11 Tax Tips That Could Save You Enough To Buy A VW Bug




Alicia Ostarello
Alicia Ostarello
I can’t claim to know everything about doing taxes as a contract worker. But I can tell you that eight years ago, what I lost in taxes could have bought me a well-cared for ‘71 VW Bug. With my mom’s patience, my tax guy’s genius, and seven more years of working under 1099’s, I’ve learned a few things. If you’re a freelancer (or thinking of transitioning into it), here’s what I wish I’d known before first getting my tax on: 
If you are on a 1099, your employers are not taxing your income. 
Which means, when you go to file your taxes, you are going to owe the IRS a number that will shock your socks off...unless you itemize your taxes with deductions and write-offs. 
Yep, you are now one of those folks who has deductions.
Welcome to some hard-core #adulting. Itemized taxes are way more complex than the standard Turbo-tax plug and play you’ve come to know and love. 
Deductions: a definition.
I like to think of deductions (aka write-offs) as business expenses. Any cost related to me making an income is a deduction. For example, if I buy a latte while discussing a writing project with a client, that’s an expense I can write-off. 
Receipts are friends, not fodder for the recycling bin. 
Write-offs require proof. In the United States of Taxlandia, you must be able to show and tell about each of your purchases in case the IRS audits you. The old school way of doing this is to collect receipts, and write on each how the cost is related to being a writer, and sticking that receipt in a sacred place (I use an dilapidated shoe box). 
No receipts? No problem. 
Retrace your credit and debit spending online, looking for statements that jog your memory. I highly recommend getting a business-expense credit card, which you’ll only use for write-off friendly purchases — seriously, a game changer come tax time. 
There are a magical number of things you can write-off. 
Remember, write-offs are about costs related to making your income. Anything you pay for that enables you to do your job is a write-off. Here’s a quick list of things I’ve written off in the past: 
     -My cell phone plan and my smartphone upgrade
     -Netflix subscription (oh, how I miss the days of blogging about movies!) 
     -Printer toner, Moleskin notebooks, earbuds
     -50+ square feet of my apartment, where my work station is set up
Anything you spend money on that helps you do your job is on the table, though I recommend you talk to a professional before setting anything in Formica (or the stone of your choosing).
Don’t be afraid of your losses.
Have a client who didn’t pony up after receiving an invoice, or was your printer stolen? So long as you have a paper trail, you have a case to report, and thus write-off, your losses. 
Track transportation expenses…
Oh you better believe you can write off work-related mileage, bridge tolls, and even car maintenance. Keep a notebook in your glove compartment with the date, mileage, and cost of all driving activities to make reporting these deductions easy-cheesy.
...and medical expenses, too. 
Medical expenses include that time you tried acupuncture, sports massage, and naturopath subscribed supplements, to name a few. 
No more drop and dashing at the library. 
Any time you donate gently used books, that funky Niagara Falls t-shirt, or your collection of Parenthood (wait! I’ll take that!), stick around for a receipt. And hang-on to emails showing you donated to a GoFundMe and your local NPR affiliate. Provided you have the paperwork, those are tax-deductible, too.
Hire a pro. 
It can be tricky to catch all the bits and bobs floating about in your expenditures – and one misstep plus bad-luck fairy dust can lead the IRS to your door (yikes!). A tax pro might seem like one more hard cost to swallow, but I can’t sing the praises of these good eggs enough. 
Good luck out there, and let me know if you have any favorite tips for keeping your IRS payment low!
When Alicia was 17, she wrote an essay titled "I Am a Snail Watcher." The themes of that essay—noticing tiny details, celebrating small victories, and rooting for the under-appreciated—still apply to her daily life and affect her writing.


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