finance foundations

30 Badass Tax Deductions To Take If You Freelance in Hollywood

This is the fun part.

You know how you read about executives in John Grisham novels, casually making extravagant purchases and shrugging it off with the line, “don’t worry, it’s a business deduction.”

Presumably, the executive employs shady business practices because he possesses a wizard of an accountant, capable of moving debits and credits like Scouts across the Stratego board.

Turns out, you don’t need Itzhak Stern to get the deductions you deserve. What you need is:

Optional: find an accountant to help you file — an option I’d recommend.

Now, can you take the extravagant deductions these executives brag about: a new entertainment center with the 4K flat screen and Bose surround sound? I wouldn’t recommend it — it has to be a legitimate business expense — but always consult with your tax professional.

Onto the list of deductions!

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Best Tax Practices For Hollywood Freelancers

(This is the second post in the Tax Tips for Hollywood Freelancers Series on Fighting Broke. You can read part one here.)

We’re two weeks away from the deadline to file your 2013 taxes.

If you haven’t filed yet, this post will guide you through organizing all your information, before hauling ass to your tax professional.

If you’ve already filed, then you’re probably thinking, “whew! Glad I’m not one of those suckers who still hasn’t filed their taxes. Now I don’t have to worry about it for another 365 days.”

But ask yourself this: if you freelance and pay self-employment tax, when’s the best time to get organized for filing your 2014 taxes?

Your buddies, employed by the man, they can get away with starting in January 2015. As a Hollywood freelancer, though, the best time for you to start is:


Or a month before that.

Filing your taxes is essentially a constant work-in-progress, and here’s why…

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Tax Tips for Hollywood Freelancers: An Introduction

Two days before the deadline to file my taxes, and I’m squirming in my Ikea chair at H&R Block. 

“Did you have any business expenses?” the accountant said. “Did you buy any business cards? Any office supplies? Do any printing?”

She was trying to help. She was trying to find enough deductions to get me over the standard deduction…

Except I couldn’t conjure up more than $5,500 worth of deductions in 10 minutes.

So I had no choice but to pay taxes owed in one lump sum: around $10,000.

It had been a rough year. I’d been freelancing, picking up a number of side gigs to keep myself afloat: I worked as a casting assistant, a production coordinator, and a script reader. I had been so focused on first finding work, then actually doing the work, I didn’t study the business of freelancing.

This accountant tried giving me a crash course, except it was too little, too late.

I remember stepping out of the dumpy H&R Block building on Sepulveda, and kicking stones on the pothole-ridden parking lot. I was frustrated with the accountant, and frustrated with the whole H&R Block experience.

Mostly though, I remember how shitty it felt, barely scraping by in Los Angeles, uneducated and misinformed about protecting the business of me.

Crossing the lot, I promised if I freelanced again, I’d be prepared.

So when I learned I’d be freelancing again, I started doing my research. I scheduled an appointment to sit down with my (new, non-H&R Block) accountant, and got all my questions answered.

This series details what I’ve learned about self-employment, taxes, and deductions…

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How to Fly for Free (Part 3) – Update: First Bonus Earned

There are quirks you get used to, living in Los Angeles:

Rain makes national news.

Outdoor tennis in February.

You start believing that thoughts like “…do I have enough chia seeds?” is socially acceptable behavior.

One thing I can’t get used to, however, is missing out on people’s lives back east: birthdays, bachelor parties, weddings… the sort of events that bind friendships and provides photographic evidence for blackmail in years to come.

Unfortunately, regularly springing for plane tickets can be a real bitch on your bank account.

This is the major reason why I got into the credit card miles game — because I want the option to go back east, whenever I want…

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