How I Went From Never Using A Planner To Using One For Literally Everything

A few years ago — right around when I started working at TFD, actually — I decided I was going to try out bullet journaling. I had always been attracted to the idea of being the type of person who uses a planner, but I’d never gotten a system to stick. I’d try sticking with a planner for a few weeks, then abandon it after it felt like it required too much time and attention. The bullet journal, on the other hand, offered complete customization and flexibility, two features I never associated with a “traditional” planner.

Fast forward nearly three years, and I have made the 180-degree switch back to a traditional weekly planner — but this time, after more than a year of using no handwritten planning system, I have fully stuck with it for five months (and counting). Here’s how I’ve managed to make a planner habit stick for the first time in my life.

Discovering My Planner-Friendly Personality Type

As many people reading this will know, I have become somewhat obsessed with the concept of habit building. I read Gretchen Rubin’s book Better Than Before, which helped me learn many things about myself — including the fact that, according to her personality categorizing system that she calls “the Four Tendencies,” I am definitely a “Questioner.” This means that, while “Obligers” need external accountability in order to get something done or achieve a goal, I respond most to internal accountability. (“Upholders” respond to both internal and external accountability; “Rebels,” well, who even knows what’s going on with them.) I will pretty much only do something if it makes logical sense to me to do it — e.g. I will stick with a resolution if I’m serious about it, but I won’t wait until January 1st to start it, because it’s an arbitrary “starting over” point.

How I Know I’ve Always Been A Questioner

While I’ve only recently discovered this terminology for personal tendencies, I know my Questioner nature has been true for me pretty much my whole life. I never had a boyfriend in high school, even when all of my friends did, because it never made sense to me to go on a date with a dude simply because he asked me out on one. I only ever did the exact amount of math homework that helped me feel like I understood a concept; anything beyond that felt like dedicating way too much time to math. I completed a totally-optional thesis my senior year of college only because I knew my advisor would let me write about a television show even though I was an English major. I kept going to work when a terrible startup job wasn’t paying me — not because I felt accountable to my boss (“boss”), but because I felt accountable to myself in case there was even a tiny chance that I would ever see the money I was owed. (Spoiler alert: I didn’t, but you can read all about that here.)

Knowing myself better and thinking back on what’s helped me stick with projects and make good decisions in the past have made it easier to figure out how to achieve even bigger goals. At this point in my life, if I make a promise to myself that I’m going to do something, it makes logical sense to me to hold onto that promise.

Why Bullet Journaling Didn’t Work For Me

Now, at first thought, the bullet journal seems like the perfect solution for a Questioner like me. You aren’t bound by arbitrary timelines and starting on a certain date. You can use any type of template you want. But I found that the most effective way to utilize one was to set up the month’s pages at the end of the previous month, or the week’s pages every Sunday — and I just couldn’t commit to scheduling and planning on specific days. Plus, while the original bullet journal isn’t remotely about making planning “pretty,” I like pretty things, so if I was going to bother putting time and energy into it, I was going to make it colorful and cute. It took up so. much. time. My bullet journal felt like would invite a spontaneous form of planning, but it ended up being an even more rigid system to me than using a regular planner. And because it required so much time, I’d often leave it unattended for weeks before getting back into the groove of it.

Why My “Normal” Planner Works Better

I started using a planner right at the beginning of this year, about a month and a half after I got serious about regular exercising. At that point, the main purpose of my planner felt really simple: to keep track of the days I would plan to go to a group exercise class. Writing them down made them feel like more of an obligation than simply telling myself I would go. Of course, plans often have to change, so I started recording when I actually made it to a class in my planner as well. On my monthly calendar pages, I simply make a little pink dot on each date I made it to a fitness class. This way, I get a big picture idea of how frequently I’ve made time for exercising, which is extremely motivating because I never want to break a good streak.

Planning Ahead = Making More Room For Fun

Very soon after I started using my planner for exercise, I started using it for pretty much everything else, too. For instance, it has helped me get super on track with my savings goals for the year (which is very important this year in particular, considering that I’m getting married and attending three other weddings in different states).

Getting to know myself and my tendencies better has also meant accepting a very core part of my personality: I take so much more pleasure in planning than I do in spur-of-the-moment decisions. This goes for everything in my life, from planning out vacations to planning ahead when I am going to treat myself. If I know we’re going to go to our favorite bar on Friday night or we’ve scheduled a pizza night on Sunday, I’ll get so much more joy out of those things. Not only will I get to take pleasure in the cocktail I get or the pizza I eat, but I will also get the privilege of having those things to look forward to.

Of course, you don’t need a physical notebook to plan ahead for these types of things. But writing down everything I have to look forward to makes it feel more real. Being “addicted to your planner” almost feels like a joke — like a quality you’d assign to a caricature of an organized, Type-A personality. But for me, it doesn’t suck the joy out of things that are supposed to be fun. Planning helps me enjoy things even more.

Using Scheduling As Stress Relief

Now, planning ahead also means you have to plan for the not-fun stuff. You can’t effectively use a planner if you’re not also writing down doctor’s appointments and networking events. But to me, there is nothing more stress-relieving than taking time to plan ahead.

Here’s the thing — once I have a system in place, I don’t like change. Case in point: Peter and I recently discovered that, because we are getting married this calendar year, we will have effectively been married all of 2019 when it comes to filing our tax returns. This means that we needed to look into how to switch my Roth IRA over to a Traditional IRA, because our joint income puts me over the income requirement for a Roth. It’s an extremely privileged position to be in, but the thought of changing up my system was giving me a lot of anxiety. Instead of dealing with it on the random day we realized we needed to make a change, I had us schedule a date and time two weeks out, when we would look into opening a new account and re-assigning my yearly contributions. That way, it was out of my mind — I knew I didn’t need to immediately worry about it, but I also knew it would eventually get done.

Conclusion: I Have No Interest In Not Planning

Back to Better Than Before, and to quote Gretchen Rubin:

“Habits make change possible by freeing us from decision making and from using self-control.”

I’m now in the habit of using my planner, which means I don’t have to think about it — I just do it. This makes it easier to hold myself accountable for things I want (or need) to do, from getting my butt to pilates to staying on track with my weekly spending. It’s not about trying harder; it’s about having to try less. It sounds counterintuitive, but putting a “restrictive” system on myself actually feels more freeing. I can spend a little time planning in exchange for a lot less time making decisions — and a lot more time simply enjoying my life.

Image via Unsplash

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