(Cross-posted from my roam-blog)
Productivity Origin Story
Growing up, the one thing I wanted more than anything else was super powers. It wasn't until the middle of 6th grade that I finally gave up on trying to nurture my not quite nascent telekinetic abilities and turned to (slightly) more practical avenues. Taking a cue from all the Kid's Science and Physics books that surrounded me, I decided I was going to make cool things and be an inventor. To me, "inventing stuff" served the same psychological slot that super powers had. Maybe I'd never be Spider-Man, but I could be Batman!
The only problem with that plan was... I sucked at making things. My PVC pipe air cannons leaked. My potassium nitrate smoke grenades shot out more flames than smoke. My microwave magnetron Tesla Coil plugged in and did nothing. And I never came up with a remotely plausible idea for an invisibility cloak.
As I made my way through high school, two things began to change. I read Outliers by Malcolm Gladwell, and I started getting into magic. Outliers told me, among other things, that if I could just dedicate 10,000 hours of practice, I could be a world class expert - and as anyone who's ever read a YA novel knows, the hero is often the best in the world at a certain skill. Meanwhile, magic was giving me a visceral experience of the previously abstract truth that I Can Make Progress Via Practice. Every sleight of hand move was difficult at the beginning. Then I'd practice it. Then it would become easy.
This was the first time I began to be convinced that I could become better at something, as opposed to simply being good at something from the start. It was exhilarating! As high school turned into a gap year which turned into university, Outliers was joined by books like The Talent Code (expanding on the deliberate practice formula) and DeepWork (cut distraction, focus is everything), hours of podcasts with Tim Ferriss (meta-learning and sneakiness) and Jordan Harbinger (a bajillion guests who wrote self-help books), and a deluge of blog posts from the like of Scott Young (meta-learning and focus) and others. The sorts of people who love to hustle but hate to identify as hustlers.
Many of the themes (focus, commitment, deliberately working towards a goal) had a trad ring to them, reminiscent of the sort of advice I'd been getting from my parents my whole life. Now the advice felt like mine because I'd found it on my own terms and from people who I thought were cool.
One was "It's not gonna happen unless you make it happen." Another was "Talk is cheap, either do something about it or shut up."
Lots of great things came from spending several years on that trajectory. This post is not about the great things - it's about the bad ones. As with any cluster of advice, aphorisms, and motifs, there are multiple plausible ways to fill in the details in ways that either harm you or help you. These two morphed into a beast where I felt like I wasn't allowed to want anything I didn't immediately know how to get, and that I wasn't ever going to get anything I didn't already know how to get or was working on, and so I always felt like I needed to cram a life's worth of ambition into every single day.
Yeah, it was a little crazy.
Juggling Deflating Balloons
For many years, all I noticed was the feeling that "I liked too many things". Here's a sample of some of the hobbies I've spent time on:
- Close up magic
- Lock picking
- Modding nerf guns
- Making catapults
- Rock climbing
- Making weapons for LARPers
- Sword fighting with said weapons
- Card Games + Game Theory
- Sketch comedy
- Freestyle rap
- Standup Comedy
When I was younger I leisurely ambled back and forth between different activities. But as the years went by, it began to feel like I had tens of partially deflated balloons in the air, all slowly falling. The problem wasn't that there were so many balloons, but that I felt I couldn’t let any of them touch the floor. When I realized weeks had gone by since I last touched a hobby, I frantically ran over and launched it into the air again, only to soon realize that another balloon was about to touch the floor, and ran off once again.
It was this constant tension, a slight unease that cyclically reared its head. I’d be having a blast doing stuff that I liked, and out of nowhere “FUCK I haven’t played ukulele in a week, I can’t let that die!”
This post will explore how this came to be. To understand why I felt compelled to have so many balloons in the air in the first place, we'll investigate my relationship with boredom. To understand why I felt an intense, almost moral, imperative to keep my balloons from touching the ground we’ll explore the development of my desire to be seen as impressive and to be “taken seriously”.
Fear of Boredom ≈ Fear of Losing Autonomy
As a kid there were two distinct experiences that blended together to shape my relationship with boredom.
The primary experience was that of being trapped by authority. Being stuck somewhere at some boring event, often with lots of boring adults, and not being allowed to go do something more fun. School, church, dinner parties, weddings, etc. The memories are foggy but I remember finding such things excruciating. It was made all the worse by the fact that I always had a book with me, but was never allowed to read it. I could straight up just not have been bored if it wasn't for the fact that these lunatics weren't letting me. The message I got was that what I cared about just wasn't important.
This wasn't just boredom, but a loop where boredom triggered plans to relieve boredom, which butted up against not having enough autonomy to enact the plans, followed by trying to suppress my urge to do something else, then experiencing boredom, and looping back to the top.
The other key experience was genuine boredom, typically born out of cycles of hype and fading novelty around things I was building:
"Once I build this trebuchet, I'll never be bored again cuz I'll always have this super awesome trebuchet to play with!"
*gets bored after a day*
"I'm gonna make an air cannon! Once I build this air cannon I'll never be bored again cuz I'll always have this super awesome air cannon to play with!"
Sometime between 8-12 years old I began to notice this cycle and go "Huh. There isn't one thing that can make me happy forever, is there?" The ephemerality of my own enjoyment felt spooky. Today, I could tell you all about the mechanisms that govern what feels interesting to me in a given moment. I could tell you about decently reliable plans to rekindle interest in projects and ideas I feel tempted to give up on. But back then? All I understood was that sometimes things you had always thought tasted good sometimes just... stopped tasting good, and you never knew when it might happen.
This discovery fed directly into feelings around "boredom as being trapped by authority". Boredom born of fading novelty could trigger the fears associated with boredom born of being trapped. Noticing I was starting to lose interest in a project could trigger the familiar feelings of despair and lack of autonomy, even in situations where I did have autonomy.
Top it all off with various flavors of shame ("You shouldn't be bored, there's plenty of things in this house for you to play with") to create an emotional context where boredom was an experience that really scared me, and I would do a lot to avoid it. I see my proclivity to collect hobbies and interests largely as an attempt to safeguard against feelings of boredom, which in turn is a way of safeguarding against feelings of being helpless and trapped.
This loop, plus just being open and curious to things, explains why there were so many balloons. But it doesn't explain the way in which I felt I couldn't let them hit the floor.
Needing to be "Serious"
As mentioned, I held an intense, almost moral, imperative that I could not let any of my hobbies or interests decay or get dropped over time. If it had been too long since I'd last done something, I felt compelled to rush over and practice, launching the balloon back into the air for a while. This pattern began to crystallize in high school and intensified in university.
One of my earliest memories related to this: at school, I'd told my friend Ethan that I was going to make us metal gauntlets so that... well... I can't remember if there was a reason. When you're 10, having metal gauntlets and being able to punch things with a metal fist is sorta a terminal value. Anyways, my plan for making them involved no metal-working, and instead was based on the idea of holding onto a magnet and sticking our hands into a bucket of iron filings.
After weeks of bugging my science teacher, he gave me some iron filings. I finally gave it a shot, and whaddaya know, it... just got my hands really dirty. "I totally should have seen this coming. What a dumb idea! I can’t believe I was talking it up so much!" I realized I'd been doing shit like this for years and was mortified. "From now on, I'll only hype up an idea when I think it'll actually pull through!"
Flash forward to high school. I've accumulated several hobbies besides making things. One day I brought some of my lock-picking stuff to school. Some kid at the lunch table said he was impressed that I did lock picking. Another kid responded with,
"Yeah, he'll be on lock picking this week, then probably back to magic next week, then on to something else the next week."
On its own, not a particularly scathing review, but he said it in a way that I took as a thinly veiled put-down. I was suddenly aware that other people could dock me impressiveness points via asserting I wasn't that serious. This was a scary thing to young me, because as I've written about briefly here, the bulk of my personality that developed across adolescence was centered on the premise of "Be so radiantly impressive that people just give me attention so I don't have to ask for it." That became the one script that I leaned on so heavily, and to such great success, that I became the only way I knew how to meet my needs.
(note: this looks superficially similar to Paul Graham's Keep Your Identity Small, which I don't find to be a useful frame as it makes identity and identifying-as-something a black box and just says "Don't do it." I much prefer thinking of identities as strategies you've become dependent on because it gives a more gearsy model.)
Being accused of not being serious or of being a “poser” became The Bad Thing that I fought against, and all of the pop-psyche on deliberate practice and focus became The Tool I used to fight against it. This synthesized into a particular mindset. I felt like I wasn't allowed to want or desire something unless I had a concrete 12-point plan for making it happen; if I wasn't working on something, I needed to make it super clear that I didn't have any prideful illusions of "doing it later". This tied deeply into my mindset of "Fix the problem or stop complaining about it." The future only existed if it was on a Google Cal event. To let a balloon touch the ground meant to never see it back in the air again.
Besides making life unnecessarily frantic, this mindset also made my world small. In high school, most of my challenges were things that I was actually able to deal with simply by Trying Harder and applying Focus and Effort. In university I had huge success with strict discipline as a strategy for attacking heavy course loads. But despite immediate gains, it imposed constraints on what I felt I was allowed to desire, which shrunk my conscious experience of the world. My dreams and ambitions lived in a strange kind of limbo. Since I didn’t know how to accomplish them, I couldn’t admit that I had them, so I had to engage in strenuous mental gymnastics to push them out of my mind while simultaneously making sequitous moves in their direction, all while swearing I was "just messing around, of course I’m not serious".
Commands to follow norms presented as claims about the world
This dynamic, the felt necessity of being provably “serious”, was a force in my life for many years before I gained any reflective awareness of it. Certain things simply felt clearly good, or clearly bad, and if I felt so inclined to introspect, the feeling came ready with a little soundbite about how you need to be proactive to get anything good in life. It took a particular series of events to set up the self-investigation needed to break through this confabulation. One of those particular events was a call with a friend who probed me on why it felt so wrong and awful to want a thing and not be actively working towards it. I eventually got to:
"Because if I'm not working towards the goal as we speak and I only have vague intents to get around to it later that makes me just as bad as the sort of beanie-clad loser hanging out at Starbucks on his MacBook talking about the novel he's totally going to write when he hasn't produced more than 100 words in over a year."
.... wait wut? As soon as I said that I was shocked. I didn't know a single person who resembled this hypothetical Starbucks-goer at all. Like, at all. How the fuck had I managed to arrange my life around not being similar to a person that I've never even met? Eventually I traced the image back to a Cracked article I read back in 2012. All it had taken was one listicle from a comedy site to convince me it was bad and shameful to act or look like this archetype I’d never even interacted with.
It was beginning to dawn on me that, while I had no problem ignoring or disbelieving authorities who supposedly "knew best" when it came to everyday facts about life and the world, I absorbed everything that anyone said about who they saw as contemptible or praiseworthy. It's the signal that's always present no matter how much the channel might seem like meaningless noise. If your friend tells you Ashley's a bitch because she was sleeping with Rachel's boyfriend, you may or may not have learned something about Ashley, but you definitely learned something about what sort of behavior is gossip-worthy and what can get you bad-mouthed.
The juxtaposition between the intensity with which I was avoiding the hipster archetype and its concrete irrelevance to my life was just too jarring to be ignored. This disconnect opened a path to see how a lot of the motive force behind most of my productivity, focus and "have a plan or it ain't happening mindset" was driven by this mimetic aversion (the less-famous sibling of mimetic desire). I began the hunt for formational memories. One of the clearest examples I found was that of my interaction with the magic community.
Status Games in Magic
In high school I spent a lot of time lurking on online magic forums. Often, old-timers (and magic is mostly old-timers) would talk about having to "pay your dues" and "working in the trenches". Get a restaurant gig where you perform 5 nights a week for a few years. Put in the hours performing. Hone your craft. Before I ever had Cal Newport, I had these guys telling me I needed to practice.
Telling new magicians to practice is a good thing. You need to practice to get good. It's also true that there's more going on here. Often, these discussions would be started by someone bagging on those darned edgy youths over at Theory 11 or Ellusionist, with their cool magic trailers that all the kids were throwing their parents money at. "I can't believe this kid plays some dubstep, gets a piercing, and suddenly they're The Best Magician In The WorldTM. They're not even that good! I've been doing restaurants for 20 years and I tell you, this sloppy shit would never fly in the real world."
At the same time that they're trying to make claims about what makes good magic and what will make you better at magic, they're trying to renegotiate how status is allocated in their community. Here’s the subtext of the above rant:
"I've put a lot of hard work into magic, and I see someone who hasn't worked nearly as hard (or as LONG) as me getting lots of hype, attention and status. That is not how our community should work. Status should go to those like me, who have put in the work."
This isn’t unique to magic. In any community there will be various status hierarchies that people are trying to negotiate and enforce. And it's not an entirely useless pursuit. It is 100% possible for groups and communities to collapse and be sucked dry because bad actors figured out how to play the status norms, drain capital, and permanently damage a culture that cared about something precious. In the communities I've been a part of, the stakes have mostly been "who gets to be the cool kid?", but in general the stakes can be much higher.
Constantly negotiating the norms of how social (status/prestige) and material (gigs/loans) resources are allocated is just a thing people do, and I don’t begrudge them for doing it. I will begrudge you if I think you are pushing for shitty norms, and I HELLA begrudge the way that these negotiations get disguised as concrete claims about how things work. This obfuscation led me to generate all sorts of unnecessary problems for myself.
Example: it was a big deal for me when my junior year I took a hiatus from magic and working restaurant gigs. Just months before, this would have been impossible because taking a break felt like quitting. Even though I knew that I loved magic and would come back to it in a year, how could I prove that to anyone else? Why would anyone believe me? “YOU WILL LOOK LIKE A FOOL IF YOU AREN’T VISIBLY DOING!” There was a poisonous, incessant focus on being able to prove something to others even when it literally did not matter.
Blending Is and Ought
Suppose you asked me, "Do you think you actually won't be able to succeed unless you have a concrete plan, or is it that you expect other people will deride you if you don't have a plan?" The whole problem was that my mind was muddled enough that a clear distinction between the two didn't exist. And I don't think that's an accident. Everywhere I look in my life I see concrete claims about how the world works ("if you don't have a plan, nothing will happen") being blended into imperative commands to follow a particular norm ("don't ask for any resources unless you have a legible plan we can sign off on").
"Describing how things are is almost always understood to be an implicit justification for how things should or could be. Hume’s Is-Ought Problem is notable precisely because everyone ignores it."
The aforementioned blending has confused my thinking and made it hard to understand reality on its own terms, un-warped by whatever social context I've most recently decided is cool and that I want to be a part of.
Making the problem worse, it generally is taboo to explicitly talk about a community's norms. Doubly so when talking about the norms for allocating social and material resources. This creates a sticky situation where there's a real need to be a part of the ongoing negotiations of the norm landscape, and these negotiations can't be pursued straightforwardly. Everything must be laundered through a front of "we're just reasonable people rationally debating how stuff works." Ought gets laundered through Is.
This laundering will always produce a distorted reality. Grinding on your magic skills in restaurants every night for years will do amazing things for you. It's also not the only way to succeed. Planning is amazing for helping you figure out hidden assumptions. It's also not the case that nothing can happen without a plan.
A recurring pattern: Shared Success Scripts
Figuring out how I came to believe the things that I believe is hard. The motivated blending of Ought commands and Is claims makes it extra difficult to do detective work on my worldviews. If look at my own life and squint, I can sort of make out three loose partially overlapping phases to the process:
- Notice my worldview is motivated by something other than what I thought it was.
- Begin to see the cracks in said worldview.
- Ask, "given that this worldview doesn't do what it says on the label, what are the actual repercussions of living like this, and who does it benefit?"
This post has focused on a subset of worldviews that I call shared success scripts. The online magic world had a shared success script about "paying your dues". For many decades in the United States there was a shared success script of, "going to a good college lets you get a good job lets you get a good life" (it’s still common, but narratives are more fragmented across the board these days). These are scripts in the sense that they're simple to follow (though maybe not easy), and they tie into a narrative about why you'll end up achieving a particular local flavor of success. It's shared because everyone (relative to some community) knows it, even if not everyone acts on it.
Shared success scripts take a while to saturate a community, but once they're in, they provide a Schelling point for allocating social and material resources. I expect most communities past a certain age develop shared success scripts of one type or another.
These scripts often do the sort of Is/Ought blend I described earlier. Concrete claims about the world, blended with commands to act a certain way. Piecing them apart is vital. That's the beginning of step 1, notice that there's a difference at all. It's really hard to do step 2 until then. When a script is whole and fully blended in your psyche, going against the script feels like, well, just failing.
A Serious Paradox
There's a contradiction buried at the heart of this all. My drive to be "taken seriously" nudged me further towards being hyper-attentive to what other people thought. At the same time, my idea of being a "serious person" who was "radiantly impressive" involved not being beholden to what other people thought.
Sometimes it boggles me the number of contradictions I have managed to actively maintain for years. Other times I just try to feel grateful for what I've been able to work through so far. Other times I put on my detective hat and keep snooping.
I think part of why I didn't notice this paradox for so long was because all of the people I found impressive were far away. Some background first: skills like magic and parkour have huge immediate returns on impressiveness. The bottom 10% of magic tricks can still knock the socks off of laypeople, and the bottom 10% of parkour can still be cool to people who've never done it. So at the same time that it was really important to me that I impress my friends, I knew that was going to be pretty easy. The people that I was actually anxious about being able to impress were people I never got to interact with. For a long time I couldn't find other people who did magic or parkour. I couldn't find people who read the books I'd read. When I found forums online I only ever lurked. And I didn't even consider trying to talk to the actual content creators and authors I admired. (I'm just a kid, why would Tim Ferris respond to my emails?)
I never knew if I could impress the people I wanted to because I had never met them! I had this whole panel of judges that I'd assembled in my mind, all of whom I felt an intense desire to prove myself to, and none of whom I was able to actually talk to. This lack of feedback meant that whether or not I felt good about myself was completely at the whim of the emotional wound that drove me to be impressive in the first place.
Besides creating an unresolvable tension, this distance also made it easy to not notice the way I was following a script. Compared to my irl peers, I was an iconoclastic rebel veering off of conventional wisdom and living beyond a script. But only compared to them. I mistook finding a script that spoke to my needs with being scriptless. I think this would have been much more transparent if I'd actually interacted with communities of people I admired.
(aside: that's actually one of the reasons I've loved being on twitter the past year. It's been alarming and insightful to see how quickly my attitudes change based on my social environment.)
Having gotten a better grasp on where I got my script from, let’s circle back one more time to examine the contents of the script. We'll do it by tracing how I noticed what was going on the first place, through each of the three phases I mentioned.
Dissecting My Worldview
Back at the beginning of the post I described two throughline attitudes as:
- "It's not gonna happen unless you make it happen."
- "Talk is cheap, either do something about it or shut up."
Tweak them slightly to get
- "It's not gonna happen unless you have an explicit plan."
- "Talk is cheap, either show us your plan or shut up."
To tweak the two attitudes one more time, I'll culminate with the framing:
"I need a legible plan for inevitable success, otherwise I'm not allowed to desire something."
Legibility is an amazing concept. It highlights the difference between easily understood by others, and easily understood by you. My illegible handwriting does in fact have the structure of language embedded in it, it's just not standardized enough for most people to perceive it. In this framing, everything becomes really obvious.
I lived in a world where my desire was capped by what courses of action I knew I could make legible for others. Did that person just scoff at a colleague for repeatedly insisting he's totally gonna get the work done later? Cool, I now believe the future doesn't exist unless it's in a GCal event I can wave in your face. "See? It's right here!" How did I learn what types of actions had legible narratives of success around them? Cal Newport, The Talent Code, older magicians, kids shit-talking each other, my dad telling me to work hard, etc.
Phase 1 and phase 3 we've already looked at. The dissonant image of the hipster slacker made me first notice something else was going on, and examining the transparent case study of my interactions with magicians filled in my understanding of why these ideas were being pushed in the first place. Phase 2, noticing the gaps, is what I want to focus on next.
Or at least, it’s what I’d be focusing on if I wasn’t trying to end this blog post, which is already quite long. There’s a whole nother feature-length post to be written. Which of the concrete claims fail? When do they fail? If not time-boxing your deep work to optimize your UltraLearning for deliberate practice, then what? Don’t I actually need to stick with something to get good at it?
These are all very important questions, far too important to be left rhetorical. They’re ones that I’ve spent a lot of time struggling with. The post you’re currently reading was actually intended to directly deal with those questions. But as I dug into it, I realized that the most impactful change factor for me was understanding the warped motivational dynamics I was embedded in. So that’s what you got a post on instead :)
Tune in next time for illegible strategies to pursue awesomeness!