Using Apps to Organize Your Life

If it weren’t for the software I use to keep my life running smooth every day, I’m not entirely sure I could survive. My responsibilities include a full-time job, a relationship with my wife, three young children (each with their own needs, appointments, etc.), other family events and obligations, two dogs, a house to manage and maintain, a car, personal projects, way too many bills, and now schoolwork (my wife and I recently decided to go back to college).

I don’t know if this is a typical load for most families, but to me, it seems excessive when I write it all down. It certainly feels like a lot while living through it, so I need tools that work for me so I can put my energy and focus on actually getting things done.

And work for me they do: school assignments and work tasks are always completed on time; I almost never forget anything important; appointments and events don’t creep up unexpectedly; bills get paid on time; I’m on top of routine house and car maintenance; I’m able to attend all school events for my children. All in all, I’m generally prepared for most things. And on top of all that, I still have time for my family.

However, without the various apps and services I use to keep my life on track, I’d be a total mess. And in fact, I used to be. It wasn’t until I took the time to organize every aspect of my life with digital tools that things started to finally run without a hitch.

Trial and Error

It took a long time for me to get to this point, and indeed there were times in the past where I have felt completely overwhelmed (even with fewer responsibilities). My setup required a lot of fine-tuning over the years. But finally, over the past year or so my efficiency has been at an all-time high, and I attribute this directly to the software I use to stay productive. Taken together, these tools take on the role of a very good personal assistant that can handle anything I throw at it.

The good news is, my setup is relatively simple to replicate and some parts are highly interchangeable. The most difficult part is getting in the habit of using the tools on a regular basis, but it really doesn’t take too much effort as long as you stick with it for a few weeks. Once you see how efficient you become, like me, you may wonder how you ever got by any other way.

As a side note, this is one area where macOS and its integration with iOS really shines, and is one of the main reasons I find it totally debilitating to use non-Apple platforms. I have used Windows, Linux, and Android for extended periods of time, and during those times I was never able to replicate my setup in a way that matched the level of efficiency afforded by my Mac and iPhone for my productivity needs.

Calendar

The built-in app on both macOS and iOS are sufficient for my calendar needs, which are pretty basic (by design). The only thing I put into my Calendar are actual events. No due tasks or assignments or anything of that nature—strictly events. This includes things like appointments, school field trip days for my kids, vacations, birthdays… you get the picture. I use separate apps for non-event items.

I have two iCloud calendars so all of my events are synced between my Mac and iPhone (no local calendars) and are always backed up online:

  • Calendar: events that are relevant to me only.
  • Family: a shared calendar with my wife, for events that pertain to both of us (family events, appointments, etc).

I also have some Google calendars hooked up to the app that are for work events, meetings, off days, etc. These are calendars that are managed by my company, so it’s not really something I have a choice in, but they are there for me to see along with everything else.

This part of my setup is pretty interchangeable in that most people either use Google Calendars, iCloud, or some other widely-used calendar service that can be managed with just about any app, whether it is native or web-based.

I personally prefer the built-in Calendar app (in both macOS and iOS) over third-party alternatives, even though there’s really nothing about it that makes it necessarily better. I like the full-month view, as well as the UI for managing events. It’s simple, and free.

Event Metadata

A really important detail: for any new event that is added, I always fill in as much metadata as possible (start time, an address if applicable, any relevant notes, etc.). I find this practice really helps make life easier when the event inevitably comes up. This is especially true if an event was added really far in advance and the details of the event are no longer fresh in my memory (or easily available). Don’t wait until later to add metadata, or you’ll risk forgetting.

So to recap: use a Calendar app to put all of your events into, but put only events in your Calendar—don’t fill it with to-do items, reminders, or junk. And don’t forget to add event details!

Reminders

I use the built-in macOS and iOS Reminders app extensively. Its interface is similar to a task list, but as with Calendars, I have a strict rule for what goes into this app: things I need to be reminded of on a specific date and time. I do not use this app as a to-do list, or for due tasks that belong to a specific project (I’ll get to that next).

I’m sure there are other great third-party apps that provide more features, but this is the only app that I trust to give me a notification exactly when it’s time (on both my Mac and iPhone). This is true even if I don’t have the Reminders app opened in the background, which some third-party apps require for proper notification delivery. Reminders has yet to fail me even once.

Lists

The key to using Reminders effectively is to take advantage of separate lists. Here are mine:

  • Reminders: My “default” list for general reminders that don’t fit into any of the other lists.
  • Finances: Bills, payments, and anything money-related.
  • School: Anything related to the kids’ school that I need to be reminded of.
  • TV Shows: My wife and I watch several TV shows, and it’s a pain to keep track of when seasons start, what day episodes air, etc. I’m reminded of when shows like Better Call Saul and Game of Thrones are ready to watch, to name just two of our favorites.
  • Movies: When movies my wife and I want to see are either going to be in theatres, or available for purchase.
  • Music: Same as movies, but for music albums.
  • Recurring: Any reminders that need to be repeated. For example, I have reminders for watering the grass every Wednesday and Sunday night, a monthly reminder to change the air filter in my house, a weekly reminder to put the trash bins on the street, etc.
  • Future: Things that are pretty far in the future that I don’t need to see in my general “Reminders” list, which can get pretty full at times.

Splitting everything up into multiple lists really helps keep everything very organized. I also sort items by date so “sooner” items show up on top. The Reminders app is probably the least interchangeable part of my setup because I don’t know of any other app that does the same thing as reliably.

Once I got in the habit of using Reminders for anything and everything I need to remember at a specific date and time (that isn’t considered an “event”, which goes in the calendar), my life has been running so much smoother. Before I used this app, I would often forget even simple things like putting trash bins on the street every once in a while, bills would occasionally be late, etc. Even small things like that add up to big stresses in a busy life. Now none of those things happen.

OmniFocus

Tasks that are “actionable” and cannot be classified as events or reminders get put into OmniFocus, my current task management app of choice.

Inbox

Ideas, things I think of as I go, and tasks that don’t yet belong to a project get dumped into the OmniFocus Inbox for later processing. Since I check the app every day, whatever gets put into the app is not something I’ll miss.

Loosely following GTD principles, about once a week, I’ll think of anything and everything that needs to be done for the following week (or beyond) and dump them into the Inbox. When I get time, I’ll process the items into their own projects or move them to the Reminders or Calendar apps as appropriate. Everything gets processed out of the Inbox though—nothing stays.

Projects

I have several projects set up for short and long-term groups of items I’m working on. For tasks that have specific due dates, it can sometimes be confusing whether to put it into OmniFocus or Reminders, but as a rule of thumb, if the task is part of a specific project or isn’t something that I need to be reminded of at a specific date and time, it’ll go into an OmniFocus project.

Forecast

The thing that sets OmniFocus apart from the competition for me is the Forecast view, which shows upcoming tasks and Calendar events. With this feature, I don’t have to open both OmniFocus and Calendar to see everything that’s coming up in my life.

You can definitely get by with a different app for managing your daily tasks and projects, and there are a ton of free options available, but unless the app has an equivalent to the OmniFocus Forecast view, you’ll need to be sure to also check your Calendar daily for upcoming events (so you can be prepared for them before they come up).

1Password

Most browsers have built-in password managers, but those don’t hold a candle to 1Password in my opinion. In fact, I have Safari’s password saving feature turned off and I rely exclusively on 1Password for all my passwords. Why? Because not only does 1Password do a better job of saving passwords (and filling forms), it also stores a whole lot more than that.

Of course, I use 1Password to store all of the hundreds of logins I have accumulated over the years, but it also holds my credit/debit cards, bank accounts, social security numbers, software licenses, etc. I also have a few “Secure Notes” for things like health insurance information and things like that.

What makes 1Password even more useful is all the meta-data that can be stored with each item, as well as the ability to add custom fields. For example, for many items I have a “Security Questions” section that is useful when I can’t quite remember exactly what answers I entered. There are several other examples like this where the ability to add custom metadata comes in very handy.

Having all of this data accessible from a single source on both my Mac and iPhone is very convenient, and I never worry about losing it ever since 1Password switched to cloud-based storage. I tried a few other alternatives and none of met my needs as well as 1Password has, and for such a reasonable price; it is well worth the $3.99 I pay every month for this.

Notes

Everything else that doesn’t get put into any of the previous apps and services—and I want to keep—gets saved as a “note” using the built-in Notes app. For a long time, I used a plain text setup for all of my notes, but I found it cumbersome to view and edit notes on mobile. Since I have both a Mac and an iPhone, this is the fastest, most reliable solution. It works well, meets my needs, and it benefits from the extra dollar I spend a month on iCloud storage.

I also have some “pinned” notes for frequently accessed items (this feature was added in High Sierra). Other than that, my usage here is pretty straight forward.

iCloud Documents

I have the iCloud “Desktop and Documents” feature turned on, and pay an extra dollar each month to get more iCloud storage space. Everything stored in my Documents folder is automatically backed up to the cloud and accessible on all of my other devices (my Desktop is generally always empty). Files that I need saved, such as receipts that have been saved or scanned in, vehicle registration copies, tax returns, work-related files, etc., gets stored in my Documents folder (within sub-folders, of course).


Combined, every app and service I mentioned helps to organize (almost) every aspect of my life, and being able to rely on all this software helps free my brain’s resources to focus on the things that really matter. This results in higher efficiency with much lower overall stress. Instead of wasting “spare cycles” on organizing everything, I can rely on specific software on my Mac and iPhone to keep my life on track.

Additionally, I have found that this setup scales really well, and I think that’s due to using a handful of tools to handle very specific parts of my workflow. It is also relatively inexpensive to replicate, and there are even free alternatives to some of the paid software and services I use. Almost every part of my setup is interchangeable, and can be swapped out for a different alternative if I ever wanted (or needed) to.

One area of my life that I didn’t cover is how I manage my personal finances and what that setup looks like. However, that topic will have to wait for another post as it’s outside the scope of this one. For now, I wanted to focus primarily on the “organizing” aspect of my digital productivity setup.

I’m also curious to hear about what apps and services others use to manage their lives, and particularly if there exists a similarly effective setup for Linux, Windows, and Android users. During the times I have spent using those platforms, I was unable to find solutions to my problems without accepting severe compromises in efficiency—there was always something that was missing or had to be worked around.

I’m sure my setup can be optimized further, and I do sometimes have a compulsion to try new things, but so far, everything’s been working great and I feel like I have finally hit a sweet spot in my digital productivity workflow.

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