I’ve started asking people for prompts for these vomits. The first one I got that I liked was “write about playfulness as a discipline/practice”.

“The best ideas always come as jokes. Make your thinking as funny as possible. ” – David Ogilvy

“Forget being a comedian, just act like a reporter. What’s the question that hasn’t been asked? How come white kids don’t get shot? Have you ever watched television and seen some white kid got shot by accident? [laughter] You laughed right away. I just asked a question that no one had ever asked.” – Chris Rock

I have always, always believed in the importance of playfulness, silliness, humor. I think it’s very important. Arguably the most important thing! I take it as seriously as I can without being solemn. (John Cleese explains the distinction very well; solemnity is really a sort of ego-preservation).

One of the ways I compress and condense my worldview is the idea that “One should imagine Sisyphus LOL-ing“. Constant happiness is too much to expect from life, and not necessarily a good thing. It’s better to navigate by excitement and curiosity.

I’m working on a book of essays called “Naughty Boy” – it’s partially because that’s what I was called a lot as a kid, by my parents, by my teachers. It was a label that stuck, that weighed on my mind. Part of the reason I’m doing it is to reclaim the term, to take ownership of it, to acknowledge the validity of the claim, and also to really consider it thoroughly. I think being naughty can be a good thing. What IS naughtiness? It’s deviance from social expectations. You’re naughty for doing something you weren’t supposed to do, that you were told that you shouldn’t do. You’re naughty for thinking improper thoughts, for participating in improper acts.

Well, I want to make the case that “properness” is extremely overrated, and that pretty much all good and interesting things come from improper people doing improper things. When I think of “proper”, I think of upper-class aristocrats and royals and their manners – and where does that come from? Where does the king get his power? If you trace it back, it begins with conquest. And conquest is a rather naughty thing, don’t you think?

But I digress. What is play? Play to me is a state where you’re somewhat indifferent to the outcome of what you’re doing. It’s about enjoying the process of a thing, tapping and fiddling and messing around to see what happens. You haven’t decided what you want yet, not exactly. You just want to have fun. You just want to dick around. You take things apart, put them together, turn them upside down, inside out, string them together… all just to see what happens. To feel what happens.

How do you… practice playfulness as a discipline? There’s a bit of a balancing act here – I’m not a fan of overly scheduled playdates. Play should be wild and random, it should be free-range, exploratory.

I wrote a twitter thread once about games and meta-games. One way of thinking about playfulness is that it’s about being detached to the specific outcome of a particular game, and having more fun instead with the meta-games of what games you’re playing. Children are pretty good at switching around – I find myself thinking of Maurice Sendak’s quote about how children move back and forth seamlessly between fantasy and reality in a way that adults tend to forget how to do.

I do think it’s possible to get serious about being a good player – loosely, I imagine it’s like getting good at improvising as a musician. Getting good at improvising actually takes a lot of practice – and for some people this seems like a paradox that makes the whole thing sound silly and stupid. But it’s not. Being interesting when you’re being spontaneous requires having a range of options to choose from. Without having deliberately practiced and experimented, most people end up defaulting to a very small handful of fallback choices. Being flexible, avoiding functional fixedness, being able to reimagine things – all of this requires practice and experimentation. And it’s definitely one of my favorite things to do. I highly recommend it.

I tweeted somewhere else – a crazy thing is that a seemingly meaningless existence can become more meaningful just by thinking about it. That’s play! “Suppose…”, “imagine if…” “what if we…” “let’s try…”.

I’ve alluded to it but I think it’s worth being clear about the following distinction: there’s a sort of “shallow play” and “deep play”. Shallow play is superficial, cosmetic, dicking around. There’s a place for it. It can be fun. It’s the equivalent of “noodling around” on your guitar. I’ve definitely “noodled around” for a lot of vomits. It’s not a bad thing to do in of itself – it can have a sort of calming effect, and sometimes you do accidentally surprise yourself. The holy grail, though, is “deep play”. Deep play is when you play with real stakes, for keeps – you go hard. You really reconsider things. You really experiment. You do things that could have potentially “permanent” consequences.

Doing effectively and functionally as an adult requires also being able to be responsible. Sendak pointed out that children can move back and forth between reality and fantasy easily – and a part of a reason why that is the case is that kids don’t have bills to pay, and they don’t have a lot of responsibilities. The adult creative, the adult player is a lot more interesting in a way, because they have to be able to put things out of their mind but also be able to bring them back in. It can be intensely playful to take a bunch of drugs and make a huge mess… but then you’ll also have to clean it up afterwards.

Different people will bring different attitudes and assumptions to the table when you talk about playfulness. I think most people have a playfulness deficit. I hung out with musicians and theatre types when I was a teenager, and I think those folks can be a little “too playful” sometimes – where the problem isn’t actually that they’re playful, but that they use their playfulness sometimes as a sort of avoidance mechanism – to avoid responsibilities, to avoid difficult conversations and so on. I think at the heart of it all, playfulness should be something that guides you to engage more intensely and truly with the world.

I was actually “engage more intensely and truly with reality”, but sometimes some “escaping reality” is a good thing – because you’re only really escaping “mainstream reality”, which is simply the majority sect of magical thinking”. Still, it’s complex and layered. Sometimes taking a break from things can give you perspective that is useful to you when you return. And still, ultimately, I think there’s something unpleasant about an obsessively utilitarian model of the world. Sometimes escaping into an alternate reality – into play – is worth doing because it’s fun. And life is too short to be solemn.