Now that the tax man is going into hibernation for another year, make next year's process less chaotic by ditching the receipts-in-a-shoebox system: Use technology to organize your finances (and save money too!).
Start by tackling the receipt issue. Digitize a dump all that paper with the Fujitsu ScanSnap S1500 ($400). Drop up to 10 sheets of paper in the hopper and in seconds the pages will be scanned and stored as PDF files on your computer. As a bonus, the ScanSnap is great for more than just receipts: I now scan bank statements, insurance and real estate documents, old tax returns, and any other information I want to keep without keeping the paper it's printed on. Fujitsu.com
If you'd rather someone else to do the dirty work, sign up for Shoeboxed. They'll send you a postage-paid envelope for all your receipts. Just mail them in and Shoeboxed will scan, organize, and store the details in a secure online account, ready for you or your tax preparer to retrieve. You can also send photos of receipts from your phone to have them processed, so getting organized becomes as easy as shooting a photo, crumpling the receipt, and tossing it in the wastebasket. (Sadly, there's no tax break for shooting perfect free throws.) Monthly fees start at $9.95. Shoeboxed.com
The best way to get out from underneath repressive reams of receipts is to avoid them in the first place by digitizing your finances. The process is relatively painless with Mint, the free money-management website that will keep track of your bank accounts, investments, credit cards, and loans, while also suggesting ways to save money. Every time you pay for something, Mint sees it and categorizes the purchase, so you can quickly get a sense of the big picture about where your money is going. (Be prepared to face the truth: I am not proud of my $800/year Starbucks habit.) It tracks and organizes your expenses without requiring you to ever touch paper. Mint also has fantastic budgeting and goal-setting features as well as spiffy iPhone and Android apps and, most importantly, it incorporates the same security features that banks use to insure your private information stays private. Mint.com
Now if I could just find a way to have my laptop gently nudge me when I'm at Starbucks and ask, "Do you really need that latte?"