stuff. “Big fish, small pond” and all that jazz. I’m generally uncomfortable with that talk. There are enormous problems with elitism and hubris. Just from a practical standpoint, exclusive cliques don’t work out well, whether they’re out on the playground or running the country. Once you start reflexively screening out people or ideas based on the perception that they’re somehow “beneath” you, you’ve started concocting your own downfall.

Still, it rings true. Most people can't do what I've been doing. It remains to be seen how much that's worth, but it's a Good Thing(tm) to remember. Keeps the old morale up.

Anyhoo, a little self-pat-on-back post here, but it's what was turning over in my head on the BART this morning. Stay tuned to see how it all shakes out!