Photo by Cathryn Lavery on Unsplash

My to-do list is almost always the first app open after I turn on my phone in the morning. And for as long as I remember, I’ve relied on it as a second brain. Besides being a planner and doer, I crave productivity. I get an endorphin kick when I check things off my list and hear that satisfying “ding”.

I’m the kind of person that can’t resist trying out new productivity apps. But of all the ones I’ve dabbled with, the best tool for me was always Wunderlist. It was simple but effective. I used every single feature: drag-and-drop tasks, multi-list creation, cross-platform syncing, due dates, reminders, notes, file attachments, sort by creation date, starring, sub-tasks, and theming. Microsoft eventually bought the company and shut it down in 2020 after releasing their own to-do. It’s pretty much a re-skinned, soul-less version of the old app, but it does the job.

The way I use my list has evolved over time. While it all started as a single tactical list, I’ve refined my tactics and broadened my usage. I added an immediate next step to every item on my to-do to avoid project paralysis as popularized by David Allen’s Getting Things Done. I added monthly and annual goals, though a spreadsheet turned out to be the best long-term solution. I added tidbits I didn’t want to forget but rarely needed to retrieve — what are your go-to karaoke songs?. I added tips and reminders for getting better at my hobbies. I added random ideas for side projects or articles. I even added a list for mental models and frameworks that I try to apply, to varying degrees of success.

But as much as I rely on my to-do, I always try to be wary of task bloat and especially of interpreting the number of “dings” as a measure of productivity. I wrote in my 2018 review how it’s easy to be infatuated by mindless progress. Deciding what not to do is as important as deciding what to do. And I often wonder if I rely too much on lists as it is. Would I be a mindless zombie without it? When does a second brain effectively takes over for the first?

Endlessly curious, always optimizing. Startup and product enthusiast. vincenttsao.com