Assumed Audience: anyone who has ever struggled to start something new and unknown and therefore difficult and intimidating.

I am sitting here on a weekday evening, trying to figure out exactly how to start building rewrite. There is an enormous amount to be done, and I genuinely have no idea how to do… almost any of it. I asked myself: “Where would I start if this were a web app?”—because web apps are my bread and butter, the place I have spent the majority of my time over the last half decade.

But the answer is that I still don’t know. I have only started two completely “greenfield” projects in my entire career. In every other case someone else had done this part, and in most cases I was working with a product manager or someone like that, who was divvying up the tasks. And those two greenfield projects were (a) extremely well-scoped and (b) of a very different sort than this one is. The last time I started a truly greenfield app, it was for a web app… but a web app extremely heavy on words: exactly my home terrain, as it were, on the web. Not that different from a blog.

This is not like that. The problems to solve—managing references, dealing with PDFs, writing large documents, building up projects, you name it: they are all completely new to me. And it’s just me: no product owner handing me feature specs.¹ I’m out of my comfort zone even in terms of the technologies I’m using: no deep comfort with the web stack here to fall back on.

Can I do this? Yes. I can. I’ll figure it out. I have figured out hard things before. But it doesn’t change the fact that starting is hard, and I have no idea how to begin.

I’m going to start anyway. Most of what I build these next few weeks will almost certainly get thrown away. That’s okay. I’ll have started. That’s enough for now.

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An aside, a confession: I have made an enormous amount of progress on my website redesign over the last month. Some of that is because it’s just plain fun. Some of it, though, is because it’s easier to keep working in my comfort zone than to buckle down and get started on the hard new thing where I have no comfort at all. Time to get into it.

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1. however ill defined!↩