The Calendar Invite That Almost Drove Me Mad

Look, I thought I was losing my mind.

There I was, scrolling through my calendar when I saw this meeting: “Sync with Natan.” My immediate reaction? Pure panic. Did I schedule this with myself? Was future-me trying to warn current-me about the post-apocalyptic outcome of the accelerated rise of AI? Had I finally snapped under the pressure of too many design critiques?

And that’s when it hit me - this was the perfect example of something I’d been thinking about for ages: Context of use.

Two People, Same System, Completely Different Experiences

Here’s what actually happened. My friend Esther wanted to catch up, so she created a calendar invite titled “Sync with Natan.” From her perspective? Makes perfect sense. She’s syncing with Natan, so she calls it “Sync with Natan.” Clear, logical, done.

From my perspective? I’m staring at my calendar, wondering if I’ve developed multiple personalities. “Not again!” I thought to myself.

Same system. Same data. Completely different contexts.

When Standards Meet Reality

ISO 9241-210 talks about human-centred design requiring “an explicit understanding of users, tasks and environments.” The calendar app understood Esther’s task (schedule a meeting) and environment (her calendar interface). But it completely missed my context as the recipient.

The system knew who created the invite, but somehow forgot to tell me that tiny, crucial detail. It optimized for the creator’s mental model while ignoring the recipient’s experience entirely. It makes you think - could an AI layer help contextualize this? Maybe, but sometimes the simplest solutions work best.

Here’s the thing - this isn’t just about calendar apps. It’s about recognizing that users exist in contexts we never considered.

My Proposed Solution

I’ve been tweaking my own calendar invites using nothing but organic intelligence and this simple format: “Natan <> Esther.” And if Esther sends me one, I see “Esther <> Natan.”

Why does this work?

• The initiator’s name comes first - instant context about who reached out
• It’s bidirectional - both people understand their role immediately
• It acknowledges perspective - the same meeting looks different depending on where you sit

That scrappy mentality of “make it work for everyone” is exactly what we need more of in UX.

Context Is Everything

I’ve seen this pattern everywhere. Email threads that don’t show who started the conversation. Shared documents where you can’t tell who made which changes. Apps that assume everyone has the same mental model about how things work.

When I’m rushing between meetings, trying to figure out if that 3 PM slot is something I scheduled or something someone scheduled with me, that context becomes the difference between showing up prepared and showing up confused.

Progressive disclosure with purpose: Don’t just show information - show the right information for each user’s perspective.

Symmetric experiences: If your design works great for Person A but confuses Person B, you haven’t solved the problem yet.

The Real Challenge

Next time you’re designing something - anything - ask yourself:

• What context is invisible to my users but crucial for understanding?
• How does the experience change based on who’s initiating versus receiving?
• Would this make sense to someone in Berlin, Lagos, São Paulo, or Mumbai encountering it for the first time?

Sometimes the best solutions are the simplest ones. A little visual cue, a name placement, a tiny detail that acknowledges: “Hey, we know you’re not the one who started this.”

That’s the beautiful grind of figuring it out - taking something that technically works and iterating on it to make it actually work for everyone involved.

Remeber… Context of use.

But that wasn’t even the biggest issue with Esther’s invite - it had no agenda :P

What context failures have you encountered lately? I want to learn from your experiences - drop me a line and let’s keep this conversation going.