I bought a stock investing education program. I'm sure everyone has heard of it. It's called Investools. The cost was about $5,500. My question is can I deduct the cost Investools off my taxes? No. The IRS has a publication 529 which covers "Miscellaneous Expenses". It specifically prohibits deducting "Investment-related seminars". Go to http://www.irs.gov/publications/p529/ar02.html then scroll down to the section called "List of Nondeductible Expenses" and you will see "Investment-related seminars". You can not deduct any expenses for attending a seminar for investment purposes. Now, if you have set up your stock trading as a business which means you derive most of your income from trading, then you may be able to deduct the investment seminar as a business expense, not as an itemized personal deduction. For more information on setting up your stock trading as a business, you need to consult a tax specialist. Do not ask such important legal tax questions over the Internet. As you can see from the comments below, some people have no idea what they are talking about and will give you the wrong advice.