Obsessive compulsive planning and how it drives me a little nuts

I wonder if anyone else feels like they’re constantly living in a planner. You know what I mean? There’s this fine line between being organized and being a little obsessive about it. For me, it often feels like I’m wading through a sea of checklists and schedules, and the irony is that while I think I’m gaining control over my life, it sometimes drives me absolutely nuts.

I’ve always been someone who thrives on planning. I love the feeling of crossing things off my to-do list, and I often find myself meticulously planning out my days, weeks, and even months. But lately, I’ve noticed that this obsession with planning can spiral into something more constricting. It’s like I’m wrapping my life in a tight little bow, and when something doesn’t go according to plan, it throws me into a bit of a tailspin.

For example, there was this one time I meticulously planned a weekend getaway. I had every minute accounted for—what time we’d leave, where we’d stop for lunch, and even the exact time we’d check into the hotel. But then, a couple of things fell through. A friend had to cancel, and traffic was a nightmare. Suddenly, all my well-laid plans unraveled, and I felt this surge of anxiety. It was almost as if I had lost a part of myself because I couldn’t keep everything on schedule.

Reflecting on it now, I realize that my need for control often stems from a deeper desire for certainty in a world that can feel overwhelmingly unpredictable. There’s comfort in knowing exactly what’s coming next, but I’ve started to question if this is truly healthy. Am I missing out on spontaneous moments with friends? Am I making memories, or just ticking boxes on my planner?

I’ve been trying to find a balance—allowing for a little chaos while still appreciating the structure that planning brings. I’ve started incorporating “free time” into my schedule. Sounds silly, right? But allowing myself to have unstructured moments has actually been refreshing. There’s something exhilarating about not knowing how the day will unfold.

I’d love to hear from anyone who feels a similar push and pull between planning and spontaneity. How do you navigate that space? Do you find it challenging to let go of your plans, or do you embrace the chaos? I think talking about it can help us all find a little more freedom in our days.