I love thinking about career paths and how people get from A to B. It's my favorite thing to teach as well--and I'll be giving a class at Startup Institute this Tuesday night about it. They're a career accelerator, which is a pretty neat concept--doing what YC and Techstars do for startups, but for your career.
Anyway, 2015 marks a couple of big career anniversaries for me.
Twenty years ago, I got my first job. I started working in 1995 at the age of 15 in the mailroom at Waterhouse Securities (which became TD Waterhouse) at 100 Wall Street.
Ten years ago, in 2005, I started working for Union Square Ventures as their first analyst.
I've always thought about plotting where I was in my career against where I thought I should or could have been at my age. Sure, there are outliers who start companies at age 19, but that didn't seem like a fair comparison. I was aiming more for the top quartile--who was at top of my field that didn't seem to get there via a fluke--whose career might actually be replicable.
When I was working for USV, I learned of Chamath Palihapitiya's career. At 28, he became the head of AOL's Instant Messenger (AIM), which was a big deal at the time. When I was 26, I called him up and asked him about his background to try and figure out how, in two years, I could be running AIM (or rather, the equivilent impactful job).
What I learned was that Chamath's career path was the product of three things: First, being really good at what you do, obviously. Second, was taking risks. He didn't aim to become the head of AIM. He joined a startup that wound up getting bought by AOL. He later took a similar risk by joining Facebook when it was just a year old or so.
I reiterated the notion of risk taking when giving career advice the other day and how when I joined Union Square Ventures, it wasn't the USV it was now. Fred and Brad didn't have the reputations they do now. Barely anyone had ever heard of them. Getting a job at USV was much easier then than today--but that job isn't the same as when I had it. When I took the job, the New York startup ecosystem was nascent. You could literally get to know everyone in the local tech community at the time. Now, the community is orders of magnitude larger and the number of investors who invest here has grown significantly. In other words, it's all baked now. You can't rise up as fast taking a job at a VC firm in NYC the same way you could 10 years ago--and you can't get that USV job as easily as you could. Plus, even if you could work for someone like a Fred Wilson now, would it make as much sense to do so, or would it be a better option to figure out who the next Fred Wilson is? Who's the VC that everyone *isn't* trying to network with.
The third important ingredient for Chamath was making an ask. He didn't apply for that AIM job. He asked for it because it was the most interesting thing to do at AOL at the time. If he didn't get it, he was going to leave.
That's one of the reasons I like to mark my career over time--because I want to understand how what I'm doing now compares to what I *could* be doing at this stage. Back to Fred--he became a partner at a VC firm after apprenticing there 7 years. He was 33. He was 36 when he started his own fund, Flatiron Partners. I started my own fund at 32, so just to mark time against the career of an industry leader and mentor, that seemed pretty good.
Things didn't always match up well.
When I turned 30, I found myself at perhaps the lowest career point I've ever had. I was down to the last few weeks of capital at my startup, after almost two years of work. It wasn't clear where I'd work once it went under, and I certainly didn't feel like I had much in the way of any skills to offer.
Somewhere I must have made a wrong turn.
When I joined USV I was 25, working for an quickly up and coming and visible VC firm.
Now, at 30, I was a failed startup CEO who was going to be out of work soon. Oh, and in between those two jobs I was a product manager for a year for a product that didn't really go anywhere.
On the experience versus accomplishment chart, I felt like I was in quite a trough, having peaked quite a while ago.
Little did I know that I was about to start the biggest continuous upswing of my career. I suppose I could have seen that the pieces were there--but that's the problem with these kinds of charts. They only measure accomplishments. They don't measure skills, network, and the changing nature of the ecosystem around you.
At 30, I had built one of the best professional networks in New York City--a market that was on the verge of passing Boston as the second largest startup ecosystem in the country. That's why I got hired by First Round--to help them build a presence in NYC. I had something VC firms were interested in.
Sounds pretty good when I put it that way--but it didn't feel like that at the time.
The point is--it's good to measure yourself, where you've been, and where you are now--but keep in mind that the measurements are probably lacking in their ability to predict the future. They're too focused on jobs and titles, versus the actual predictors of creating opportunities for yourself: what you have to offer and who knows about it.