## Set up Trello so your brain does not derail
Let me explain the main trap I fell into when I tried to use the Pomodoro technique with Trello: moving cards between lists messed with my flow more than it helped. I originally thought I was being clever. I had a board with lists for “Inbox,” “To Write,” “Doing – Tomato #1,” “Break 🍅,” and “Done Today.” So during a writing session, I’d drag a card across the lists as I worked through each Pomodoro. That turned into chaos fast 🙃
The catch? Moving cards manually during Pomodoro breaks is a trap. First of all, you’ll forget. Then when you remember halfway through Tomato #2, you end up losing half the break trying to fix the board. One time, I started dragging two cards at once and accidentally dropped a planned post into a client deadline list. No undo.
So here’s what finally made it simple: I stopped moving cards around during the Pomodoro entirely. I made a Trello label called “🍅 Focus” and that label is the only thing I change when I start a Pomodoro. That way I can filter my board to show only what I’m writing right now, without reshuffling my life.
If you’re brand new:
– Trello is a kanban-style tool where each card is a task (like a writing topic)
– You can organize them into columns (lists), add tags (labels), and even build checklists or due dates inside each card
And once you start pairing it with focused writing sessions, there are a few setup quirks you’ll want to fix early:
– Use separate boards for writing-only cards, or your brain will start scanning unrelated tasks
– Don’t use due dates for Pomodoro timing — it’ll just clutter your calendar
– Avoid browser Trello during Pomodoros — desktop Trello lets you Command+Tab quickly without seeing 35 other tabs
If I forget to filter by label before a session starts, my brain instantly tries to do 10 other tasks. So I automate it with a Zap: “Start focus timer → add 🍅 Focus label to currently selected card.” Yes, I once accidentally applied that label to every card in the board 😬 But if you’re careful with your Zap filters, it works.
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## Use a quiet Pomodoro timer for writing flow
Let’s talk timers. I used to think it didn’t matter what Pomodoro timer you used. Wrong. I used TomatoTimer dot com for maybe 3 years and thought I was fine… until I tried MacBreakZ. Huge difference. The audio fade, the screen dimming, the way it *politely* interrupts. It changed how I feel about writing sessions.
Here’s where it gets annoying: most Pomodoro timers reset your session history the second you close the browser tab. And if you’re toggling between Trello, a writing doc, and maybe a research tab? You *will* close that tab by accident, like I did 2 minutes into break number 3. Poof. No more tracking.
After nuking my session tracking like 12 times, I switched to a desktop Pomodoro tool. There are a few decent ones:
- Be Focused (Mac): great native app feel, can label tasks per Pomodoro
- Flow (Mac/Windows): gorgeous fade transitions, but labels don’t always save right
- Pomodone (Mac/Windows/Web): connects (sort of) with Trello, but also introduces a 5-second delay before every timer
Pro-tip: whatever timer you use, disable ALL sounds except the break alert. Your sessions should feel immersion-like. If the timer clicks or dings during writing, it yanks you out.
Oh — and if you have Focus modes on macOS or Android — set up an automation so that when Pomodoro starts, DND goes on. I had this weird bug where Slack notifications still slipped through until I toggled Slack’s “Respect OS DND mode” setting. Look in Preferences → Notifications. It’s not on by default 🤷
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## Build one card per session not per project
This one tripped me up way more than I’d like to admit. You might be tempted to make Trello cards for big projects: “Finish Blog Post on Zapier Tricks,” “Write Notion Automation Course,” etc. But those projects are way too big for one Pomodoro. So what you end up with is a single bulky card that constantly gets moved but never marked done.
Instead, I started making Trello cards per Pomodoro session. Literally:
– “Write intro paragraph for Zapier post”
– “Revise section about Airtable edge cases”
– “Create example for broken RSS Zap”
That way, the moment one Pomodoro ends, I can mark the card Done… and it feels *very* satisfying 🙂
Side effect: my Done list becomes a timestamped log of what I actually worked on. I used to feel like I “got nothing done all day” until I looked back and saw I had crushed six microcards.
To automate this:
– Use the Trello card template feature to make a blank Pomodoro card titled “🍅 Write [task here]”
– Set up a Zap (or use Trello Butler) that auto-generates a new card in your Inbox list every morning prefilled with the template
– Once you’ve picked your Pomodoro focus, edit one detail and drag to the Today list
I had a weird glitch with Butler once where it created two of the same card if I had another rule running that also watched the Inbox list. Stack those rules carefully or they’ll overlap and explode 😑
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## Automate transitions between sessions and breaks
This part feels magical when it works — like your workspace resets itself and your brain just follows along. I used Shortcuts on my Mac to do this:
1. When I start a Pomodoro (triggered manually), it:
– Opens my writing doc
– Filters Trello to only show 🍅 tagged cards
– Starts a 25-minute timer
– Pauses Slack
2. When it ends, I get a subtle notification saying “Time to stretch 🍎,” then it:
– Clears the Trello filter
– Plays lo-fi
– Starts a 5-minute break timer
But here’s the dumb thing I ran into: Trello’s web app doesn’t expose filters to browser URL parameters. So when I tried to make a link that opens Trello and auto-applies “Focus” label filtering, it just did nothing. That meant I had to keep one Trello tab open and use Keyboard Maestro to simulate the filter steps 😩
Still worth it, because it makes each break feel *official*.
Later I tried Raycast instead of Shortcuts (which is way nicer if you live in Alfred-style workflows). You can build a Pomodoro command that calls Trello APIs directly to apply labels or move cards. But uh, don’t try this unless you’re comfy with tokens — Trello revoked my test token twice because I forgot to scope it properly 🫠
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## Deal with Trello weirdness before it derails everything
Alright let’s talk bugs. Trello is friendly and colorful but it has one very specific thing that drives me nuts: label sorting *breaks* when you use more than five labels on a card. When I started tagging things by topic (e.g., “Notion,” “Email,” “Style Guide,” “Pomodoro-Writing”), the label picker would just rearrange randomly. This sounds small but when you’re in a flow and trying to find the right filter fast, it’s infuriating.
Also, card ordering inside lists isn’t reliable when you have two people editing the board at the same time. When I was co-writing a newsletter, my writing partner would reorder cards while I was mid-session, and suddenly the card I was typing notes in would jump away.
And of course, Trello quietly resets your card templates’ checklists if you duplicate a template from mobile. I discovered this the hard way when I created five Pomodoro tasks during a long train ride, and every single one had an empty checklist despite the desktop template having all my writing steps preset.
So:
– Make labels visual (colors only) and limit to 4 per card
– Lock down mobile usage to *read only* when mid-session
– Use Firefox containers or Brave workspaces to isolate your writing Trello from everything else
– If card sort order matters, don’t share the board during deep work
I still love Trello for this — but I keep the chaos contained now. Most of the battle is just making sure the board doesn’t become another source of decision fatigue during the day ¯\_(ツ)_/¯