0601 – consider the end-game

So we’re now 60% through with this word vomits project. A lot has changed. All I knew in the beginning was that I wanted to be a writer, and that completing 1,000,000 words would make me feel more legitimate as a writer. And hopefully, ideally, it would itself make me a legitimate writer somehow. I knew that the goal was too vague, but the hope, or the plan, was that I would figure it out along the way. Well, we’re along the way. We’re more than halfway along the way. It’s time to start figuring out with much more precision than when I started.

I’ve been reading some horror stories online about how there are published writers who have gotten great reviews for their books, and yet they’re broke. A part of this is because of bad deals with book publishers, who only really give great deals to proven rockstar authors. That’s just the name of the game. Another part of this is, more simply, that they don’t have enough fans, enough followers, enough supporters, enough readers, enough people who’re willing to say yes I’ll pay $20, $30, $50 for something that you write. A thousand readers who’ll pay $10 each is $10,000. Probably about 1% of readers will pay, so vaguely I think we’re working with numbers like 1,000,000 readers -> 10,000 customers -> $100,000.

I find myself thinking about how my boss once talked to me about the process of recursive calibration and optimization that needs to happen. You might start with “build a billion dollar tech company”, and then have to break that down into “make product” and “acquire customers”, and then break those down further into progressively more nuanced and complex bits.

There’s a similar thing with a writer’s career, I think. Which is to produce work, and acquire paying readers or patrons. Write the damn things, and make the damn money. But those things are of course more complex than that, so we can break it down further.

Body of work + pool of readers -> monetization. Each of those things is infinitely more complex as well. Well, let’s dig into them.

Body of work.

I have many different things that I’d like to write about. I don’t have infinite time to write about everything that I’d like to write about, so I’ll need to prioritize. To prioritize what to write about I’ll need to have a framework of prioritization. First I’ll need to have a list of all or most of the things I want to write about. I think the state of this is pretty well covered. Next I’ll need to know what to write first. There are a few heuristics I can use for this.

One is the path of most interesting, which is the most fun and engaging thing to do as a writer. This fun aspect is important, because if I’m not having fun I’m not going to be able to keep going. But there are more variables to consider. Another is, what will people want to read? (This already overlaps with the READERS segment, and we haven’t even gotten around to talking about it yet). I could write about something utterly obscure and unique to my life, like say, how I feel about some piece of furniture in my house, or I could write about the challenges I’ve faced in putting together a home as a Singaporean at a young age. Of course, I can do both in the same article – the point there is that every piece of work needs to have an audience in mind, and needs to be pushed out to that audience.

Pool of readers.

So far I’ve been writing word vomits primarily for myself. I intentionally cloistered myself away from the public domain. I chose to force myself to write 1,000 words in a rambly, unedited format so that I’ll be a turn-off to most readers. There was a time where I’d just comment on political issues and it would get me lots of hits. And maybe there may be some sense in going back to doing a bit of that, just doing it in a more intelligent way that doesn’t offend my own sensibilities. As long as I’m writing something that I think ought to be written, I think that’ll be alright.

I used to be moderately big on Quora, I had millions of views on my answers over there. It might make sense to point some links from there to my blog. Actually why haven’t I done this already? I’m going to do this right after I’m doing with this vomit.

I have also had some moderate success here and there from writing on reddit, and there are many different subreddits I could approach. In fact, it would be possible to work backwards for writing projects from the subreddits that I would want them to be successful in. I’ve been trying to gain weight all my life, I’ve made some progress, it might make sense to package all of that in a smart way for folks on /r/gainit. I’m willing to start pretty much anywhere for this, so.


I’m not too obsessed with making money from my writing ASAP. I wonder if that’s true, or if I’m saying that as some sort of defensive mechanism to avoid taking this whole pursuit seriously. I should get to an intermediary state ASAP instead of overthinking this. And the simplest intermediary state I can think of is – charge a very nominal amount of money for an ebook. Less than $10. Maybe $5. (This also makes me realize something about monetization – the people I think i’d most like to write for also probably are the least likely to pay me. It might make sense to write something about my experience as a marketer and start selling that first, just to get into the practice of selling words for money. I could do an ebook about the 7 sins that I used to obsess about, or about my thoughts on MBTI. Those are things that have ready audiences that people care about and will be willing to pay for. Those things don’t seem super exciting to do in of themselves, but they seem quite interesting once I frame it in terms of making my first few dollars as a self-published author. I don’t know if I want to be self-published all the way, but it makes sense to start and get to that as soon as possible.

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