My productivity system

I’m going to describe how I get stuff done. Writing it down in this post is a somewhat morbid exercise as this post is doubling as a way for someone to come in and take over if I’m incapacitated.

The tools are less important than the capabilities afforded by them.

For the most part I use the free applications provided by Apple. I consider the cost of the software to be part of the premium paid for the hardware and the applications are pretty easy to use.

The system is designed to delegate remembering things to the system itself; this requires trusting the system I built.

Wake up, check calendar, check today reminders, and go from there.

I use Apple’s Calendar app to track scheduled events; I try to minimize recurring events listed on the calendar, which is different than my work calendar. The app is available on all my Apple devices and in iCloud, which keeps the events synced across all my devices and available through the web.

The events may be things that must be done on the specified date and time, or, they may be agreements I’ve made with someone else that can be renegotiated.

A semipermeable hard landscape, if you will; somewhere between the calendar described by The 7 Habits book and the one described by Getting Things Done.

I use multiple calendars within the app.

• I have a shareable calendar I use for my events, which I can share with friends and family.
• Becca has shared her calendar with me, which lets me see her schedule of things; similar to my shareable calendar.
• Becca and I have a calendar for events where the two of us will be involved or needed. The first two calendars let us see where each other are prior to discussing possible joint adventures.

These are the main calendars and others may come and go.

I also use the Calendar app to remind me of people’s birthdays, which are stored with contact information in the Contacts app; more on that later.

Calendar is the app I look at first most days because it shows the somewhat hard landscape of my world on a given day.

I use Apple’s Reminders app as my main tickler file; mentioned in Getting Things Done. It’s available on all Apple devices and through the iCloud website, which keeps the reminders synced across devices.

Reminders are placed in lists and lists can be grouped together. There are a lot of other features, but these are the two I use most. It’s worth noting that I typically turn off notifications for all applications, including the Reminders app.

The vast majority of reminders are set to repeat, which is easier done using an app than with pen and paper because every time I mark the reminder as done it sets itself to go off again at a later date.

I check the Reminders app after looking at the Calendar app; mainly for the automatically generated “Today” list, which shows all items I’ve set to do that day or any past due reminders.

I use this app for most things maintenance.

I should note, with most of these reminders, I don’t need to wait until the date to perform the associated action. Instead these reminders act as, well, reminders; an accountability partner poking their head up and saying, “Hey, just in case you haven’t done it already, you should do this thing.” If I’ve already done something near when a reminder shows up in the Today list, I can just mark it as done and move on.

What I appreciate here is the “set it and forget it” nature of things. Once I put the reminder in the app and set the interval, I can look at the Today list and work off that instead of digging through all the lists individually.

Let’s look at some of these lists in more detail.

Growing up in a military family we moved a lot and I still move every couple years myself. Whenever we moved I’d get contact information for friends and family in that place. Despite both of us promising to keep in touch, we never did. I’d inevitably apologize when I’d get back in touch with someone, usually with self-deprecating humor: I’m a terrible friend.

In 2019 my mother passed away and I was also getting disenchanted with social media. When the 2020 pandemic started I decided to create a system to help me out.

The Rotation is a list in the Reminders app.

Each reminder is the name of a person with whom I have taken on the responsibility of reaching out to on a regular basis to keep in touch in a more intimate way than, “What do you mean you didn’t see my post on social media?”

How it started: I looked at the Contacts app and my social media accounts and started reaching out to folks to have a catch-up conversation. Based on how that went, I’d fill them in on what I was doing and I’d ask if they wanted to be on the rotation. And, if so, how often did they want to hang out and talk. Then I’d create a reminder and set the interval starting from that day; could be as short as one month all the way up to a year—haven’t had anyone go beyond one year.

How it’s going: When their name pops up on the Today list, I send them a message using their preferred method, which is captured in the Contacts app. The message is asking if and when they want to have a catch-up conversation; this is the first step to marking the reminder done. Once we figure out a date and time, I create an event in the Calendar app; this event may shift, but it’s the second step toward marking the reminder done. When we have the call, I update the reminder with that date, and mark the reminder complete; this ensures we don’t end up in a situation where we talk and the next day I’m sending them a message to catch-up again—the interval is maintained based on the last time we talked.

There’s no rule, edict, or custom saying I have to be the one to initiate; in one case, as of this writing, a friend has taken on the task of reaching out to me instead of me reaching out to them. Further, we don’t need to wait the entire duration; the other day a friend called out of the blue and we caught up then. The interval is a rough maximum, not a bare minimum and I’m agreeing to be the one to reach out if things go quiet for a while.

I’m building the list slowly. In some cases it’s folks I knew in my primary and secondary school days and ran into online. In others it’s people I’ve worked with in the past. I’m also looking at folks I’ve only known through social media and seeing if they want to try and have a relationship beyond the Internet.

Some people are only meant to be “Facebook friends” and there’s nothing wrong with that. Further, some people start as close friends and become “Facebook friends” and there’s nothing wrong with that either.

If incapacitated, these folks should be notified, however, they may not be one of the key people listed in the Contact app section below.

This is a group of lists in the Reminders app and stores recurring maintenance tasks.

I have a list for:

1. weekly,
2. monthly,
3. quarterly, and
4. annually.

These names are something of misnomers. The weekly, for example, is really less than a month, so, things that are done every other week are listed here as well.

Paydays and paying bills go in the weekly list. Downloading statements and reconciling accounts go on the monthly lists. Reconciling the 401k account is an exception because I do that quarterly because it’s easier that way. Testing the batteries in my tracking devices is in the quarterly list. Stuff related to taxes are in the annual list.

Some of the reminders have their dates modified based on when I get them done; going through the Finder app, for example. Others works differently because there’s a specific date at which I should start thinking about them each interval; taxes and waiting for tax forms, for example.

The shopping list is an exception to the guideline of the reminders being recurring maintenance tasks. I typically have one of my AirPods in my ear and, when I notice I’m running low on something, I’ll ask Siri to add an item to my shopping list. Then, when I go shopping, it’s all right there in the app on my phone.

Becca and I have shared lists we can use as ticklers to talk about later or coordinate around a particular event. When my mother passed away, for example, Becca, my sister, and I created a shared Reminders list because we all use Apple devices and it made things easier to track; once we finished handling mom’s remaining business with the living, the list was deleted.

Just because you create something, doesn’t mean you can’t delete it.

I have various other lists I use as a way to capture things outside the main action list. They sorta fall into the “someday/maybe” category from Getting Things Done; part of what I call The Forge.

The Forge is the generic name I give to things I’m just sorta thinking about doing; these may never happen and may be removed, but I get them out of my head. The Crucible is reserved for things I’m actively pursuing, near-term.

Most of my near-term, one-off actions goes into a notebook; paper or digital. With either version I try to distinguish between three roles. With the paper notebook, I use different color inks. With the digital notebook, I use different line weights.

1. Personal: black, thin.
2. Professional: varies, medium.
3. Employment (or client): green, thick.

I do this because it helps me see, at a glance, where I might be falling behind or where things might be backing up.

I use Apple’s Contacts app to store contact information and related details for individuals; however, it’s becoming way more than that.

I take notes about people, have their birthdays there, which also appear on my calendar; instead of depending on social media platforms to let me know.

The Contacts app is quite capable. Every time I think about getting a fully-fledged relationship management software, I try to see if I can accomplish something similar with what I have, and I haven’t found the combination of the Contacts app and the other free apps listed lacking in that regard.

Key people is a group in the Contacts app and is a list of people who should be contacted should shit go pear-shaped. The idea is that at least three of those people would be able to work together to handle whatever is going on; they are the break-the-glass crew.

There are other groups for medical, insurance, and so on.

I use Apple’s Notes app for many things. Mainly I track my online accounts, share notes with Becca for a regular check-in she and I have, scan documents, and, well, taking notes.

I have a bunch of pinned and locked notes. They store lists of all my online accounts. As soon as I sign up for something, or, let’s be honest, discover I had an account somewhere I forgot about, I put it on a list in one of these pinned and locked notes. I have a monthly reminder set to go through the list and delete things, update passwords, and so on.

Becca and I share a note of topics to discuss during a weekly check-in we’ve set up with each other to handle the business part of partnership.

I use Apple’s Mail app for consolidating all my email accounts into one email client. The major affordances I appreciate here are the rules, the ability to mark addresses as important people, and the integration with other apps (which has been the biggest surprise with the suite of productivity apps from Apple).

Despite rules being available in most email clients, in this case, I have to say none of the clients I’ve used has had the same robust, easy to use, and constantly applied system I’ve experienced with Apple Mail. I have rules that automatically delete emails from recruiters when I’m not actively looking for a job; when I am looking for a job, I turn that rule off and I see those emails again. If I sign up for a newsletter or similar recurring mailer, I’ll create a rule that automatically routes it to a folder for future reading; if I unsubscribe later, the rule is still there and I don’t get a cluttered inbox if I sign up again. I even have rules that color-code emails; green for finance-related things and red for stuff using deprecated email addresses. But, the big thing for me is the simplicity of it. For example, if I’m looking at an email for a newsletter I’ve signed up for that I don’t have a rule for, when I create the rule (or want to add it to an existing rule), the app uses the email I’m currently viewing to auto-populate form fields; for example, moving stuff from this address to that folder—the from address will be pre-filled with the sender of the currently selected email.

The important people feature is basically a rule, but there’s a shorthand way of creating it. Instead of creating a rule that says, “If sender is X, do this thing.” You click a star in the interface and when emails come in from that address again, they’ll be highlighted with a star; these are the only emails I let pop notifications on my phone, and I have to check manually, so, the notification is more a checkin saying, “In case you missed it, this important sent you an email.”

Regarding the integration it’s kinda trippy to drag emails over to Notes or Reminders and have the app do something constructive with it. Calendar can pick up on possible invites in emails. Reminders can be dragged to the Calendar to create events. That sorta thing.

I use the Numbers app for creating spreadsheets and I have to say, of all the spreadsheet applications I’ve tried, I appreciate it the most. Similar to all the apps listed so far I can have the files sync across all my devices and be available on the web using the iCloud website.

The main spreadsheet I have is related to my finances; called Allocate Funds—see my personal budget.

I use the Pages app for writing books and publishing the ebook versions and, similar to the Numbers app, I have to say it’s my favorite full feature word processor. And, again, I can choose certain files to be synced across all my devices and even share files directly with someone using their iCloud account; good for editing and proofreading.