As soon as Disney’s acquisition of Playdom closed, e-mails from recruiters started appearing regularly in my inbox. Most of them I essentially ignored: I’d been having a great time at Playdom, and while I didn’t expect to stay there for the six years that I’d stayed in my previous job, I certainly wasn’t planning to leave after just over a year. So I sent polite notes back to the recruiters saying that I wasn’t interested, and promptly forgot about them.

Eventually, though, one of those e-mails snuck through my defenses. It was from a startup that I had vague warm feelings about, enough so that I clicked through to their job ads; and, when I did so, I found that they used both Ruby on Rails and Scala. These are two technologies that I’m quite interested in, and that I wasn’t likely to get to play around with at Playdom; also, at that point I was in a bit of a rut at my current role at Playdom. So I responded to that e-mail in a more positive fashion.

That was the first chink in my armor; a little while after that, I got an e-mail from an industry recruiter whom I’d noticed appearing on my twitter followers list a week or two before. So, out of curiosity (or perhaps vanity), I responded to her as well.

This was the middle of December, so it was close enough to Christmas break that not much happened with those conversations for the rest of the year. But the conversations had planted a seed in my brain, enough to shift my mental story so that, when relatives asked me over Christmas how work was going, my answer was “fine, but I’ve been a little bored recently”.

Changing Stories

In retrospect, that was the key turning point. Before, the dominant stories playing in my head were all strongly in favor of my being at Playdom: the story about being in the games industry, the story about how Playdom was on the right side of an Innovator’s Dilemma market shift, the story of being part of a startup destined for great things, the story of learning new technologies. The first two stories were holding up fine; but Playdom wasn’t a startup anymore (and I was a late enough hire that I didn’t have much of a financial incentive to stick around waiting for options to vest), and there weren’t any technologies on the horizon at Playdom that I was actively excited about, so the third and fourth stories were losing their power. And we hadn’t had meetings within Playdom for a while that were reinforcing those stories or generating new stories to replace them. (Playdom had an all-hands meeting in early February that excited me an a couple of ways; if that had happened in December, maybe I never would have responded to that earlier e-mail.)

This meant that my brain had a narrative gap that it wanted to fill. And, right at that moment, the best new stories were coming from seeds planted by recruiters: maybe I wanted to be at a startup again, maybe I wanted to explore Ruby or functional programming. The very act of talking to recruiters and companies gave this a boost: such conversations inevitably turn fairly soon to the question of what you’re interested in, so unless you want to sabotage your chances immediately, you’ll come up with an answer expressing a story leading away from your current company and towards whomever you’re talking to. Yes, you’re doing that because of your audience; still, telling them those stories has a cumulative effect, and if you spin enough such stories, they’ll combine to lead you in a different direction.

Crafting a New Story

But that travel is more haphazard than I’d like. And potentially dangerous: if other people are driving the conversations and leading the stories, they’re not particularly likely to go in directions that will turn out well for me. So that suggested two courses of action:

  1. I should think hard about what I wanted.
  2. I should talk to as many people as I could manage, to maximize options and prevent any single external story from having undue influence.

The outcome of the first course of action was:

  • I wanted to explore different technologies, Ruby and functional programming languages in particular.
  • I wanted to be some place that was into the technical side of agile, that focused more on craftsmanship.
  • I wanted to be at a startup again, and a smaller one: I’d tried 50-person and 100+-person startups, I’d tried large companies, and it seemed time to head down to the 25-person range.

None of which I was likely to get at Playdom. Now, I like playing and thinking about games, which meant that I liked being in the games industry; but I like thinking about programming, too, and about everything entailed in the art of creating software. And when it comes down to which of those two I’d most be able to make a rewarding career out of, I don’t think there’s much comparison: I’ll do better (both personally and financially) if I follow my nose as a programmer. So it wasn’t crazy to think that I’d gotten most of what I was going to get technically out of Playdom, and move on.

And the outcome of the second question was that I should cast my net more broadly: in particular, I talked to a couple of recruiters that had helped me land with Playdom originally. One of whom was at a different firm, so now I was talking to three recruiting firms plus a handful of companies that I’d met through other means, mostly LinkedIn e-mails that they’d sent.

Going for a Ride

Let me tell you: those recruiters did not mess around. They all did a very good job, and I’d happily work with all of them again: they’d come up with a first pass of ten or so companies that seemed to them to be plausible fits, I’d look at them and agree that all of them were plausible but pick out a few that particularly caught my eye for some reason, and they’d both set up conversations with those few and use that information to come up with further excellent suggestions.

The upshot of this was that I was spending a lot of time on the phone talking to various companies, and some amount of time (mercifully mostly on evenings or holidays) interviewing in person. (It was quite lucky that it was good weather, because I spent a lot of lunch breaks sitting in a nearby park and talking.) And it was nice to feel wanted!

But also a little disconcerting. I’d like to pretend that I’m so super-awesome that anybody would love to hire me; the truth is, though, that while I’m fairly sure I do have several good attributes, there’s also quite a bit of luck involved. I know several other people whom I have a lot of respect for who have had more protracted job searches recently; I’m not about to chalk that up to some sort of essential difference, it means instead that right now I’m in a situation where people are happy to work with me to spin stories where I sound good. So I need to understand what’s going on there, and see how to best take advantage of it and set myself up in the future.

I wasn’t consciously thinking about this during the job search, but I turned 40 last Tuesday. I’m in an industry that, to some extent, overvalues youth; so far I haven’t had any problems with that, but it’s an example of how future job searches could be a lot more prolonged and a lot less fun than this one was. Which helped confirm my feeling that now was the right time to leave Playdom: from a strictly mercenary point of view, it’s almost certainly going to be the case that I have a significantly higher expected value from playing up the story of “being part of a company that has sold for a good amount recently in a high-profile industry” than from the Disney stock options that I’d be giving up by changing jobs.


The upshot of this was that I decided that I needed to change the story that I was telling myself and others still more, and to do so by increasing its ambition. Following the nose of technologies that I’m interested in but not yet fully fluent in remained important (both for personal fulfillment reasons and for setting myself up for further growth), but I didn’t want to go too far in that direction at the expense of underplaying everything that I’ve learned over the last decade.

Also, I ended up prioritizing functional programming languages over Ruby: Ruby’s been around enough that I’m definitely playing catchup there compared to a lot of other programmers, whereas I’m hearing a surprising amount of buzz about Scala while not yet getting the feel that there’s a huge amount of existing expertise in the language. (And I’m quite confident that my brain will do well at turning me into a very good Scala programmer: it’s good at that sort of thing.) I’m pretty optimistic that going in that direction will open up a lot of interesting doors a few years from now, positioning me well on the adoption curve.

In terms of company size, I should go still smaller: coming into a 25-person company would be interesting, but even then you’ve missed a lot of the early decisions. I didn’t quite want to be a co-founder or first hire, but being in the 10-15 person range seemed like it would be a plausible fit.

And then there’s The Innovator’s Dilemma. You can never predict what will turn out to be successful, but I figured there’s no sense not swinging for the fences. Which meant looking for companies that could tell a story involving disruption on a significant scale, and companies whose founders have the chops to pull it off.

This all adds up to a great story going forward: I’ll have worked at multiple successful startups, I’ll have had increasingly important roles within those startups, I’ll have a lot of experience in dealing with very large quantities of data, with cloud technologies, with new programming paradigms (or with half-century old programming paradigms that are making a deserved resurgence!), I’ll have the agile chops to look beyond my day-to-day programming to help the effectiveness of the organization as a whole. That is a story that I can get behind, and it will convert my getting older from a potential liability into a tale of valuable experience.


At least that’s how I’d like things to go; then again, I certainly wouldn’t have predicted two years ago anything that has happened since then, so I don’t want to get too tied up in this particular story! I’m very glad to have spent time thinking about it, but in the mean time I need to dive in, start programming, work as hard as I can to help make my next company successful, and see where the future leads.

Which means I needed to pick the next step in my future! I was very fortunate to have the opportunity to talk to some very interesting companies indeed; I ended up joining Sumo Logic, and I’m super-excited about them. They have a great disruption story, their founders can pull it off if anybody can, I interviewed with all nine of the current employees and am very much looking forward to having all of them as colleagues. What they’re doing and the way they’re working fits well enough with my prior experience that I should be able to hit the ground running and contribute well, but there’s enough new that I’ll come out of it knowing quite a bit more than I know going in. It looks like a great fit from my point of view, and they seem to agree; I’m looking forward to spending the next several years with them, it’ll be quite a ride.

And I will pay more attention to the stories that are going through my head in the future: they are powerful, they control me more than I realize.

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