Fortunately for me, I keep records sufficient to piece together what I need for reporting. There is plenty of redundancy between my bank records, invoices, receipts, and 1099s. Ultimately, it becomes a task of story telling through numbers.
I am a bit obsessive about writing down notes; however, I'm lousy at keeping my notes organized and consistently in one place. Sometimes I write them on paper, sometimes in Evernote, sometimes I text message them somewhere, or I'll record an audio note. The end result is that much of my data is scattered, and ultimately may as well not have been recorded.
But, thanks to redundancy, my income tax story can still be told by gathering corresponding information from other sources.
One thing that is different in this year's tax preparation is that Evernote plays a larger role than in previous years.
The key differences are that I adopted a simpler method of record-keeping. Rather than create a note for each transaction within Evernote, I make one note for related transactions. So, for example, my Smartsheet subscription will generate 12 invoices in a year. Rather than make a note for each of the invoices, I stuff all 12 invoices in Smartsheet 2014, or as is now the case, Smartsheet 2015.
But, that is not all. It also helps to use the features inherent in PDFs, such as combining multiple documents into a single document. Rather than have an Evernote note with 12 documents, it makes sense to combine the 12 statements into a single document. Obviously, it is beneficial to have some type of software that allows you to edit PDFs.
I should like to add that having fewer, more comprehensive notes in Evernote makes it so my information is easier to find. One does not feel like one is wading through murky waters. It is more like splashing in kiddy pools.
Learning to use PDFs as one would use paper documents has been the greatest improvement I have made in better using Evernote. This includes highlighting passages and writing notes in the blank spaces like one would do with a book or report. It is for this reason I would recommend having a PDF editing application such as Adobe Acrobat, Foxit Phantom, or one of the Nuance products. I think most of us consider PDFs as read-only files; but, when you dig in a little deeper, they can do so many more things. And, when combined with something like Evernote, then so many more options open up.
Another thing I have come to realize is that paper notes are great for working. But, once they have done their job, it is vital to scan or make data entries. Yes, it's a pain to have to touch information twice; but, if you neglect to do it, you'll have the tax-time crunch waiting for you. Therefore, it is important to schedule some time, regularly, to "transcribe", for lack of a better word, all your paper notes into digital format.
For a while, I would take photos of my text, or scan my notes. However, plain text is so much more usable. Although I spent so much times fawning over PDFs, they are best suited to original documents rather than scanned documents. If you go through the trouble of writing notes, it is best to type up your handwritten notes rather than scan. You get much better information density with plain text than with scanned handwritten notes. I'm talking about usable information per KB of storage.
I won't go on. I'm tired. Brain dead. And I need a shower to clear my head and go to bed. But, keep in mind how keeping better notes, not merely keeping notes, can improve your tax time experience.