When should I start preparing for filing my taxes?

You should start preparing for tax day at least a month beforehand. You, like many others, might think that you can handle anything the tax gods throw at you a week, a few days, a day before your taxes are due. But the wise will know that anything can happen when you're filing your taxes. So if you want to play it safe, and have a sound mind as you go through the process, start a month in advance. Get a feel for what to expect, and make sure you don't have to rush things.