Life as an Arcade

Rick Webb
Rick Webb

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Note: I wrote a post a little while ago that was a sort of rambling, personal, essay in the form of an email to a friend. Probably slightly-too-personal, and not very self-helpy. Really not the sort of thing that you’re supposed to post to Medium if you’re a go-getting tech dude. No rah rah, no promotion, barely anything from my current career. Just. Musing. It was kind of fun, so I’m going to do more of them. This one started out as a journal post today.

My whole life, my basic MO has been to get to know a field — a topic, a career — just enough to grasp its basic workings, and then I get bored. I’ve been doing this my whole life. I’m as yet undecided on whether this is a good thing, a bad thing, or a neutral thing. In my brief time in each of these fields, I’ve sussed out the basics and had some modicum of success, and then moved on.

The best analogy I can think of is being in a video arcade. You walk up to one game, and you try it out. Sometimes you do great, sometimes you die instantly in a minefield or a hail of alien bombs. When that happens, you deposit another quarter, and try again. You keep doing that until you get the gist. To extend this metaphor, I basically play the game until I can get on the high score list. Not the top slot mind you, just anywhere in the top 10.

Now, this is just one Asteroids machine of many throughout the world. Each one has a top 10 list. There is no real correlation between the top 10 scores on your machine and all the other machines. Your machine may have been reset last night, and only like 100 people have played it since, and the #10 score is only like 40,000. Somewhere else in the world, there’s an asteroids machine that’s never been unplugged since the day it was placed in that arcade in (Wikipedia tells me) 1980.* That game might have a high score of 1 million. And, of course, both of these scores are just the highest score on that machine. A theoretical maximum also exists. A perfect game.

I am not a perfect game player. I am a high-score-on-that-machine-and-move-on player. Now, some of those machines might have (relatively speaking) high scores across all machines, and some may not. So, by the time I’ve gotten on the high sore list of that machine, my skills in that game may be, like, nationally ranked, or just best-on-the-block.

Then, of course, there’s natural talent. Some of these machines I could walk up to and start playing and be preternaturally good. I might be a natural. A prodigy. I might get on the top 10 immediately. Now, I admit, when I encounter such a field (remember, this is a metaphor here), I tend to stick around a *little* longer. Maybe a few weeks, months or years. But in the end, the “browsing the arcade” metaphor holds, and I will move on from that field.

So, then. I may have gotten really good because the machine in my arcade had some really high scores relatively speaking. I got really good at math in high school because my school had some amazing mathematicians, for example.

Or I may have gotten really good at something because of some innate natural talent that I milked a little further. I happen to be very, very good at Ping Pong. No idea why. But once I got really good and started beating everyone at the student union, I just gave up and moved on, rather than, you know, pursue an illustrious career in ping pong.

This, to me, is a really interesting little nugget: you can get good at things for different reasons. Both of these reasons, you’ll notice, have little to do with “passion.” That’s a topic for another occasion, I think. We can safely limit ourselves here to a passing acknowledgement that passion probably influences which arcade game you step up to next: we’re not necessarily trying every single game in the arcade in order.

This is something I am just really coming to terms with about myself. I’ve known it for a long time, but I’ve never really thought about the ramifications. It was always obvious to me that this was the right approach. I’ve never questioned it. It’s only occurring to me now, really, that other people do not take this approach. That, maybe, leaving a career or abandoning a field or hobby right when you get good at it is a wee bit self defeating. I am undecided on this topic.

A few tableaux:

Yesterday: I was on a call with a portfolio company at the fund I work at. Their product is awesome, and they are, in bro parlance, crushing it. It’s a product related to one of my old fields. A field in which I managed to obtain some notoriety (I guess that particular arcade game in the gaming parlor hadn’t been unplugged in a few years). They asked me for intros and whatnot, and I thought to myself how I barely even talk to people from that world anymore. And I was SO INTO IT. For several years. But, like, in getting these guys’ update it was super clear to me I barely even know what’s going on with that field anymore, and I have lost touch with many of my friends in that industry. That was not a super great feeling.

Also yesterday: we had some dudes come to our new house to help us with some Ethernet issues. They saw my studio. All my musical gear. This has happened a few times now. The electricians. The movers. A couple neighbor kids. They ask if I’m a musician. I am currently trying to be a writer and an investor but there’s just one little computer and some books in the corner of my office for these particular pursuits because, well, they don’t take up as much space as keyboards and guitars. I never know what to tell these people when they ask if “I am a musician.” I know they really mean am I some sort of professional, and I am not. I gave that whole thing up, inexplicably, even though our band was really good and people went to our shows and we had fans and everything. But when that band encountered a few problems, I just moved to another game in the arcade. I remember knowing very well at the time that the problems were surmountable, but I also kind of knew this was pretty much it. If I kept going with the music thing, the BEST thing that could happen is I’d be drinking in night clubs even MORE often, and on the road with no money even MORE often and, also, I felt like the secret nut had been cracked, so, really, what was the point? Everything beyond RIGHT THEN was going to be… just… tactics. So I moved on. And now, in my basement studio, I just sort of dodge their questions. I say (not fully honestly) that this is the first time in years I’ve had it all set up and I’m going to play around again, so… “we’ll see!” (always end on a note of optimism).

A few days ago: my friend Doug and I were on a good weekend vision quest in fields of mud. At some point in the weekend he asked if I would ever “take a job” again.† I didn’t waste much time before I said “no way.” What’s the point. I had jobs. I was good at them, I did well. But the same things happen each time.

This calls for a bit of a tangent:

There are two currents of my personality that intersect, but are not as related as they seem to be:

First, I’m terrible at keeping my head down. If you’re not a leader at a company, just a regular worker, it seems to me in 90% of corporate America your success is at least partially defined by your ability to keep your head down. Hunker down, ride out the absurdity, and don’t get too involved in the bumps and scrapes of the every day drama. And I am just not good at that. I sometimes envy people like that, and I’ve occasionally attempted to get better at it, but I’ve had to come to accept it’s just not in me. For better or worse.

Secondly, I’ve had a temper my whole life. It’s much better these days. There hasn’t been an “anger bagel” incident in years (long story). The Webb Advisory hasn’t had an emergency update in three years and counting. I’m trying, getting better, and keeping my mouth shut. But I’ve never been especially good at it. Lately I’ve learned to control my temper by doing what I think is hugely responsible and adult — just getting out of the room. So I walk out when things get tense. Apparently that is still a pretty dramatic, annoying thing, when people get upset and just walk out of the room. But for me it’s such a hallmark of maturity.

In any case, both of these elements make it hard to work a regular job in a non-leadership position, I was explaining to Doug. Because you want to do right, you want to participate, so you try and help and say something when you think something’s off track. I still believe it’s the right thing to do. But many, many people don’t want to hear it. So they tell you to shut up, which kicks in the temper, so you walk out. Two separate habits, but lethally intertwined.

ANYWAY, I was explaining all this to Doug, when it struck me: this is actually related to my arcade approach. Doug is a polymath too. Even ignoring the arcade thing, we read books on millions of topics, explore different things, get obsessed about all sorts of things. We don’t fit into the usual “engineer” or “product designer’ roles. We have opinions on all aspects. And there’s really only one place for polymaths in companies: leadership.

Now, some great leaders manage to harness polymaths in their organizations. I’ve had a few bosses like that, and I am forever in their debt (thank you, Derek).

And there are some polymaths that are able to compartmentalize: I know I am a decent designer, too, but they want me for my back-end coding chops, so I’ll just park the rest outside. I’ve not been able to do that in my life. Spoilt by too many years in leadership, when it was a trait that was important to build. Too much experience knowing that all fields, all bodies of knowledge, converge and are useful. The realization that I am blocking much out only to be a cog in a larger machine is, I suppose, too much for me. I guess, despite my best efforts, I’m too individualist? No, that’s not it. It’s because I’ve learned through the crucible that I’m not as helpful to the greater whole playing that of a limited-knowledge cog.

So, then, I suppose the arcade approach to life has its pros and cons. It turns you into a polymath, which I am not too cynical to say I believe to be an unqualified good thing. But it also leaves you with a trail of past lives. And… I guess I’m coming to terms with the fact that it has a downside.

Now, several of these “arcade games” lasted years. My time at Barbarian Group lasted a decade. It’s a fallacy to say that the arcade theory keeps you from learning how to handle obstacles or doesn’t build fortitude. I mean, we’ve all experienced the sensation of playing a new game and dying immediately, over and over. Then we look at the 12 year old kid playing it and kicking ass, and thinking “I HAVE to learn how to do this.” Then we play for hours, days, weeks until we’re pretty good at it. No, the arcade approach doesn’t mean giving up. It means developing a competency, even a mastery, no matter what it takes, but once you have it? Move on. Good or bad, I’m still not sure yet. Hell, I’m only now realizing there were other approaches to life. But at least I’ve come to terms with the fact that this is a part of me.

* Did you know that Asteroids earned $150 million in unit sales and $500 million in coin deposits? In 1980? That is $1.5 billion in today’s dollars.
† I have a job, btw. And I like it. He meant a full-time, operational thing at a product company. We both knew that.

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Rick Webb
Rick Webb

author, @agencythebook, @mannupbook. writing an ad economics book. reformed angel investor, record label owner, native alaskan. co-founded @barbariangroup.