Originally drafted on April 8, 2026.
Revised on April 9, 2026.

The only thing that rivals my interest in how people manage their money is how they manage their calendars. This fascination makes a lot of sense when you think about how for those of us who work for a living under capitalism, money represents a conversion of time. My fascination with calendars and schedules and time management is extensive (no doubt this is a very Capricorn/ruled by Saturn trait). I have several calendars scattered around my apartment, I have done my own personal time management studies, I have worn the same watch for so many years that I have a semi-permanent watch tan, and one of my favorite things I’ve ever written was titled “How to ask a busy person for something.”¹ Like most women with interesting lives, being busy is a family tradition. My late grandmother famously had an answering machine recording that went “I’m probably out at a committee meeting somewhere.” 

Historically I have been both extremely protective of my time and also view scheduling things very far in advance with friends and family to be the highest expression of devotion. My calendar management is also wildly complicated by the fact that for the last several years of my life I’ve had varying eldercare responsibilities for my late father, and increasingly now my mother. Eldercare is challenging for many reasons, but one of the hardest is because unexpected health crises and other various emergencies come with the terrain of eldercare, and therefore can lay all your best laid plans to waste. 

I am self-employed, which means my scheduling practices can be a real double-edged sword. On the one hand I have more flexibility and much more control over my calendar than most salaried workers (a huge reason why I love self-employment and am extremely reluctant to return to traditional work). But on the other hand, that flexibility can often mean that if I am not incredibly vigilant, my calendar can lose some of the sturdier scheduling guardrails that people with a regular office schedule often have built into their weeks. 

Back when I was married, my ex-husband and I shared calendars and also had a standing time in which we went over our calendars for the week to discuss things like errands/meal plans/etc. But now that I am in my hot divorcée era and beginning to rack up a full dance card, managing my calendar has become a completely bonkers exercise in trying to maintain a delicate balance of my very strong preference for scheduling things way in advance while leaving open pockets of time for more spontaneous meetups with new friends/dates as well as long-time friends who tend to prefer more last-minute hangouts. 

Just like the way you manage your money as a young person is not necessarily the way you should manage it later in life, so it is with calendar management. So now I am in this new season of my life where I’m trying to figure out how to manage my calendar to reduce overwhelm and maximize FUN. I’ll follow up with a part two soon to articulate what I’m starting to deploy/what I’m thinking of doing. In the meantime, if you’ve ever confronted a similar challenge, I’d love to hear how you reorganized your calendar/schedule to support a major life transition.

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