How My Girlfriend Solved My Biggest Problem with a Hybrid Calendar

Entirely simple, but I completely missed it.

The intro to this piece has turned into an ersatz essay, so I’m going to start with a bit of TL;RL (that’s “too long, read later” because of course you’ll come back to read my magical prose, won’t you, dear reader?)

Here’s the rules that will make a hybrid paper/digital calendar work withouthaving to have a daily or even weekly “copy everything” session:

1. Never accept a digital invite until it’s in your paper calendar.
2. Never create a digital event unless it’s already in your paper calendar.
3. If you can’t check your paper calendar to see if a time is available, do not add it to your digital calendar. Instead, create a reminder to check later. Then see #1 and #2.

That’s it. Three rules — two from my girlfriend, one from my nesting partner when I told her about the first two. 

The magic sauce is that these rules are constant and in-the-moment. There’s no “I’ll reconcile these later during my weekly review” or some balancing-your-calendars session that gets put off/shortened/delayed because you found something more fun to do. 

It’s a brilliant system, and it’s worked for my girlfriend for most of her very-successful-professional life. If the measure of a person can be indicated by the intelligence of their partners, I’m one helluva guy.

However, they must keep me around because I’m pretty, because I’ve been trying to figure out how to do this for…well, for most of my professional life, and I’ve never been able to make it work. 

Let me explain why…essay incoming.

Why a Hybrid Digital/Paper System Seemed Both Necessary and Impossible for Me 

In case you’re new here, let’s get one thing clear: I almost always prefer paper to digital. I won’t go into all the reasons why here, and yes, I recognize the hypocrisy of typing this on a digital device and posting it to a digital platform. We’ll probably have to deal with that later, but it’s the reality of the world I live in that it would be much harder without certain digital tools.

Such as: the Calendar

Do you remember the old “Dayrunner” magic? That book with sections and the waterproof plastic cover and an address book and pen holders and little vinyl zipper pockets?

No? Well, pull up a chair to the fire, young’un, cuz we used to have pages of inserted business cards, and weekly reviews, and when Saint David Allen brought the GTD down from the mountain we combined with with Merlin Mann’s 52 Folders and thought we could conquer the world…

Spoiler: we couldn’t. In fact, even Merlin Mann now has basically apologized for creating a system that seems great on paper (ha!) but doesn’t really survive contact with the chaos of the real world.

OK, with some real worlds. I will admit, there are some people for whom these simplified calendar systems work wonderfully. I would respectfully also suggest that these people tend to have very consistent lives, at the very least where they can sit down as a household and update and make sure everybody is on board with where and when they’re going to be in the next week/month/year.

If they are able to thrive using only a paper calendar, they probably also have a good innate sense of time; when they think “I need to remember this tomorrow afternoon” when tomorrow afternoon comes they have a little pingin their brain that says Hey! Time to do the thing!

Yeah. That ain’t me.

Shared Calendars Ruined the Analog Dream

Plus, there is the undisputed convenience of a shared digital calendar platform. Just this morning, I sent out the final invitations to the five members of a particular subcommittee for my day job. In the analog calendar days, I would have had to contact each of them via phone*, and then hope that they (or their secretary) penciled it into their calendar so they’d be ready the day of.

Instead, I first created the event in my digital calendar, invited the chair of the committee and my boss to see if the time worked (it didn’t) and then adjusted it to a day that did work. Then today I simply added the emails of the rest of the committee members, and instead of being interrupted, they can read the auto-generated email invite at their preferred time, and with a single click:

• let all of us know if they’re coming
• Add it to their calendar
• Get a reminder before the meeting
• Have the ability to join the meeting just by clicking the little video camera icon

Yes, I know you know this; I’m pointing out how much we take for granted with the convenience of such things. 

I confess, I was an early adopter. I thought that when things went digital, it would be a blessing — so compact! So flexible! I was teased for being the first one in my crowd with a pager (what are you, a drug dealer?), a cel phone (Oh, so important you don’t have time to find a land line, huh?) and a palm pilot (What happens when you run out of battery, huh?). I just put my head down and watched as slowly everybody else started using those things — or their updated combination, the smartphone — themselves.

But as the tech companies started realizing just how much of our attention they could hijack, and how vulnerable we humans are to targeted advertising, I began to notice that my digital tools were a trap.

I’m being disingenuous; it didn’t need to be a company targeting me. I could do it myself, because if I have pictures, books, movies, or even just notes available to me on my device, I’ll jump to one of those the minute I reach a point of discomfort, whether I’m online or not. 

That’s not even particularly ADHD; it’s just human. We evolved the very sensible survival instinct that discomfort is bad, avoid it and it sometimes takes literally the threat of eternal torture and flaming damnation to get us past it.**

A Hybrid System: This is the Way, Except…

So obviously if my phone is the Dastardly Device of Distraction, I should just go to a paper calendar, right? 

Not if I want to have access to and communication with my coworkers. Or my poly partners. Or, back in the day, my kid’s school schedules. To be a semi-functional somewhat-productive adult in my world, I have to use a digital calendar at least some of the time. 

But maybe I could limit that to only meetings that I had with other people, or that I wanted other people to know about? 

The problem with that is breaking one of the key principles to personal organization: a Single Source of Truth. It’s the place that you trust to tell you accurate information you want. Two calendars*** that have differentinformation on them is a trap worthy of Admiral Akbar; the probability of double - or triple - booking is all too real.

Trust me. I’ve done it. 

For a while I was able to use Google Calendar as my Single Source of Truth. The joke was It’s not real if it’s not on the calendar. For a while, it fit all the schedules of the people and events I needed to keep track of, and it worked fine…until it didn’t.

Three reasons:

1. Platforms began to put up walls between their formats, making iCal and GCal and Outlook and others less inter-operable — unless you wanted to pay extra for some app. *** *
2. Google began to (or, maybe more accurately, we learned how much) mine our data and use things like what is on our calendar to market products to us and people we included in our calendar.
3. Google lives in the most Dangerous Domain of the Dastardly Distraction Device: the internet. “Let me check the calendar” devolved into doom scrolls and side quests way too much. 

Paper is only part of the answer.

There are a lot of ways to keep track of your schedule with paper. I’m not even going to list them here. For a while, Bullet Journaling worked for me, but the reason it’s not good for me is the need for a consistent time to spend reconciling, updating, and migrating tasks. 

I love thinking on paper — don’t get me wrong. But the umpteenth time I’ve migrated an event happening in six months to a new notebook I begin to question whether that’s the best use of my time.

Ironically, given the amount of time I’ve spent exploring tactile cognition, I could make a pretty good argument why it is the best use. But it’s still annoying, tedious, and so my own paper system is an FrankenPKM of BuJo Rapid Logging, Sketchnotes, and a little GSD *****

But the calendar was never something that I could make work…until I realized that my girlfriend had been using a paper planner for as long as I’ve known her, and never had an issue with her various digital commitments.

Asking her how she does it was long overdue. And yet, once she explained it, seemed blindingly obvious. 

The moral of this possibly-too-long story? The one thing I wish I’d known sooner?

Trouble figuring something out? Ask my girlfriend. 

* for those of you saying “or letter”, I’m not that old!

** there’s a reason it’s called the “Judeo-Christian Work Ethic”

*** or, let’s be real, I’m a polyamorous Grandpa with a side gig, six calendars

**** Don’t even get me started on the ick of facebook events.

***** The unruly sibling of David Allen’s GTD (Getting Things Done) known as “Getting Shit Done.”