I first considered using a physical planner after a disastrous day, some time ago, when I entered an important meeting into my "work" calendar instead of my personal one. I ended up missing lunch with a friend who understood the mix-up, but didn't (understandably) argue when I admitted that I was descending into flakiness.
Originally, I thought that keeping the two spheres separate and un-synched would help me be more organized. In a sense, it did — if knowing half of my schedule really well at any given time, and constantly forgetting the other counts. There really were some upsides to bifurcating my calendar in the digital world: not receiving a million alerts and notifications on days when I had work and personal meetings was a big one. But obviously, a big perk — namely, seeing conflicts ahead of time — was something I missed out on.
So, although it felt slightly strange to think that a notebook could do what technology couldn't, I decided to test out a few physical planners. I started on a Sunday evening with several spread around me, and went through the calendar and text messages on my phone to see what I had planned, promised, and put off for the upcoming week.
I thought my main dilemma would be knowing what to put in the planners, versus what I had already put in my phone. In fact, I learned that my real problem was how poorly I had organized events in my phone in the first place. There were meetings with unconfirmed times, or meetings that just didn't show up at all for some unknown reason; and I was counting on my memory to remember they existed. Some days or weeks didn't necessarily have conflicting times, but they were overbooked, making it unlikely I'd be able to be punctual or at ease when checking them off.
After seeing how many holes I caught in just one week, I decided to go through the following week in advance, too. It's not like I had never looked through my calendar before; I just tended to look at my calendar on a day-to-day basis — either the night before, the morning of, or relying on pop-up notifications throughout the day. That kept me on task (ish), but it didn't leave much of a margin of error.
In the end, I realized that I could still use my phone to view the play-by-play action of my days and weeks, but a physical planner was much more useful in creating a structured, bird's-eye view. Figuring out how to balance the two does take time, but more importantly, it takes commitment. Creating a routine of when I'll go through my planner and phone calendar is key. Without that, neither works very effectively.