The 15th
I have two kinds of problems, the urgent and the important. The urgent are not important, and the important are never urgent.
Each year on my birthday, I pull up time.is and quietly watch it tick from 11:59:59 to 12:00:00. This moment is quite emotional, and it inevitably surfaces scary questions. Do I feel like I've spent this year well? Am I becoming the person I want to be? The moment allows me a rare opportunity realign myself, and over time I've come to treasure it.
But once a year is actually quite infrequently to think about these things; quarterly feels about right. So now, on October 15, January 15, April 15, and July 15, I break whatever my usual routine is, and spend a chunk of the day asking this sort of question and broadly considering the state of my life.
What does it actually mean to spend a day considering your life? Tactically, I've found that some constraints are useful. Until I've finished my consideration, I don't use the internet. To prevent myself from just spacing out, I force myself to sit down with an empty document and write. At this point, the thoughts almost always flow easily.
This habit forces the important to supersede the urgent at least once each quarter.