Can’t Find a Good To-Do List App? Blame Microsoft Outlook ‘97



My father brought home our first family computer sometime in the 1990s. We set it up in our living room, then went on a Best Buy shopping spree. My dad bought Microsoft Office. I bought several video games, including the new Microsoft Flight Simulator.


Hailed as a technological masterpiece of unparalleled accuracy, Flight Simulator perfectly captured what was like to be really bored.


The first Microsoft Office didn’t include an email client. Staying in touch with contacts and remembering calendar appointments was still a manual process. You had to use a planner - a little notebook, usually divided into weeks and months, where you scribbled phone numbers and upcoming tasks.


Then, with Office ‘97, a new player emerged: Outlook. Seemingly designed for the types of guys who wore calculator wristwatches, Microsoft built Outlook around a geeky fad called “email.” Email was a recent invention that let nerds send letters to each other via telephone. One the install screen, Microsoft had listed its top 3 features:


“Auto-clipart intelligently suggests appropriate clip art!”


To me, Outlook sounded even more useless than Flight Simulator.


Even so, email caught on, and Outlook remained. Even as AOL Instant Messenger became all the rage in middle school, adults glued themselves to Outlook. Hidden inside that interface, almost like an afterthought, were several pixelated icons:


  • journal

  • tasks

  • notes

  • contacts

  • calendar


Outlook was built like the menu at Denny’s. It contained a relatively small list of ingredients, repackaged and combined in different ways to create a sense of variety.


In their attempt to impress us with a massive menu of capabilities, Microsoft had repackaged the same basic concepts a dozen different ways. It was clear they had lots of ideas, but the technology didn't exist to reinvent the wheel for all of them.


Built to add to Outlook’s menu of capabilities rather than to be a powerful tool in itself, Outlook’s task feature was basic and non-inventive.


Before Outlook, most people used planners or notebooks. Now, they had a better way to keep track of tasks, but it came with a catch. It wasn’t the best way. It was just Microsoft’s way - their version of a Denny’s breakfast omelette.


Almost a quarter of a century later, the Outlook way has become the default way we communicate. It’s what we think of when we think of task apps because it’s what we’re used to. We expect our Apple Reminders or our Wunderlist (now Microsoft To-Do) to work like calendar appointments with check-boxes.


But why? There is no good reason, other than the force of habit, for this default way of thinking about to-do lists. Most of the tasks I need to get done don’t need to be done at a specific date and time. I may need to get my wife a birthday present sometime this month. But, Todoist, Remember the Milk, or any other to-do list app will make me assign a date and time (or leave the task in a blank list).


Before Outlook, back in the days when business-people had planners (or secretaries), task lists weren’t bound to dates and times. They had sections for weeks and months. You noted your tasks wherever, and however, you saw fit. If you had to get a suit dry-cleaned sometime next week, you made a note for the week. You didn’t have to choose a date or time.


There are lots of ways to conceptualize a to-do list, and different methods will work for different people. But, scroll through the iOS App Store today, and you’ll see hundreds of Tto-do list apps that all work around the arbitrary due-date mentality.


That's why we created Stongweek. Using a task list app shouldn't feel like Microsoft Outlook with a fresh interface. It should feel like your personal planner.