Man, organizing stuff is a nightmare. I’ve tried all the fancy apps, the expensive planners, the bullet journal craze—all that junk. Every time I start, it looks great for three days, and then it just turns into a pile of guilt sitting on my desk. So for October 24, I decided to chuck all the complicated nonsense and just go back to basics. A quick look inside, nothing fancy, just what needs doing.
The Brutal Truth of October Setup
I grabbed the biggest piece of plain card stock I had lying around. Forget the pre-printed calendars. They never have enough space where I need it. First thing I did was just draw 31 messy boxes. They look like a kid drew them, honestly. But that’s fine. If it looks too perfect, I won’t use it. If I can’t scribble on it, it’s useless to me.
I always begin with the stuff I absolutely cannot change. I pulled up my old, unreliable digital calendar just to verify the immovable anchors of the month. These are the things that will cause a major financial or social disaster if I miss them.
- I blocked out the non-negotiables first: Those three days I absolutely have to travel for that one client meeting out of state. I used a thick, angry red sharpie for those. No moving them. They are sacred.
- Then I looked at the big looming deadlines. The major projects that need shipping before the last week of the month. I assigned each of those a specific color—yellow for Project A deliverables, blue for Project B final review. I didn’t worry about specifics yet, just the target completion week. I slapped down the color block over the entire week if necessary.
- I slammed down the personal stuff next. The dentist appointment that’s been rescheduled twice (I hate the dentist). The kid’s school play. If it involves pants and leaving the house, it goes on the calendar. I used a plain black pen for these because they are annoying, not urgent.
I realized pretty quick that Week 3 was packed solid. Absolute gridlock. It looked like a traffic jam painted in highlighter. I saw that if I didn’t intervene, I would be working 16-hour days and eating instant noodles. So I pushed back the smaller, flexible tasks—the “nice to finish” items—from Week 3 into Week 4. I used Tuesday and Thursday slots specifically, because everyone knows Tuesday is the least productive day of the week, so if I schedule deep work then, it has a chance of actually happening.
This isn’t high-level corporate planning; it’s just surviving the next four weeks without collapsing. The whole process, from finding the card stock to scribbling the last reminder for groceries, took me maybe 45 minutes, maximum. I tacked it up right next to my coffee station so I literally cannot avoid looking at it every single morning when I go to fire up the espresso machine. That’s the key, right? Making the system unavoidable.
Why I Finally Decided to Stop Messing Around
You might be asking why I’m suddenly obsessed with this quick, ugly calendar setup. I mean, I’ve been winging it for years, right? I used to think I was invincible. Well, something happened last month that just… slapped me awake. It put the fear of God into me about relying on my own memory.
My buddy, Mike, the one who always bragged about being able to juggle five projects at once, the one who never needed a calendar because “it was all in his head”—he got hit with a serious, sudden health scare. Nothing catastrophic, thankfully, but it was enough of a wakeup call. He had to shut down for two weeks, completely. Everything he was juggling just dropped. His entire schedule, which was only ‘in his head,’ vanished. Clients were scrambling, thinking he’d just abandoned them. His wife was furious because she didn’t know who he needed to call back or what deadlines were burning.
I went over to his place after he was cleared to work minimally, just to help him sort through the wreckage. We opened up his laptop, and it was pure chaos. Notes scattered across twenty different text files, emails unanswered for days, and commitments he’d completely forgotten about until a client called him up yelling. He looked at me, totally exhausted, and just said, “Man, I thought I had infinite memory. I thought I could hold it all.”
That hit me hard. I’ve been running the same dangerous game. I used to pride myself on that mental agility, thinking I didn’t need external systems. I laughed at people who needed color-coded schedules. But seeing Mike sitting there, completely overwhelmed because he hadn’t written anything down, it scared the hell out of me. It wasn’t about being perfectly productive anymore; it was about damage control when life inevitably decides to throw a wrench in your gears and you can’t function.
So, the October calendar isn’t about being perfectly optimized for output. It’s about creating a physical backup system. If I get taken out by a bad flu, or something worse, someone else needs to be able to look at that ugly poster board and figure out what commitments I have pending. It’s the minimum level of adulting required, honestly. I put the pen down and stepped back, realizing that this quick 45-minute setup wasn’t just a plan; it was insurance against total collapse. I looked at the red blocks and the blue blocks, and I felt a tiny bit less anxious knowing I’ve got the next four weeks physically mapped out. Let’s see if this basic structure holds up through October. I’ll keep you guys updated.