My Experience with Planners

I started really using a planner just before COVID, in eighth grade. I’d had schedules before; our family had calendars on the fridge, and my mom kept track of events for me. But I think I’d started thinking about journaling even earlier, though I can’t remember exactly when. I don’t know when I first made a schedule, but I do remember always being the kid who was on time, always worried.

Specifically, I remember this one day, when I was maybe in the first grade. School started at 1:30, but the clock said 12:30. Because the small hand on the clock had already moved slightly past the 1, I thought it was 1:30 already. I completely freaked out. Full-on meltdown. That moment really captures how much time and structure mattered to me, and how even then I wanted to be where I needed to be on time.

When I got my first planner, I was so excited. Not just a regular school planner; I’d had those before. This one was pink, had stickers, and a ton of space to write whatever I wanted. That blank-canvas feel was amazing. I went all in. By the end of the year, I switched to a notebook because I wanted even more freedom. That’s when I tried bullet journaling and that’s when the adventure really started.

Bullet journaling is a customizable system where you design your own planner pages from scratch: everything from calendars to to-do lists to habit trackers, often combining functionality with creativity and design. For me, bullet journaling started off as freeing. I had so much space to do whatever I wanted. But at the same time, my creativity hit a block—like 15 or 20 designs in, I had no idea what else to draw. It hadn’t even been a full month, and I was already stumped. I started getting annoyed with how meticulous it was. Starting on a blank page sounds nice in theory, but there’s so much effort involved. Even centering a title is tedious when there are no grid lines or reference points on the page.

This is also when I started realizing I was annoyed at paper itself. In the eighth grade, my daily routine wasn’t that complicated: school, homework, lunch, maybe volleyball. That was it. My to-do list was essentially the same every day. But to feel accomplished, I needed to write those things down so I could cross them off. And, rewriting the same tasks every day was just exhausting.

At some point, probably thanks to COVID, I started shifting to digital tools. I still had a physical planner, still read physical books, and still kept a physical book log. But things like Zoom meetings started going into my Google Calendar automatically, and it just didn’t make sense to write down a Zoom link on paper when it was obviously a digital thing.

What I noticed immediately was just how convenient digital planning was. Repeating events? Easy. Editing something? Done. Adding links or locations? Seamless. I stopped writing “class” and “homework” every day because one recurring event took care of it. I even shared my calendar with my family instead of telling them my schedule every night. They could check anytime. That kind of visibility just wasn’t possible with a physical planner.

What I’m trying to say is: the benefits of digital planning were immediate. Repeated events, shareability, the ease of edits, adding links—everything just worked. But what I miss about physical planning is how it challenged me creatively. Now, everything is online—Google Calendar, Notion, etc.—and while it’s super convenient and efficient, it doesn’t leave room for the little things. The mini drawings, the spontaneous notes, the details that made me happy that day. There’s something soulful about those little moments on paper that digital hasn’t captured yet.

Every now and then, I try out new tools for to-do lists. I’ve tried Google Tasks, Docs, Sheets, Trello, Habitica, Notion, Obsidian, Evernote, Apple Notes, and most recently, FigJam. It’s a Figma product that’s helped me be more creative again. I’ve been using sticky notes to track tasks, and FigJam makes it easy to add doodles, stamps, and other little things that feel personal. It solves a lot of that blank-canvas fatigue with easy templates and accessible customization.

But even FigJam has its trade-offs. It doesn’t have the same structure for recurring events. Sharing and syncing with others is more limited. So I keep ending up in this cycle: I want the creativity of paper and the structure of digital, but no one tool really gives me both.

That’s where I think AI can come in. Not to take over the planning process, but to help guide it. I don’t want something that automates every part of my life, but I do want something that can support me with smart suggestions. Maybe it could say, “This task has been on your list for a while: do you want to try getting it done this week?” Or, “These three things seem related, maybe you can group them together.” Or even something simple like sorting tasks by time or energy level so I don’t have to do all the thinking myself.

I think that’s what the next step could be: a system that blends structure with soul. Something that keeps the flexibility and creativity of FigJam but adds the intelligence of a good assistant. It doesn’t replace your choices, it just helps you make them more clearly. It notices patterns, offers support, and still gives you full control over how your day looks.

That probably means I won’t be going back to paper anytime soon. But if the right digital tool existed—one that understood both my need for creativity and my need for structure—I wouldn’t feel like I was missing anything. My laptop might not smell like paper or have washi tape, but if it can help me stay organized and still feel like me, then that’s good enough.