Planning to the Extreme: How Hyper-Organization is Driving me Insane


I know some people (myself included) are in the school of thought that too much planning is never a bad thing.

“Measure twice, cut once,” amirite? My friends, this couldn’t be more wrong.

I’ve mentioned a few times in my previous posts that I have OCD and extreme social anxiety. Well, part of that means I’m obsessed with planning. Every. Little. Detail. All. The. Freaking. Time.

woman with a clock face

If I haven’t planned for it, it can’t happen. And if it does happen, I can’t handle it.

Now, this isn’t very practical for a mom, or even a regular human being. Especially when you take BVTMB writer Sarah’s “Murphy’s Law of Parenting” into account.

I’ve basically got two options: plan for everything or change how I react to unplanned episodes.

Since planning everything would make me go insane and leave me a hot mess curled into a tiny ball in the corner of my room,  I’ve had to learn how to deal with unexpected events. 

Some of the best advice I’ve found for dealing with my need to plan has been in articles like this one from the Harvard Business Review. So, here’s my top three ways to get over my obsessive need to over-plan and swallow that chill pill I so desperately need.

Think of plans as trail maps, not treasure maps.

hiking no planning
Sure, take a map, but don’t plan out your journey to the last detail. Have fun!

Sure, you’ve got a destination, but there are many little branches from the main trail, and lots of awesome sights to see along the way. One of my favorite local hiking spots has about 50 different ways to get to the amazing mountain spring at the end. And if I put my head down and followed the main trail, I’d miss seeing the tiny waterfalls fed by the rain and snow melts, the huge, moss covered rock where dozens of people have left their initials, and the multitude of mushrooms pushing through the undergrowth and decaying leaves. I’d be missing out on LIFE, and for what? The satisfaction that I got there quickly? That I did it, “My way?” Totally not worth it. I’d rather take the extra hour meandering through the woods than get there out of breath and sweaty from trucking it to the end.

Don’t get so self-assured that other people’s ideas seem inferior.

I know I’m super guilty of this. I think my ideas are the bee’s knees. And while, admittedly, I’m brilliant most of the time, there are so many people whose brilliance is a match (if not superior) to my own. By letting go and listening to input from the people I’ve surrounded myself with, my plans and ideas can only benefit. There’s a reason I decided to hang out with these people, and I shouldn’t hinder myself by neglecting their opinions.

There’s no consequence for failed plans.

Having been in school for the past five years, I tend to think in terms of right vs wrong for my life. But really, if things don’t go my way, what’s the worst that will happen? For instance, if my daughter decides to wear shorts on a cold fall day, how will my forcing her to change make the situation better? I’ll tell you now, it won’t. She’s as stubborn as I am and fighting about her cold legs will only result in tears (from us both) and bad attitudes for the whole day. Instead, I let her wear shorts. She’s got extra clothes, including pants, at school and in her backpack. By letting her make that mistake and decide on her own to change, I’m empowering her decision making for the future. Sure, I know I’m right, but I’m not failing as a parent by allowing her to make her own mistakes— I’m actually teaching her a valuable lesson.

Stressing out and being a compulsive over-planner isn’t good for me, my daughter, or the people around me.

I’ve got a choke-hold on the events in my life, but by holding on so tightly to my plans, I’ve turned myself into an over-planning monster. Because I’ve got a mental disorder that compounds this problem, it’s really important for me to peel my fingers back one at a time and let go of what I can.

mother and daughter
I want unexpected and silly moments with my daughter, not ones that are staged and planned to the point of ridiculousness.

Since I’ve got the fate of a tiny human in my hands, I want to make sure that I’m setting an example for her that will enable her to achieve everything she wants in life. And most importantly, to not worry about planning like I do. It’s with this goal in mind that I wake up every morning and tell myself to take a chill pill, go with the flow, and let life happen.


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