The Best Digital Life Organizer Apps and Where They Break
1. Sorting tasks in TickTick with smart lists that misfire
I used TickTick religiously for about eight months and swore by the smart lists until a recurring task started showing up everywhere except where it was supposed to. You can set filters like tag:@work AND priority:3, but the actual logic sometimes treats that as an OR if you saved the list too fast during a sync lag. Wild.
Their UI makes you think you’re building real logic stacks, but under the hood, it’s interpreting filter strings in a way that’s, well, inconsistent. Adding parentheses doesn’t help. Forget nesting. You’re better off stacking singular filters in separate pseudo-smart lists if you want any kind of native backup plan.
The bug? One day a task tagged both @admin and @deepwork just ghosted both smart lists. Never rendered, even though a manual search kicked it up instantly.
After spending too long toggling custom filters on and off, I discovered this random fix: export the list, make an edit in Notepad to remove rogue carriage returns (yes, really), then bulk import. Suddenly everything sorted correctly again. No UI change. My guess: formatting corruption silently broke the logic tree.
2. Using Notion for project tracking until rollups collapse
Notion’s databases can feel like magic, unless you’ve tried to do anything with rollups that count tasks across filtered relations. At a certain point, the counts just stop updating. Or worse, they spin for twenty seconds, then show obviously wrong data.
I hit this when building a weekly dashboard that tallied completed tasks by category. I used a relation property to link tasks to weekly sprints, then a rollup to count “Done” statuses. Everything worked fine—until someone duplicated a template. The new week’s rollup started counting tasks assigned to the old one. Even though the visible relations looked isolated.
What actually fixed it
- Deleted the template block (not the database template—just the block)
- Unlinked and relinked the affected entries manually
- Rebuilt the rollup from scratch, one column at a time—Notion doesn’t sanitize nested relation states on duplication
Notion support is still holding out that this isn’t a bug. It absolutely is.
3. Obsidian plugins that overwrite internal IDs without warning
I have synced vaults between desktop and mobile and one day I lost two weeks of zipped meeting notes—just gone—because the YAML headers were overwritten after a community plugin tried to auto-tag a page as “Archived.” Turns out the plugin re-saved the file with a freshly generated UID using the current timestamp.
Nowhere does it say it’ll overwrite the id: field, and even skimming the README again didn’t help. I only discovered the change after diffing synced vaults through GitHub Desktop on one machine. Obsidian didn’t throw any sync alerts, because technically, the file updated just fine.
The quick fix was disabling the plugin and hand-patching every file it touched using a grounded ID list I luckily had lurking in a JSON cache. Normal users wouldn’t even notice it’s broken—until your Eleventy export or Dataview automation fails silently.
4. Airtable automations fail silently unless you check run history obsessively
Here’s the situation: I set up an automation in Airtable to send a Slack message when a record’s status hit “Ready.” Simple enough. It worked great during testing. Then it stopped working randomly after a field re-order. No errors. Just silence.
You actually have to dig into the Run History to even begin troubleshooting. It turns out Airtable pins automations to field IDs, not field display names. Reordering columns? Can break formula parsing or field mappings.
This diagnostic trail isn’t visible unless you expand each failed run effort manually. I now keep a dummy trigger that sends alerts any time a record passes through the automation at all—just so I know it’s triggering. Waste of a run? Sure. But more predictable than playing Airtable Clueboard.
5. Cron job setups in Make that forget filter context on rerun
There’s a particular behavior in Make when you use a schedule to run a scenario with a bulleted filter chain: the first run behaves exactly as designed. But if you manually rerun the last execution later, it reuses certain module states but drops the scenario-level filters like datestamps.
Example: A scenario that fetches WooCommerce orders created after 12 AM today worked fine on its daily run. But when I used “Run once” mid-afternoon, it pulled in the entire week—even though the initial module filter still showed “Date created: after {{now;startOfDay}}.”
The issue is that {{now}} gets interpreted at run trigger, but in a rerun that anchor doesn’t refresh. It uses whatever UNIX stamp it originally got. You can’t see this unless you crack into the run log JSON tab.
Half an hour disappeared into trying to “fix” correct logic because of stale token resolution. The workaround is annoying: use a custom webhook trigger even for one-off tests, just to force token regeneration.
6. Apple Reminders sync delays that sabotage location triggers
This one’s pure chaos. I tried relying on Apple Reminders to ping me on-location at the post office when mailing something time-critical. Set it the night before. Set it to “Arriving at location.” Worked in testing. Next day? Nothing.
Here’s the bug: reminders created within an hour before iCloud Drive re-authentication (or time drift sync events, which happen invisibly) sometimes drop off the sync queue. They exist locally on one device but won’t register location state until they’re cloud-pushed. So the phone never knows to fire the reminder.
You see them in the Reminders app like everything’s fine. But look at iCloud web view? They’re missing. I even had one disappear after editing the note field. Remade it. Then it synced and fired—while I was already leaving the post office.
I now create duplicates for any time-sensitive geo-reminder, from a second phone signed into the same iCloud account. Horrible solution. Semi-reliable.
7. Toggling filters in Todoist with keyboard shortcuts adds invisible states
I was flipping between views using F + filter keyboard combos in Todoist (e.g., F p1 then F overdue), when I noticed that sometimes the results count stayed flat even though the query changed. UI updated. Results didn’t.
Culprit? Those shortcuts trigger an async stack update that doesn’t fully flush unless you use the mouse once between commands. It’s not documented but if you inspect the backend requests, you’ll see multiple overlapping calls, and only one is acted on.
I flagged it to support and their reply was basically, “Use the mouse for now, we’re reviewing keyboard interaction state.” Hardly helpful. But here’s what does work:
- After two successive keyboard filters, press arrow-down or tab once to force UI reconfirmation
- Wait for the keyboard hints to complete slide-up before next input
- Toggle back to Inbox and forward again if trashing completed tasks in the same flow
The mistake is assuming you can keyboard-navigate Todoist like a terminal app. You can’t.
8. Google Keep labels shift entries out of visible order silently
I thought I lost a whole checklist about client onboarding. Just vanished. Turns out, Google Keep is still weirdly aggressive about collapsing or hiding cards if you label them and then filter by multiple labels. Especially if some were added through voice.
The page looks like everything’s loaded—but swipe or scroll fast and one or two notes won’t actually render until you let go and wait. If you hit a filter toggle mid-scroll, the rendering context drops them entirely. I only found mine again by unarchiving from search. There was no way back to it through the UI.
Behavioral bug? Assigning two or more labels via Assistant sometimes stores them out of order in metadata. They’ll appear under one filter but not both. You can delete a label, reapply it in the right order, and—bam—it’s back in the feed.
I don’t trust Keep for even short-term data anymore unless I screenshot key cards. Just not worth guessing which filter didn’t apply when you needed it.