A person wearing a yellow shirt.

Little Gestures Planner-Types Find Extremely Satisfying

“Planning is overrated.” – said no planner ever.

The planner-type is a special person. A person who feels that they can control the universe around them. A person who reins in the chaos and unpredictability of life with calendars, schedules, and agendas. Yes, the planner-type is a special person. I would know. After all, I’m one myself.

Most people have some system for planning. It’s often crude, but it works. Well, it works until it doesn’t. It only takes a busy day for the common system to fall apart. But that would never happen to you. And on the off chance it did, you would see to it that it wouldn’t happen again. Because you like to plan. And so do I. Here are some little gestures you will find extremely useful and satisfying. From one planner to another.


What’s mine is yours

In passing one day, my wife mentioned something that has since been a game-changer for us. The ability to share our calendar. It’s simple to do. You simply create a new calendar category and share access to it. Instead of now asking my wife if she has plans in three weeks, I can just check the calendar. Instead of her wondering what I’m doing on Tuesday, she can just check the calendar.

Our collective planning efforts have become streamlined. Further, decision-making has become easier. The question of, “What did you say you were doing next week?” is no longer a thing. We both have access to the data. The first planning gesture is to share your calendar as needed.


The power of maybe

“Are you free next Wednesday at 11 AM? Or is Thursday at 2 PM better?” Assuming you schedule meetings manually, like me, this is a common scenario you encounter. But what happens if the person doesn’t respond for a few days? You’re left with an unresolved feeling in the back of your mind.

The solution is simple. I add both events to the calendar. In front of each of them though, I write MAYBE. For instance, Wednesday at 11 AM would show – MAYBE: Meeting with Charlie. It would also show that for Thursday at 2 PM as well. That way I block out the time on the calendar but know things aren’t solidified just yet. The second planning gesture is to add tentative events to your calendar using the word MAYBE.


Reading between the lines

I have diagnosed anxiety. I also have a desire for control in a chaotic world. Hence, my gravitation towards planning. Being the planner I am, I like to see the days on my calendar filled with dots. A dot representing an event on a particular day. Dots are good. No dots are bad. At least, that’s how I used to feel.

Maybe it’s because I now take medication for the said anxiety, or because I have a young daughter and my life perspective has changed, or maybe it’s for a slew of other reasons. But now I don’t stress about the dots as much. I know the no-dots are just as good as the dots. Because the no-dots, the white spaces, represent opportunity. Where the dots represent a guarantee of action, a white space represents the promise of spontaneity. Something I’m trying to embrace. The third planning gesture is to welcome no-dot days.


A thousand times, yes

What if every meeting you scheduled offered promise? What if each call brought hope? Promise for a new friendship, hope of something new to be gleaned. That’s what I strive for with the meetings I undertake. Now, full disclosure, I have more control over my time than most. However, even if you have zero say over such matters, this is something with wider implications than just who signs your paycheck.

What if everything you added to the calendar – meetings, events, activities, appointments – were skewed towards fulfillment? Meaning that the meetings you actively set up, the events you had the ability to select, and so on, were generally focused on creating a meaningful life for yourself. Instead of seeing your calendar as a collection of requests and chores, it would be a space of purpose and meaning. The fourth planning gesture is to build your calendar on fulfillment, not guilt.


Separation anxiety be gone

I strive for simplicity. So naturally, I loved the idea of keeping everything within my calendar. From the time I would awake to when I would exercise, have lunch, and read. But I quickly realized the calendar is not made for such things. Making a minor change, like when to shower, would be a multistep process. What seemed minimalistic was actually complex and annoying.

So instead, I use two things to plan. First, obviously, is my calendar. The second though is a Google Doc. This Google Doc is where I undertake all of my day-to-day planning. It’s ideal for this function due to its ease of editing. I can easily move tasks around. Conversely, my calendar is used for major events. For example, meetings for the week or dentist appointments go on the calendar. It is the macro. My Google Doc focuses on the nitty-gritty. For example, when I’ll wake up, get dressed, and start writing for the day go on the Doc. It is the micro.

This has allowed my calendar to be what it is – not my daily planner, but something more macro-centric. The final planning gesture is to separate your micro and macro planning. It may feel more complex at first. It’s not.


Moving forward with little gestures

From one planner to another, know that these little gestures have vastly improved my time. From avoiding scheduling conflicts with my wife, to embracing the spontaneity of no-dot days, to more thoroughly planning my time, and everything in between. They can help you as well. For your reference once again, the little gestures for better planning are:

  1. Share your calendar.
  2. Add tentative events with MAYBE.
  3. Equally embrace dot and no-dot days.
  4. Fill your calendar with fulfilling events.
  5. Use your calendar for the macro and a separate doc for the micro.

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