Whoops. Before I write about my filing system, I decided to excise this long section on what should go into my tax-deductible-o-riffic folder. It's surprising how much stuff is in there. Here is a partial list.

  • Donations to a registered non-profit (duh.)
  • Volunteering costs - for instance, if you live in Needham but travel regularly to Cambridge to volunteer, you can deduct commuting costs for your "I Save the World!" work. (People with 1cc office hours take note.) You can claim 14 cents per mile plus parking and tolls, apparently.
  • Work-related expenses up to $17,500 annually. You need documentation that you needed whatever you're claiming for your job (a letter from your boss or such), and that over 50% of the time you use it is for work. If you have a computer that you work from home on, etc., this counts.
  • Work-related educational expenses that pertain directly to your field. If I (for instance) took a RF seminar, this would be deductible, but if I took a cooking class, it wouldn't be. Yes, everything's connected, but I don't think I can persuade the IRS that my engineering work is so interdisciplinary it involves souffles. Not relevant to me and probably most readers, but it also doesn't count if you are required by law to take the class (so mandatory professional development stuff for nurses and the like can't be deducted).
  • Job-related association dues and subscriptions to trade magazines and journals.
  • Tax prep fees are deductible! Financial books and software count for this.
  • Medical expenses greater than 7.5% of your adjusted gross income. I hope I never have to take advantage of this one, but just in case, the it's-deductible list includes insurance, co-payments, transport to and from medical care, and prescriptions.
  • Catastrophic loss is tax-deductible. Theft, flood, fire, and the like. I never want to have to use it.

'Course, this list wouldn't be complete without a shameless plug for a certain soon-to-be-available-again tax-deductible donation option. It may not be the right laptop for you or your kids if you're looking for a replacement for a $2k machine, but they're sure doing students in places like Peru and Nepal and Uruguay a lot of good - you might also consider banding together with a team to sponsor/start/run a local pilot. </shamelessplug>

Now, folders.