Event Creation Still Largely Feels Like an Unsolved UI Problem

From my 2011 post linking to Fantastical 1.0:

Fantastical’s primary innovation is its natural language parser for event creation — you type something like “Yanks-Rays tonight at 6:40” and Fantastical not only parses that into a new event, but, using some very clever animation and design work, shows you what it thinks you mean before you hit return to actually create the new event. Watch their screencast to see what I mean.

Four years ago I wrote a piece called “Deal With It”, about how some UIs feel like going uphill and some feel like going downhill. An uphill UI feels like you’re fighting against the app; a downhill UI makes it feel like the app is helping you along. The example I chose to illustrate my point was event creation in iCal (uphill, and steep) vs. 37signals’s Backpack (downhill). Fantastical is an even better downhill UI for event creation.

A friend texted me after my post earlier today, in which I wrote about Fantastical’s new AI-driven email forwarding service. My friend wrote that he does this sort of thing with ChatGPT frequently, using photos of event posters he sees on the street or screenshots from event images in Instagram, with a prompt like “Create a Google Calendar link for these.” He concluded, “IMO calendar event entry is one of the most tedious UI problems that we’ve never truly solved.”

I hadn’t revisited my 2007 “Deal With It” piece in a while, but I just re-read it, and it holds up. I still feel like the UIs that most annoy me are the ones that give me the most fields to deal with. I mention instant messaging vs. email a lot in the piece, coming out squarely on the side of IM for communicating with friends, even for things that I admit probably should have been an email. The predominant messaging platforms of 2007 are now long gone — AIM, ICQ, Yahoo, etc. But those platforms lost only because they were surpassed, not because the basic idea was wrong. Messaging itself — iMessage, WhatsApp, Signal, etc. — is a zillion times more popular today. I almost never today think “Maybe that should have been an email...” when I text a friend. There’s just so much less to deal with. Today it’s more likely that I’ll send someone an email and think to myself “I probably should have just texted them that...”

This is one way to frame the explosion in popularity of ChatGPT and its many competitors. They help you accomplish tasks that would feel far more tedious to do on your own than just telling them to do it for you with a sentence or two of plain English describing what you want done, perhaps including a photo or two. LLM chatbots are able to turn feels like pedalling uphill tasks — often just everyday ones — into feels like coasting downhill tasks.

★ Tuesday, 3 June 2025