What I Learned in my First Year as a Freelance Writer

Before I went freelance, I worked for several years as a writer, content creator, and marketing strategist in an agency setting. As a creative, I often felt like the 9-5 was not sustainable for me. While the salary and stability of full-time employment was comforting, I wanted a better work-life balance, the ability to take projects that I cared about, and an opportunity to scale my income without taking the traditional management route. 

After years of dreaming about it, I quit my job in February 2020 to pursue a career as a freelance writer. Within three months, I secured a full client load and surpassed my monthly income goals. The path to success is rarely linear, and I found that my first year as a freelance writer presented many challenges and a wealth of learning opportunities. While I’ve picked up several nitty gritty lessons of business ownership, these are the four that helped me build a fulfilling and successful business as a freelance writer.

You’re never going to feel ready.

As a perfectionist, one of the most important lessons I’ve learned is that sometimes you have to build your plane while you’re flying it. Self employment can be overwhelming, and I think you’ll never feel 100% ready to take the leap. When I first started reaching out to potential clients, I didn’t have a website, brand, social media presence, or even pricing. But I was confident in my professional experience and my ability to deliver exceptional work. 

To my surprise, every single person I reached out to resulted in paid work and a steady stream of income for my first several months. So much of business ownership is learning as you go and refining your process. I never would have built the business I have without the confidence to get started, even before I felt ready. 

It’s okay to say no.

When you’re first starting out, it’s hard to turn down paying work. However, if a project comes your way that just doesn’t feel like a good fit, it’s absolutely fine to turn it down. The first time I received a proposal that didn’t feel like a good fit, I grappled for days with the thought of turning it down. I reminded myself that I chose to be a freelance writer so I could work with clients I love, write about things that interest me, and get paid what I’m actually worth. 

If I’ve learned anything over the last year, it’s this: continually accepting work you hate doing will never create a business you love. Of course, there will always be seasons where you have to take some projects just for the paycheck, and that’s fine. But if you have a clear idea of what your ideal project looks like, it’s okay to pass on work that doesn’t align with that vision. 

It’s not all about being creative.

While being a freelancer is creatively fulfilling, writing is only one aspect of my job. There are a million administrative aspects of running your own business, from finances and billing to project management and business development. I’m a one woman show, so everything that makes my business successful is my responsibility. I learned early on that having the right set of tools to manage the administrative aspects of my business is so important. I use Quickbooks to invoice and manage my financials, Google Sheets to keep track of my billable time and projects, and ClickUp to manage my deadlines from various clients. 

Freelancing full-time often attracts creatives, and I think it’s a great avenue for writers, graphic designers, artists, and more. A fair warning to my fellow creatives: there are so many skill sets you will have to learn to manage a full-time creative business. It’s not impossible, but it’s a steep learning curve. Do your research, figure out a system that works for you, and never underestimate the time and knowledge it takes to run a business by yourself. 

Embrace the ebb and flow.

Shifting from being an employee to an entrepreneur is honestly terrifying. As a salaried employee, there’s a sense of security in your monthly income that business ownership cannot provide, especially in your first year. But there’s also freedom to charge what you’re worth and take work you enjoy. I would love to tell you that it’s smooth sailing from the moment you get your first paycheck, but it’s not.

There’s an ebb and flow to freelancing that affects both your workload and income. I’ve had months where I had a full workload of exciting projects and made more money than I ever could have dreamed in a salaried position. I’ve also experienced lulls where both my project load and paychecks were light. It’s not an easy adjustment, but I’ve learned to appreciate the busy times and embrace the down periods. When I’m feeling anxious about the uncertainty of freelance work, I often remind myself that no job is guaranteed. I’ve worked at giant media companies and small startups, and not one job could promise security. At the end of the day, I would rather fail trying to do something that makes me happy than never try at all.

If you’ve considered pursuing a freelance career as a writer or creative, I hope this offers encouragement and a realistic perspective of what that transition can look like. From one creative to another, I’m always happy to answer questions big and small about building a freelance business. Email me at sarahrearickroy@gmail.com to chat!