The 9 Movies Every Freelancer Should Watch

By Shelby Deering November 21st, 2014

The life of a freelancer is rarely glamorous. We don’t wear designer gowns or expensive suits while we type on our laptops. When we do travel, our assignments typically don’t take us to Paris or Milan. And there certainly is no red carpet.

In Hollywood, the portrayals of freelancers and reporters are glossy and dramatic, even if a movie is based on true events. But hidden between the generous expense accounts and overly pretty people are genuine moments most freelancers can relate to. Here are 9 movies about our profession that have some wisdom to offer.

1. Almost Famous

Most freelancers do at least some work that simply pays the bills. Those assignments are necessary for sustaining careers, but whenever you have the chance, go after those stories that stir your soul, just like William Miller did for Rolling Stone in the 2000 film Almost Famous. When you finish your karaoke version of “Tiny Dancer” and have to start that next project, remember to make time for the topics you’re most passionate about.

2. Capote

Truman Capote was a gifted storyteller, and his New Yorker piece turned non-fiction book In Cold Blood has become more than just a good piece of writing. In the eponymous film, Capote has to interview several grieving, shocked sources and manages to put them all at ease by sharing relatable stories from his own life. Don’t be afraid to put your own personal details into an interview. Honesty and openness are keys when trying to establish trust.

3. Sex and the City

We can all agree Carrie Bradshaw’s life doesn’t represent the realities of freelance life. She wouldn’t be able to buy $500 shoes on an income that consists of a weekly column and the occasional Vogue piece. But one aspect the show and movies get right is that writing—especially in the first-person point of view—ebbs along with life’s changes.

As Carrie begins research for her next book, she tells Mr. Big, “I used to write about finding love. Now I want to write about what happens after you find it.” Keep your writing fluid as life evolves, and try not to get hung up on stilettos that cost as much as your rent.

4. Sideways

Miles is a perpetual pessimist, particularly when it comes to Merlot and his own writing. After getting rejected by a publisher, Miles says, “I thought this one had a chance, but I was wrong again. I guess I’m really not a writer. I guess I’m not much of anything.”

We’ve all been there, and we’ll all probably be there again. Don’t let those rejection letters, unanswered emails, and ignored pitches bring you down. Dust yourself off, remind yourself that you’re awesome, move on to the next opportunity, and drink a little more Merlot.

5. Julie & Julia

Julie Powell escaped the drudgery of her daily life by blogging for one year about her experiences cooking every recipe in Julia Child’s debut cookbook. Eventually, she parlayed that creativity into two nonfiction books.

Powell’s relatable story is a reminder to push out of comfort zones and stagnant careers. Set a goal to write for 10 national publications next year. Cover a topic outside of your area of expertise. Test your limits with a challenge, and you might surprise yourself (and get your blog turned into a film).

6. Dan in Real Life

The line between a freelancer’s career and personal life is always blurred. In Dan Burns’s case, his work as an advice columnist clashes with the the messiness of his daily life. The story is a reminder that success is never as simple as it may appear in an advice column. Instead of pretending obstacles and snags will go away, accept them and try to confront your issues in your work.

7. The Rum Diary

Hunter S. Thompson used his own experiences in Puerto Rico to create the fictional American journalist Paul Kemp. Kemp takes a reporting job at a newspaper, only to find himself in a heap of rum-fueled trouble when his assignment takes a dangerous turn. The lesson here is to investigate the reputation of your clients before you sign a contract or agree to take on work. Now, we can research with a Google search, but since Kemp’s story takes place in the 1950s, he didn’t have that luxury.

8. Philomena

After political journalist Martin Sixsmith gets fired as a government advisor, he stumbles upon an unexpected story about a woman’s search for her adopted son. Although Sixsmith isn’t initially interested in writing a human-interest story, he follows through on the idea and immerses himself in the reporting(and eventually turned his journey into the nonfiction book The Lost Child of Philomena).

Losing a steady job can crush any freelancer’s ego, but it helps to embrace the chance to do something new and evolve professionally. There are plenty of stories out there worth telling, and sometimes, they fall in our laps in unexpected ways.

9. Nightcrawler

Lou Bloom takes a sharp turn down the dark side of crime journalism, providing footage of gruesome accidents and crime scenes to local news stations. Bloom is a prime example of what happens when the drive to get ahead as a freelancer starts to consume the rest of your life. It’s good to occasionally put in extra effort, but it’s also smart to step back and set professional boundaries.

So now that you have some movies to binge watch, sit back, munch on popcorn, and learn what to do (and not do) from these films. Who knows? Maybe your freelance career will be turned into a movie someday. There might be a red carpet in your future after all.



Image by Andy Kropa
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