the anti-schedule nearly broke me / #16
on structure (or the lack thereof), spiraling, and starting over (again)
It started innocently enough.
Six weeks into my sabbatical, and I had a rhythm: morning meditation, workouts and cardio sessions, deep work blocks that produced, framework sessions that felt purposeful. Even family time had its own distinct shape.
The system was working — until I decided it wasn’t.
Maybe I’m being too rigid, I thought, staring at my carefully structured day plan. Isn’t the whole point of a sabbatical to break from structure, and explore?
So I tried the opposite. I started what I called the Anti-Schedule Experiment.
In my April 20 newsletter, my note read:
This week's experiment: operating on my anti-schedule — sleeping past my alarm, gym in the evening, creative work at night. Spoiler: I really don’t like the anti-schedule.
This was a spoiler that turned out to be a prophecy.
I wanted to follow my energy instead of a calendar. Trust instinct over time blocks, and to access that mythical float through days, getting in a state of spontaneous genius, free from reminders, alarms, or task lists.
After all, hadn’t I left the corporate world partly to escape the tyranny of the calendar, and of being at the mercy of people who could double-triple-quadruple book my time? The neatly sliced 30-minute blocks dictating when I could think, eat, or exist?
So I cleared the board. Turned off reminders. Flipped my schedule upside down. Ditched the habit tracker.
When I had woken up at 6:30am to work out, I was now gleefully hitting snooze and drifting through mornings. The structure I’d once seen as discipline started to feel optional.
I’d scroll. I’d snack. I’d lie on the bed and think about writing, but never quite start — so I turned to my Kindle instead. Reading is self-care, right?
The days stretched wide — and somehow, still ran. Fluidity!
Freedom, baby.
It’s 3PM on this Sunday. I haven’t worked out. I told myself I’d go this morning. Then later. Then after lunch. Then after writing this piece.
I still don’t know if I’ll go, or not. (Editor’s note: She did, and she ran a 4km. Please clap.)
And this wasn’t a one-off. This had scarily become the pattern. Intentions evaporated in the open space where structure used to be. What I thought would be freedom felt more like drift.
And the worst part is, I saw it happening in real time.
No, actually, the worst part — it was only meant to last a week. It’s been a month now, like spurts of acceleration in the engine but going back to the default.
The aftermath of the anti-schedule, in metrics:
Writing output: ↓ 78%
Workouts: vibes-based, occasionally fused into a single “okay, I stretched, that’s enough” session
Creative work: functionally absent
Sleep: irregular and mediocre. Naps are up, though
Family time: physically present, mentally buffering
Screen time: from under 2 hours, to 6+ hours per day last week
Journal entries: one night was just: “haha”
Negative self-talk: now available 24/7, a subscription I didn’t know I signed up for
But the real cost? A steady, low-grade anxiety. Like I was squandering something important.
Probably because I was.
I’ve built systems for teams. I’ve designed products for users. I know how to reduce friction, create flow, and make things feel intuitive.
And yet, when it came to (re)designing my own time, I somehow decided I wanted to ship a featureless prototype. No guardrails, no feedback loops, no triggers. Just the illusion of freedom.
It’s the UX equivalent of “click here” (terrible UX writing, that needed to be said)—
—and then... nothing.
Creativity needs constraints. Otherwise it’s just chaos in a nice font.
In my disproved hypothesis, structure was the enemy.
But now this is how I see it: Structure is a taut line between freedom and discipline—too tight, and it snaps; too loose, and it sags.
But just enough tension? That’s where momentum builds. That’s where energy transfers. That’s where you can walk across.
I had let the line go slack, too fast, too much. So I drifted.
So… Now, I’m rebuilding. Not going back to rigidity (or what I thought was rigidity!) — but forward to something more livable and sustainable.
Morning anchors: A consistent start (meditation, writing, movement), no fixed time, but a defined opening
Themed time blocks: Creative, admin, social etc. Not hyper-specific, but enough to shape the day
Bookends: Back to my brief morning log, and in-depth nightly journal: something small that mark “I’m on” and “I’m done”.
I’m calling it designed flexibility. It’s not going to be perfect, but at least I know what I’m building toward now; three weeks overdue.
Whether we realize it or not, we’re always operating inside a system. The question is whether it’s one we chose, or one we defaulted into.
I spent a month in default mode. It really sucked. It looked like freedom, but felt like a blur.
But it wasn’t chaos that wrecked it: It was the absence of design.
Tomorrow, I’ll be up. I’ll be moving. I’ll be writing.
That's the design, anyway. The implementation is where it gets interesting.
Other things
Trying to read Dopamine Nation and getting distracted by shiny things around — a real meta case study coming up soon
Went for my dental check-up, and she said she had no notes; my dental health is excellent, and I should keep doing what I'm doing. This is the adult version of getting a gold star and a sticker at the dentist's office.
Until next time,
Jalyn