Comment You'll never know what you'll need your records... (Score 1) 366
I'm not sure why everybody "don't worry about it." If you have things archived digitally it doesn't interfere with your life. And frequently proper documentation can be the difference between success and failure in a dispute with a company or organization or even a lawsuit. It's also often interesting to see how you were thinking or what you were doing in the past.
Personally, I store as much as my information in PDFs, JPGs, and select documents that I change often in MS Office formats (worse case scenario if MS goes out of business I can print them as PDFs too). The frequently-changed documents are the ones with the notes about miscellaneous projects I have. Most projects have their own documents. I organize these in a simple directory structure with folders such as Finances and Photos. I make sure to separate things I rarely or never access with subdirectories so they don't clutter things up. It's not as fancy as having everything on Evernote or the cloud but it works and is in your control.