The Problem With Calendars, Organizers, and Planners

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I am part of the “productivity cult”. But I think it’s time to recognize that there’s a problem with calendars, organizers, and planners. Try as they might, there’s just not one solution that works for everyone all the time—including me.

I’ve been trying for years to find the perfect planner that fits my needs. The problem with that is all the planners out there were designed with someone else in mind—their creators. So far the closest design I’ve found to the only planner I’ve ever used start to finish is from Erin Condren.

But it’s still not hitting all the marks.

So what’s the issue with all of these organizational tools?

The Problem with Calendars

I have two different calendars to true up with each other. The first is my Google Calendar, which tracks all events, appointments, and trips for multiple projects and responsibilities. In GCal, you can have multiple individual calendars, and I have many that are color-coded.

Doing it this way lets me see my week in colors and identify open spots for other tasks or things I haven’t scheduled yet.

The second calendar is my work calendar. My office uses Outlook, and my meetings don’t automatically move over to my Google Calendar. G-Cal is the core of where I run my life. So I have to make sure all my work meetings line up in Google, since I don’t access my work calendar outside of work hours but still need to know what’s going on in the next few days or weeks.

Paper calendars present a different problem. What if you write an appointment and it gets canceled or moved? With a pencil, it’s relatively easy to erase and rewrite. However, many people use pens in their paper calendars because it doesn’t smudge. There are erasable pens like the Frixion pens, but I can’t stand how they feel on paper.

Another problem is communicating your calendar with others. What if you need to coordinate with your spouse about who’s picking up the kids? If you both have your own calendars but don’t synch them up, you might accidentally leave the kids at school.

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The Problem with Organizers

The definition of “organizers” depends on the person. I think of organizers as the system where I keep my life organized. Think “The Container Store for Your Life.”

Maybe this includes habit trackers, goal-setting sheets, vision boards, notes from work meetings, brainwaves on post-it notes, and a million different lists for all the things you want to have, do, or be.

In the world of calendars, organizers, and planners, organizers cover the broadest range, up to and including their calendar and planner siblings.

The problem? There’s so many things to organize! I’m constantly testing how to best slice up my life. I usually fall back on five core areas:

  1. Personal
  2. Work/Professional
  3. Blog (including Podcast)
  4. Virtual Assistant
  5. Book/Author

But the “Personal” bucket has a lot of stuff in it.

How you organize your life depends on what’s going on in it. If you’re still a student, you’d obviously have a “school” bucket.

One tool that tries to solve this problem is the Bullet Journal method. It’s the most versatile way of organizing and planning your life. However, it depends a lot on you coming up with your own structure and then sticking with it.

If I try putting everything related to those five core areas into one bullet journal, I’d have a heck of a time finding any one thing in it.

The Problem with Planners

Raise your hand if you’ve ever bought a planner and then stopped using it a few weeks later. Yeah. Guilty. It’s not just a problem of motivation or discipline to stick with it, it’s a problem of design.

Everybody and their sister is developing their own paper or PDF planners to sell online. This is great! Most of the time, what works for one person will work “well enough” for someone else who doesn’t have the time, capital, or creativity to design their own.

Ruth Soukup’s Living Well Planner has changed the lives of thousands of people. What works for Ruth also works really well for a lot of other people. I tried it for eight months in 2019 and found that it just doesn’t work for me.

What’s it For???

Sometimes planners have a specific purpose. Do you want to accomplish a specific goal? Use this planner. Do you want to just keep track of what’s going on each week? Use that planner. Maybe you’re a teacher or a lawyer and all those other planners don’t fit your needs. That’s okay, use these planners over here.

The biggest problem is that it takes time and money to find out if a planner works for your purposes. All About Planners tried 52 planners in 52 weeks to do that work for you, but even that experiment didn’t turn out as planned.

The only planner I ever used start to finish for an entire (academic) year was the 2011 school planner my community college gave to every student. It was relatively thin, with a flexible plastic cover, tight spiral binding, and a weekly horizontal layout with plenty of space to write in homework and other to-dos or notes. I’ve been trying to find a commercial replica of this planner for over eight years now.

Paper or Digital?

People swear by one or the other. Nobody agrees. What works well for Debbie doesn’t fit Morticia’s needs.

I use both analog (paper) and digital tools. That being said, most of my calendaring, organizing, and planning happens in my digital tools. The analog stuff is more for cementing ideas or taking quick notes.

I love checking things off a list or crossing something out. It feels like an accomplishment in and of itself, which is part of the draw of having analog to-do lists.

The problem? It takes a long time to set up paper calendars, organizers, and planners. Sometimes I wonder if I ever forget some to-dos when I’m writing them by hand. In the time to write one down I’ve thought of two more and those push out the original thoughts in my head. As David Allen says, your head is a terrible office and can only consciously hold four to-dos at once.

Choosing paper, digital, or a combination of both is a unique decision that I can’t make for you. I just know that a combination works for me in different ways.

One Tool or Multiple?

I would love to find a single tool that handles all my calendars, organizers, and planners and handles them well. And that’s the kicker, isn’t it? Every tool I use has a downside.

Airtable is amazing at record management but lacks a rich text editor to take lengthy notes or write blog posts inside each record on my content calendar. This would be a game-changer.

Notion is a beautiful note-taking and organizational tool with that rich text solution to Airtable, but the tables are clunky and offline mode needs serious improvement. If I could access everything offline, I would use this for almost everything.

Evernote used to be the titan of digital organizers. Unfortunately, their improvements have not caught up to the needs of their customers. Its offline mode is the best, but lacks too many other features to be anything except the tool with which I write content when I’m on an airplane.

Clickup is new. It’s a combo-platter with all or most of the functions I want, but lacking in a few key areas like offline mode and word counts in their rich-text editors.

Of my analog tools, I have an Erin Condren Life Planner (which isn’t getting as much use as I’d hoped) and multiple notebooks. I’m picky about notebooks because the feel of the paper matters a lot more than you’d think. One notebook I tried using as a bullet journal barely got any use because the paper felt awful under my favorite pens. I did purchase the Erin Condren Winter 2019 surprise box, which included her Petite Planner Folio system and that has become a staple of my paper planning process.

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Solving This Issue is Hard

Calendars, organizers, and planners form the structure of keeping our lives on track.

I’m of two minds.

Spending all that time experimenting with different tools takes away from time spent on “more productive” ventures like writing blog posts or prepping a speech. But that time investment into the “perfect tool” is an up-front cost that will save me the time down the road when I keep getting frustrated with my organizational system.

Ideally, I’d have one tool that does it all. But since that’s not possible, I’ve settled for experimenting with different things to find what works the best for me. You should experiment too as much as you’re able.

But, if you’re strapped for time or the money to try multiple systems, reflect on what you need a system to do—and then research what’s already out there.

Erin Condren planners look like the most versatile especially because she offers multiple different planners and you can customize most of them in terms of layout. My EC planner goes through 2020, but I bought some of her “Petite Planners” to keep testing out what works for me and what doesn’t.

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