Ugly Outlines, Clean Drafts
Introduction: Why “Ugly” Wins
I’ve fallen into the trap more times than I care to admit: sitting down to “outline” an idea, I open Notion or Obsidian or some new flavor-of-the-week outlining tool. Ten minutes later, I’m fiddling with nested bullets, collapsing toggles, and dragging things around like I’m arranging furniture in a dollhouse. I’m no closer to writing. In fact, I’m further away.
Digital tools invite polish too early. Paper invites motion. There’s a difference. One demands structure; the other forgives mess. That’s why I’ve learned to reach for an index card or a notebook when an idea starts tugging at me. The uglier the outline, the faster the draft.
The Five-Rung Ladder Outline
The backbone of my process is something I call the ladder outline. It’s literally five rungs, stacked vertically like a ladder. Each rung gets no more than two words. That’s it.
Airport
Lost bag
Dinner
Rainstorm
Hotel lobby
That’s a ladder. Five beats, each one a foothold. No bullet nesting, no Roman numerals, no endless sub-points that make you feel like you’ve done something before you’ve actually done anything. Five rungs give just enough structure to keep me moving forward without giving me a place to hide in “planning.”
Ugly? Absolutely. But it works.
Why Only Two Words?
Two words per rung force me to commit to essence over detail. “Lost bag” tells me everything I need to recall the story of scrambling through an unfamiliar airport with no luggage. “Hotel lobby” brings back the smell of rain-soaked carpet and that awkward conversation at the check-in desk.
If I let myself expand into phrases, sentences, or god forbid—paragraphs—I’ll start editing before I’ve even begun drafting. Two words keep the door propped open without letting me barricade myself inside.
Checkboxes and Momentum
Each rung gets a checkbox. When I draft through that beat, I check it off. It’s corny, but that little square carries weight. Crossing off a rung is like topping a hill on a bike: you feel the momentum pick up.
There’s something about seeing progress in black ink. Not theoretical progress (like fiddling with a digital outline that auto-saves in the cloud) but physical progress. You scratched the box. It’s done. Move to the next one.
Drafting From a Card—No Tabs, No Clicks
Once the outline is done, the card sits next to the keyboard. That’s the whole scaffolding for the draft. I don’t click between tabs. I don’t scroll back and forth through notes. I don’t get lost in formatting.
One card. Five rungs.
The draft unfolds on screen, and the card keeps me grounded. Ugly on the desk, clean on the monitor. The outline doesn’t nag me for attention. It doesn’t ping me. It doesn’t crash. And, most importantly, it never lures me into pretending I’m “working” by reorganizing instead of writing.
No app notification has ever popped up on an index card.
The Midday Reset: Scan and Adjust
Here’s where paper pulls double duty: the midday reset. By lunchtime, most mornings have gone a little sideways. Meetings, distractions, new emails—momentum drifts. That’s when I flip back to the outline.
Did I hit the first couple of rungs? Am I drifting into tangents? Do I need to add a note for tomorrow? A quick scan keeps me honest. Sometimes I’ll snap a picture with my phone and toss it into my Paperless-ngx pipeline so it’s archived and searchable. That way, the ugly outline has a digital shadow, but its primary job was already done hours earlier: it got me moving.
Ugly vs. Perfect: The Trap of Digital Scaffolds
Let’s be clear: digital tools have their place. I’m not anti-technology—I run half a homelab in my basement. But digital outlining tools are too good at pretending to be work. They let you keep polishing a scaffold instead of building the house.
Perfection in scaffolds is procrastination in disguise. I’ve built gorgeous digital outlines that led nowhere. I’ve built ugly ladder outlines that carried me through entire essays, talks, and even projects at work. The ugly ones win every time.
North Star in the Wild
This connects directly to my broader North Star approach. The North Star system isn’t about building the most beautiful constellation map of your notes—it’s about moving, card by card, step by step. Ugly outlines are just one of the tools that keep the orbit stable.
If you’ve read North Star in the Wild, you know the pattern: paper first, server backed. Capture it quickly, draft it cleanly, store it securely. The outline is the capture. The draft is the clean. The archive is the backup. Each plays its role.
A Real Example: This Post
Here’s the ugly outline that started this very essay:
Ladder outline
Checkbox
Draft from card
Scan midday
Cross-link NS
Five rungs, two words each. That’s all it took. The rest you’re reading now. Proof that ugly works.
Closing: Ugly on Paper, Clean on Screen
Every clean draft I’ve ever published began its life as an ugly outline on a piece of paper. Ugly is honest. Ugly moves. Ugly doesn’t care if the ink smudges or if the words aren’t clever. Ugly does its job and gets out of the way.
So the next time you sit down to outline, resist the siren song of the perfect digital scaffold. Grab a card. Draw five rungs. Write two words per line. Then put it by your keyboard and start typing.
Ugly on paper, clean on screen. That’s the rhythm that keeps words flowing.