How I Finally Got My Weekly Calendar Workflows To Stick

1. Default calendar views hide more chaos than they reveal

Default weekly view looks clean. Monday’s meetings stack politely, Thursday leaves room to breathe. But that neat illusion collapses the moment you start marking actual task blocks—deep work, breaks, prep time. Turns out I was dragging events over white space that was already claimed by Google Meet links I wasn’t invited to (auto-synced from a shared calendar I never cared about). Double-booked but no warning—because Google Calendar doesn’t count subscribed calendars in its conflict alerts unless you have “Make changes” access. Love that.

Had a chaotic Monday where three team members were waiting on me separately, because none of us realized I’d blocked time for each of them on different calendars—and all of us thought I was free. I only noticed because one of them showed me their screen and it looked totally different from mine. That’s when I stopped trusting the default views entirely.

Solution: I now rely heavily on custom Agenda views in Fantastical (on iOS) and a stacked week view in Notion synced via Cron. I color-code my calendar only and grey out every other shared layer so I can still see potential conflicts, but they don’t trick my eyes into assuming a free block.

2. Toggling calendar visibility breaks down in team sync scenarios

There’s a weird mental model break here. People get used to toggling calendars off to simplify what they see—but that doesn’t actually remove those obligations from your day. I kept toggling off my team check-ins so my focus day looked clearer, then completely forgot I still had to prepare notes for one of them. Because visually—it vanished.

I ran a dry-run with a colleague once to test this: we both subscribed to each other’s calendars in Google, then both created blocks across a typical Tuesday. When we sent the day’s plan to our manager, they called out three double-bookings that neither of us saw—because we’d toggled each other off, assumed nothing overlapped. Lesson: toggling doesn’t mean it isn’t scheduled.

There’s no built-in logic in Google Calendar to alert you to conflicts across toggled-off calendars. If the calendar is hidden, the system doesn’t factor it into any alerts—not helpful.

What fixed it for us wasn’t a new app, but adding a Zap triggered when either of us made a “focus block” labeled with a specific prefix (we used [DEEP]) into our calendars. The Zap pings Slack with a quiet status update like: “Avi scheduled deep work on Tuesday 9–11AM. You may want to reschedule anything overlapping.” Works well when people respect the prefix tagging.

3. Structured weekly time blocking collapses without real friction buffers

If I had a dollar for every overly-ideal week plan I made in Notion and then never followed… You can’t block 8 hours of meetings back-to-back and expect yourself to switch instantly between topics. Or schedule “writing time” in a 30-minute slot right between two Zooms. That’s fantasy planning.

I only truly got calendar blocking to work once I started programming in calculated friction buffers. These aren’t breaks (though sometimes they are). They’re 10-30min blocks labeled by buffer type:

• Context reset (for switching between different projects: marketing → tech)
• Debrief capture (dump thoughts from a meeting before they vanish)
• Re-route overflow (if you didn’t finish that task, this is your slot)
• Inbox cleanup (light admin moments just to recover sanity)
• Schedule triage (look at tomorrow, not just now)

Put three of those in your week and suddenly your calendar stops feeling like it’s lying to you. You don’t get to Friday wondering what derailed everything. Because you buffered for it by design.

4. Multi-app calendar sync loops can undo each other silently

This one almost broke me. I had Notion syncing with Cron, syncing with Google Calendar. At the same time, a Zap was pushing events labeled #admin into my Todoist, and then another Make scenario was updating those Todoist tasks back into my Notion weekly dashboard. Sounds clever, right?

Worked for about an hour. Then I noticed random tasks duplicating or disappearing. Here’s what happened: the time format rounding between Google and Cron didn’t preserve seconds. So a 10:00:15 event got rounded to 10:00:00 in Cron, which then pushed that update back to Google, which pinged the Zap again… triggering a loop. Worse, one sync tool saw the update as a “new” event and created a fresh task in Todoist.

Undocumented behavior: Notion’s calendar view does not trigger an update webhook if the only change is to color or tag—so the downstream task manager never got the category updates unless I tweaked the title again manually. No doc ever pointed that out. I only caught it by watching the Zapier task history obsessively for two hours.

Break the loop by introducing a middleman: I now push all calendar items into Google Sheets first, then filter deduplicated rows before syncing elsewhere. Not elegant, but at least it lets me watch what’s happening with actual timestamps and detect feedback cycles.

5. Color coding becomes signal noise without rigid naming conventions

I used to think calendar color coding would save me. Meetings = red, deep work = blue, admin = grey. Naive. The issue? Every app has its own palette, and some sync services ignore them entirely. I once color-coded a Notion board so beautifully, only for it to sync into Google Calendar as identical pale green blocks. Thanks, Cron.

Worse, if you collaborate with teammates using different naming, the colors don’t mean anything when side-by-side. Green might mean “client work” to you and “personal block” to them. On one shared team calendar, I watched someone assume I was free “because your calendar was grey, not red.” Turns out their red meant ‘off limits’, mine meant ‘still okay to double book if urgent.’ It’s unsustainable.

The “aha” fix was absurdly low tech: we standardized on emoji-prefixed event titles for internal events. 🔴 = hard meeting, 🔵 = deep work, 🟢 = available for booking. Every recurring block respects emoji logic now. You can spot it instantly—even when synced through four platforms.

Bonus chaos: Apple Calendar on iOS totally strips those emojis in the notification banners. Don’t rely on mobile push based coloring.

6. Planning your week on Friday afternoon almost never works long term

I kept trying. Friday 4PM: open Notion dashboard, pop open upcoming events, start dragging blocks around. It always felt productive—but most of that work got overridden by Sunday evening thoughts, or random Saturday messages from clients.

The behavior flaw is timing. Late Friday you’re already mentally checked out, and by Sunday your priorities have shifted or new context landed. But the plan feels “locked”, so you end up forcing your week to fit a context that’s 48 hours stale.

Now I run a “quick scope” toggle in Superhuman during Sunday email review. Any task that feels heavy gets starred. Then Monday 8AM, I pull up that list and structure the week from that—not from the calendar events. Only after that do I start moving events around.

Cron is better than Google for this, because it lets you drag-reschedule with keyboard macros. Hold Ctrl+Arrow and slide a task across the grid. No context switch needed. Still wish there was a “tentative block” mode where items could go grey until confirmed by actual calendar availability… but we work with what we’ve got.

7. Conflicting time zone conversions pretend they’re helping but they lie

I once booked a full week based on Pacific time—only to realize half those meetings were imported from Outlook invites coded in EST but synced through Google. Visually they looked aligned. Then someone dropped a “thought you were showing up at 10” message in Slack and I realized I’d trained my entire week to a phantom time zone. The difference? Meetings from Google Meet auto-adjusted correctly; iCal ones did not. Fantastical showed the time as sent, not as interpreted, causing the inconsistency.

I now rely on the somewhat hidden “event time zone” toggle inside Cron. You can specify a different time zone per event—not just per calendar—so if your teammate sends an invite coded in their zone, you can override your view without overriding the sender’s actual source calendar.

This also got me weirdly deep into ISO 8601 formatting. If your task manager stores time as YYYY-MM-DDTHH:MM:SSZ but adds a local offset incorrectly before syncing to the calendar—suddenly every recurring task is an hour off. Not a bug, just silent drift. Only caught it when I scanned the raw webhook logs buried in Zapier’s “View sent request” tab. Looking at that was probably the turning point where my Sunday mornings started including JSON diffs.