Not the worst it’s been, but heading there. (Brigid Schulte)

My desk has been worse. Teetering stacks of a mishmash of my lives at work and at home — papers and notebooks and files and magazines and stuff to read and receipts and scribbled reminders and bills to pay and doctor’s instructions and Girl Scout cookie forms and towers of business cards.

If I didn’t do something soon, I knew I would soon be right back in the thick of the clutter, hyperventilating, wasting frustrating hours looking for things, forgetting to do stuff I’d promised, and unsure where to start each day. In other words, overwhelmed, overloaded and disorganized.

So, with the dawn of a New Year, I decided to start with a clean slate. I wanted to figure out how to organize my desk and my office to help me do my best and most important work, rather than get in the way.

And, because I tend to get myself in trouble when left to my own devices when it comes to the stuff of life I don’t want to do, like cleaning my desk, I enlisted the aide of Andrea Hancock, owner of Dexterous Organizing in Washington and a member of the National Association of Professional Organizers.

Before she begins projects that are sometimes like archaeological digs, Hancock asks clients a deceptively simple question: Why do you want to clean your desk?

WHY: The question, she said, is critical. Maybe you want to be more productive and streamline your workflow. Maybe you just want to stop feeling so stressed out and disorganized. Or maybe you want to create time and space for other, new, or more important things, instead of pawing through piles of papers and stuff, or searching through chaotic digital files, all the time. Whatever the reason, you need to understand yours.

“As it gets tough — and sometimes it does get tough — you have to have the why,” she said. “Otherwise, people may just fall back into the same patterns that led to the paper piling up in the first place.”

UNDERSTAND PAPER FLOW: Next, Hancock helps people figure out how paper and e-mails and stuff flow into the office, and what needs to happen to them, how they’ll flow out. What’s working? Where do things get stuck? How does stuff “marry” with their To Do lists and calendars? “A lot of times, the problem starts with people just not knowing what to do with the things that flow in,” she said, “and then not creating a regular time of day or a time of week to deal with it.”

CREATE A SYSTEM: That’s where creating both a system for handling the stuff that comes in, and setting aside a specific time to handle office administration come in. “Most paper has an expiration date,” Hancock said. So, whether you’re picking up something from a teetering pile, or opening today’s mail, Hancock suggests thinking of paper in three different ways:

  • Active: That’s the stuff that usually goes up on a corkboard, or gets stuck to the fridge. Maybe an RSVP to a wedding, or a note from the dentist to make an appointment. Once you do it, you can throw it away. “If you get a wedding invitation, most people might set it down and say, ‘Oh, that’s nice.’ But if you’re in the habit of using an inflow-outflow system, you put it on your calendar, and note the RSVP date,” she said. “Then when you’ve RSVP’d, you decide whether the invitation is archived into a memorabilia folder because it’s so pretty, or you can toss it, so it’s not cluttering your life.”
  • Action: Hancock suggests keeping an ACTION file on your desktop for things that may take longer before you need to, want to or can take action on them. Perhaps it’s a reminder to get your oil changed. Tax receipts. Or a credit card slip from a store where you may want to return some merchandise within the next 30 days. And once they come due, you either throw them away or put them in an archive.
  • Archive: This is for papers that you don’t need in your physical area as often, but want to make sure they’re easily retrievable. Past years’ taxes. Ideas for a new project. I use filing cabinets. Hancock goes a step further. Her goal is to have a largely paperless office this year. So she has two scanners, and during her office administration time, scans receipts, business cards, documents and papers for storage in the cloud on Google drive, Dropbox or Evernote, then tosses the paper.

MAKE TIME: Hancock herself uses Monday for planning and organizing. And she suggests giving yourself a good hour, or an hour and a half to start. Once you start noticing your patterns, and setting up a system that works for you, you may not need as much organizing time, she said. She also suggests not expecting that you’re going to get to the bottom of everything in that hour, but to see it as an investment for creating a productive workflow in the long haul.

In talking with Hancock, I realized that I always feel too guilty to take time to sort through piles, file things or even gather receipts. I can’t tell you how many times I’ve eaten reimbursements because I didn’t get my expense reports in on time. Not smart. I know.

But I’m usually already feeling so pressed, slightly panicked and behind in work, and that there’s always more and more important and productive stuff I should be doing anyway, like writing and reporting, that I’ve never made a regular time for administrative stuff. I even tried delegating, hiring a personal assistant through Done for You Solutions. But since it turns out that she’s in the Philippines, it’s not like she can come in and do my filing. So officey stuff, if it gets done at all, tends to happen in one herculean, insane burst. After which, I’m so burned out, I don’t want to think about it anymore, much less do anything, so the piles start to build up again.

Hancock hears that a lot. “Sometimes we do organize receipts when we’re avoiding more important tasks,” she said. “But if you’ve set up a consistent time for office administration, then you’re not procrastinating. You’re doing what you set out do. And the more you do it, the more you’re realize that organization is supporting all of the other, more important aspects of your life.”

CREATIVITY AND CHAOS? This is where it’s important to note that you may not want your desk to be neat as a pin, especially if you do creative work. Kathleen Vohs, a social psychologist, and her colleagues at the University of Minnesota ran a series of experiments and found that people in orderly environments were prone to healthier eating and generosity, but tended to be more conventional in their thinking, whereas people in messier environments were more creative. (Vohs et al measured this by asking people to come up with different uses for a ping pong. People in neat and messy environments came up with the same number of uses, but those in messier digs, apparently, had more interesting answers.)

And I’ve seen the desks of such intensively creative types as Mark Twain, Steve Jobs and Albert Einstein, that some claim to be slovenly. I disagree. Their desks aren’t tidy, but I would hazard a guess that most of the stuff on their desks and their shelves dealt directly with the work they were most interested in concentrating on. I doubt these guys had doctor’s appointments and their kids’ ACT sign up forms polluting their piles, or their thoughts or workflow. They had wives or assistants for that.

So, since my piles were polluting my thinking, my creativity at work, my efficiency at home and my time, I did find an afternoon on my calendar to begin my dig out, using Hancock’s system. I’ve now got an Action pile on my desktop for work, and one in the kitchen for home stuff. My work Active files are sorted into magazine holders on my desk for easy access. And I’ve archived notes and documents I want to keep for now in my filing cabinets, and even tossed an entire drawerful of stuff I haven’t looked at in more than a year to make room for what I hope will be new thoughts and new projects.


ACTIVE files in folders along the back. ACTION pile to the right. Everything else ARCHIVED. (Brigid Schulte)

I’m not ready for a scanner. I’m still not sure what to do with the stacks of business cards. I’ve got work to do on how I track To Do tasks (resetting Wunderlist) and schedule (Google calendar is my go-to right now.) And you don’t want to see the dining room table finally covered with the receipts I dug out, sorted and now have to figure out what to do with ….


Still To Do … (Brigid Schulte)

I do want to be creative. But I also want to breathe, pay my taxes on time, and get my kids to the dentist. Maybe my walls can be messy?

What are your strategies for making sure your office space helps you do your best and most important work? Share them below.

Andrea Hancock is one of our Time Hack experts. Interested in making the most of your time? Fill out the Time Hack form here.