5 Skills You Need to Grow a Successful Freelance Writing Business
And my honest advice after 4 years of freelancing.
There’s a honeymoon phase when you leave a traditional job to pursue freelancing full-time.
My honeymoon started in July 2019. I had a renewed sense of purpose — an inexplicable zeal for life and work, something I hadn’t possessed in a long time. After succumbing to burnout in the corporate world, I couldn’t wait to build a business and blaze my own trail.
I don’t have any statistics or survey results to throw at you, but I assume most freelancers experience something like this when they first start their careers.
Despite having a grand vision for my writing business, my expectations were still somewhat down to earth. I was a decent writer and I believed in my abilities — but still, I knew it would take a while to develop the necessary skills to build a legit writing business.
Over the last 27 months, I’ve diligently honed my craft and become a legit business owner. I feel like a new person…I can’t even fathom it sometimes. I blinked and now people come to me with freelancing questions.
Today, I want to shed light on the critical freelancing and writing skills that we need to succeed in this line of work. (Yes, I meant to separate “freelancing” and “writing” — they’re unique and often exclusive skillsets.)
Here are five of those skills and how I approached developing them.
1. Voice, style, and story
As a writer, you have a unique voice, style, and story. Together, they comprise your writing personality, which distinguishes you from the masses. It draws people to you and keeps them coming back for more. Without these elements, we’re just…normal.
Strive to be weird.
Inject your words with personality. Be vulnerable. Be charismatic. Be angry. Be giddy. Be pensive.
Be human. It resonates with people.
Why does this matter from a freelance perspective, especially if you’re ghostwriting for businesses? In most cases, companies request your services because they admire your writing voice and style. They want their business’s personality to reflect the same core traits of your personality.
Tips for developing your voice
This is a two-parter. First, you have to accept your own writing personality.
And it starts with baby steps: opening a blank document and sharing thoughts. There’s no word count goal or limit. There’s no format requirement. You could dump your stream of consciousness out like a box of Legos on a glass dining room table. Your rough draft could be as coarse as sandpaper. Who cares?
With enough repetition, you’ll shape your writing personality. Once you do, you can work out the kinks and format your content to appeal to other readers, which brings us to part two: accepting other people reading your work.
Hitting publish gets easier each time. Sharing your hard work with social media gets easier each time. Getting public feedback gets easier each time.
Just know that it will happen with enough practice, eventually. Don’t believe me? Commit to writing for three months. You could write every day or once a week, it doesn’t matter. By day 90, I guarantee you’ll reread day 1 and cringe. This happens to me whenever I read my old writing. It’s painful. I squirm in my seat.
If you’re like me, you’ll heavily criticize your word choice, grammatical structure, and writing personality. You’ll think, “Man, this sucks. I would rewrite all of this.” But guess what? That means you improved.
2. Thick skin
If you screamed your personal thoughts through a megaphone in Times Square, there’s a good chance someone would either find a way to take offense or ridicule you just because the opportunity is there. It’s not unlike the concept of writing for online audiences.
As a writer, you’re bound to endure your fair share of public criticism. It’ll even be malicious sometimes. This accentuates the need for thick skin, or else we risk letting it affect our writing personality and ego.
That said, even thick skin is penetrable.
I’ve had my fair share of haters over the last few years. I’m not ashamed to admit it — it got to me for a while. I’ve written about overcoming haters already, but I will share this: it gets easier. There will come a point where most knit-picky comments don’t get to you.
Tips for thickening your skin
Unfortunately, thick skin is formed by experience. So, you have to roll with the punches for a while.
It’s difficult to ignore people who publicly lambast our hard work — it’s even more challenging to avoid fighting fire with fire. That said, there’s a practical way to deal with haters. I outlined my process already here.
3. Word output
The more you write, the more full bodies of work you can produce. The more eyes you can reach. The more projects you can take on.
Of course, there’s a trade-off: writing at high volumes is mentally taxing. It’s like exercising a muscle — you have to keep pushing yourself to increase your strength.
But word output is also a two-parter. Volume matters, but so does efficiency. You have to train your brain to produce at least semi-coherent thoughts without tripping over itself or doubling back due to perfectionistic tendencies. Some people are plagued by these tendencies more than others. I am certainly one of those people.
Tips for improving your word output
The key is embracing terrible writing. I don’t mean to suggest that you should lower your personal standards, but normalize the concept of a rough draft. Many writers, including myself, expect their fingertips to produce pure, vivid, synchronized content on the first try.
In reality, writing and editing are separate skills that activate different parts of the brain. And doing both simultaneously is a waste of time.
Perfectionism is a bitch. Speaking from experience, it handicaps our ability to produce high volumes. Sure, a paragraph sounds masterful by the time you’re through with it — but it’s not an efficient use of time.
Gamify writing if you need to. Set yourself up against the clock. See if you can cross 1,000 words in an hour. Keep upping your target word count.
4. Business mindset
One of the earliest mistakes you can make as a freelance writer is underestimating the “freelance” half of your title. Freelancing is an entirely separate operation from writing. It requires a different mentality and skillset.
For instance, you have to think strategically about time management and business reinvestment — such as subscribing to certain tools like Monday.com or outsourcing activities like bookkeeping.
I had the added benefit of working in an analytical, business-oriented role before becoming a writer. Still, it takes a while to grasp small business activities like financial planning, marketing, networking, and so on. I think that’s what can make freelance writing so hard — you have to be a good writer and business owner.
Tips for developing a business mindset
I have a bunch:
- Track your time. This helps you not only improve writing efficiency but also identify the highest-earning project types and clients.
- Value your time. Reserve specific windows of the day for emails.
- Leverage inbound marketing to acquire clients. It’s much easier to land high-paying clients when they come to you versus you pitching them.
- Clients are equals, not your bosses. If you disagree with a deadline or a rate, say something about it.
- Increase your rates regularly. At least once a year (view it as a cost of living adjustment).
- Start an LLC.
- Give yourself a title.
- Give yourself a salary. (Make that income goal happen.)
- Give yourself vacations.
5. Financial confidence
Freelance writers often start their careers with minimal financial confidence.
For starters, you have to build your income from scratch as a freelancer. And unlike the guaranteed salary of a corporate role, your income can be unpredictable — many gigs and writing opportunities are one-time or temporary by nature.
Meanwhile, you have to pay for stuff. Rent doesn’t disappear. Food still costs the same for entrepreneurs. Bills don’t have an “I just started freelancing” clause that entitles you to discounts.
This is not only stressful but can also encourage you to fill your schedule with low-paying gigs, creating a vicious cycle of financial instability.
No one wants that, which is why you’ll quickly realize that building a business requires you to alter your view of money. You have to learn to live within your means and be comfortable with potential dry spells.
Tips for building financial confidence
To combat financial stress and instability in the early stages of freelancing, I highly recommend saving 6–12 months of runway before you jump into this venture. This can be hard to hear because it usually means pushing your “leap of faith” to a later date while you save money.
Even if you never tap into your runway, it provides invaluable peace of mind. It made all the difference for me. My runway gave me enough financial confidence to set my rates high from the get-go, which led me to better clients and an easier schedule.
Long-term consistency is the key to success
Improving as a freelance writer is frustrating because most of these skills are developed by experience. You can’t flip a switch and thicken your skin — or write 10,000 words without breaking a mental sweat. It takes time.
That’s why long-term consistency is the key to success. If you commit to writing for a long enough period of time, you will get better. If you commit to growing a business for a long enough period of time, it will grow.
I have a saying: the “free” in freelancing is deceiving. It’s really easy to envision running a bountiful business, working from wherever you please, and living a fulfilling life. It’s really hard to actually get to that point.
Freelancing isn’t a nonstop flight to your dreams and riches. It’s more like walking 2,000 miles across the country without a map.