How a Coupon Organizer, an Excel Sheet, and Dropbox Help Me Survive Tax Season

How a Coupon Organizer, an Excel Sheet, and Dropbox Help Me Survive Tax Season

How a Coupon Organizer, an Excel Sheet, and Dropbox Help Me Survive Tax Season | brokeGIRLrich

Tax time is here again, and I thought it would be a good idea to share how I tackle my taxes each year. Now, I know taxes are one of those things that no one really enjoys, but having a solid system in place makes it a whole lot less stressful.

For me, this year, like most years, I had a mix of 1099s and W-2s to handle. But nothing, and I mean nothing, will ever top the year I worked with Ringling Brothers. That year was a tax nightmare. I ended up with W-2s from 26 different states. Can you imagine the chaos? That’s the year I realized that sometimes, you just need a tax professional to help get your life back in order.

That said, even if you decide to bring in a tax pro, you still need a reliable system for keeping track of all the deductions you can claim against your 1099 income. The IRS likes to keep things simple with their guidelines: deductions must be “ordinary, reasonable, and necessary.” But let’s be honest—if you work in the arts, there are probably a lot of things you could argue fall under that umbrella. For instance, if your job regularly requires lifting 50 lbs., shouldn’t a gym membership count as a necessary expense? Spoiler alert: it doesn’t. But I digress.

Today, I’m not here to debate what you can or can’t claim. I just want to share how I keep track of my deductions. I’ve developed a four-tiered system that works wonders for me. Ready? Let’s dive in.

First off, I use an Excel spreadsheet to track everything. Each category of deduction gets its own tab—think meals, tools, education, rent for office space, fees, retirement contributions, health insurance, and so on. Every time I log an expense, I make notes about it, just in case I need to explain why it’s “ordinary, reasonable, and necessary.” For example, if I’m claiming an educational expense, I’ll clarify why that particular purchase is educational (even if it’s not super obvious from the receipt). Once I’ve entered all the expenses, I use a formula to pull the totals from all the tabs into a main summary sheet. That’s probably what your tax preparer will want to see, because, let’s be real, they don’t care much about all the justifications unless you get audited.

Now, for the digital receipts—I’ve got a system for those too. They go straight into a Google mail folder labeled “Taxes 20XX,” so they’re easy to find when I need them. For physical receipts, I take a picture of them and upload them to a Dropbox folder labeled the same way: “Taxes 20XX.” The physical copies? Those get thrown into a coupon organizer that’s also labeled to match the categories in my Excel sheet. It’s a bit of a paper chase, but it works.

And here’s my little tip for when I’m on tour: I keep all my receipts in one place—specifically, the laptop pocket in my backpack. Yes, I know it’s a little weird, but it’s a lifesaver. That way, when it’s time to sit down and organize everything, I don’t have to dig through multiple pockets, bags, and purses. Everything’s in one spot, ready to go.

I know, it’s not the most glamorous or high-tech method, but this system has worked for me for over 10 years. And honestly, that’s what matters. It keeps me organized and helps me stay on top of things come tax season.

So, what about you? What tools or systems do you use to keep track of your taxes?

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