Ask the Experts

Dear Organizing Coach: How Can I Take the First Step in a Daunting Project?

With each passing day, your cluttered home office becomes more impenetrable. It’s gotten so bad, in fact, you can’t bear to enter. How can you take the overwhelming first step in a monster project you dread? Find out here.

Q: “My home office is the only area I do not clean and organize at least twice a year, and it is a mess, which is why I do not sit at it. I keep organizing my 3 kids’ areas, the fridge, and the closets — donating, selling, or trashing unused items regularly. But I can’t do the same with my own desk and office. I even bought folders and whatnot, but can’t get myself started, out of the fear that it would take me forever.” —SuperMom

Hi SuperMom:

Let me assure you that you are not alone on this one. First of all, we need to get you into that office more than twice a year! And if we can do that, organizing and maintaining it won’t take you nearly as long as you might think.

Look at it this way: You go to the dentist twice a year for a check up and cleaning, but you still maintain your dental health several times a day by brushing and flossing. You need to give your office the same type of attention! And here are a few strategies to get you started on a healthy routine.

1. Schedule “Office Visits”

Pick a time slot when you know you will have a few uninterrupted hours to work every week or every few weeks. This step is critical for success. If you don’t plan the time, your likelihood of doing the work is slim. Next, add this time slot to your planner or calendar like you would a doctor’s appointment or night out with friends. If you give this task the same importance as your other appointments, you are more likely to honor it in the same way.

[Free Resource: 73 Ways to Organize Your Life Today]

2. Use My “Triple S” System: Short, Simple & Specific

Try to accomplish everything in one session and you’ll end up overwhelmed and frustrated. Instead, set specific intentions each time you enter your office. “Today, I will sort all the financial documents.” “Thursday, I will declutter the old health insurance files.” “Saturday morning, I will tackle the weekly mail.” In other words, break down this project into manageable parts to feel more in control.

3. Make It Fun!

Crank your favorite music and throw yourself a dance party. Set a timer and play “Beat the Clock” by seeing how many papers you can shred before it goes off! Grab your favorite candy or snack and “have a treat while you make it neat!” Infusing energy and play is a wonderful way to get you moving!

And if you are looking for more tips and tools, please check out our website at We have tons of FREE resources, videos and materials on this subject.

Organization guru Leslie Josel, of Order Out of Chaos, will answer questions from ADDitude readers about everything from paper clutter to disaster-zone bedrooms and from mastering to-do lists to arriving on time every time.

Submit your questions here!