I've decided that I just don't have the time to be filing and filing, so I'm attempting to go paperless. I went to Staples a little while back and bought a scanner to scan in bills and paperwork. It's a
Canon CanoScan LIDE 90 (
CNET Review).
the LIDE is nice because it gets all the power it needs over the USB line, so no brick and no second plug. That makes it convenient. the form is nice (light and thin) for a decent price and decent quality. The secret is to be able to tuck it away, get it and attach it when it's needed, and then tuck it back away when you're done.
... Hmm, that sounded dirty...
On my MacBook Pro, the software's really pretty painless, although I don't like how the default software always wants to open up its own organizer/filer when it's done, I'm much happier just in the file system!
Here are my secrets to scanning happiness:
1. Get a shredder
Sounds lame to say that part of scanning is to buy a shredder, but if you're going to be dumping out all the files and paperwork, let's not do stupid things. I like the shredder I got at Fry's, but to each his/her/their/its own. This is not only a perfect opportunity to get organized, but an amazing de-clutter opportunity. Make the most of it!
Last and not least, never underestimate how catharsis of shredding a bill. I've never felt so free as when I've shredded my monthly mortgage bill.
2. Make sure you're saving to open file formats Of the aborted or painful times I've tried to go paperless in the past, the downfall was always with how onerous the technology was/is and how painful and time-consuming it is. In the old days, it was slow 100dpi scanners and PaperPort. If you've used and love PaperPort, I'm sorry. I hated it. It basically kept things represented internally, with everything proprietary. All those records are sitting dormant on my PC collecting electron-dust because I don't have the software and the format is so closed.
Nowadays, most scanners will save right to PDF, so you're not even dealing with pictures, either. I love this, especially on my mac, because the PDF capabilities are so well integrated, but I hear from LifeHacker that there are options for PC people, too (I just haven't booted my PC in about 7 months, so how would I know). I like the PDF because it's a very open file type for what I need, and it's very easy to use, and the drivers now make them moderately compressed (no more 10MB single page scans).
Another feature of using PDF -- just stack your monthly statements/bills in the same PDF! Why deal dozens of files for a single vendor? I just have one landscaping PDF file, and every month, I take the new scan and just append it to the existing bill. Sure, you want to why I bother, and the simple reason is that a person rarely cares about finding all the June bills, but if you have a problem with the gardener overcharging you (I'm looking right at you, Mr. Lee!), then it's a very common occurrence for you to always need the current and last couple bills, why not have them in the same file where you can attach notes and running commentary easily?
3. Use the file system for organizing 
We're all so used to using the file system for storage, I would think that any halfway-decent geek just doesn't need a database or a proprietary format for storing their PDFs, just use the ol' FS!
Most software for scanning should give you a way to save files, just make sure you get to choose. If it's going to demand you scan and save to its database/software and then do an export, I say start looking for other software. Like I mentioned earlier, this is one spot where I think the CanoScan could improve. Whenever you scan something with the one-button press, it lets me decide where to save the file, but then it opens up its manager which takes a good 30-45 seconds of spinning beachball land to figure out that there's a new file. In the meantime, I've already renamed the file and moved it to its final resting place.
4. Store immediatelyOne thing that I have in common between my scanning and archiving habits and in my file management habits at my new job: Looking for, retrieving and touching old files is not desired. Just get it in, get it stored, be done with it. I scan page after page of the important stuff (no, I don't scan junk mail, I'm not in this for the geek points), and then save the PDF and move them to their location in the tree. I've seen so many people (and I did this in Windows) who move them to "new" or "need to pay" or something, then try to move them where they belong later.
a) This is annoying. If the scan is a 401k statement, it belongs with the 401k statements, not a "to be read" or "new" folder. Get it filed! if you don't, the system breaks down, and the first time you can't easily find the thing you need to find or you miss that you need to pay that bill, then your filing system has failed you (or vice versa).
b) In my approach with PDFs and storing multiple bills in the same PDF, this isn't even possible! I'd be moving around my entire history of gardener bills every time a new one came in, that's hardly a good move.
5. AliasesIn my former worlds (windows 3.1 - windows XP, OS/2, and so on), when I tried this, I learned this lesson early, but then how do I easily see the bills that I have to pay?? I used to make copies, or in (ewww) PaperPort, I'd make the scan a different color on the label, or put a post-it-note on it to tell me to pay it by Tuesday.
This one time [at band camp], I went to delete the note and whoops! I deleted the doc instead! That was the end of that tool. I then went to making copies of documents in multiple folders. First, one went in its final location (see tip #4), and then another one went in "pay"... until one day instead of copying I moved the file (again, my whoops, but seriously!) and when I paid it, I deleted it. I Didn't realize it until the next month's bill came in and I had that panic attack of "Where's March's bill?? wtf!"... by then the ubiquitous trash can had long since been emptied.
This is easily solved in OS X with Aliases in a folder on my desktop named "Things to take care of" (btw, not just scanned documents go here, but any form, email reference, or other major item I need to handle at home). Finish the task, delete the alias, job done. Never "touch" that original file, don't even look for it. Just do what you need, annotate the alias, and delete the alias. The annotation is an added bonus because you can open the file from the "take care of" folder and put notes inside the PDF when you pay it (like "I paid this!") and it updates the original (stored in its nice little virtual cubicle) without you having to hunt for it.
See now, that's not so hard, is it? On the note of converting any cabinets/boxes or other stores of paper records... I say don't try and go crazy. If I ever need something out of a file, I take the opportunity to scan the file, if it's not too heavy and doesn't give me Carpal Tunnel syndrome shuffling papers through the scanner. I've seen people with the "I'm going to go completely digital and scan everything I own" twinkle in their eye, and they're funny to watch (as long as they're not related to you and your safety and well being does not depend on them).
Good luck, I think it's worth it!
