Professional Unfulfillment

I’m just trying to sort through some feelings. I don’t mean for this to come off as a humblebrag or anything else. I’m just trying to work through things, so I’ll be talking about how I feel about things. If you’re sensitive to that sort of thing, skip this post. I’m probably going to sound like a jackass.

Over the last fifteen years, I think it’d be very difficult for me to make a serious argument that things haven’t gone well. I assumed it would take years to get a game design position, much less a position where I’d do anything other than execute on whatever someone else told me. Instead, I made quick career progress, got to work on a wide variety of fun stuff with a decent hitrate for success, I founded a company (mostly) that did *extremely* well, we made a number of things all of which I’m quite proud of, and yet, I find myself feeling like basically my professional life isn’t even close to being a success. In many ways, it feels like a total failure.

I think the problem is that we achieved a certain level of monetary success that allows us to be comfortable, but not to have *control* over our lives – that is, we don’t have enough that we can essentially not work for the indefinite future & do crazy shit like travel the world. Well, I mean, we certainly could in the short term, but my worry is that unfortunately, both of our careers have “short fuses”, where if you’re out of the industry for a few years, getting back into it is not all that different than starting completely over. So I don’t feel like we can fully take a break and not suffer the consequences of that in the longer term.

And the frustrating thing about that is essentially the result we got was the *best* we could. We made what has been at times the #1 grossing app in the App Store, and over its lifespan, one of the most financially successful games on iOS, period. And you’d think that might be enough to retire on, but due to the circumstances of how it was started, and how it all ended, nope. And I’m realistic – we’ll certainly try to make something great again, but hitting that sort of financial jackpot is *always* a huge roll of the dice, even if you’ve done the best work you can. No one can predict with any degree of serious accuracy what will succeed. So we’ll give it our best shot, and see what happens.

But that’s not really what it is. Because I don’t really care about the money. I mean, I care, sure, but it’s not like I set out to make $. I set out to try and build an amazing team that could make amazing games. And I *did* succeed at that. Much, much better than I would have hoped. For a while, it was *exactly* what I wanted. And maybe that’s part of the problem. I know it’s possible. Or at least, I know it *was* possible. And as much as I want it to be possible again, I don’t know how it’ll work out. Sometimes, I just want to work with the same folks again, and try to recapture that magic. But time has passed. Everyone’s at a different phase in their lives now. I constantly worry that one day, when we can secure funding, or whenever it makes sense to hire someone, that we’ll hang our shingle out there… and no one will show up.

That *constantly* terrifies me, and I feel like the fact that it does is a fundamental indicator that things aren’t right.

All I want is to love what I’m working on, and work with people that I care deeply about, who are also passionate, and driven, and creative, and crazy. I want for us all to work in service of the same cause – to make something awesome that no one’s seen before, that people *love* to play. And for all that to happen so many things need to line up just right. Because what it comes down to is that at this point in my life, I don’t *want* to start over. I don’t *want* to start with a team of strangers, even though many of the strangers that we hired in the past are now close friends. I want us to start this thing with people we care about, because the *reason* we’re starting this thing is to make something better, not just for players, but for the team. Even before, the driving force was always to try and make a company that treated its employees extraordinarily. Not just with perk-related bullshit, but by actually caring about people, and building a real team. And right now, we’re not there.

I feel like for a while, even though he has *no idea who I am*, Stewart Butterfield & I lived in semi-parallel worlds. He was running Tiny Speck, which made Glitch, and we were building Fleck. Two games that some folks put in the same pool, and we had such similar arcs to the games, from smallness to a passionate userbase that never grew to ultimate failure. And Tiny Speck continues on into Slack, where they’ve now achieved the double-whammy – tremendous financial success *because* they’ve built something people absolutely love. I’m jealous. Honestly. I don’t mean that in a mean way, I don’t wish them ill. I’m just jealous.

I guess it took him from Flickr to Tiny Speck to Slack, and for me, I’m maybe in the middle phase – the entire arc of the previous company was the first act, and the third act is where it comes together. Maybe I just need to be patient, work out where the funding comes from, and just keep cranking away at things until we crack that nut. Maybe I’m just insecure, and I think the team I wanted to work with doesn’t want to work with me anymore. I don’t know.

So much is going so well, and that one thing eats at me constantly, because if it’s true, it means everything I thought I’d succeeded in over the last six years wasn’t actually a success. And even dealing with that potential is a frustrating, strange, and bitter pill to swallow.