Why You Shouldn’t Pay Your Dues

career, writer's room
work frustration

We’re all paying our dues.

Just read any “millennial struggle” article, about the challenges in breaking in, standing out, or moving up.

Like, this one in the NY Times:

This is especially true in more creative fields, whether it is filmmaking or publishing. “It’s fashion,” said Dawn Joyce, 24, when asked why she has gone through four internships since 2010. Those include unpaid stints at a major fashion magazine, where she mingled with Zooey Deschanel and Julianne Moore at photo shoots, and at a public relations firm, where she held front-row seats for late-arriving celebrities like Selena Gomez. “I consider myself to be pretty jaded already.”

“I have seen a lot of people beside me quit,” Ms. Joyce added. “It’s sort of like, ‘Let’s see who lasts the longest.’ ”

Yes, the industry is tough.

Yes, it’s easy to feel jaded.

Ms. Joyce sees internships as the endurance test to pay her dues.

Which is a mistake. She shouldn’t be paying her dues. 

I’ll explain what I mean, but first here’s what I don’t mean..

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Life Beyond Taxes


In this Fighting Broke series, we covered

  1. Tax Tips for Hollywood Freelancers: An Introduction
  2. Best Tax Practices for Hollywood Freelancers 
  3. 30 Badass Tax Deductions To Take
  4. 7 Mistakes to Avoid When Claiming Tax Deductions

For all the lessons covered here, the most important thing is this…

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7 Mistakes to Avoid When Claiming Tax Deductions


We covered what qualifies someone as a freelancer.

Then I gave you some best practices and tools to simplify the process.

And then we went over 30 tax deduction all Hollywood freelancers should take.

However, confusion regarding taxes always abound. It took me a long time to wrap my head around the intricacies, and today, even with the help of an accountant, there are still some things I miss.

Consult with your tax professional before you file. Before that, here are a list of 7 common tax mistakes freelancers make…

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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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