Six secrets to organizing difficult things

Organizing most things is generally fun, relatively easy and comes with the benefit of a big visual payoff – think cleaning off desks, arranging closets and making kitchen counters sparkle. But occasionally, we must all face organizational tasks that are, for lack of a better word: painful. There is not much fun involved in organizing your really important information just in case of an emergency (which is really a matter of when, not if) or going through the possessions of a loved one after they have past away.

Unfortunately, when things are not enjoyable, we tend to avoid doing them. The longer you put difficult organizational tasks off, the more likely you are to either (a) be putting yourself at risk, or (b) carrying some degree of misery and stress unnecessarily.

On July 5th, 2010 my mom, stepbrother and sister-in-law were killed when the small plane my mother was piloting crashed after a landing gone awry. It’s been two years now, and yet those words still seem unreal.

About a month after the accident, my despondent (and beloved) stepfather asked my siblings and me to help him clear her things from the house. He found the constant reminders of her too much to bear, a sentiment we all understood. So, still reeling from the losses, my brother, sister, and I began the bittersweet task of dealing with the detritus of mom’s life: her clothes, her papers, and various odds and ends; in short, her clutter.

As we waded through her things, the smallest things would bring me to my knees, like the three Disney books she had clearly purchased for my oldest son’s fourth birthday, which fell just four days after the plane crash. At first, I refused to claim them, unable or unwilling to accept that she would no longer be present to celebrate those kinds of special days with us.

In the end, I took four large boxes of her things and two massive bags of her clothes home with me. Once home, I promptly stashed them in our basement guest room, the room we lovingly call “The Waiting Place,” and closed the door. Every time we had a guest or I played with the boys in the playroom, the closed door to our Waiting Place taunted me. The longer I avoided it, the more intensely I felt the weight of what I knew I should be doing, and the more I felt the weight of the “should,” the worse I felt about myself.

Finally, about two weeks ago, I faced what I had been putting off for twenty-four months. It wasn’t easy. But it wasn’t as hard as I had made it out to be in my head, either. In fact, by the time I had finished, I felt wonderful: flooded with happy memories, grateful for having a wonderful, inspiring mom, excited to hang some of her pictures, and proud of myself for finally ridding the Waiting Place of the jumble of her things.”

Six Secrets for Organizing Difficult Things

As I reflected on our various experiences in tackling difficult organizational tasks like this one (and organizing my wills), I noticed that getting un-stuck took all (or at least some combination of) the following strategies.

1. Set a Timer for 15 Minutes & Just Start Already!

Our brains are not always the most reliable gauges when it comes to predicting how long a task will take – or how painful it will be. If you’re feeling stuck, grab an egg timer, set it for at least fifteen minutes, and force yourself to focus relentlessly on the job at hand. It is highly likely that you will make significant progress and won’t want to stop when the bell rings.

2. Use an If-Then Statement to Get Yourself to Follow Through.

We often make good intentions, like “I will start project X first thing tomorrow morning.” But when tomorrow morning comes…it’s easy to get distracted by something “more important.” Many studies by clinical psychologists have shown that deciding in advance when and where you will take specific actions to reach your goal (e.g., “If it is 11am on Saturday, then I will go through my mom’s things.”) can double or triple your chances for success.

3. Carve Out Quiet Time to Make Progress:

If you have small children, a cell phone, a smart phone, a computer, or a home phone, you are at risk of being interrupted just as you start to tackle your project. Obviously, that makes it much harder to make any real progress. Organize a babysitter if you need one, and turn off all communication alerts so that you can work uninterrupted on the task at hand.

4. Ask for Help:

Sometimes just having someone there with you while you take on a task makes all the difference. If you’re scared to tackle something, maybe all you need to do is call up a best friend, ask your spouse, or reach out to an expert.

5. Anticipate Moments of Joy.

Even if the job itself has nothing inherently exciting or happy about it, you will still experience moments of joy when you realize you are making progress, and eventually complete, the project. When you do something hard, you can’t help but feel a sense of accomplishment; “Hey! I am doing what I said I could!” That, in turn, boosts self-esteem, which feels wonderful. It also makes you more likely to take on and complete other difficult projects – setting off a positive chain of continuous improvement.

6. Focus on the Benefits.

There is a saying that you get what you focus on. When you’re putting something off, you do so because you are paying more attention to the pain of getting the job done than on the good that will come from having crossed it off your list. Break your old pattern of focus by grabbing a pen and paper and writing down all of the things you will gain by following through.

What do you think is the most difficult thing to organize? What are you putting off?