Trello Calendar Power Up Is Not Just for Dates
I used to think the Calendar Power-Up in Trello was a checklist with a pretty face — just drag the card to a due date and call it content planning. Nope. It gets messy fast when you’re juggling drafts, edits, collaborations, and links to Google Docs or WordPress posts that aren’t published yet 🙃.
Once you enable the Calendar Power-Up (it’s one of the core free ones), you’ll see a new “Calendar” tab at the top of your board. Sounds cute until you realize:
– Only one date per card shows up automatically. So if you use checklists to track draft deadlines, review dates, or go-live timing, those don’t appear.
– No recurring tasks. Want to post every Tuesday or schedule weekly content refreshes? Nope. You’ll need to manually recreate all of them or use another Power-Up like Card Repeater (which is incredibly clunky with blog stuff).
– If you change the due date on the calendar directly and it’s already linked to another tool like Zapier or IFTTT, the automation can fire early. That happened to me with an automatic Slack post — full post promo went out two days before the content was reviewed. Awkward.
That said, seeing your entire editorial pipeline on an actual calendar saved my brain more than once. When I forget what I’ve committed to writing (hi, every other week), the visual layout keeps me semifunctional.
Bonus tip: Use emojis in your card titles to make the calendar layout easier to scan — 📝 for drafts, 👀 for in review, ✅ for published. Yeah, it’s silly, but way faster to scroll.
Custom Fields Save My Life Weekly
I resisted Custom Fields for way too long. Genuinely thought, “I’ll just type it in the description box.” Terrible idea. That method goes downhill fast when you’re trying to filter out what’s a sales post, what needs SEO optimization, and which post had an interview that still hasn’t been approved 😑
When you enable the Custom Fields Power-Up, you get to assign new standardized fields to every card on your Trello board — like Post Type, Platform (e.g., Substack, Medium), or Editor Assigned. You can set these as dropdowns, checkboxes, plain text, dates — and yes, you can color-code them.
Here’s how mine usually look on a Blog Planning board:
- Stage: Idea, Drafting, Editing, Scheduled, Published
- Content Type: SEO, Case Study, Email
- Primary Link: URL to the Google Doc or CMS preview
- Assigned To: Writer, Editor, Guest Contributor
- Needs Graphics: Checkbox to remind me not to ignore visuals again
The coolest trick: once you’ve set those up, you can search or use filters based on fields. So if I’m prepping just email posts for next month, I filter the board for Content Type = Email and Stage = Drafting. Snap, there’s my (usually late) workload 😛
Also, one weird issue: checkbox fields don’t show in the board search if your board is large (more than about 50 cards in my case). That seems like a rendering issue, but Trello support just shrugged.
Card Repeater Is Predictable but So Clunky
So this is the one I almost hate recommending, but it’s still kind of essential. Card Repeater lets you create recurring tasks in Trello — like “Write Monday Newsletter” or “Check blog analytics every Friday.” Thing is, it doesn’t clone the card to the same list unless you get very specific with how the original was structured.
Setup is a pain:
1. Create the template card.
2. Add **Card Repeater** Power-Up.
3. Tell it what list to clone into, and on which schedule (weekdays, monthly, etc).
4. Save and pray.
Here’s what happened to me: I had a repeating card to “Update Affiliate Links in Top Posts” every first Monday of the month — nice in theory. After about three months, the new cards started appearing in random lists. Sometimes they’d wind up in the backlog, once even in my archived list, which should literally be impossible. Couldn’t replicate the bug consistently, but it still happens.
Also, there’s no visual cue that a card is a repeat-template unless you label it. I forget, clone the card manually, and then Card Repeater spits out a second card right after. Duplicates galore.
So, set a bright red label like “Repeats Monthly” and archive these template cards into a dedicated list (NOT the board archive) to keep them from cluttering up your workspace.
Butler Is Powerful Until It Confuses Itself
Ah yes, the automation darling — Butler. It’s one of Trello’s built-in Power-Ups now, which is both good and bad. Good because it’s free and somewhat integrated. Bad because the interface feels like it’s mimicking a 1990s rules engine from Outlook, but with more cryptic bugs ¯\_(ツ)_/¯
I use Butler mostly for these types of blog automations:
– When a card is moved to “Ready to Publish,” set the due date to tomorrow
– When a label “Content Approved” is added, move it to “Scheduled” and add a checklist: Twitter, Email, LinkedIn
– When due date is marked complete, archive the card
You’ll think these rules are working perfectly… until they overwrite each other. I had a few rules where the label triggered a due date change, and another rule where a list move triggered another label. End result? Two rules firing at the same time and Butler just skipped one entirely with no alert.
If you add more than about six rules on a board, you *must* test them one by one. I basically have a sandbox board just for this 🙃
Also, even if you delete or disable a rule, there’s a delay before the update fully applies. For about 15 minutes after disabling one auto-archiving rule, Butler still ran it. Like it had cache trauma or something.
Board Sync Power Ups Only Work Halfway
This one will drive you crazy if you try to manage multiple blogs or client content from different boards. There are Power-Ups like “Unito” that offer Trello board mirroring, and they’re supposed to let you sync cards between boards — status changes, due dates, comments.
Cool in theory, but in practice:
– Comments only sync one-way unless you’re on a paid tier
– Moving cards across lists sometimes reassigns them accidentally (especially if users aren’t on both boards)
– Custom fields don’t always sync correctly, especially if one board has more fields than the other
You’ll get weird phantom cards that update some properties but lose attachments. I had one being synced from a client board that showed up in mine, but none of the attached briefings were usable. They looked attached but clicking them gave a “file not found” error.
There are moments where it works beautifully — like having a client mark a blog post as “Ready for Review” on their board, which slides into my “Needs Editing” list automatically. But until the sync features become truly reliable (and affordable), I’d rather copy cards manually and sleep better.
Other Power Ups That Sound Fun But Ruined My Flow
Sometimes I experiment with new Power-Ups during harmless re-org sessions and suddenly regret everything. Here are a few that technically work, but felt awful for blog workflows:
- Voting: Sounds fun for choosing headlines, but honestly just creates tension with teammates when everyone votes for their own idea 😛
- Google Drive: Heavy on permissions. If you’re not logged in as the exact same email as the one on the doc, Trello shows nothing.
- Slack Integration: Doesn’t honor filtered card types. Every card pinged the blog channel, even when it was a typo fix.
- Planyway: Gorgeous on mobile, but very desync-prone with due dates. Missed two scheduled blog launches because of it.
- Time Tracking Power-Ups: Unless you bill clients hourly for blog posts, it’s overkill. Mostly built for dev work, not creative drafting.
Best combo I’ve found so far for actual working blog flow:
– Trello Calendar + Custom Fields
– Butler (with debug testing)
– Maybe Card Repeater, if you like punishment
I used to try five or six Power-Ups together for a completely automated editorial calendar, but all I got was wasted hours and a card that said “Publish ????” scheduled on the wrong week.