Casting off for new shores

One thing I’ve learned this week – even if you know about the sunk cost fallacy, it can still somehow creep up on you unexpectedly.

Writing has been a lifelong dream for me. For about as long as I can remember, I’ve always been fascinated with stories, and would constantly dissect and re-imagine them in new ways.

But it never felt like the right time to actually write. The reasons are varied, complex, mostly depressing, some aggravating, and all in the past – the sum of it is that I’ve never really been able to settle on something that I actually wanted to do, and as a result of that paralysis, have done largely nothing.

Last year, May 2016, I redid this blog – archived all the old content, changed the domain name (supremely happy to have landed, let me tell you), and wrote this introductory post.

Fast forward a year, and while I’ve done some measure of that privately, I haven’t done nearly enough of it publicly. What I have done, instead, is retreat back to the same comfort zones I’ve always had.


Towards the end of 2016 I started getting agitated that I wasn’t making progress with my writing, and decided to tackle it as a pure productivity problem. People are writing and publishing books every day – there has to be a system that will work, right?

That’s where the idea for Write500 came from – my own desire to set specific goals that I could hit, every day, and make progress as a result.

But then my comfort zones kicked in.

When I talk about the “sunk cost fallacy”, the first assumption you might make is that I’m referring to the time I spent on this specific project – which is a factor. Over the last few weeks I’ve been working on Write500 more or less because it exists, and because I know there are people that are interested in how it evolves. Not so much because I think it can actually solve the problems I need it to solve.

So that’s one level of fallacy right there – working on something because I’ve been working on it before, and the cost of killing it is somehow (inexplicably and irrationally) unacceptably high.

But there’s another level to this, and it’s only in this last week that it’s really been driven home for me: My career so far is, itself, a sunk cost.

My approach to solving problems is almost always rooted in software, which shouldn’t be a surprise – I learned to program at a very young age, and because of my knack for it, I was able to get a job, which I was then able to turn into something resembling a career.

As a result, when I’m deciding the best way to add value to the world (which I believe is something we should all try and do, in our own way), my main inclination is almost always software. I keep coming back to it, thanks to how far its gotten me in life so far.

Over the last year though, that inclination’s been challenged somewhat. Last year around this time, I was in the process of handing over my biggest freelance client to another agency, thanks almost entirely to burnout.

The idea of working late nights developing software for paying customers had lost its appeal entirely, despite how absolutely brilliant it was to be able to monetize my nights and weekends, and build up some savings as a result.

I’ve had a similar inclination at work, too – whenever a new problem presented itself, and if it could be solved with some custom development, that would always be the first suggestion I’d make.

Which had not been a problem, really, up until the end of 2015 – I had latitude to develop things that I thought needed to be developed. The change of my job role had also forced me to change the way I solve problems – including occasionally not solving them at all.

I imagine it’s at this point that a lot of developers would quit out of frustration – feeling like they’re adding no value, or taking umbrage at not being able to use or grow their skills.

I didn’t quit, though, and I ended up learning something new: That it was possible for me to be productive (and add value) without writing a single line of code.

I’m sure that seems obvious to a lot of people, but it’s only recently become clear to me how big of a mental shift this actually is. And it brings me back to the thing about writing.

I’ve wanted to be a writer for as long as I can remember – the idea of spending time in my own world, creating characters and stories within it to share with other people – is incredibly appealing.

But with my very narrow view of problem-solving, I’d always look at my lack of writing as something that could be solved with software. And so instead of actually writing, I’d set out to shave as many yaks as possible.

It’s the old “if all you have is a hammer” adage – the problem of me not writing started to look like a nail. A problem that could be solved if I just found the perfect combination of tools, frameworks, and the right approach.

Which as it turns out, is horribly wrong – at least for me.

Most of my work on Write500 was underpinned by that. The first, most basic thing it was meant to do was deliver daily writing prompts (a tool I always wanted to build anyway). But beyond that, I wanted Write500 to solve two other problems: Be a daily go-to tool to produce new content, and be a revenue-generating SaaS product.

Except that neither of those things (and it’s obvious now) actually move me any closer to me being a writer. It’s actually the exact opposite: I’m creating new tasks for myself that specifically prevent me from writing, but justify it by telling myself that once I build this, I’ll be equipped to write.

Which is bullshit, and I think I always knew it was bullshit, but I let myself believe that anyway.

Another big dimension to all of this is that I’m doing all of this work in my spare time. What little of it I have, anyway. Time to work on these sorts of things is a scarce resource for me, and I haven’t been making very good use of it by focusing almost entirely on things that move me in the exact opposite direction of my goals.

And so last night, while processing all of this (and failing to fall asleep) I came to the eventual realization that I have to kill Write500. Specifically, the extensions to it – the daily prompts thing is still quite useful, and low-maintenance on my part.

Once I actually go through the process of producing and publishing something, I’m sure I’ll uncover lots of problems from that experience – and I might find a gap that could be filled with software.

For now, though, I’m rolling everything back and parking this project. A part of me still hates to do it, but the reality is that I have limited time available to me, and I’m not actually making the progress I want to make.

Instead, I now know I should be focusing on the things that are outside my comfort zone: Namely, writing things I think are shitty, and sharing them with people that might have nothing good to say about it. Which will be a start 🙂

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