Which System Would You Pick? The Answer I Didn’t Plan For
Last Tuesday, my friend Lila showed up at my apartment with oat milk iced coffee, her laptop open to three different productivity app tabs, and a whole lot of stress. She’s switching to full-time freelance next month, and everyone she follows online has been yelling that the right system will make or break her whole year. Half the people swear by rigid time-blocking and habit trackers that would make a 1950s housewife blush. The other half swear that systems kill creativity, you just have to go with the flow and trust your brain. She leaned across my coffee table, spilled a little of her coffee on the corner of my beat-up thrifted notebook, and asked me straight out: which system would you pick?
I froze for a second, because I’ve been through this enough to know there’s no sexy answer. Three years ago, I would’ve given her a 10-minute rant about time-blocking, how I color-coded my Google Calendar down to 10-minute water breaks, how I never missed a deadline, how it fixed all my messiness. That was when I was working that dead-end remote admin job, the one where I had nothing to do all day but tweak my system. I once turned down a spontaneous walk with my neighbor, the one who brought me homemade soup when I had COVID, because my 2 p.m. block was reserved for answering junk email. I stood in my doorway and lied and said I was too busy, and she hasn’t asked me to come along since. That’s the thing no one tells you about rigid systems: you start prioritizing the system over the actual life it’s supposed to organize.
I got so obsessed with checking off blocks that I’d procrastinate on a 10-minute task just so I could move it to the next day and have a full, perfect row of checkmarks. I’d stay up an hour late just to finish a trivial thing so I didn’t have a blank spot on my calendar. By the end of that year, I was burning out so bad I’d sit on the floor of my closet for 20 minutes in the middle of the day just to not have to look at my screen full of colored blocks. So I threw it all out. I deleted the calendar apps, I threw out my fancy overpriced bullet journal, I decided I was going loose, no system at all, just go with the flow like all the cool anti-system people said.
That lasted six months. I found a grocery list for lemons and adhesive bandages in the pocket of my winter parka three months after I’d needed them. I missed my cousin’s baby shower because the reminder was written on a post-it that fell behind my desk and I never saw it. The most embarrassing one was the dentist appointment: I wrote it on a scrap of receipt, stuck it in my jeans pocket, washed it, and showed up a week late to a cleaning I’d waited three months to get. The receptionist gave me that quiet, pitying look, the one that says you can’t even keep track of a single appointment, and I stood there red-faced rescheduling, and I knew the no-system thing wasn’t working for me either.
So what do I have now? It’s not one or the other. It’s a mess, honestly. I keep all my work to-dos in the default Notes app on my phone, no folders, no sorting, just one long running list. Every Sunday, while I’m waiting for my tea to steep, I cross out all the stuff I didn’t do (most of it wasn’t that important anyway) and move the three things that actually have to get done that week to the top. That’s it. No fancy rituals, no 30-minute weekly planning sessions, no journal prompts to reflect on my progress. Doctor’s appointments and birthdays go in that thrifted notebook by my front door, the one with the coffee stain Lila left, so I see it every time I leave the house. I track how many times I walk my dog on that terrible cat calendar my cousin gave me for Christmas, just a little tick mark on the day, because I wanted to make sure he’s getting enough exercise. That’s the only habit I track. Everything else, if I forget it, I forget it.
Last month I had a big client deadline, and I got anxious, so I tried time-blocking again, just for that week. I blocked every hour out, got all colored up in my calendar, and then my dog ate a whole chocolate bar off the counter and I had to spend four hours at the emergency vet. The whole system fell apart by 10 a.m. on Monday. A couple years ago, I would’ve spiraled, thought I was a failure for not sticking to the plan. This time, I just texted my client, explained what happened, asked for an extra day, got it, and sat in the vet waiting room eating bad vending machine chips while my dog slept off his stomach pump. It was fine.
Lila was expecting me to say “this one app!” or “go 100% rigid!” or “just relax!”, but I couldn’t. I just pointed to the notebook, the cat calendar, the messy Notes app on my phone, and told her I pick the system that doesn’t make me feel like crap when I don’t follow it. Some weeks I’m more rigid, when I’ve got a lot going on and I need that structure to feel grounded. Some weeks I’m more loose, when the weather’s nice and I want to take off for a walk in the middle of the afternoon without checking if I’ve got a block open for it. It changes. I still forget things sometimes. I still feel the urge to over-organize when I’m scared of everything else being out of control. But I don’t beat myself up for it anymore.
I don’t have a perfect conclusion. I don’t know what’s right for you, or even for Lila, for that matter. She went home and tried my messy half-system, texted me yesterday that she forgot a 15-minute check-in meeting but made it to her niece’s soccer game that she would’ve skipped if she was blocking all her time, so that’s a win in her book. I guess that’s all you can ask for, right? A system that lets you have the win that actually matters, even if it’s not the one the system planned for. (Word count: ~1150)
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