Unless you only have a few trades, it is worth your time to learn how to get your data in a file format that a computer can use.   You can then deliver the data to your Tax Preparer or you can deliver a Schedule D to your Tax Preparer.  Either will improve accuracy, save time and cost less.

Have you noticed that most web-based reports, including 1099 documents, are (.PDF) pictures of your data?  Do you get that unsettled feeling when you think about how to use that data?  What if you could get real data and use it yourself or give it to your Tax Professional?  The answer is it will save time and money.  This is why we must think differently and sort out a more efficient process. 

Paper and pictures are for people, but computer like data.  Have you ever tried to work with a .PDF picture of transactions to generate something by using Excel?  The average user can only open a .PDF, save it, print it or e-mail to someone.  These document are good as a visual reference but are a real pain to use their content. 

Consider the following choice.  You have 200+ trades and you provide your Tax Preparer a paper copy of a 1099 document.  At this point someone must type the data into a program to generate the Schedule D and the tax return.  Did you know that this is expensive work?  The reason is because it requires a combination of clerical data entry and knowledge of how to generate tax lots plus knowledge of how to resolve issues that occur with the data when trades don’t reconcile.

Action Step - Let's spend a few minute to sort out a road-map for your data. 

1. Log into your brokerage account and find the tax information page.
2. Mouse around with the search feature.  Try a search for "Tax Tools" and "History." 
3. Look for the data download section and see if there are instructions on how to get data for usage by tax software.  They might offer a download to Excel or other software.
4. Make a few notes regarding the download formats supported and the software supported.
5. Print out samples of the pages for future reference or to give to your GoTo Tech person.

If this is your first venture in this area then take a break after 15 minutes and reward yourself for covering new ground.  Next time it will feel faster and easier.  If the pages are confusing then send e-mail to support and ask for help.  Ask them your questions.  Your goal is to pick a data format that will allow you to get your tax year Buy and Sell information in a file.

If you are going to generate some of the tax documents yourself (like the Schedule D) then contact your broker early and ask for guidance regarding data download.