why i plan my schedule six weeks in advance

​since about the middle of 2015, i’ve gotten real rigorous about my calendar game. i’ve always been a calendarer, but after my 2015 reflection weekend, i really stepped it up a notch.

this increased rigor regarding my schedule has had many impacts, but the one that most of my friends encounter is this: when people want to hangout, i schedule it (on average) six weeks in advance.

this has prompted all sorts of interesting (hurt, annoyed, frustrated) comments from people:

• “wow! you’re really that busy?”
• “oh, you must not care about hanging out with me that much.”
• “i don’t even know what i’m doing in six weeks; put it on your calendar and remind me two weeks beforehand.”

here’s a little more backstory: in 2015 and 2016, i took 1-2 days during the first weekend of january to reflect on the previous year. the 2015 reflection was at a coffeeshop called simon’s too on mass ave with my dear friend, annemarie. i forget where the 2016 reflection happened… i used this holstee tool. it basically lead me to this process:

• make a list of your priorities,
• review how you spent your time* last year,
• check to see if how you spent time lines up with your priorities,
• if they match on all accounts, change nothing; if they don’t, make changes.

i saw that my time didn’t match what was important to me. and i know from the getting things done methodology that most people struggle to achieve their high level goals/vision because they have insufficient mechanisms for connecting minute-to-minute decision-making with the big picture ideals. all of this lead to me thinking at a very granular level about how i spend my time each week. based on my priorities, i determined that the following categories were how i wanted to spend my weeknights:

• personal projects
• friend/group projects
• close friend hangouts (these are recurring with certain people and only certain people)
• friend hangouts (these are for when someone wants to get a drink or coffee)
• wildcard or network-building
• preparing for the week

this has had lots of impacts on me and my time. it’s made me think clearly about: who my close friends are and how i want to cultivate and invest in those relationships, what do i want to spend my energy on outside of work, how do i want to use my social energy when not with close friends, et cetera.

the different catgories don’t have to be on the same day week to week. normally i plan for network-building things to happen on saturdays, but if something comes up on friday, i have no problem swapping it from saturday to friday and then moving what was planned for friday to saturday.

that said, some of the categories are much easier when they are regularly scheduled. for example, preparing for the week almost always happens on sundays. that way, food i cook lasts the whole week without going bad.

close friend hangouts are also easier on fixed schedules. it helps both parties stay committed to seeing each other when (1) we know exactly how to plan other things around the time and (2) we don’t have to worry about it being too long before we get to see each other again.

anyways, when all of this thinking combines with the number of people i know and the rate at which i make new connections, it results in my schedule being planned about six weeks in advance.

so in early august when i schedule our dinner date for mid-september, now you know why.

ps - wow. realizing that this should have been multiple posts and this is sort of all a jumble, but i just couldn’t stop.

pps - i was encouraged to write this post after a real good conversation with my friend, dan schenk, at haley house last week. thanks for asking and subsequently prompting the writing, dan!

ppps - my thinking about all this stuff has been shaped by more than just what’s included up there. i know i’ve had conversations with my friend, ofer, about these things, but many friends as well.

* note: the word ‘time’ can be replaced with any list of resources: ‘time and money’, ‘time, money, and energy,’ whatever you want to and have ability to measure.