Seven Films That Get Freelancing Right - UnderPinned

I became a freelance writer fully expecting the Carrie Bradshaw lifestyle.

You know – writing one article a week, yet earning enough to live in a luxury Manhattan apartment and supplement my ever-growing wardrobe. I envisaged my days spent brunching with the gals, then popping into Jimmy Choo on my way home to pick up a lil’ something with my spare change.

Carrie Bradshaw lied to me.

If you’ve ever been freelance, you’ll know that working for yourself is more living in your pyjamas than designer gowns, and you’ll spend your days worrying over whether you’ll have enough work to pay the bills rather than if you can secure reservations for the latest restaurant.

But some films do get freelancing right. If you’re in the mood to watch something that you can relate to, here are the seven films that represent the freelance journey.

Jerry Maguire (1996) – A guide to faking it until you make it

Jerry is tired of slaving away for a big company only to have his efforts taken for granted, so he decides to set out on his own. Sound familiar? There are few films that are more relatable to freelancers than Jerry Maguire. Jerry only has one client, yet refuses to compromise his business ethics to land ‘easy’ wins. There’s plenty of client-contractor conflict in Jerry Maguire too that you’ll definitely relate to as a freelancer. Self-employment lessons aside, this is a really watchable film with plenty of award nominations to back it up.

The Social Network (2010) – Because we all want to know how they did it

How can there be a list of films to inspire freelancers without featuring The Social Network? This is a biopic about the foundation of Facebook, from its humble beginnings of a college campus social network to the biggest website in the world. The film offers stellar performances from Jesse Eisenberg and Justin Timberlake, as well as a fascinating insight into the social network we love to hate. And while Facebook may be the bane of many of us self-employed people’s lives, it’s hard to deny the incredible drive of Zuckerberg and his ability to carve a niche no one knew existed.

Indie Game (2012) – A showcase of the little guys taking on a giant industry

You might not have heard of this documentary, but Indie Game is a must-watch for freelancers looking for inspiration. The film follows the journey of three independent video game designers as they release ‘Super Meat Boy’ after two successful Kickstarter campaigns. The documentary is less about the video game and more about its developers’ creative process, as they strive to create a product that harks back to their childhood in an era of ultra-HD gaming. The developers face marriage strife and health issues, as well as a potential lawsuit, before finally releasing their video game to critical acclaim. Indie Game is a must-watch if you are currently struggling with the motivation to keep following your own dream.

It’s a Wonderful Life (1946) – Proof of why you should never give up your business dreams

It’s a Wonderful Life is often revered as one of the best films of all time, but its message to small business owners is often overlooked. If you’ve never seen it (where have you been?) the synopsis is this: George Bailey runs local bank Bailey Brothers’ Building and Loan, but when the bank faces closure and the local community risks losing all its money, George plans to kill himself. A guardian angel called Clarence then visits George to show the way the world would be if he had never been born. The message? Never feel like what you are doing doesn’t matter. Bailey Brothers’ Building and Loan is a key part of its community as an alternative to dastardly big business, and It’s a Wonderful Life serves as a highly emotional reminder that your business is important too.

Joy (2015) – A true story of battling self-employment with raising a family

Many of us freelancers are doing so to support our families, and no film captures that quite like Joy. This drama-comedy tells the true story of Joy Mangano, a self-made millionaire and single mum from humble beginnings. Joy creates a self-wringing mop that becomes an overnight success. While the story behind the product’s meteoric rise is interesting, this is a film for anyone who has struggled to balance family loss and conflict with chasing his or her dreams. Joy has a happy ending though, and it’s a joyous (pun intended) watch full of career motivation.

Fear and Loathing in Las Vegas (1998) – A snapshot into the wild side of freelancing

Hunter S. Thompson is one of the most maverick and outlandish freelance writers of all time, and the film version of his autobiographical novel Fear and Loathing in Las Vegas is a wacky insight into the world of self-employment. Okay, most of us freelancers won’t experience a drug-fuelled psychedelic business trip featuring giant lizards, but the moral of this story is that freelancing can be a wild ride, full of insane opportunities and wonderful anecdotes. If you feel like your work is getting mundane, live vicariously by watching this film.

Ghostbusters (1984)  – A lesson in nailing your marketing

Who you gonna call? Ghostbusters! Everyone knows the song, which showcases exactly how brilliant the Ghostbusters marketing is. Not only have Peter Venkman and Co. created a solid marketing campaign, but they have used their unique skillset to fill an underserved niche in the market. Take note, fellow freelancers: Ghostbusters is Small Business 101, except with some cringe-worthy CGI spooks thrown in.

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