My Writing Workflow is All Messed Up

A nice thing about having written a blog for awhile is I can go back and see if my younger self has an answer to a current dilemma. Here’s me, 9 years ago:

Life is short and the considerable time I spend wondering which app has the best Markdown implementation is time thoroughly wasted. Write more, shop less; all of this will end someday.

Oof. As the kids say, I feel seen.

To my younger, apparently wizened, self I say to hell with it. I’m going to ponder the dumb question of how I write anyway.

Jason Snell kinda opened this whole thing back up for me with a piece on his search for the perfect iOS writing tool. His issue is that he can’t quite find a solid iPad app that comports with his Mac writing workflow. My problem is that I don’t even have a decent writing workflow on my Mac anymore. It’s all just gotten away from me.

I used to push text around from folder to folder, app to app, without much care about how it got there. Dropbox, for the longest while, was the linchpin of such operations. Then, at some point, I started preferring library type apps, like Ulysses, Drafts and Vesper. I loved being able to dash off a note and know it would be saved somewhere. I didn’t even need to name the files; there were no files, practically speaking.

But it wasn’t to last. My Ulysses library has grown bloated. A bad sync years ago has left me with multiple copies of a ton of sheets, and no easy way to weed out the duplicates.1 Drafts, similarly, has become a silo of disorganization, a messy hoard instead of a manageable archive.

And so I am drawn to the idea of keeping my writings organized on disk instead of loaded in a library. At present, I have no idea how to do this. Should the files just be named whatever I want to call them, or have date-based filenames? Should I make a bunch of subfolders with dates? How granular? It’s a processn…

These days, on the Mac, I prefer writing in BBEdit for reasons I can’t quite explain. It just has a certain solid feel to it, the kind of feeling that great Mac apps have. Organically, I’ve found over the last few months I just end up there. Most any note I have to jot down or text I have to paste, it’s happening in BBEdit.

So, assuming I settle on a naming organization, the questions become: where do I save these files and how do I access them on my iPhone and iPad? iCloud Drive seems to work well enough for saving. It even retains the different versions of the file so I can go back in time and see if I scratched out a brilliant idea.2

As to working with documents on other devices, I’ve been messing around with Taio. It’s a powerful app, but something is missing. I don’t quite know how to explain it. In exactly the same way BBEdit feels solid Taio just…doesn’t.

I don’t know, I’m still tinkering with it. Around every corner writers (including, to an extent, Snell) are recommending iA Writer. I haven’t used it since the whole patent thing, but maybe it’s worth another look on iPad.

If I ever settle on a form of document organization, I’ll need apps to conform to my system and not the other way around. Maybe soon I’ll wrap my head around all this and have a better writing workflow. Yeah, that’s it; it’s just around the corner.


  1. It should be easy to figure out which documents contain the exact same text, and it would be if the duplicate files were just some text files on disk. ↩︎

  2. I didn’t… ↩︎