Tax paperwork handling strategy - which has been successful for you every year

Wondering if anyone has a better way of handling tax paperwork recurrently every year.

For example:

1.)Any kind of spreadsheet as a checklist to refer?

2.)Any app to handle paperwork

The reason I ask is , I have to tendency to procastinate on work, which I find overwhelming. And this falls under that bucket, and trying to understand how the other smart folks(YNAB makes you and me automatically under smart category :)) are handling this monster.


Thank you!

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  • I keep a directory on my computer that contains a text file for organization. each year i create a new directory, copy the text file, and look over it for any account additions/subtractions or employment changes. I also review it throughout the year as changes happen). The text file serves as both a checklist (I use a hyphen to denote a checkmark) as well as any notes for myself or the accountant that would not be readily apparent just from the documents themselves (totals for charitable donations, property taxes, etc.). The directory also stores the documents themselves. If an institution only provides snail mail, I scan it and store it.

    Documents/Taxes/<YEAR>/Docs - contains paperwork

    Documents/Taxes/<YEAR>/Returns - contains tax returns

    The Taxes directory and children are stored in Dropbox.

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