Freelance Writing 101: Expert Answers to Your Burning Questions

Welcome to the world of freelance writing, where creativity meets flexibility! If you’ve found yourself on this page, chances are you’re curious about how to make the leap from a 9-to-5 to the freedom of freelancing.

This blog post is your ultimate guide, packed with insights from Dita Squires, a seasoned freelance writer and content strategist. Dita has a rich history of helping companies like Ecolab, Deluxe Corporation, and Great Clips, Inc. tell their compelling stories, elevate their brands, and drive engagement. Her experience is a treasure trove for anyone looking to dive into freelance writing, especially in the dynamic realms of marketing, creative, and digital work.

We sat down with Dita to get her insights on everything from managing your first client to setting your rates and juggling deadlines. So, grab a cup of coffee, and let’s unravel the secrets of building a successful freelance writing career with Dita Squires as our guide.

How did you transition into freelance writing from a traditional 9-5 job?

When I was a journalism student at the University of Minnesota, I was introduced to a section editor at the Star Tribune who hooked me up with a few freelance research projects. The experience planted a seed; I loved the ability to moonlight, fitting in the work around my class and internship schedule. After working full-time for a few years in advertising and then corporate communications, I was pregnant with my first child and decided I wanted to earnestly pursue a flexible working schedule. A few weeks before my son was born, I resigned and reached out to my contacts to let them know I was going to be a freelance writer. I signed my first contract one week after having my son, and my business grew from there.

How do you set your rates as a freelance writer, and how often should they be adjusted?

When I was getting started, establishing my rates was tough. Do you base your rates on your years of experience? Should they flex to match the value of the project? Do you adjust them based on the size of the company? Initially, I undervalued my services, charging the equivalent of my salaried hourly wage at my previous job. However, this also gave me the opportunity to get a foothold in several industries and gain valuable experience.

A few years in, I began freelancing for a few ad agencies. The rates they paid contractors were much higher than what I was charging, so that gave me a better sense of where I should be. It helped me create my own rate sheet, which I keep on my desktop and revisit annually. From highest to lowest, my rate categories are: 1) Direct client rate, 2) Agency rate, 3) Contract and nonprofit rate. To expedite proposals, I also have general rates with word counts established for types of content such as blog posts, social posts, ebooks/white papers, case studies, emails, web copy, and print ads.

How do you manage your time, juggle multiple clients, and meet deadlines as a freelance writer?

Strong organization and time blocking are vital to my business. I often have competing deadlines, as well as large-scale projects that require daily progress. To ensure I don’t miss deadlines, I have a very structured writing calendar that breaks projects into manageable daily chunks, defining bigger blocks of time for work that requires deep thinking. I also note any checkpoints along the way so I keep clients updated on progress as needed. 

One important thing is to know thyself! My best productivity is before 1 p.m. and, if needed, after 7 p.m. It’s harder for me to maintain momentum in the mid-afternoon, so I often plan tasks like proposals, billing, and client meetings and/or communication during that timeframe. 

One goal I try to uphold is to finish a project a day early so I can sleep on it and give it one final review with fresh eyes to catch grammatical issues or clumsy phrasing before I send it off. Of course, it doesn’t always play out this way – especially with rush jobs – but I try!

What are the biggest challenges you’ve faced as a freelance writer, and how did you overcome them?

My number one challenge over the past 25 years has been learning to say no to work.

Because you don’t have a steady income as a freelance writer, and you never know what’s around the corner, I am inclined to say yes to projects, even when my plate is full. I do think there’s a time and place to be hungry and take whatever opportunities come your way if the terms are acceptable to you, but there’s also a stage when you must be more selective and manage this career with a marathon mindset. Today I’m better about asking clients if there is any flexibility in their deadlines and, if not, declining the project. Sometimes they come back with magically extended due dates, and sometimes, they don’t. Either way, it’s okay. Writing is mentally demanding, and if you sacrifice your sleep and health to take on every project that comes your way, your work and, ultimately, your business will suffer.

How do you handle client feedback and revisions? And how do you navigate challenging client relationships?

In general, I don’t struggle much with implementing client feedback. I know there are often larger dynamics at play involving people and preferences that are outside of my knowledge and/or control. If I feel the feedback will dramatically alter the tone or rhythm of a piece, I will talk to the client about it, asking questions to ensure I have clarity about the situation and how it differs from our initial conversations about the project. In some cases, a client will request edits that are grammatically incorrect. Usually, a simple explanation of why something needs to be tweaked does the trick!

I’ve been very fortunate in that I’ve had just a few challenging client relationships over the past 25 years. I do believe that people usually give you signs that they’re going to be trouble. For instance, I’ve had potential clients who drag out the proposal process beyond what I believe is reasonable. If a formal proposal is followed up with a flurry of questions, requests for more info, dead air for weeks, suggestions to meet again, conversations around pricing and timeline adjustments, and general indecision, that’s a red flag for me, and I won’t pursue the work. If someone is excessively needy or if they act like a jerk, I’ll gladly step back.

How do you keep up with current writing trends and industry changes?

Read! Read books, read magazines, read blogs, read ad copy, read the newspaper, read billboards, read direct mail, read through your inbox. Take note of fresh approaches, words, or phrasing that resonate with you, tactics that are effective, and those that aren’t. Bookmark industry websites and articles that address topics and trends relevant to your work.

Finally, what are the top three pieces of advice you’d give to a budding freelance writer?

Once you have your online portfolio ready, I think these three steps will get you rolling:

  • Get one client: Lean into your network to find one client. Reach out to your former employer(s) and see if they have any projects that would benefit from external writing support. Message your former co-workers, friends, and family to let them know about your new venture and to ask for referrals. Sweep LinkedIn and job boards for contract work.
  • Make yourself indispensable: Make your clients wonder how they would survive without you. Ask questions. Solve problems. Be proactive. Go above and beyond. Deliver quality content on time and on budget. Become a vital member of the team.
  • Tap into work pipelines: Build mutually beneficial relationships with companies like Celarity that can bring you ongoing contract and project-based opportunities. By connecting with recruiting firms and advertising agencies, you can spend more time accruing billable hours and less time on sales.

Now It’s Your Turn

So, there you have it – your primer on forging a successful path in freelance writing. It’s a journey filled with its own set of challenges but also brimming with opportunities to grow and shine.

At Celarity, we’ve seen more and more companies eagerly seeking out freelance talent, and we believe there’s never been a better time to explore this career path. If you’re thinking about giving freelance writing a shot, or if you’re already in the mix and looking to level up, we’re here to help. Drop us a line, and let our team of recruiters connect you with gigs that match your skills and passions. Let’s make your freelance writing dreams a reality!

About Dita

Dita Squires a freelance writer and content strategist who helps companies tell their stories and elevate their brands while driving engagement and response. Her clients include Ecolab, Deluxe Corporation, Great Clips, Inc., and Children’s Minnesota, and she has ghostwritten three books for clients which yielded book deals from three unique publishers. 

Learn more and connect with Dita!

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