5 Things Being a Freelancer Taught Me About Pursuing a Creative Career
Lessons on Freelancing and Pursuing Your Creative Passions
Welcome to this week’s Sunday Evening edition of The Backlot, which includes stories from my recent experiences working in indie filmmaking, helpful resources for emerging filmmakers, and other posts covering topics in the film industry.
NOTE—The Sunday version of the newsletter is free. The mid-week version is a paid subscription, which you can subscribe to below.
This week, we’re exploring the broader landscape of freelancing and a few of the things I’ve learned over the years…
🎞️ Five Lessons from Freelancing
🎬 Community Thoughts and Open Discussion
🗞️ Three Movie Recommendations
A Few Things I’ve Learned About Freelancing
This week, I want to share a bit of my freelancing story with you because these experiences have played an important role in navigating my career as a filmmaker.
All throughout my life, I’ve been obsessed with living an alternative livelihood and diverting from the status quo. For as long as I can remember, I’ve wanted to do something different than work the office job and settle down. Not that there is anything wrong with that, but it’s just never been for me.
Therefore, in the Spring of 2021, after working as a communications specialist for a conservation non-profit organization in Baja California, Mexico, I fully committed to the freelance lifestyle.
I started writing as a journalist and blog writer, finding work with any publications that would pay me to write about my knowledge of environmental issues.
At first, I had no idea what I was doing. I wasn’t a trained journalist, and although I was a good writer, I had very little to show for it besides scientific research papers and a few conservation blogs.
Truthfully speaking, I went into freelancing rather blind. It took years of learning from failure to scratch and claw my way toward any resemblance of a sustainable life. Still, through those experiences, I learned a lot about myself, running a business, and building a career in written and visual media.
Plan Ahead
One of the most important things my father instilled in me growing up was the importance of good preparation. He always preached that a few hours of preparation could prevent stress and anxiety in the future.
And let me tell you - he was absolutely right.
As a freelancer, your ability to properly prepare can make or break your career. In this lifestyle, there is a critical need to plan ahead because, unlike other jobs, you are solely responsible for getting the next contract, meeting the next deadline, and finding the next paycheck.
That’s because freelancing is a less-than-stable existence and more of a feast-and-famine lifestyle.
In one month, you’ll be working on several different contracts, making a lot of money, and growing your business. The next month, things will slow down, clients will be harder to come by, and your income will drop significantly.
This is a necessary understanding of being a freelancer because it happens to all of us, and we have to learn to ride the highs while preparing for the lows.
One of the best ways to prepare is to make time throughout your week to work on your business's future. Whether it’s a few hours or an entire day, it’s a good idea to work on finances, track your taxes and fees, or send pitches for future contracts.
The more time you spend preparing for the future, the better your chances of weathering the next storm when it comes. Because trust me, it will come.
Learn About Running A Business
In the spirit of planning ahead, one of the best investments you can make as a freelancer is to learn about running a business.
As a contract worker, you comprise the entire company. Unlike jobs that have a variety of departments to support their employees, in freelancing, you are in charge of everything, including negotiating contracts, marketing your services, keeping track of finances, securing health benefits, and paying your taxes. All the while, you continue to produce the best work you can for your clients and collaborators.
For these reasons, it’s important to invest in business skills that help you learn and improve in each of these aspects.
For myself, this has included reading books about running a small business, taking classes on entrepreneurship, and learning from others through their experiences.
Nowadays, there are plenty of good resources out there. Some of my favorites include Freelance to Founder and The Writer’s Co-Op.
Separate Yourself From the Business
Okay, I’m not just talking about legally separating yourself from your business, although that can be a very good idea under the right circumstances. I’m referring more to the mindset of separating your business and your work.
Many freelancers, especially in film, writing, and art, do it so they can make a living from their passions.
That’s why, at first, when you start marketing your skills and passions to clients, it can be a difficult transition because getting feedback on your work can be very hard, especially when it’s responsible for your livelihood. This dependency on these passions can make struggles to get new clients, make money, and find success feel personal and like an insult to your work.
Instead, it’s quite the opposite. Freelancing is a business. Your passion is now your product. This means it’s not always about whether your work is good enough or worthy of payment; it’s more about the business aspect of things and how you market, produce, and share your work.
That’s why it’s important to see the gap between these two things. Everything that happens as a freelancer isn’t a reflection on yourself; it’s a reflection on the business.
Consider them two separate entities: the passions are executed by the worker, and the business is executed by the entrepreneur. In this way, the bumps in the road are less about yourself and more about the reality of running a business.
All your efforts toward your art doesn’t always correlate to its success as a product or service, and it’s important to realize that. It will make you more resilient, empathetic of your client’s concerns, and practical about your business's needs.
Make Connections
For myself, this was one of the hardest things about becoming a full-time freelancer. As freelancers, we often work remote jobs with clients and collaborators who live in different countries, time zones, and hemispheres.
We can spend a lot of time on our computers, working alone, and never leaving the house. In my experience, this loneliness and lack of community can be especially hard because it deprives us of the necessary connections we need as human beings.
That’s why it’s important to find a community of other freelancers with whom you can talk, share experiences, and form relationships. This community can be virtual or in-person (although I would advise in-person) and can help you overcome the hard times, provide feedback on your work, and give you friends.
For myself, the need for community pushed me to start working at coffee shops and co-working spaces. Spending my time in these places allowed me to connect with others who were seeking the same types of connections.
Over time, this slowly built a network and community around my work, allowing me to have people to talk about life with, learn from their shared experiences, and, frankly, keep me sane.
Learn to Turn Off
This may be the single hardest thing to do as a freelancer. Over the years, I’ve experienced numerous spurts where I've found myself working ridiculous hours, constantly thinking about work, and never taking time to relax.
As freelancers, we do not have time to clock in and clock out. We often set our own hours and work at a pace dictated by the project, deadline, and our personal preferences.
This can be incredibly rewarding because it allows you to make your own schedule and find time to do the things you want to do in life.
It can also be one of the most dangerous aspects of being a freelancer. Since we are responsible for our finances, future projects, and success, many freelancers find themselves constantly thinking about work and worrying about the future.
This is especially true during harder times when there are fewer opportunities. We find ourselves constantly searching job boards, sending pitches, and networking. This constant work mindset can cause unnecessary stress and anxiety and can affect our relationships outside of work.
As someone who has done this many times, I can honestly say that it can be incredibly detrimental to your mental health and can quickly lead to burnout.
That’s why we have to find times to clock out and take breaks from our jobs. We have to allow ourselves to curate a work-life balance that gives us time away from the constant grind of running our own business.
Over the years, one of the best ways to help me log off is establishing boundaries around my hours. For example, unless I am on a deadline, I will have a hard shutdown time during the day, after which I don’t allow myself to work.
In addition, I also ensure to schedule a full day off during the week when I am not allowed to think about work, which helps me prioritize other passions and keeps me inspired and creative for the week ahead.
For others, I know individuals who turn off their work inbox after a certain time each day, schedule relaxation breaks throughout their daily routine, and take a few days off every few weeks to combat burnout.
Final Words
Now, I don’t share all of this to deter you from being a freelancer or pursuing this kind of lifestyle.
Instead, I share these experiences to help others understand the reality of a freelance career. It’s not working a four-hour work week or logging in from a remote island destination. Freelancing is hard work and requires dedication, resilience, and belief in yourself.
If you can manage those things, then it can be an incredibly rewarding lifestyle. It can empower you to dictate your own life, manage your own projects, and curate your own schedule. It will also give you an invaluable skillset that is hard to come by anywhere else.
As for film, since this is a filmmaking newsletter, I’ve found all these experiences to be invaluable for my career as a writer and producer. They’ve helped me navigate the highs and lows of this industry, trusting in the process and approaching each project with the mindset of a business owner.
For that reason, I think there is a lot we can learn from working as freelance artists or creatives. There is a power in living this life, and learning to wield that power can be liberating, opening up a whole new realm of possibilities.
A Quick Discussion on Community
Moving forward, I’m very interested in which topics, ideas, and questions you are interested in hearing more about.
These newsletters are a way for me to share my experiences, explore different topics, and learn about the industry. They are also about the community around filmmaking, and therefore, I want to know if there are ways this newsletter can be more beneficial.
I also want to open this platform up for other filmmakers to share their stories. Over the next few months, I will be sharing conversations with a few different filmmakers and writers who are navigating their own routes in the industry. I’d love to expand on those conversations and welcome others to this platform because the more we can share and learn from one another, the better we can become together.
With all this said, feel free to leave a comment or message me below. I’d love to hear your thoughts on The Backlot, filmmaking, freelance life, or even just your favorite film you’ve seen recently. Let’s start a conversation.
Three Film Recommendations
This week, for our film recommendations, we’re sticking with the theme of living an alternative lifestyle and finding ways to pursue a life of passion and excitement…
The Secret Life of Walter Mitty (2013)
Anyone who knows me knows this is my favorite film of all time. The Secret Life of Walter Mitty, based on the short story, is a film about it never being too late to follow your dreams. The film follows Walter Mitty, played by Ben Stiller (who also directed the movie), who is a negative asset specialist for Life Magazine and has to track down Sean O’Connell (Sean Penn) for the final photo of the magazine's print cover.
The film is an ode to pursuing your dreams and taking risks to become the most authentic version of yourself. Combined with some brilliant cinematography, great performances, and an outstanding soundtrack that includes Arcade Fire, Jose Gonzalez, Of Monsters and Men, and Kristen Wiig singing Space Oddity, the film is an underrated masterpiece.
Not to mention, Sean Penn as Sean O’Connell might be one of the coolest characters ever on the screen. I mean, photographing Ghost Cats in the Himalayas - that’s rock-star shit.
Where to Find - Rent of Amazon Prime or AppleTV
Hector and the Search for Happiness (2014)
Most people recognize Simon Pegg from the Three Flavors Cornetto trilogy and, more recently, the Mission Impossible movies. Although each of those movies is brilliant, I’d argue Hector and the Search for Happiness is Pegg’s most authentic role.
The film follows Hector, played by Pegg, a therapist in London who feels his efforts to improve his patients' lives are pointless because he doesn’t understand happiness himself. In a roundabout adventure, Hector travels around the world to try and understand the meaning of happiness; encountering overworked businessmen in Hong Kong, drug lords in Africa, and his ex-girlfriend in Los Angeles, Hector slowly begins the understand the true meaning of being happy.
It’s an exciting, funny, and very emotional tale about the reality of finding happiness and discovering this power within ourselves.
Where to Find - Free on Amazon Prime
Flora and Son (2023)
On the more recent side, last year’s Flora and Son follows a woman’s efforts to help her rebellious son by involving him in music. Led by Eve Hewson, Bono’s daughter, who plays Flora, the film is an emotional, sometimes cheesy, and personal story.
Throughout the film, Flora connects with an online music teacher, following her own passions and finding a way to connect with her rebellious son. The story is about this mother-son relationship and how learning to reconnect with yourself can help you connect with others in your life.
The film also comments on the power of the internet and its ability to connect us with people around the world who can have a profound impact on our lives. This part of the film is also a very creative way to tell a story around what I only assume was a budgeting or scheduling issue to fly Joseph Gordon Levitt to Dublin.
Where to Find - AppleTV
On Wednesday, in the paid newsletter, we will be diving into the streaming landscape for documentary film…
🎞️ The State of Documentary Film: Episode III - The Streamers
🎬 Other Latest News and Updates from the Industry