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If you feel stuck or exhausted in a complex creative project, consider if it might be time to pause, take stock, and “start over” — i.e., shift to making a second draft.

First drafts are hard. Going from zero to one takes extraordinary effort. Once you got something, you can build and refine — which you must do since first drafts are far from perfect. But at some point, you must get perspective and start a new take on the material.

That’s where I find myself. A couple of weeks ago, I started work on the second draft of Duly Noted. I’m tackling this phase with renewed energy and focus, so I thought it’d be worthwhile to share how I went about it.

1. Take time off

I wrapped the first draft the week before Thanksgiving. After that, I decided to give myself two weeks off the project to focus on other things. During that time, I read other stuff, started a new client project, and prepared for the current cohort of my IA fundamentals workshop. IOW, I wasn’t on vacation — just taking time off from the project.

2. Review draft one

After two weeks of not thinking much about the project, I held my nose and read through the first draft. I started by exporting it as an EPUB, which I uploaded to Apple’s Books app on the iPad. This is where I read many other books; i.e., I tried to make the context similar to the one where I usually read.

3. Critique the draft

I went through the draft, annotating my impressions. I tried to imagine the book was written by someone else. What did they get wrong? Where did they leave logical gaps? Shifts in tone? Etc. I highlighted and made comments in the ebook, which I synced to Obsidian via Readwise.

4. Revisit the outline

My outlines are two-dimensional matrices: I note chapters in the horizontal dimension and “beats” in the vertical dimension. Beats include the main points that need to be in each chapter, explanatory material, examples, opening and closing framings, etc.

After months of working on trees, branches, and leaves, it’s useful to examine the entire forest. Does it make sense? What empty patches emerged in revisiting draft one? Is it flowing? Are any ideas in the wrong sequence? (They were — I moved three chapters and several beats.) This work is straight-up information architecture that leads to a more cohesive narrative.

I’ve traditionally done this work in Tinderbox, but for this draft, I used Apple’s new Freeform app just for testing. Of course, the two tools aren’t comparable, but I like Freeform’s relative simplicity and (especially) its availability on the iPad, where I do much of my thinking.

5. Start a new draft

This is where I find myself: starting a new draft in my writing app. I used Scrivener for draft one, but I’m considering writing draft two in Ulysses, where I wrote Living in Information. (I’m excited to try the new version of the app, which better supports larger projects.)

Of course, I’ll reuse lots of what I wrote in the first draft. But starting anew allows me to restructure the project based on the revised matrix from step four. Ideally, the result will be a book that flows nicely and feels cohesive.


The first draft is how I externalized my thinking and found focus for the material. But it’s a lovely mess.

Re-starting with a new structure based on what I know now is tremendously energizing. I still have a long way to go, but I’m excited. Among other things, shifting tools gives me a bit of that new notebook rush.

If you’re feeling stuck, consider whether it might be time to leap to draft two; shift levels of detail and work using different modalities and tools. You might fall in love with the project all over again.