0616 – micromanage your time

I’m on the train now, I’m on the way to work. I’m still a littitle bit mindblown at how long it took me to write that last word vomit and how it delayed the start of my day. I need to hold these things very vividly in my mind. I need to make it a point to turn off the WiFi whenever I’m writing a word vomit.

Now I’m on the train. I’m on the train for around two hours every single work day. I should be spending this time as productively as I can. nobody will hold it against me if if decide to spend it talking to people or playing silly games. but then I would be wasting a great oppurtunity to do a lot of writing. if I could ab test my life I’m pretty sure it would be clear that writing during my commutes would be a great idea. it would mean that I get almost two word vomits done a day. that would guarantee that finish my word vomit project before the end of 2017. hopefully I’ll be done before I turn 27. that would be a nice birthday present to give to myself. a million words. take it and go run. run into the future.

So I’m still thinking about principles and decisions. what do I choose to do during my commutes? I typically choose to spend it on social media- twitter and Facebook and reddit. catching up on what other people are saying. what other people find funny or interesting or entertaining or outrageous. and I know from experience- wrote about this extensively in 2013- that this might SEEM relaxing, but it’s actually a whole new anxiety. I might actually be better off just meditating during my commutes, breathing as deeply as I can.

Thinking again about Cal Newport. An interesting life doesn’t come from endless introspection. I agree. I know I set out with this writing project with some introspection in mind, but the point also was to exhaust myself. to empty my tank and see what happened next. I think I need to start writing for the public again. I’ve surely said this before. the mistake I’m making is that I keep thinking everything neefs to be incredibly epic. I can break it down into littler steps. thats how books get written, bit by bit.

I have spent so much time in Singapore’s trains now at this point. 2 hours a day. 10 hours a week. let’s say it’s 8 hours a week. that’s a full day every 3 weeks. a week in 21. a month in 21 months, then. 12 months in a year. I’ve been working almost 4 years. so I’ve spent over 2 months in transit.


Okay now I’m in office, and it’s 130pm, and this commute vomit is only half complete. As I recall – I started the vomit around Khatib or YCK, and switched out at points here and there. That’s 500 words. I think 1,000 words in the commute is possible, but I have to start the moment I get the chance, and I have to avoid being distracted by random things.

I think it’s possible. I want to make it a priority. I want to make it a thing that I work on.


And now here I am, with 450 words left to go, and work to do. What do I do now? I guess I just gotta keep chugging with stream of consciousness stuff. Let’s zoom back to see what the original intent of this post was. Oh, I was exploring how strange it was that I wasn’t writing more word vomits. That I wasn’t writing more. That I wasn’t making the decision to write. That I didn’t finish what I started – when I look through my evernote, it’s clear that I often start things without finishing them. I think there’s a tactic or skill to be developed there – whenever I’m going to abandon something, I should first write a couple of lines of notes to myself for what I was thinking about and why I abandoned it. Notes to my future self who’ll eventually rediscover it and then have to figure out what to do with it. It’s like commenting in your code!

300 more to go. 1:57.

I was thinking this morning about doing pushups. About how I will have to do as many pushups as possible for my IPPT physical proficiency test, and how I have been putting off doing pushups I suppose because I know that it will be uncomfortable. I know that I can comfortably do 5, maybe 10, and it gets uncomfortable and frustrating when I get up to around 15-20. My goal is to do 50, but I haven’t been making progress because I’ve been hesitant to get started at all. Hey, I could do 5 pushups right now. I’ma do them.

It’s 10:36pm and I’m in bed. My cat is next to me. I want to be asleep by 11pm. So I have 24 minutes to finish this vomit and another one that I have half-written. And then I want to reflect really quickly about my work day, and then I want to go to sleep.

What’s the central idea in this word vomit? The point I’m trying to remind myself of here is how I still fundamentally misunderstand the nature of how things get done. I need to unlearn and re-learn what it means to have productive moments – how to get stuff done before going to sleep, how to get stuff done after waking up, how to get stuff done at work. I need to be a lot better at managing my time, and I’ve said that a lot but I haven’t made progress I think because I haven’t paid attention to it at a micro-level enough. I need to examine my time much more closely. What gets measured gets managed, right? Micromanage your time, Visa.


0615 – measure your time

I woke up at 9, rolled around in bed for a while, talked to my wife for a bit, and now I’m out of bed at 10:26 with my laptop trying to write a word vomit. And now I spent 30 mins doing nothing much and not getting the word vomit done. This is what needs to change. I don’t have much of a problem with the rolling around bit, but I should be writing a vomit as quickly and early as I can before my mind gets cluttered with other information that I wasn’t actually interested in.

I suppose that should be one of my principles. I remember reading a quote – people will be offended at being told what to think, but they’re generally fine with being given things to think about. And once you’re in that scenario, you can generally, or at least probablistically be steered to think one way or another. Either way, that’s what’s on your mind. That’s the trap with things like advertising – we don’t get to test the null hypothesis.

I want to really sit in my chair, with my laptop on my lap as it is, at 10:57am, and be here now. Really take in the reality of my experience and how close I was to giving up on this word vomit. If I am to make 2017 the best year yet, I need to be a lot more decisive and intentional.

I wanted to make sense of what a decision is. What is it? The word decide technically means ‘to cut off’. And that’s something I’m definitely very bad at doing. In a way, it seems like most decisions are about decisions to stop doing something, to finish something. To end the current status or setting, so that we might switch to something new. So “deciding to go for a run”, in a sense, is “deciding to cease rest”. Now I’m thinking about the Da Vinci quote – something about motion being created only by the destruction of balance.

I need to destroy the balanced equilibrium that is my way of life so that I might level up, do new things, do better things. I was also thinking that I need to apply my review process (which I currently do every week to make sense of my fitness goals, reading goals, etc) to my work.

11:21am. Wow. It’s so easy to get sidetracked and to lose steam. I should turn off the Internet while I’m writing. I’m going to do that right now. And I’m going to finish this word vomit in the next 4-5 minutes.

Right. So – a systematic breaking of equilibrium. Of re-evaluation. Of decisions. The point is to return to the center again whenever mistakes have been made, as long as there is space to continue. Let’s get meta within the context of this word vomit. I was hoping to be done with it before 11am, and then 11:10, 11:20, and now before 11:30. At what point do I give up? I think 11:30 was pretty close to my give-up point because I need to send an update for work and I want to get to office in time for lunch.

But how do I make it such that I get my stuff done by 11, so that I can leave 30 minutes early and feel nice and comfortable? That’s the million dollar question. If I can solve that, I can improve my quality of life dramatically by just making better decisions. What if I had gotten out of bed at 9, done my word vomit by 930, and left the house by 10 am? That would’ve been beautiful. What if I was fast asleep by 11pm instead of 1am, and woke up at 6 or 7am instead, and was done by 730? Then I would have had time to go for a run, or do some squats. My hamstrings are still quite sore from deadlifts though, so probably not.

I have made a lot of grand promises and gestures over the past decade, and most of them have not worked out. So I know that I cannot grand-promise my way out of it. I cannot spend my time and energy looking forward indefinitely. I DO have plans – I’ve had them for years. The thing is not to focus on the long-term but to focus on what I’m doing right now in service of that long-term goal. It’s not necessarily short-sighted to focus on the present. I think there’s a limiting belief there that I need to correct. Something about the distinction between being long-sighted and short-sighted. I’d like to think that I’m long-sighted but I’m really short-sighted, and I’ve been avoiding things that I think are short-sighted but would actually help me achieve my long-term goals. It’s all about each boring brick, one by one.

Wow we’re still not done. See, I chronically underestimate things. I underestimate how long it takes to write a word vomit. I overestimate how much time I have. I underestimate how much time I spend when I get distracted by things. I overestimate my capacity to do things. I need to write these things down in more concrete, examinable terms and then really internalise what that means to me. I’ve been navigating using flawed instruments that have consistent, systematic errors about them. So they’ve been leading me away from my destination, reliably.

Let’s recap. I need to make better decisions. I need to make decisions faster. This is so that I can achieve my goal of being more free. Freedom has a price. It’s worth paying. I need to redo my assessments of my own effectiveness and efficiency. I need to do this every single day so that I develop it. It’s like a muscle. I have to use it over and over so that it becomes a thing. I have to write on my whiteboard that this is a thing. I have to set reminders so that this is a thing. I cannot drop this now, I have come too far, I have spent too much time for me to mess this up again. I have faith. But I gotta verify.


0614 – Kissinger Before Sunrise

I was reading an interview with Henry Kissinger, and he talked about how him and Enlai from China used to meet secretly in 1971 – and in order to build confidence, they’d discuss their world philosophies. “We sounded like two college professors discussing the nature of the world and its future”.

> This sort of dialogue is not apparent in contemporary U.S.–China dialogue. Leaders meet and have useful conversations in the sense that there are practical items—a lot of items—that they have to work through. Yet the Chinese leave such conversations frustrated. The primary subject they want to discuss—philosophical in nature—is never raised, which is “If we were you, we might try to suppress our rise. Do you seek to suppress us? If you do not, what will the world look like when we are both strong, as we expect to be?”

It’s funny for me to contemplate this because in my teenage years I was very much in love with ‘philosophy’ and ‘what does it all mean’ and ‘how should things be’ . And I remember hearing from ’serious’ or ‘respectable’ people – or ordinary young people who aspired to seriousness and respectability – that things like philosophy are an indulgence, a waste of time, and that if you wanted to do something serious and important like say work in the Ministry of Foreign Affairs, then you have to be good at doing the practical things. I disagreed vehemently then, but over time I grew to kinda not get involved – and at some point I grew weary of all of the wannabe philosophising altogether, because which didn’t seem to go anywhere.

And now it’s becoming clear that these heart-stories, seemingly trivial or childish beliefs, are axiomatic. Of law, of work, of love, of family… at the heart of everything is – what is the story you tell yourself, about who you are, what the world is, and how we are to meet it? Philosophy isn’t just something for college professors or for idealistic filmmakers. It remains true that philosophy is at the deep heart of all of our human systems.

(I’m thinking now about a quote… something along the lines of “Anybody who thinks that they’re an independent thinker unconstrained by history without need for ethics is probably a slave to the thinking of some defunct white economist from 200 years ago”. Something like that.)

I’m thinking now about what I enjoyed about The West Wing. I find myself thinking about an episode where a black man made the case for reparations for slavery. And Bartlett asking “What is the virtue of a proportionate response?” And Sam Seaborne saying that schools should be palaces, education should be the #1 source of government spending, etc. It must be one of the reasons why the show inspired so many people to get into politics – because they saw the full picture, they saw how it was a vehicle for them to express their values and beliefs. It was cheesy and corny at times, sometimes preachy, heavy-handed and more than a bit smug and eager to deliver smackdowns. But ultimately I think it was more wholesome to consume than something like House Of Cards (I gave up halfway) not because “good is better than cynical”, but because it raised questions that the latter didn’t. About how to make decisions in difficult times. About how to operate in uncertainty. About values and principles.

I’m thinking now also of Simon Sinek, and about how people don’t want to buy what you do, they buy why you do it. It’s about having the same beliefs. Do you believe what I believe? And I’m thinking now about how Apple was under Steve Jobs, and how everyone felt confident that you could trust that someone like Steve Jobs would guarantee that your products were great. What other brands are like that?

Now I’m thinking about Alain de Botton’s – The News: A User’s Manual. He talks about how every piece of news is part of a bigger narrative, a bigger conflict along really big questions. Every boring news article is actually in fact a drop of paint on a much larger canvas – about questions like, how should we allocate our resources? What are our priorities and why?

What ARE my values and beliefs? I stopped writing this here because I didn’t think I could answer the question in a succinct manner fiat the time I was writing it. Revisiting it a little later, I find myself thinking that maybe I shouldn’t be in a rush to try and figure everything out all at once. I wonder what Nassim Taleb would have to say about it. On one hand he said something like “you should be able to describe the point of your work while standing on one leg”, and on the other he expressed disdain for anything that was overly simplistic, bureaucratic, procrustean.

So what is it then? What are my values? Now I’m thinking about Dalio’s Principles. The point of having Principles is to allow you to make decisions in advance. And if I’m honest about my personal history, I’m not very good at making decisions, and not very good at making decisions in advance either. I’ve gotten slightly less terrible at it, but I still find myself not fully believing myself when I say something like “I’m going to do this, then I’m going to do that”.

There are a whole bunch of possible statements I think I would be able to agree with, but I’m not sure which would stand out as the guiding principle. Which is most important?

Thinking about my experience in the past couple of years, I think an important thing that I should focus on is expanding the amount of freedom I have. What does that mean? It means I should avoid unnecessary commitments, it means I should move fast instead of slow when I can. There might be a better way of phrasing it. But basically whatever it takes to get out of stasis, out of the death that is living in a shell, in a loop over and over again.


0613 – make 2017 the best year yet

The year is coming to an end, and whenever that happens I get into a rather wistful and contemplative mood. There’s a sense of winding down, of taking time to reflect upon the past. I was looking through my archives and it looks like I’ve been doing this consistently for almost all of the 2010s so far. There are two or three instances that I tend to write about – I write at the end of the year to review how it’s gone, I write at the dawn of the new year to plan ahead, and I write on my birthday (which conveniently falls in June, right in the middle) to take stock of how things are going.

Here’s what I’ve noticed from examining my past few years’ worth of notes.

I have the same recurring goals over and over again. They’re the most fundamental of goals. Sleep more, sleep better. Avoid cigarettes. Eat healthier. Exercise more. Read more. Write more. Spend less time dicking around on the internet. Spend more time with loved ones. Make time to try new, different and challenging things. Grow as a person.

I don’t make a lot of progress on these goals. When I compare myself today to myself from 2-3 years ago, there’s obvious progress. But it’s not as dramatic as I’d like it to be. I’ve gotten rather bored with how often I’m repeating myself, and I’ve definitely gotten bored of saying that I’m bored. I’m trapped in this little cycle. Which is frustrating, because I already feel quite trapped by my circumstances – living in a small flat, struggling through a lengthy commute, day after week after month after year. It’s silly if I’m also going to trap myself in old patterns of thinking, patterns of behavior.

A friend repeatedly says that 27 is the year that everything changes. You’re too close to 30 now to keep dicking around. Your time is too precious, and you’ve wasted too much already. Well I hope he’s right. But I can’t depend on hope alone, either. I have to put in the effort. I have to change something about how I’ve been doing things. I find myself thinking that there are parallels between the way I’m currently operating and the way I used to play video games as a child. I’ve written this several times now surely – 0194. I couldn’t break through the plateau until I stopped making the fundamental mistake, which was spending way too much at the start on infrastructure and then getting eaten alive by the maintenance costs. You have to grow organically.

If I’m forced to draw a parallel, just for fun, I think the mistake I make here is that I think way too big and plan way too far ahead. And I probably incur some sort of maintenance costs from that. What I should I be doing instead? The same thing with the city – start really really small. Focus on an hour at a time, a day at a time. You win the year by winning the months, the months by winning the weeks, the weeks by winning the days. I’ve been hit hard by the fact that I always think “1 word vomit a day isn’t a big deal”, and yet every year I publish far less than 365 word vomits. If I had just stuck to 1 a day, I would have been done by now. It’s a sobering reminder of the power of accumulation. It’s actually worth doing 5 pushups a day if you can, run for 5 minutes if you can. It seems trivial but it’s really not, it really adds up. So maybe that’s what I’m going to do in 2017. I’m going to focus on the smallest wins – smaller than anything I’ve done before. I’m not going to try to win the whole year. I’m going to try to win the first week. And then the 2nd week. And I’m going to do weekly and monthly reviews. I’ve already been doing weekly reviews for the past 10+ weeks – they haven’t been perfect, but they’ve been done.

There’s two things that I need to focus on to get that right. I need to have a daily routine where I check my calendar several times, and I need to update it regularly. I’m doing that now. I need to make sure every day is as filled as I possibly can fill it – not with what I’m planning to do, but with what I actually did. If I can do this every day, I will be able to see a much clearer picture of how I’m spending my time – and I can make adjustments accordingly in real time.

It’s still November. I want to be doing this for all of December and January and I want to do it for as long as I can. If I screw up for a week or a month, I want to get right back on track. It’s all about focusing on what’s in front of my face, on what I can do now that will contribute towards my larger vision, towards my larger goals for myself. There’s no point trying to over-articulate those bigger picture things until I can get to the relative cutting-edge of whatever it is that I’m working on, because that will give me the perspective and context I need in order to make bets.

I was re-reading Cal Newport’s So Good They Can’t Ignore You. While I thought I had internalised the idea, there are still a few useful points to reference and ruminate on. I thought he made a great point about the necessity of career capital, and about how courage is insufficient early on but necessary later once you’ve paid your dues. There was a great bit about how… something along the lines of – if a little introspection, day-dreaming, imagination and idealism was all it took to change the world, tonnes of people would be making massive impact.

The thing that I want to do is HARD. It’s PAINFUL. Most people QUIT. And I have a long history of quitting when things get hard and painful. The path I have taken so far has not been the most efficient, has not been the best. But I am not down for the count. I’m coming back. I will be better and stronger because of it.


0612 – contemplate how the world works

“what is something i believe about how the world works, which i haven’t actually tested yet?”

The older I get, the clearer it becomes to me that I don’t really understand how the world works. I mean I have some rough basic ideas but I’m not sure how useful they are. From first principles of course we have basic physics – that the Earth goes around the sun, that entropy is always increasing, and so on. It’s fascinating stuff, but it doesn’t tell me a lot about how to live my life, apart from things like “don’t jump out of tall buildings”, “don’t stare into the sun” and so on. Maybe there are some implications down the line that I’m not thinking of.

But when someone says “how does the world work”, they usually mean the human world in particular. How do I fit in, how do I interface with it? How do I make a living? Once upon a time the world was simple – it was just the group of people that you lived with. You go hunting together, eat the food, groom one another, have sex, make babies, raise them together, and sleep under the stars. (Maybe.) But as settlements and civilization became a thing, “the world” got more complicated. Kingdoms emerged. Food surpluses. Specialized warfare. Conquest. Money. And then these groups coalesced and fought and traded and rubbed against each other in all sorts of ways. All sorts of things developed in parallel – technologies, philosophies, art, culture, humans trying to make sense of themselves and one another. Immensely complex system, extensive histories, all sorts of accidents and missteps, all kinds of madness, anger, hate, suffering, joy, happiness, discovery, oppression, slavery, control, power.

If we’re talking about civilization, we’re talking about power. We’re talking about militaries and technologists and financial services and legal systems, all populated, staffed, run and coordinated by people working as parts of superorganisms greater than themselves.

The concept of man as a solitary creature, as an individual – is a recent one. People didn’t start thinking of themselves as Individuals with a capital I until a few centuries ago, maybe a couple of millenia at most. For most of human history we lived in groups, and our lives depended on our groups. A lot of us in modern civilization aren’t so directly dependent on a core group of people the way our ancestors were, but even that depends on our reliance on broader systems. We can only develop the illusion of being self-made when we live in a place that has laws, that has law enforcement, rules, cultural norms of fairness, opportunities, etc – all of which are things that depend on other people doing their jobs. We live on the benevolence of strangers. This I think is self-evident to anybody who pays enough attention. Even if you live in a cabin in the woods that you built with your bare hands, you couldn’t have done it the moment you came into existence. You depended on your parents to nourish and nurture you when you were a weak little baby. For most of us, we needed to learn language – which is a massive collaborative effort happening in real time. People need other people, no matter how cool we pretend we are, or how much we love solitude.

In the real world, every product we buy is designed and assembled by countless others. Even a humble pencil comes from multiple origins – the graphite, the wood, the assembly, the delivery to the store. A massive, elaborate dance just to get you the pencil. And where did the money come from, the money in your pocket that you take out to pay for that pencil? It was printed by your government, which has a ministry of finance, perhaps a central bank, some elaborate monetary policy. And how did you get that money? You probably had to earn it, selling your labor to an employer for a wage. Or maybe you’re an entrepreneur – you still have to make stuff, and that probably involves getting raw materials from somewhere, hiring some people, so on and so forth.

The world works in an incredibly elaborate and intricate fashion, depending on the collaboration of billions of players. It’s amazing that it works as well as it does. IT does fail from time to time, sometimes over and over again in the same conflict zones. And yet it works most of the time, which is quite a miracle. I’m surprised it doesn’t break more. I suppose the reason for that is that most people are interested in having a good, happy life. Everybody wants a good time. Everybody wants to spend time with people they enjoy, eat good food, look attractive, pursue their curiosities and imaginations, so on.

All of this is true but I find myself still thinking that there’s something amiss. If I truly understood how the world truly, truly works, then I wouldn’t have any sort of stress or nervousness about it. But I do. There’s more that I’m missing.

One way of approaching it is that everything is fundamentally made up of cause and effect relationships. Every event has a cause or multiple causes. As humans we are all meatbags with neurons firing in our brain, awash in hormones and chemicals. Our brains are wired in certain ways (and everybody’s brains, while possessing similarities, is also unique). An important thing to do for a good life is to figure out what are your unique desired end-states. What is it that your brain enjoys doing? Now the first answer for most brains is probably heroin, and that’s a bad answer because heroin has some drastic, damaging effects on the body and you won’t enjoy it for very long. So you need to pick more sustainable desired end-states. For me I think it happens to be writing. I enjoy words, I like playing with words, I fantasize about reassembling words into superior configurations as I see fit. But that’s just part of what I care about. The brain has many different desires, many inconvenient, many conflicting. I also have to think about survival, how to put food on the table, and if I want to have kids and things like that. That’s a lot of cost-benefit analysis to be done. Sometimes I wonder if it’s actually worth it, or if it’s all just rationalization. I think there is definitely value in having a thinking, first-principles sort of attituide to life. After all, random improvisation will never get you to the top of a mountain, or an Olympics gold medal. Not all mountaineers or Olympians are happy, of course, especially if they fail, or if they felt pressured or coerced into it.

I guess here there’s an interesting point to be made about social pressures. Again, the modern world we live in is very different from the set of habits and impulses that our brains have. We have incredibly outdated software, and we’re using it in an environment that it wasn’t “designed” (selected, to be precise) for. So we find ourselves getting into angry internet arguments with total strangers. Why? Legacy issues. Vestigial remnants of whatever it is that helped our ancestors with their strifes and squabbles. We have minds designed for operating in scarcity, and we (at least those of us with internet connections and indoor plumbing) live in a world of abundance. Obesity is going to be more common than starvation before you know it (if it isn’t already).

Go back to the question. How does the world work? It’s a massive network of humans who are vaguely pursuing their desires and goals – but mostly just in a superficial way, just to keep up with their peers and neighbours. Mostly the world works according to peer approval, which is quite a sham because all the little emperors are naked and none of us really knows what we’re talking about.

I think the thing I haven’t tested enough is – if the world is so fundamentally colaborative and so fundamentally networked, it means that I should be spending more time talking to individuals, helping individuals. Yet here I am spending so much of my time writing in solitude. That’s gotta change, most probably.


0611 – face your fears

I’m going to list out things that I’m afraid of. I’m going to try and avoid virtue-signalling and be useful to myself.

I’m afraid of making mistakes. Why? Because I’m afraid people will think I’m stupid, or incompetent.

Reality: It’s okay to make mistakes, the worst mistake is to be paralyzed with inaction. I don’t need to make big public mistakes. Instead, I can share my work with people I trust and get corrections and recommendations before I share it with the world at large.

I’m afraid of making decisions. Why? Because I’m afraid that I’d get things wrong.

Reality: It’s better to get some things wrong than to do nothing at all. If you want to have a good life, you’ll want to make as many good decisions as you can. And it’s a good idea to just practice making as many decisions as possible. Live an intentional life, don’t defer to the default setting. When you were a kid, you didn’t trust yourself to make good decisions and you were willing to drift along. But you’ve learned now that you can get better at making decisions, and that drifters don’t drift anywhere great. Nobody drifts to the Olympics, or to the top of a mountain, or to anything worth doing. As Chris Hadfield said, don’t let life kick you around into becoming a person you don’t want to be.

I’m afraid I’ll never accomplish anything great.

Reality: That’s a good fear. But that doesn’t mean you avoid trying. Great things are achieved with baby steps. What are the baby steps that you need to take in order to achieve the great things that you want to achieve?

I’m afraid I’ll never be able to become a productive person, that I’m cursed to constantly be playing catch up with my life.

Reality: Other people have had this fear too, and overcome it. It’s all about learning a new skill. Didn’t you once believe you’d never be able to squat your bodyweight, or that you’d never be able to play music? You can become a productive person. You just need to be clear about how and why.

You already know that obligation debt is a painful, miserable thing. You have a very good reason for becoming a productive person. You’ll be able to contribute more. You’ll be able to be a force for good for everyone in your life. You can challenge and inspire your friends to become better. You can repay debts to everyone that you feel obligated to. You can come out on top and have a net surplus. So that’s that for the why’s.

Now, the more important things – the How. Listen, I know you look at your history and you see a series of mistakes. Like every minor success is just a stepping stone to the next failure. But here’s the thing, that’s entirely a function of your perspective. (Your perspective in turn is colored by things like your physical state, so make sure you’re getting enough sleep, exercise, healthy food, human contact and so on– because if those things are on the fritz then your perspective is going to shit).

Decide that you’re going to level yourself up. That you’re going to learn how to do things that you weren’t able to do before. You are capable of learning and growing. You’ve learned to cook, haven’t you? You’ve learned to navigate an unfamiliar environment (the kitchen), to use unfamiliar tools (pots and pans), to work with unfamiliar material (pasta, meat, oil, spices), to put them through an unfamiliar process (cooking), and you’ve created something amazing – food that’s so delicious that you actually look forward to eating it again. You did the same thing when you bought a squat rack to teach yourself how to squat.

You can do the same thing with your time. Remember how scared you used to be of food prep, of going into a kitchen, feeling like an idiot about it? Now, remember how scared you used to be of schedules? Of deadlines, and so on? It’s the same thing as the kitchen. You’re going to navigate an unfamiliar environment (clocktime), use unfamiliar tools (calendars, task plans, sub-steps), put them through an unfamiliar process (careful monotasking interspersed with reflection) and create something amazing – an output that exceeds your commitments. And you’ll feel great about it. You vaguely know this to be true from moments of accidental or incidental effectiveness. Let’s make it your new default state, as if you were going to be cooking every day. As with cooking, don’t start out with massive expectations of getting everything done. Just think of it as dipping your feet in unfamiliar waters. You just want to get used to what it feels like, and then you can start experimenting.

I’m afraid I don’t have enough time, and I’m afraid to face that so I have this habit of ignoring the problem and hoping it goes away. Of course, it never goes away, but eventually I get too tired or exhausted to be able to do anything about it, and then nobody can fault me for it because I sat there and ran out the clock. Nobody will ever have the patience to spend their entire life policing me; they have their own life to live too. So as long as I’m sitting here running out the clock, I have some sort of autonomy or control over my life. It’s a very shitty, limited autonomy, like a tiny-ass blanket that doesn’t cover anything, but it’s all I knew at some point.

Reality: You already know the answer to this. Yes, you don’t have enough time, but that doesn’t mean you give up and avoid your problems. That just makes things worse. If you don’t have much time, you’re going to have to be smart about it. You’re going to have to renegotiate. Simplify things. Do some bare minimum for each thing. Make some progress. Let go of this sad life of misery and guilt. Throw away the safety blanket – set it on fire and watch it burn.


0610 – disregard current affairs, focus on priorities

So Donald Trump is going to be the next President of the United States. Social media is blowing up about it, even in Singapore. What a big deal it’s going to be, why it’s bad, why it’s maybe not so bad, so on and so forth. I’ve already spent probably a day’s worth of time distributed over a few days just reading about this guy. Probably more than a day. And that’s an annoying thought. It means that I’ve given away control of my mind to forces beyond myself. And what am I going to do about it? How am I going to personally make a difference to the Government of the United States? I’m much less than a drop in the bucket.

I’ve tried to internalize this point several times but I still haven’t fully gotten around to it. One interpretation is that I’m just lazy and indulgent. Another part of the equation I should keep in mind is the fact that humans are probably wired to obsess about current affairs. To our ancestors living in small tribes, little hunting parties, every single bit of information about everybody else in the group was highly important. But that is no longer the case. We’re swimming in far too much information that’s not actually directly relevant or impactful to us. Who’s going to write the article about how it’s so much more important to just focus on the difference we can make, to ourselves? (Somebody’s probably written it. I know Gary Vee mentioned something like it at his speech at Inbound, and I already know the arguments against a statement like that – how naive, how ignorant, how privileged, way to disregard the real struggles and frustrations of marginalized peoples).

Yeah, there are real people with real problems. How much of my time and energy should I devote to trying to make a difference to them? There’s this thing going around about Teenage magazine and how someone submitted a question for Dear Kelly, about what to do after being raped by a friend. And the advice column replied that she should regret having lied to her mother about where she went, and be thankful that her rapist wore a condom so that she’s unlikely to get pregnant or any STDs. Of course this is slut-shaming, focuses on the victim and so on. A friend of mine shared the news, and there was a guy asking questions like “isn’t it tedious to have to worry about consent all the time”, and I left a comment in support of my friends’ POV – that consent, while tedious, is still more important than one person’s pleasure. I do sincerely believe that. And I do think I helped make my friends feel a little better, knowing that there’s someone in their corner. But how much time should I spend doing things like that, and what is the opportunity cost of that? That’s the real question I need to ask myself. What could I be doing with my time instead, and what should I be doing? Is it a higher priority for me than finishing my writing project ASAP? I need to be clear about this. It’s not as simple as “how selfish should I be”, because in the long run one of the best things a person can do for their friends is to be as self-actualized as possible. I truly believe that.

I spend too much time on reddit and Facebook. This is a fact. Why do I spend any time on there at all? I find myself thinking vague thoughts like “looking for inspiration”, “catching up with news”, “catching up with my friends” and so on. But what is the point of all of that? Okay, a part of it is just wired into me as something that I tend to want. I think it makes far more sense to meet people 1-1 and devote my time and energy entirely to them in those interactions. I think it makes more sense to organize dinner parties and have people over. Spending time discussing things on Facebook doesn’t really change the world all that much, as the latest US elections have shown.

Perhaps reality is still far more complex than I’m making it out to be and I’m just clutching at straws here, circling around what I think is the most important thing. And the most important thing is that I need to define what my own most important thing is, and then prioritize that above everything else, and do that as well as I can. I think a person can reasonably work their ass off for about 4 hours a day and then go on to do other things. I think as long as I DO work my ass off for 4 hours on my top priority each day, I can then go on to have fun doing things like defend my friends on Facebook – if that’s what I want. Virtue-signalling all day every day. (Deciding to forgo virtue-signalling is just a sort of 2nd-order derivative to virtue-signalling, for virtue-signallers with more refined tastes.)

There is no escaping the game of virtue-signalling. The question is whether the signalling is cheap or costly. I was thinking the other day that life is all about accumulating your personal favorite class of prestige or status. Status in the form of signifiers is hollow, status in the form of human relationships is somehow more deep and true. People who are genuinely motivated by things like honor (the way Taleb talks about it) seem to be somehow more righteous, more good. But isn’t that also more of the same thing, in a sense? Yeah, yeah, I’m an idiot for suggesting that, failing to kapish the problem. I don’t know. We’re all a bunch of monkeys playing status games, some a little more refined than others, some supposdly more meaningful than others, my game is bette or more interesting than your game.

I recognize that I cannot opt out. I recognize that trying to opt out is just another way of playing it. So I have to figure out what’s the game that I really, really want to play. And I’m tired of first-order virtue-signalling on social media because that stuff seems hollow. I want to be more useful. The best way to be more useful is to fundamentally improve myself in a way that legitimately challenges and inspires the people around me. To do that I have to challenge and inspire myself. To do that I have to do the work towards my own goals, and demonstrate that I am happy, fulfilled, satisfied, grateful and so on. I think Marcus Aurelius probably had that stuff pretty well figured out, and he’s a reasonable person to follow about these things.


0609 – political consciousness pt 1

I was born in Singapore in 1990. George HW Bush was President of the USA. The Berlin Wall fell, East and West Germany were reunited, and the Hubble space telescope was launched. Thatcher resigned. Mandela was released. Encyclopedia Britannica reached its all time highest sales. The pope was John Paul 2. The first McDonald’s and Pizza Hut outlets opened in Russia and China. Smoking is banned on all cross-country flights in the US. Voyager sends back the Pale Blue Dot photograph. Gorbachev is elected President of the Soviet Union. The WHO removed homosexuality from its list of diseases. Microsoft released Windows 3.0. Nickelodeon studios opened. Joanne Rowling gets the idea for Harry Potter while on a train, and begins writing. Iraq invades Kuwait, initiating the Gulf war. Civil war breaks out in Rwanda. Tim Berners-Lee begins work on the WWW. Home Alone was released. Lee Kuan Yew resigns and Goh Chok Tong becomes PM. The world population was 5.2 billion.

When I was maybe 7 or 8 years old, I was watching my schoolmates playing football in the field after school. I was so engrossed that I missed my school bus. Irrationally, in tears, I decided to wander and try and find my way home by myself, navigating by landmarks. And I particularly remember feeling rather lost because it was National Day season, and all of the blocks of flats were covered in Singapore flags. These days you don’t see many people putting up flags anymore. And that strikes me as something that has changed about Singapore. It’s just an odd little detail that sticks with me.

I never knew what Lee Kuan Yew was like as a Prime Minister – by the time I was old enough to know what a Prime Minister was, it was Goh Chok Tong. So I never really learned the fear and respect that older Singaporeans had for LKY. Singapore was already prosperous by the time I showed up, and I got to witness it becoming even more so – buses became fully air-conditioned, tickets gave way to tap-and-go cards.

I remember when Princess Diana died. I remember a black car and flashing lights, and I remember a massive procession that was all over the news.

I remember thinking Sir Stamford Raffles was a pretty cool guy when I was a kid. Bill Clinton was the first US President I remember, and he seemed to me like a manifestation or representation of what was “good” about America. Tall white man, friendly, charming, charismatic. He had more personality than Goh Chok Tong, for sure. The other leaders I remembered – Mahatir in Malaysia, Suharto in Indonesia. Thaksin, Yingluck, Thailand’s a mess with coups and such. Sukarno.

I never understood the conflict in the Middle East. To this day, after all the reading and watching of histories and whatnot, I still feel like I don’t really. I don’t understand why people feel so strongly about Israelis and Jews, for example. But maybe it had to do with the fact that Hitler and the Holocaust seem so long ago that I don’t feel it. Still I feel like people who talk about these things talk in a coded language I don’t understand. Why do Malay Muslims in Southeast Asia feel so stongly about Palestine? I mean, I sort of understand, but I also sort of don’t.

9-11 was the global scale event of my time – I was 11 years old when it happened and I remember phoning at least one friend to tell him what happened. Back in the day where we had to use landlines to call one another. I remember my dad’s behavior being a little incongruous – he seemed to think that the Americans must’ve deserved whatever was coming to them, after whatever interventions they had done elsewhere in the world. I watched the news for hours – every single TV channel was being interrupted. The newscasters were worried. I watched as each of the towers collapsed and a thousand people died, as people jumped from the towers.

I remember the memes back then, too, before we stated calling them that. The “we’re going to kill you Osama” memes. Stickdeath getting all patriotic and coming up with ways and means to kill Arabs and brown people. I remember that there was a message read to us in school the next day – probably from the Minister of Education, talking about the importance of being vigilant and safe. And I think it was after that that security in schools was stepped up, with stricter controls for who could go in and out. Prior to that I seem to vaguely recall walking in and out of everywhere with no problem. Same for airport security, probably.

I remember my dad bringing me to an opposition party rally probably in 2001.

I had a world globe when I was a kid and it had the USSR on the map. I used to play Red Alert, which was about an alternate timeline where Hitler was killed and the USSR expanded westward. I had an odd fascination with them – I liked their typefaces, I thought “The Reds” was pretty cool. The Cold War ended before I was born but it seemed to echo through my early days.

I remember being 18 and watching Obama, a black man, get elected as POTUS. I was so excited. It seemed like the dawn of a new era of maturity, open-mindedness and so on. Then came marriage equality. It took me a while to warm up to caring about gay rights – when I was a teenage boy I was naively, superficially homophobic in the way that teenage boys tend to be, in groups, mocking one another.

I remember the big tsunami in 2005. My parents were in Sri Lanka at the time and I was worried that they might’ve been dead. I tried to be stoic about it and figure out what my life would be like if they did.

I remember being a little bit sad when Goh Chok Tong handed over the PM role to Lee Hsien Loong. I heard rumours of nepotism – how can the former PM’s son be PM – but I don’t think it personally bothered me too much. The SG Govt seemed infallible and could do no wrong. I think I was about 15 when I learned about things like Operation Cold Store thanks to a passionate history teacher.

When I was in the military, there was an instance where some soldier had self-radicalized with the intent of becoming a terrorist. I remember we were ushered into a meeting room and our commander (who I admired) told us we were not to speak to the media, not to blog about it, etc. I remember feeling vaguely outraged at being told not to blog (if my memory serves me well), but it wasn’t something I wanted to blog about anyway so eh. It was with good intentions I’m sure, but it just reminded me of the nature of power and security and all that good stuff.


0608 – commit to reviewing your calendar

One of the things I want to get better at doing is reviewing each calendar year.

1. I’ve always been bad at doing any sort of review in a systematic way. Think about how bad I was at keeping my files updated back in school. And how I’ve never really managed to stick to any sort of deliberate system or habit for longer than a few months. I’m trying to change that now. I feel like I’ve been trying to change this for the past 6-8 years. What am I going to do now moving forward that’s going to make a difference?

1b. I think the answer is that I’m going to change my attitude towards the importance of a daily calendar review. The costs are too high now for me to let it go. I’m approaching my 4th year of marriage, of being a home-owner, of being employed. I can no longer approach it like a beginner, like a novice. There are expectations I have to live up to, especially my own.

2. I was doing a calendar review yesterday (I know it because I put it in my calendar). I went to the start of 2016, and then scanned through my days week by weeks. I didn’t always keep great records – sometimes I’d have weeks at a time where I didn’t fill in anything, and can’t exactly be sure of what I did.

2a. A part of me wants to be okay with that, as a sort of resistance to the colonization of time. But the bigger part of me I think wants to see what it’s like when I really take my own time seriously. After all, I can always revert to living a life of indifference to time. I do remember that there was a period of time in my life where I basically just hung out with friends every day, and I didn’t enjoy that at all. I found myself weary, listless, and it was just not a good vibe.

2b. It’s also a little shocking how short a year really is. It seems like a long stretch of time when it’s laid out in front of you. But you’re going to spend a third of it asleep. You’re going to spend large chunks of it eating, showering, using the toilet, walking from place to place, and so on. The reality of it seems to be that after everything else, I only have a couple of hours – maybe up to 4 hours – that I can reliably count on to be productive with. And when I look at my calendar, I see that I wasn’t nearly as productive as I wish I was. And I don’t even think I was as productive as I assumed I’d be. That’s the scary part.

3. I spend a lot more time on Facebook or randomly surfing the internet – reddit and so on – than I realize. I went cold turkey on this back in 2013, which was good for a while, but it’s slowly crept back onto me. A part of me does think that I want to build relationships with people on Facebook for my long-term writing career, but I need to be very precise about what exactly I’m trying to achieve with that – because otherwise it’s sickeningly easy to fall into the trap of just hanging out in the common room all day. (Which was what I did when I was in Junior College.)

4. I was talking to a friend over a beer and talked about how we’re going to be turning 27. Lots of the celebrities that we looked up to – Kurt Cobain, Amy Winehouse, etc – they never made it to 28. Jimi Hendrix, Jim Morrison, Janis Joplin. All of them crashed and burned one way or another. And it looks like we’re probably going to make it to 28.

4b. I just thought that was interesting, because making it to old age in a healthy and functional way, I think, requires effort. And we’re crossing a threshold now, and once we’ve crossed it we really have to shed our old skins. We have to reimagine ourselves as entirely different people, in a new stage of life, reborn.

5. All this calendar talk is really about me circling around the idea that I don’t want to waste any more time. I don’t want to allow forces beyond my control to dictate how I spend my time – or if that’s inevitable to some degree, well at least I want to minimize the amount of time that is taken from me. Life is so short. It passes so fast. I can’t believe 4 years have already gone. It almost seemed to have vanished in the haze. It went by while I was trying to keep up and trying to get by. I feel like I “deserve” at least a decade where I feel well-adjusted and happy and in control of my domain. Of course, nobody “deserves” anything. Life will bitch-smack you in the face if it feels inclined to.

6. Another thing I’m trying to tie up here is the importance of ruthless prioritization, which I’m sure I’ve written about before. I usually write myself into a frenzy to try and get myself into the right mood for agreeing that prioritization is important, but I rarely follow up with what I think is actually most important, and then eliminate everything else accordingly.

7. Well, for the remaining two years I’m going to make it a point that my word vomits are my single top priority. I’m going to have to write at least one every single day. I need to cross 650 by the end of the year, ideally I’d like to cross 700. I know it’s possible. I just need to make it a priority. I need to do it early in the day so I get it out of my system, before I do anything else. My 2nd priority would be fitness. I need to get healthier now while I’m still young. More on that later.


0607 – be sensitive to context

Roughly between ages 13 and 23 I was thoroughly convinced that one of the most powerful things you can do is to be really good at evaluating and crafting sound arguments. Rationality! Debate! Wisdom! I rearranged a lot of my life around that wishful ideal.

The past 3 years or so have convinced me that I’ve been fundamentally mistaken.

Let me try to explain why:

1. Sound arguments are always constructed within some context. (A therefore B, assuming X, Y and Z…).

2. The moment you start getting invested in the arguments you’re constructing, you begin to get blind to the world outside of your context. It’s like how you tune out everything else when you’re trying to perform a precise task.

3. When you get it right, you’ll get tremendous validation from other people who share your context. This feels very, very good, and is very, very habit-forming.

4. Sometimes you’ll win over people who are in adjacent, overlapping contexts – and these few instances are held up as glorious victories. You will cherish these. But these people were usually more or less already exploring your context to begin with. To put it very crudely, it’s like hunting docile rather than wild animals.

5. Once you start hanging out with people in the same context, there’s a sort of natural radicalization that happens. It’s not malicious; it’s almost ‘physics’ – the most attention gets naturally funnelled to the most egregious mistakes made by people outside of the context. So there’s a sort of ‘gravity’ that ‘pulls’ everyone closer to the ‘center’. The most radical members spend the most time in it, influence it the most, etc etc.

6. Now you have an in-group and an out-group. This is almost always bad news. The “sound arguments” are now almost entirely subservient to the group needs. The gravity is too strong, it bends the light, and almost nobody realizes this. The people who do realize this will typically be ousted from the group, or quietly leave themselves. More radicalization.

7. The primary way each group interacts with the other is by focusing on the absolute worst outliers of the other group. As SMBC said, “every group is some % crazy assholes”. Every group in turn holds up the outgroup’s crazy asshole as a sort of threatening bogeyman. (Of course, this doesn’t mean that all crazy assholes are equally bad or not-bad. Some crazies cause serious harm to other people.)

8. When a ‘normal’ member of the group encounters the other group, and gets caricatured as the bogeyman, their response is naturally to get upset, offended. They might try to argue for a while, but whatever argument they come up with, however sound or calm, can always be framed as “lol why u mad tho”. You can’t argue your way out of that one, the only way to win is not to play. (Or to win some other game OUTSIDE the narrow context you’re currently stuck in).

9. The vast majority of each group then ends up being highly suspicious of one another, and ends up barely ever having real conversations with the other. Their contexts are so different that they might as well literally be speaking different languages entirely. (And in fact, if you pay careful attention, they always are. Every in-group develops its own language.)

10. The only way out of this mess, as far as I can tell, is to avoid labels, avoid in-groups, and to try and make sense of each issue independently. And never try to argue with anybody to change their mind, ever.

11. The challenge with #10 is to genuinely, legitimately suspend judgement. You do this by realizing that your judgement is necessarily limited because it’s formulated within a specific context, and that the world is always bigger than your context.

12. If you’re good at doing 10 and 11, you will cease to be surprised or shocked by things like Brexit or Trump or any other supposedly outrageous phenomenon. The surprise mainly happens because you’re heavily invested in your context – the friends you talk to, the media you read, so on and so forth.

13. Let me try to return to the starting point – why I think I’m mistaken.

14. I used to believe that the way to winning people over, to making friends, to earning respect, receiving validation, serving the world, etc – was to get really good at debate, at arguments. The idea there was that if you get good at it, you’ll get closer to the truth.

15. The reality of it, however, is that you get very good at a very narrow subset of things. You just don’t see it because you’re so focused on it that the map becomes the territory for you. You become the person who understands the map better than anybody else, but then someday you’ll follow your map right off a cliff – because the map isn’t the territory, and it can never be.

16. It is much more difficult – and far more useful – to learn to identify the context that you’re in, and to ask yourself if that’s the context that you actually want to be in. If that’s the best context for you.

17. It’s exceptionally difficult because it requires relinquishing the validation that you’ve been conditioned to enjoy from arguing on behalf of your in-group. It requires (at least it did for me) a sort of self-imposed exile. In my experience, this is actually harder than quitting smoking. And it makes sense that it would be.

18. Actually, come to think of it, a lot of the frustration, ennui, listnessless, etc that I’ve faced in the past 3-4 years has been largely caused by discovering that so much of what I had invested myself into was really a narrow game. Consider, for example, once you’re an adult, how silly teenagers seem when they get all caught up in their drama.

19. To the teenagers, of course, it’s not silly at all. Their context is all they know. If you mock your child for being frustrated by his “trivial” context (when you’re being frustrated by your much larger context), don’t be surprised if he decides that you don’t understand him. Because you don’t.


Contexts, man. Context is everything. Everybody’s is different. Yours will change sooner or later whether you like it or not. When you recognize this, you don’t need to argue so much. But of course you can’t force this insight down anybody’s throat.