2026feb27: revisiting this post while reviewing my archives and thinking that I ought to be making collections on here too. always be making collections. I gave this advice to one of my clients and he loved it

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I’ve been freshly noticing recently that when I sit down to go through my writing and notes, I tend to get overwhelmed pretty quickly. And when that happens I tend to look for a distraction, like twitter or a game of online chess. Now that I happen to be in a place where I have a bit of meta-awareness of the feeling of overwhelm, I wonder if I can intervene differently and do something about it. Or maybe even before that, I wonder if I ought to describe the feeling of overwhelm? Let’s try that.

I have a document on my Roam titled ‘substack drafts’. It’s a nested list of lists of lists, with 74 top level bullets, and 65,000 words in total. That’s basically a book’s worth of wordcount, and it suggests to me that there might even be multiple books worth of ideas in there, because a lot of the writing is sketchy and incomplete. This thought itself gives me a bit of anxiety. What am I to do with all of that? Even writing out all the top level bullet points here would take a bit too much time and space. Or would it?

Well, right away I find myself thinking back to previous times in which I’d managed information overload. I remember when I used to work on infographics in my last job with my designer colleague. One of the things I’d do is, I’d lay out all these quotes or data points on a spreadsheet– there might be 50, 100 points– and then I’d try to sort them into buckets, maybe about 12-16 buckets. Maybe I should try that?

Alright so– here are the first 21 out of 70+ drafts. That’s already more than the number of categories I’d like. This also fits nicely into 1 screen on the macbook I’m using. Before I add more drafts vertically, I’d like to move some of these to be horizontal to others that are related. What are the themes here? Digressions feels like a sub-point rather than a main essay. I think I’ll put that next to ‘cleaning up a body of work’. “Should I be capitalizing substack” is actually an essay about language, and also about media, so it could go either next to ‘understanding media’ or ‘in other words’ or ‘plaintext literacy’. Oh, and ‘hypertext magic’, ‘luckmaxxing’ and ‘becoming a legend’ are clearly all related…

After moving some stuff around, I have this. I could try and collapse it further into fewer rows with more columns, but I think that would be premature– I don’t yet know what the optimal configuration is, and new entries might change how I think about ordering them. I think it’s time to add more drafts… as I keep going I notice some bullets that are similar enough to be worth literally merging… here’s an update of where we are now:

Okay! Okay. Here are almost 60 drafts laid out in 10 “collections”. I feel some kind of vague relief at this. It’s not a perfect structuring or ordering, but I find it vastly preferable to the unordered list I had earlier. I’m still missing some entries, and there’s a whole ‘nother set of drafts on my substack itself that possibly deserves similar treatment. Funnily, I’m now reminded that I have a draft that’s about the idea of relief, too.

I have several options here. I’ve made some progress on a problem for myself in real time, so this was time very well spent for me. I decided to do it while ‘writing out loud’, so now I have the above document you see before you. If you’re reading it, it means I had hit publish. But there’s an additional little puzzle I have to solve first: does me solving a little puzzle for myself, without much explanation or detail about the specific elements of the puzzle, feel like it crosses my internal ‘publishing threshold’? Not quite. I need to add something else to feel good about sending it into people’s inboxes. But what? I could… describe more about how I’m feeling. I could… go look at the rest of my drafts and see how they fit into this. Now I gotta go to bed though… gn and let’s see if I pick this up tomorrow or some other day.

(note to self: if the above images break, I can recreate them by looking for ‘2025jul blog architecture’ on my google drive)