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I have used just about every task manager, todo list and GTD system there is from email to apps to multi-componenet systems using IFTTT and Zapier.  This is as crowded a space as messaging but without the massive user bases or valutations.

I’m reaching the conclusion, that I inevitably reach every few months, that they are for the most part, a waste of time.  Task managers are useful for remembering the backlog of stuff you need to.  The chores of both office and personal life that are likely to fall through the cracks if not recorded, organized and stamped with a due date.  Because of this usefulness, I’m not going swear off these tools, but refocus how I use them. 

It’s when we try to do meaningful work with big goals or many parts that we run into issues with these apps.  The worst part is that they don’t feel like issues.  Even the act of inputting a to-do (thanks to excellent UX from Omnifocus, Wunderlist and some others) feels good, and checking stuff off is even better.  When working on big hairy projects or initiatives these tiny tasks become mundane and less useful.  We run around between meetings and squeeze time to check these things off.  Did we get to meaningless thing Z today? 

Marc Andreesen has a minimal solution (among other productivity rules) that I find quite useful and refreshing:

I sit down at my desk before I go to sleep, pull up my Todo List (which I keep in Microsoft Word's outline mode, due to long habit), and pick out the 3 to 5 things I am going to get done tomorrow. I write those things on a fresh 3x5 card, lay the card out with my card keys, and go to bed. Then, the next day, I try like hell to get just those things done. If I do, it was a successful day.

Focusing on a small number of big things (whether thematic like: Drive project x forward today or specific like: Finalize deal/requirements/y today) is the most direct way to make sure you progress on those things.  If you don’t make progress on your daily to-do’s, as will happen many times, you record a loss and have to meditate on it. Get out of the mindset that not checking something off is not failure, just that you’ll need to strategize better.  When you learn to stop checking things off left and right you can learn to do meaningful work.  Think big and leave the machines to handle your chores.