I had an invigorating conversation with my ex-boss and mentor Dinesh about how and why I’ve been creatively stuck in lately. (We recorded it for youtube, so you can actually watch the whole thing here.) One of the things that came out of that conversation was the idea that it would be very worthwhile for me to catalogue the contexts in which I’ve been creative in the past. Right away I know that if I overthink this or try to cover everything I’ll probably be overwhelmed and quit, so I’ll just sketch out some memories.

• Answering questions. Joining and posting on Quora from about 2012-2015 or so was a very significant part of my development as an author. I think the interesting thing here is how it eventually stopped being that. The creative context collapsed. Why? Quora started to get flooded with low-quality slop, probably to try and meet their growth targets. (See: How did Quora get so bad?) But in the early days, Quora was wonderful. Lots of thoughtful people asking and answering questions. I remember being in awe at some of them, like when a retired commanding officer of an aircraft carrier showed up to answer what it’s like to run one. Being on Quora felt exciting and inspiring, like I really had the opportunity to participate in this global meeting of minds.
  • I feel like there’s two parts to this, the Q&A part and the quality of one’s peers part. I have also written a bunch on reddit over the years, though I just took a few minutes to review my past reddit posts and comments sorted by upvotes and I’m slightly underwhelmed. Oh I suppose I put most of my effort into posting on my local subreddit /r/singapore. That explains it. I’m also reminded of the prior years I spent on my local music forum soft.com.sg.
• Good conversations. Some posts I write almost immediately after having a conversation with someone. They might not necessarily be finished. Some of my friends seem to inspire me more than others. You can look it up.
  • Helping someone else with their problems. One of the best examples of I post I have about this is why were you late?, which is largely a retelling of my experience working for Dinesh, which I have often found myself sharing. ‘Stories I often tell people’ are a great prompt for this. I’m currently
• Getting mad. A significant part of how I got my start as a blogger was when I got really upset about what I considered a misrepresentation of statistics in Singapore’s national newspaper of record, The Straits Times.
  • One of my funnier and more enduring bits of satire was “how to bullshit everyone with an inspirational success story” – I originally wrote a facebook status ranting about how bad some post was, and got a couple of “why are you so bitter” comments, and then I turned it into comedy.
  • I like to help people if I can. But from time to time I get frustrated when people ask for help in clunky, tedious ways that make it hard for me to respond to. This led to me writing how to ask for help, which I update from time to time.
• Jokes. David Ogilvy said “the best ideas often come as jokes, so make your thinking as funny as possible.” A recent one that came up for me was notesprawl. This might maybe also be an example of mixing metaphors.
• Solving my own problems.
• Reader demand. I never particularly set out to write Friendly Ambitious Nerd. Rather, people who enjoyed my twitter kept telling me that they’d buy a book if I wrote one. I then thought long and hard about what I’d want my debut work to be. I already had several works-in-progress at the time, but I wanted my debut work to be accessible, easy-to-read, and something that I’d be happy to be introduced as the author of.
• Unfolding. I think it’s generally interesting how i have some forms of writing that are updated periodically over time, which fits nicely into the “christopher alexander unfolding” class of thing. It seems like it would be useful to have a master list of most updated posts.
  • I try to look for patterns in things that I’m always talking about with people.
• I have a class of posts that are basically naming things, or phenomena
• Poached – there was a period of time where I used to write for a now-defunct online magazine. There was something about that external constraint– having an editor with deadlines– that really challenged me to post something regularly. Also I liked the other authors, who were my friends, and I was in a sort of friendly competition with them. There have been two instances where I was contacted by an editor of a much more established publication, and I basically procrastinated until the oppotunity decayed out of possibility.

Having written this stuff up and then glancing at my drafts, I realize that one of the issues with a lot of my drafts is that they start from a place of excessive abstraction. Like “smartphones” or “wretchedness”. These are idea-shaped but not people-shaped. People-shaped ideas are broadly ‘easier to work on’. That’s not precisely correct.’

while writing this i googled “creative context” and the top link is some rough notes on creative context by michael nielsen. the internet is so small

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(sparring with ego) So let’s talk about (1), inefficiencies in my process. I used to rely on my commutes as load-bearing scaffolding for my creative work. I needed to go to work every day in order to pay my bills, and the commute was an unavoidable amount of “dead time”– which turned out to be a blessing in disguise, since I could use it to write, and it was a roughly fixed amount of time every day. One idea I’ve toyed with is simply getting on a bus every day just to write. It seems a little silly, but I think it could work. When I try to work from home, I end up getting distracted very easily. I could write probably write a whole post about my views on ‘distraction’ as a concept, and maybe I will. The tweet-length idea is: in order to get distracted, you first need to have something to get distracted from. Which is to say, if you don’t have a destination or goal in mind, you cannot technically be distracted from it. And I do believe fundamentally still that we gotta focus on what we want to see more of. If I don’t have a sense of what I want to be writing, then of course I’m going to get “distracted”– it’s perfectly normal to meander randomly when you don’t have a destination in mind!

A couple of other riffs on process? what is inefficient about my process? I have too many unfinished…

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