Tereza's suggestion brings up many thoughts. Have a read, then let's talk:
I'm part Czech and a piece of our New Year tradition is to clean and organize on New Years Day. I've been I known to partake in some serious Container Storgasms with my husband, getting our small and open home — which is really short on storage — into shape.
[FULL STOP. It must be repeated: CONTAINER STORGASMS! Organizing as a marital aid! I love it. Okay, back to the hack. — Asha]
My hack: if you're facing an organizing task that's overwhelming, consider bringing in a professional organizer to devise a system and structure that will uniquely work for you.
A few years ago I found myself overwhelmed with paperwork while having recently left my job…and I had a new baby, my parents were ill, and I was the executor for two (!) estates. My desk became a pileup and I didn't know where to begin.
My husband would hound me — he's a very organized guy — but his systems are incredibly complex and time-consuming and don't work at my speed.
[I can identify with this. My husband is Mr. Systems and could never understand my more-intuitive way of working. It has taken us years to appreciate each others' organizing/working strengths and weaknesses (and to accept our own), and to team up rather than work at cross-purposes. — Asha]
On the suggestion of a friend, I brought in a professional organizer for just three hours. She gave me the boost and motivation I needed. I could see the end of the tunnel and got excited about that vision.
With her support, I was able to get through my paperwork and create a gorgeous little workspace that's my "sacred refuge." I've kept it in excellent shape for four years now.
Her help cost me a total of $185. It seemed like a lot, but the strategies I learned — which were tailored to me — have more than amortized themselves over time.
Alternatively, swap "organizing services" with a friend. Having a friend help sort and file is a cheap, fun + effective way to "see" your items in a more neutral light…it can really help you to let things go. At the very least, it makes a boring, onerous job more fun.
When my mom died and I had to clean out her office, her friend was invaluable in helping me curate which 5% of her stuff had sentimental value and which 95% needed to go in the dumpster. So cathartic!
Applause for Tereza! I could not agree more. I believe every family needs a supporting cast, and a professional organizer is just such an example. Getting organized is not difficult but it DOES require the ability to think systematically. Those of us for whom this doesn't come naturally are at a disadvantage…and spouses and other family members aren't always the best "coaches." Even with good intentions, plenty of baggage can get in the way of what should be a straightforward job.
Also, some of us are just better collaborators than solo workers. I feel distracted and sorry for myself when I have to work alone for too long…but with a partner, my energy level and motivation soar.
As for the suggestion of swapping organizing help with friend, again: YES. I hate filing and have a teetering pile of papers I need to process sitting on the floor of my office. But when my friend asked me to help file her backlog? I flew through the job and had a great time doing it. Plus, I got a bonus lunch date out of the deal. (She's going to help me with my pile, too.)
There are many good books and online services that can help you get organized. But if you've tried them without success, consider bringing in a partner — either a friend or a pro.
Let's talk! Experiences, good and bad? How did you go about finding a good professional organizer in your area? Have your improved organizing systems "stuck" or do you need periodic reboots?
Another chance to swap organizing ideas: my live talk about getting organized on Monday, 1/23/12! It's gonna be a great 30 minutes — especially because I've got two fantastic co-hosts who are full of use-it-now advice: Christine Koh (Boston Mamas) and Meagan Francis (The Happiest Mom). Register now at The Motherhood (it's free).
More: Hundreds of hacks about getting organized (our most popular topic)