The Ups and Downs of Freelance Life: My Journey So Far
Freelance life often gets romanticised as the ultimate dream—flexible schedules, creative freedom, and being your own boss. And while that’s partly true, it’s not the whole picture. As someone who has been freelancing for nearly six years, I’ve experienced both the highs and the lows that come with being a sole trader. It’s a journey filled with rewarding moments, unexpected challenges, and everything in between.
The Ups: Why I Love Freelancing
Let’s start with the good stuff—because there really is so much to love about freelance life.
1. Creative Freedom and Variety
One of the biggest perks of freelancing is the variety of projects I get to work on. No two days look the same. Over the years, I’ve built Madbox Creative, a micro-agency specialising in video editing, podcast production, and videography. I’ve had the chance to work on everything from editing podcasts and short films to filming events and weddings with my team at Pink Moon Videography.
The diversity of projects keeps things exciting—no project is too strange. Whether it’s working with TV personalities, sports stars, small businesses, or not-for-profit organisations like The Music Box Yorkshire CIC, I’ve learned to embrace each project as a unique opportunity to tell someone’s story.
2. Building Real Relationships
Freelance work is about so much more than “clients.” Over time, many of the people I’ve worked with have become long-term collaborators, friends, and even mentors. Word-of-mouth referrals have played a huge role in my success—when someone trusts you enough to recommend you to others, it’s incredibly rewarding.
For example, I began working with The Music Box as a client, delivering video content for their projects. That relationship grew stronger with each collaboration, and I was recently handpicked to join their board of directors, starting January 2025. These kinds of opportunities prove just how powerful building meaningful relationships can be.
3. Flexibility and Independence
Of course, the freedom to manage your time is a major benefit. I decide when to work, how to work, and who to work with. For someone who thrives on independence, freelancing gives me the space to manage my workload in a way that suits my life.
Since being diagnosed with Multiple Sclerosis (MS) two years ago, this flexibility has been more important than ever. Some days, MS can throw a curveball, but being able to adjust my schedule helps me balance my health and my work in a way that works for me.
The Downs: The Less Glamorous Side of Freelance Life
As rewarding as freelancing can be, it’s not all smooth sailing.
1. The Unpredictability of Work
One of the biggest challenges is the unpredictable nature of freelance work. Some months are busier than I can handle—so much so that I’ve had to subcontract other freelancers to help with the workload. Other months can be quiet, which, while offering a nice breather, brings its own set of anxieties.
This instability became more noticeable after my MS diagnosis. When living with a chronic condition, unpredictability can be tough to manage—whether it’s in your health or your income. Freelance life requires a lot of adaptability and the ability to plan for the unexpected.
2. Wearing All the Hats
As a freelancer, you’re not just the creative—you’re also the accountant, marketer, administrator, and customer service rep. It’s a lot to juggle. There’s no IT department to fix things when something crashes, no HR to sort out contracts, and no finance team to chase invoices. You do it all yourself.
3. Loneliness and Isolation
Freelancing can be lonely at times. You don’t have the watercooler chats or regular team meetings that come with an office job. While I’m lucky to collaborate with fantastic people on my projects, there are days when working solo can feel isolating.
That’s part of the reason I love teaming up with people like Steve at Pink Moon Videography. Working alongside others—even for just one project—reminds me how important collaboration is, not just for the work, but for the connections and energy it brings.
Why I Wouldn’t Change the Journey
For all its ups and downs, I’m proud of the journey I’ve taken. Building Madbox Creative from scratch, developing relationships that have turned into lifelong friendships, and creating work I’m truly proud of—all while learning and growing every step of the way—has been incredibly fulfilling.
Freelancing has taught me resilience, adaptability, and the value of hard work. I’m entirely self-taught in video and audio production, having pivoted from a background in live music photography and artist management during the pandemic. That leap wasn’t easy, but it pushed me to find my voice in a new industry, and the success I’ve achieved is all the more rewarding because of it.
Looking Ahead
While freelancing comes with its challenges, it’s the freedom to create, collaborate, and tell meaningful stories that keeps me motivated. Whether it’s filming weddings with Pink Moon, producing podcasts for creators, or directing music projects with The Music Box Yorkshire CIC, I’m excited to keep working on projects that inspire me and the people I collaborate with.
To anyone considering freelance life: it’s not always easy, but the rewards are worth it. The connections you make, the work you create, and the freedom you gain are invaluable. Just remember to enjoy the ride—ups, downs, and all.
