Taxes and Filing Made Easy

Last weekend I attempted to do my taxes. Even with TurboTax, it was an absolute nightmare going through my poorly organized files of receipts, payment stubs, medical bills, tuition and loan papers, and investment confirmations. There were some things I just couldn’t find and had to make up the best I could (don’t tell).

Why do we have to keep around so much paper in our lives? It takes up space, gets lost easily, and is difficult to find…ok, maybe not if you are super organized and meticulous, but honestly, who is?

I came across this list via lifehacker of what documents to keep and what to toss:


  • Your will, living will and durable power of attorney.
  • Life insurance policies, including policies with your employer.
  • Insurance, and any death benefits that are due you as a veteran of the armed services.
  • Retirement plan documents from your pension, profit sharing, 401(k), and IRAs, along with annual statements.
  • Records of nondeductible contributions made to your employer-sponsored retirement savings plan or IRA.
  • Separation and divorce documents.
  • Real estate deeds, titles and property surveys.
  • Military records.
  • Tax returns and supporting data for at least the last seven years after the original return is filed.
  • For investments, keep buy/sell trade confirmations
  • Dividend reinvesting statements (for seven years after you file your tax return showing a gain or loss
  • Receipts for items under warranty until the warranty expires.
  • Pay stubs – until the end of the year


  • Receipts of bank deposits and ATM transactions
  • Canceled checks – save only those needed as support for tax purposes.
  • Bills – once you’ve paid them and verified that the checks have been cashed.
  • Monthly or quarterly brokerage statements
  • Credit checks on employees (even housekeepers and nannies)

What got me excited was not that I was given the go ahead to throw away all my bills, but rather a point one commenter made about scanning all important docs and saving them as PDFs, then throwing the paper away. I really like that idea, because then instead of messing around with heavy, dusty filing cabinets, you can just scan, save as, and drop in an appropriate folder. If you need it, you can find it with your trusty mac spotlight search (or equivalent). If not, it won’t bother you.
Now, all I have to do is get a scanner. Some day…some day, I will be organized.

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