0118 – What I’ve learnt from writing over 120,000+ words.

In the past year I’ve done over 100 word vomits of at least 1000 words each, which adds up to over 120,000 words. It has been an interesting experience, and I think I’m growing and changing as a writer-and-thinker.

When I started, all I knew is that I would be a different person at the end of it, and that I would have learned a bunch of things along the way that I couldn’t possibly anticipate.

While I still want to reach the 1000 x 1000 milestone, there are a few other things I now want to do as well. A few pertinent “side-quests” have popped up, and I feel like I can’t fully commit to the “main story mission” (1,000,000 words) unless I get these out of the way. I feel like the experience and powerups I’ll get from these side-quests will only add to my main mission, not subtract.

For a couple of years, my blog was centered around my Singapore-centric social commentary. A good 80% of my top-grossing hits are about Singaporean politics and media.

Since then, I’ve gotten married. I become a homeowner. I got a full-time job. I had a blogpost reach the front page of Hacker News. I became a Quora Top Writer for the 2nd year running.

My perspective has changed. My priorities have changed. My interests have changed. My blog has largely remained the same. [See: Derek Sivers’ Why am I here?]

I still care about civil society in Singapore, and I will probably continue to speak up when I feel compelled to do so, but I don’t think I’ll be devoting as much time and energy towards staying on top of everything. There are others who are more qualified than me who are making a meaningful difference.

What will I devote myself to, then? Here are some thoughts on my mind:

1: I want to write about my vision for the future of education. I find a lot of the discussions in this area to be painfully myopic. Almost everything I’ve seen involves some rearrangement of familiar elements such as “student”, “classroom”, “teacher”, “curriculum”, “degree”… all of which I think are assumptions that need to be questioned. We need to reason from first principles rather than think by analogy- I anticipate that education will be disrupted rather than reformed.

I will need to be careful when writing about this, though, and my word vomits are anything but careful. Vaguely, I think that I am the recipient of such a modern education. I don’t have a degree, ut I got headhunted to work with some really cool people nevertheless. I have skills and perspectives that not everybody else has, and they’re valuable enough for me to pay the bills with. Of course, I might be an exception or an outlier of sorts, but I don’t believe that is the case. That would be awfully presumptuous of me. At the very least, the path I have taken is open to thousands of others.

2: Related to that, I want to write about what I perceive as “modern illiteracy”. Reading, ‘riting and ‘rithmetic are necessary (and horrendously lacking in some parts of the world) but insufficient. What differentiates the “modern literate” is the ability to think, process, expound. That’s just the half that I’m familiar with. Lately I’ve found myself feeling very illiterate. I know far too little about large numbers, about businesses and corporations, about law, about nation-states, about computers and how the internet works, about financial systems. What is money? What is debt? What is insurance, and how do you make good decisions? I am incredibly unqualified to write about any of this- all I have is my curiosity, which I will have to use as a compass of sorts.

3: I want to write about marketing in a way that is meaningful to me. I already write about marketing for work, but I do that in a way that is more… “professional”? Since I’m working in this industry, I want to see how far the rabbit hole goes. I want to really sink my teeth into it, unearth the viscera.

I have a nagging suspicion that a large proportion of internet marketers or even marketers in general don’t really know what they’re talking about. I can’t just say that, of course- that’s irresponsible, accusatory, naive, ignorant. Again, just following my nose here. Why is marketing as convoluted and chaotic as it seems to be? Why are so many people simply mouthing platitudes and feel-good quotes? Where is the real work happening, where is it making a real difference, and why isn’t this data easily and readily available? I want to write about that.

4: I know that I don’t want to keep writing about the same things. I know that I want to review movies and books, but I’m not really sure why. I just have faith that I’ll be able to connect the dots when I’ve made significant progress.

5: I know that I want to do real-life experiments and document them on my blog. It’s funny, but one of the biggest epiphanies I’ve had from writing like crazy is that writing can only do so much. My writing guided me to realize that writing is inherently limited as a tool of exploration. It’s a fantastic tool, but ultimately it can only show you where you need to go, what you need to do. I attempted to do this in a very simplistic, superficial sense when I first started blogging here. You can dig into the archives and look for them if you like. They’re pretty embarrassing, vapid wannabe-motivational/lifehacker nonsense. But I’m keeping these posts around to remind me that you have to get the crap out of the way so you can get to the good stuff.

6: I know that I want to be useful. I’ve always wanted to be useful. My best writing and my best living, even, happens when I’m trying to be useful. Things start falling apart when I lose sense of that and start trying to impress people, or boost my ego one way or another.

I’m still figuring it out along the way. I know that I have a whole bunch of other things I want to write about. I want to write a history of Singapore that I personally find interesting. I want to write… there’s a lot of stuff I want to write.

The main quest still stands. I wonder what I will have changed my mind about at word vomit 200, 500, 1000. We’ll see.

Oh yeah, what have I learnt?

1: The early stuff is always crap.

2: Sometimes I’ll think something will take off, but it won’t.

3: Sometimes I don’t think something will take off, but it will.

4: Usually, if I find myself sweating (the sort of high-tension sweat I get in a high-stakes social situation, or even in poker), and I’m sort of frightened to publish, it’s a good sign. But sometimes it’s a total miss.

5: As I write more, I find myself able to sort my thoughts better as-I-go. I’m publishing this post without editing. I find that my unedited thoughts today are better than my edited thoughts a couple of years ago.

6: I warned my readers/audience that I was going to severely bore them with incoherent rambling. I expected the readership to drop. While the raw numbers did go down, I was getting great engagement. People were increasingly messaging and emailing me to tell me that they enjoyed reading my incoherent rambling. They found it more honest and compelling. I realize that my earlier numbers were entirely vanity metrics- I was getting clicks from people who just wanted to read controversial, anti-government rhetoric without engaging me. One of my most popular posts is “Sex in the ACJC”. I doubt those readers were very interested in what I had to say. Any regular reader of my word vomits, though, is a valuable asset to me (and probably a little crazy).

There ain’t no getting offa this train. I hope to do at least 200-300 vomits in 2014 as I make it a more integrated part of my routine.



0117 – sleep

I don’t really care for resolutions but I’m going to experiment with a month of sleeping early. (2014 edit: HAH.) I’m starting now to get a running start. I believe it will make me Fitter Happier More Productive. I believe it has worked for me in the past and I believe it will work for me moving forward. I find that when I sleep before 11pm, I wake up earlier AND more well rested. This was most clearly evident during my NS days and during other brief periods.

I need to write down my processes and make them more explicit. I want to increase my output. I believe that I have been sitting on a large stash of excess capacity that is continually being wasted. I think a large amount of that comes from me having unclear priorities. What is my workflow? If I were to step outside myself and observe myself, what would I notice?

Bad posture, lack of exercise, too many tabs open, too many distractions, constantly just trying to get by. I need more focus and clarity. I can’t conjure that out of nowhere; it starts with sleep. Sleep makes me make better decisions. I remember that I used to smoke more when sleep deprived. The brain just needs rest sometimes. The kind of work that I do especially demands mental acuity.

I realized this in greater detail yesterday when I was doing a pomodoro of work. I work best in short bursts. I should design that into my workflow.

I slept at 12mn last night. I was hoping to sleep at 11, but I was “doing some stuff”. I woke up at some point in the night- I didn’t check but I think it would’ve been around 4am- and I went back to sleep. I woke again at 8am. Lay in bed til 815. Reddited and tumblred till 9, which on hindsight was a bad use of my time. I should not go online until I get a chunk of stuff done. I should probably shower immediately after I get up instead of drawing it out. I’m on the way to work now though, and I’m both fresher and slightly earlier than usual.

The best thing about sleeping earlier, I think, is waking up more naturally. Less abruptly. I know that military folk train to be functional while sleep deprived, but hey. Even Napoleon supposedly took naps on the battlefield. On hindsight it’s ridiculous how little attention I give to my quality of sleep, considering that it directly influences my quality of life. I feel myself less stressed, more alert. I’m breathing more deeply. I feel less likely to want a cigarette.

It’s interesting how we take drugs to alter our consciousness, or we demonize and/or criminalize people who do, when pretty much everything we do has a similar effect. Life is drugs. Exercise is drugs. Sleep is drugs. Sex is drugs. Facebook is drugs. Smartphones are drugs. Food is drugs. Driving when sleep deprived can be worse then driving under the influence. Clearly a lot about life- if not everything about it- is about managing one’s consciousness.

If I could I would mandate that everybody experiments with their sleep and diet and Facebook usage. Since I don’t have the authority to do that I’ll have to do the next best thing: experiment myself, and report my findings. I’ve already found that I’m a happier person when I spend less time chasing hits on social media. I’ve already found that vegetable salads make me lighter on my feet and fast food makes me a little sick- salty fries burn my palate. Coke messes with blood sugar levels. Cigarettes make me snivelly and cough, they narrow my field of vision and they make the world look less colourful- this is something I’ve noticed over and over again. Whenever I go off cigarettes, colours look brighter. My sense of smell improves, as expected, but so does my sense of touch. Even my field of hearing feels “expanded”. What cigarettes seem to do is “tune out” the world.

Here’s a thought I had earlier: we fixate far too much on the people we meet. We allow them to shape our view of how the world is. In reality the world is infinitely more complex. Whatever your experience of the world is, there is more. No matter how outcast you feel, there are others out there who relate to you, your ideas, your experience. You can find a support network for almost any lifestyle you might have or background you might desire.

I’m thinking about the boys who annoyed me in secondary school. I wonder where they are today, what are they up to now? And then I realize that I don’t really care. Why should I? I have a life of my own to worry about, and people and projects that deserve my attention more. I wish I knew this when I was a kid, in a way that would’ve been meaningful to me. I would’ve worried less about their approval or the nuances of our social relations and focused more on the stuff that I personally wanted to do- stuff I sort of lost track of along the way, overwhelmed by adolescence. What do I really want to do, anyway? I want to be of use to others. I feel like that’s the most fundamental insight I have. I want to pursue my curiosity and I want to be useful to others. Or as Neil Tyson put it, learn something new everyday and help people along the way. I think that is a life well-lived.

I want to be a lot more prolific than I have been so far. I’ve written 800+ Quora answers, 15,000+ tweets, 600+ blogposts. That seems okay, but I’m sure I can do better. I’m convinced by the argument that you can’t really boost your batting average, what you can do is bat far, far more times.

My thoughts died around here as I got to work. I think I’m going to have to refactor my blog, change things up. I think I might have to revisit my ideas about scaffolding. I’ll write a separate post about that.


0116 – writer’s “block”

It’s been a full month since I last published something. When I started out I naively thought that I’d be able to publish two vomits every weekday and maybe three on the weekends. I think there HAVE been days when I’ve written 3 or 4 vomits, but I vastly overestimate myself, over and over. I overpromise and under-deliver, which leads to me living an uncomfortable life of lies and inaccuracy. I am increasingly clear that that’s not how I want to live my life in the future.

Why haven’t I been writing? Some family stuff cropped up that I didn’t know how to handle, and this external stressor just demolished my existing system. My fitness routine, reading habit and guitar practice all suffered too. I haven’t been able to write anything for Poached either, and it’s been a struggle just to stay on top of my work.

I have always been uncertain about how to operate when you’re writing about things that could potentially impinge on others. I remember when Lilly Singh uploaded a video about her family life and then promptly took it down, presumably because her family was unhappy about it. I don’t know. I don’t know and so I clamp up and get blocked, because I can’t possibly write about X when my mind is heavily preoccupied with Y. I suppose on hindsight the solution might be to write anonymously, say with a throwaway account on Reddit, or maybe to write fiction. I have little to no experience with either.

Anyway I don’t want to think about that too much right now- it makes me uncomfortable and I don’t have the luxury of going through that when I have work to do. That is something I can’t resolve in a vomit- I’ll need to set aside time to write, think, edit, revise, reflect, meditate. While I call it a luxury- because it requires time and focus- it’s also a necessity, because I won’t be able to operate at 100% until it is resolved. In this regard it is much like an injury.

So setting that aside for a while I think the most important thing for me to learn here is the importance of redundancy, of reserves, of deep assets, of emergency routines, structures, backup plans. Here I think I am arriving at an insight that only comes to me in times of difficulty, which I need to preserve to inform my “peacetime operations”. An analogy:

If I were a nation-state I’d be screwed, because I wouldn’t have a standing army or strategic reserves. I’d be a straight-talker, saying what I mean even if it offends people. This will inevitably get me in trouble. The problem is, I’m unable to empathize with venomous, grudge-holding people. I forget that they exist at all. I don’t hold grudges. I’m just not predisposed to.

I remember that there were moments as a child where I wanted to get angry and stay angry with myself (typically for getting into trouble at school), or with my parents (for trying to discipline me). “I’ll show them,” I’d mouth angrily in the mirror. It would never last- I’d stop caring about it the next day. Everything fades away, everything will turn to nothing, why be angry?

I sometimes think my akrasia- my inability to follow my own instructions- comes from a deeper wisdom that knows better than my short-sighted, fleeting ambitions. I trusted
‘chaos and randomness’ because they were easier to accept than badly made plans, or well-made bad plans, or well-made good plans that were badly timed, or badly executed… I would have to take the blame for all of it, and it seemed silly and wrong.

I responded to the systems’ oversimplistic grand plans with an oversimplistic heterodoxy- my plan was to reject the plan that was foisted upon me. I have more in common with Republicans than I thought.

It is clear to me today that my approach was oversimplistic, and that there are costs to my Diogenesian lifestyle that weren’t obvious then.

Quick parallel aside: when I look at my writing from 2009 to early 2012, I see a writer who has too much time on his hands, who presumes too much of his audience. I wrote in a sprawling, tedious manner. It was self-indulgent and unnecessarily ornate. I’m still less succinct than I could be, but now I’m pressed for time- I’m writing this on my morning commute. The biggest difference is practice, of course- the more you practice, the more you develop your aesthetic sensibility, and the more you get frustrated with unnecessary elements. I think the second biggest difference- for me, at least- is the fact that I have real commitments and obligations now; bills to pay, work to do.

Let me restate that: I think the constraints of being a working adult is forcing me to become a better writer, because I have to say more with less. I don’t have the time for long drawn out arguments on Facebook anymore- those were like little scrappy catfights more for personal entertainment and minor social point-scoring than the fundamental development of my craft. It helped, I think, but it wasn’t optimal. Still, suboptimal progress is better than optimal fantasy.

Let’s return to this idea of the random/chaos lifestyle. I thought I was being free and wild but I wasn’t- I was in suboptimal routines of my own. I didn’t grow and develop as much as I could’ve. As Scott Adams put it, losers have goals, winners have systems. I rejected goals, but I failed to build a good system. There’s the rub. The absence of goals does not make a good system. A good system has to be carefully crafted.

Earlier I talked about badly made plans, well-made bad plans, etc. All of those can be avoided through a gradually built system (as robust as possible) for navigating complexity, for exploring the unknown. It can be done, and I think I’ve done a bit of it by accident over time- that’s what experience is, that’s what wisdom is. But I think it can also be pursued and built deliberately, and that’s what I want to do.

Ok I got to work, continue in the evening