I would rather be too organized than disorganized, but I’ve been called rigid quite a few times in my life. Actually, “rigid,” with its negative connotations, is the word used by my family; my friends are kinder and call me disciplined. Finding that balance between rigid and organized is tough for us perfectionist, obsessive-compulsive types.

I was working with a client recently organizing her dresser and closet drawers. When you have a lot of clothing, as most of my clients do, drawers and closets have to be extra-organized, otherwise things either don’t all fit into the space or the drawers end up being jumbled messes. However, there’s that fine line you don’t want to cross of being so organized that the system is impossible to maintain. Unsustainable systems seem to add more guilt to the disorganization than if you had never organized in the first place. After all, you spent a lot of time or money or both to get things organized and now it’s a jumbled mess again.

Thinking things through to the point where they could become disorganized again is important. A small but simple example: long sleeve t-shirts getting mixed in with short sleeve t-shirts. It is something that irritates a lot of people because they sometimes have to unfold several shirts before finding the one they want. (These types of irritations are so “first world” and can seem silly, but when you are late for work and it’s cold out and you can’t find your long-sleeved black t-shirt, it can start your whole day off on the wrong foot.)

Too organized would be putting the black long sleeve behind or under the black short sleeve in the drawer every time you put laundry away. Putting long sleeves in a separate drawer altogether, like with sweaters for example, would be a simpler way to not mix them up. Even better, hang your long sleeve t-shirts and fold the short sleeves. More separation between categories that could get easily confused is really helpful.

You can apply this to filing, the pantry, the spice drawer and other places. The more stuff you have, the more separation of categories is needed.

Schedules are even more challenging than space to keep organized but not too rigid. It can seem much easier to just develop routines that cover all your bases, but within this, how to be flexible? First, figure out your absolute hardscape. Then add what might be nice to do each day, week and month—the meditation, the manicure, the car wash, the lunches and coffees with friends.

When you’re known as a person who gets things done, you often get asked to join boards or participate in community projects. It’s great to be of service, but wait at least 24 hours before agreeing to anything. Treat it sort of like a big purchase. Take some time to think it through and make sure you have room for it in your life. More meetings and commitments mean more hardscape schedule and less room for play and time to relax, so be sure you aren’t going to crowd out important downtime with somebody else’s agenda. Remember how Tom Sawyer got the other kids to paint the fence for him? Any volunteer projects should be in line with your interests and passions and not taken on out of pressure or because it was flattering to be asked.

Another pitfall of the overly organized is that terrible feeling of having thrown away or given away something that you later realize you need. In a fit of recycling at my own house a few months ago, I accidentally tossed an important document. I’m still mad at myself about that! I’ve done it with clothing and other things too—given, sold or thrown something away that later I regret. It doesn’t happen often, but past regrets have caused me to slow down a bit in my personal purging process.

If a client hesitates about purging an object, I always err on the side of keeping it, at least for a bit, to make sure there will be no regrets. A good way to do this is to put the “maybes” in a bin with that day’s date on it and a “review by” date. Obviously, this is for just a few things—not everything can be a “maybe”. If you have a lot of “maybes” you are probably not in the over-organized camp, but that’s a subject for another column.