Some people think their accountant is doing them a favor when they show up for the annual tax meeting. You make coffee, get your crumpled receipts envelope ready, and a few spreadsheets you didn’t touch since July, accompanied by a vague sense of dread. That’s all you need, right?
Nope. What I’ve learned over the years (and a few awkward nods from my CPA) is that tax season stress isn’t really about taxes. The reason you’re stressed is because you weren’t organized before taxes.
Most self-employed folks don’t realize that the panic you start to feel in March is the result of all the little things they ignored back in July, October, and January. I’m not going to bore you with tax strategies and loopholes because that’s not your job anyway. But I think it’s really important to know that there’s a checklist you should follow that’ll make a difference between a smooth filing and a hot mess of emails and missing documents.
If you’ve ever dumped a pile of papers on your accountant’s desk and crossed your fingers, hoping Fairy Godmother will get you out of this, this one’s for you.
What Your Accountant Actually Does for You
If you’ve ever worked with a good accountant, then you know they do so much more than just plugging numbers into tax forms. Your accountant is part strategist, part compliance expert, and part detective.
What I mean by that is, they’re constantly looking for ways (legal ones!) to lower your tax bill, spot issues before the IRS does, and make sure everything adds up. But if you hand them a mess, they can’t do their job properly.
A lot of clients assume their accountant will ‘just know’ what to do with a pile of uncategorized expenses and random documents. But in reality, they can only work with the information you give them and, if the information is incomplete or disorganized, their hands are tied. This is why accountants have a tax folder for each of their clients – to keep records clean, separated, and easy to process.
When documents come in last-minute and messy, it adds unnecessary stress and cost, both for you and for them. If you want better results, you need to make it easier for the accountant to do their job.
The Most Common Tax-Related Mistakes People Make
Has your accountant ever raised an eyebrow during your meeting? If they have, you’ve probably made at least one or two mistakes that were totally preventable.
Here’s what you should stop doing and what to do instead.
Mixing Business and Personal Expenses
This is probably the most common issue. If you use the same debit card or bank account for both business and personal purchases, it’s easier in the moment, but it makes everything harder later. When tax time comes, how are you going to be able to separate that one Uber ride to a client meeting from five others to brunch? It’s a nightmare.
The easiest fix? Open a different business checking account, or at the very least, use one specific card just for the stuff that’s related to work. It keeps everything clean, plus your accountant will be very grateful.
Saving Receipts Without Categorizing Them
It’s smart to keep your receipts, but not if you just dump them in a drawer and forget about them. You think you’ll sort them later and then April rolls around and you’re knee-deep in a pile of papers with no clue what was what. Your accountant doesn’t have time to guess, and neither do you.
What helps is keeping receipts organized from the start. Sort them by type (meals, travel, office supplies, etc.) and file them digitally or store them in a labeled folder.
No Record of Mileage or Travel
If you drive for work, that mileage adds up and, if you’re not tracking it, you’re probably leaving money on the table. You could have months where mileage could earn you hundreds in deductions, but if you don’t log any of it… Welp, kiss that money goodbye. And without records, your accountant can’t claim it for you.
However, this is easy to fix. Apps like MileIQ can automatically track drives, or you can just jot down your miles in a notebook.
Waiting Until the Last Minute
We’ve all procrastinated, right? But with taxes, waiting too long will hit your wallet because you’re more likely to miss deductions when you start late. You’re also more likely to lose important documents or rush through details that matter. And if you book a meeting too late, your accountant might not even have time for you.
Start early to have enough time to gather what you need, ask questions, and actually benefit from the advice your accountant gives you. Plus, it will take a whole lot of pressure off.
Conclusion
When you become self-employed, part of your dream isn’t to become a paperwork wizard. You just want to work, make money, and possibly write off a few meals if you can.
But if you aren’t organized and don’t do this on time, tax season will be hell (one you’ll have to pay a lot for).
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