Chris VS an increasingly large pile of receipts - From Rags to Reasonable


I’m not the most organized dude.

Actually, I wouldn’t really qualify myself as a dude… so that sentence is just chock full of words that don’t apply to me.

But as much as I’ve changed and gotten better over the last few years, one of the things that hasn’t improved is the way that I deal with receipts.

Regular readers are already sick of me talking about how important it is to keep any receipt that you plan on DEDUCTING on your tax return. If you haven’t heard it here’s the short version: it’s gotta be a receipt, and you’ve gotta keep it.

That piece of information has sunk into my brain, but it kind of has swung over to the extreme now.

I keep all the receipts.

Doesn’t matter if it’s business or if it’s the most pleasurable of pleasures. If I don’t ask for a receipt I get this kind of guilty kid feeling… like when I don’t want to brush my teeth before bed because I’m too lazy to go downstairs (even though I have significant DENTAL ISSUES).

So I keep them all. And at the end of the day I’m left with piles of unsorted receipts, most of them ones that I didn’t need to keep in the first place. All of which I have to sort through.

It’s part of the reason why tax time is a complete disaster in my house. I have to sort through the massive wads (because piles of receipts always form into wads) and figure out what was actually business, and what wasn’t… it’s really not a great system. Actually… it’s not really a system at all.

The Plan for Victory:

My receipt issues clearly have multiple facets that need addressing. Part of the reason I haven’t managed to change anything is that it seems a bit daunting to completely revamp my organizational process.

So right now I’m going to focus just on the collection aspect.

I am no longer going to collect non business receipts.

Since I generally use credit/debit cards for my personal purchases I have a record of all of them for budgeting purposes. So receipts are only needed for tax reasons.

My hope is that it cuts down on the clutter, and also cuts down on the magnitude of the next job that needs doing… sorting and organizing (and hopefully digitizing) all of the rest of them.

I will keep you posted on my quest for victory, and wish you best of luck in the battles that you’re fighting! Remember that you lose 100% of the battles you don’t fight.


Am I the only one who does this? What systems do you guys have in place to keep chaos from creeping in?