On learning, success and the year that was…

This whole year has been a lot about learning who I am. I think for a while, I had a fairly good sense of who that was. But over the past few years, I think I became so consumed with this notion of “success” that gets fueled from reading too many books about ‘Crushing It’ and less about what the internal combustion of your motivation sends you. I’ve read comments from people a lot more experienced than me, who’ll say “you need to flexibility to molt as you grow,” and I feel like that’s been an instructive piece of what I’ve done this year.

It can be so easy to delude yourself into believing you what you’re working towards, only to get there and stand around looking at it and thinking “uh, what?” When it comes to the whole notion of success, I feel like it can be such a cliche. Especially in the rapid fire world of social media. I’ve read and heard tons of stories of people who look at their high school, college or work peers and their lives, only to feel as if they’re somehow living their own lives the wrong way by comparison.

The more I’ve talked to people, the more I’ve realized how funny it is that we can delude ourselves into these beliefs. I realize that these caricatures we put out are only as reliable as what we’re seeing and that taking stock beyond the immediacy of what you’re reading is folly.

More than any year in recent memory, I’ve refocused my lens on what I’d like to be doing with my time, rather than being so focused about this go-for-broke attitude towards giving up every shred of your humanity for a slice of an elusive pie that might seem just a step out of reach, only to discover that you weren’t really close to it at all.

Taking a step back from the rat race, has helped remind me of the things that I really like and doing some of the things I genuinely enjoy doing. I think it’s probably also instructive that this is the first year since 2006 that I haven’t spent the bulk of it doing a major redesign someplace. I hadn’t thought about that before, I’m sure it’s played a part in the rewiring of my habits, as has moving and other spikes in the punchbowl of life.

While my music listening has always been robust, I’ve taken to listening to full albums in their entirety rather than just keeping my MP3 player on random. After swearing off hot drinks for years, after growing up a coffee fiend too early in life, I’ve taken to tea like I’m a character in a sepia movie set in Burma. I’m absolutely certain that thanks to Netflix, I’ve seen more movies this year than I have in one year ever. I have still quite a bit of catching up to do and I doubt I’ll ever be a movie nerd like I am a music snob, but…it’d be nice to know what people are talking about when they name their favorite art-house indie flick of the moment. Sometimes, anyway.

I think most of all, I wanted to sit here and rant a bit about the culture that I’ve seemed to observe that glorified the “art of the start.” This winner-take-all belief that dictates that if you’re starting up something and fail to make a major league exit, close on a big round of VC funding or take your company to an IPO that you 1) didn’t work hard enough and 2) you’re some kind of failure.

The biggest takeaway from the past five years of my entrepreneurial pursuits are the sheer number of things that are completely out of your hands before you even get started trying something. Preparation is a far greater indicator of long-term success, than hard work, passion or motivation. Together, they make a pretty powerful combination, but I’ve learned that the sacrifice involved in giving up everything that makes you interesting in the off-chance you hit a jackpot and can say you’ve made it; is simply a price that’s too steep for me.

Nothing I do, whether it’s offering my two cents to an institution that needs help or trying to create something useful has anything to do with the grandeur of success. It’s about the opportunity to help as many people as possible, in the shortest amount of time. Some of my most successful projects are been the sort that I don’t necessarily derive a lot of internal joy from. They’ve been the sorts of things I pour a ton of work and energy into, then eventually retreat to the background while the people inside of them do their own bidding and I eventually retreat to the background of the project.

With all of the end of decade lists being released, I feel like this is the start of my own next decade project. My mom teased me about turning 30 and making drastic change, saying “You think you’re 30 and it’s the end of the world and that you’re old and running out of time.” I denied that, but…in retrospect, that’s probably more accurate than I’d ever want to really believe it to be. I’ve broken down those thoughts, considered where I am and where I’d like to go next.

There are so many things that my precocious teenage self wanted to do when I left home nearly 12 years ago that I haven’t done yet or mastered how I’ve wanted to. Most of all though, I’ve come to realize that the only lens of success that matters is the one that bears my own fingerprints.