Freelance Writing as a Side Hustle: The Good, the Bad, and the Fatal

I have dreamt of being a writer since I was twenty years old. Fantasies of writing best-selling novels and feature articles about the latest tropical destination I had visited frequented my mind as I grinded away at my unappealing day job. Can you relate? If so, you have probably played with the idea of becoming a freelance writer.

While I have been freelancing for over a decade, I didn’t make it my sole job until a couple of years ago. I can’t imagine going back to a normal 9-5 after switching, but I have to admit it’s not for the faint of heart. This career has major perks, but it also has its drawbacks.

So, I wanted to share the pros and cons of freelance writing for anyone who is considering this as a career or even a side hustle and how to get started if you decide it’s for you.

Freelance Writing Pros and Cons

I wish I could say that this career is the easy street to Moneyville, and you will be sipping margaritas on a beach somewhere in no time, but that wouldn’t be the truth. It takes dedication and consistency to become a successful freelance writer. Before you decide if it’s the right career path for you there are some significant pros and cons you should consider.

So, I’m going to share with you what I’ve experienced personally to give you a true visual of what to expect.

Pros of Freelance Writing

Let’s start things off on a positive note and dive into the perks of being a freelance writer. Keep in mind that some pros may appeal to you more than others. But I must say, it’s a pretty sweet gig being a writer.

Freedom and Flexibility

The thing I love the most about being a freelance writer is the freedom and flexibility it offers. Of course, the hours you work will depend on your clients’ needs. For instance, some clients may want you to work specific hours, but there are many that don’t care when you work as long as you meet your deadlines.

So, they may assign you articles and give you a week to turn them in. The turnaround time depends on the company and client.

Location doesn’t matter either as long as you have a stable Wi-Fi connection. That means you can work while you travel or at the local coffee shop if you need a change of scenery from home. So, this is a huge pro for someone like me who prefers the ability to work whenever and wherever they want.

Increase Your Pay Quickly

Are you sick of waiting for a raise each year and having no control over how much you get? Well, one of the biggest pros of freelance writing is that you can increase your pay quickly as you gain experience. While some companies may pay per hour, you can find companies and clients that pay per word or article and boost your salary significantly.

When you get paid per word or by the article, the faster you write the more per hour you will make. For instance, let’s say you make $250 from a single article and write it within five hours, that’s $50 an hour! You would be a six-figure freelancer if you average 40 hours per week.

I don’t know about you, but that sounds much more appealing than Indeed’s reported average 3% annual raise most employers give. So, if you’re ready to earn more money faster, you may be able to do it by becoming a freelance writer.

Write About What You Know or Like

It may surprise you that you can leverage your current skills, knowledge, or interests to launch your freelance writing career. In fact, that’s exactly how I became a writer. I used my background in banking to break into writing about personal finance. Who would have thought my day job would provide me with the ticket I needed to start my dream career?

Now, I am a lifestyle writer who writes about anything from finances to plants! The easiest way to become a writer is to write about what you know or things that interest you. So, if you have extensive knowledge of a specific topic or want to write about things you find interesting, you can get paid to do it.

Cons of Freelance Writing

No matter how great something is, there is always a catch or two or three. While freelance writing has major perks, there are some serious cons you should consider before switching careers.

Job Instability

The thing I hate most about freelancing is that it can be very unstable. Although companies are more likely to hire freelancers during a recession because they are slashing their budgets and full-time positions, clients can still go as quickly as they come. You may have a consistent gig, but you aren’t at the forefront of the company’s priorities since you are not a dedicated employee.

When it comes to freelance writing, I tell people it can be feast or famine. So, you need to be diligent about consistently having work if you don’t have dedicated companies and clients you work for.

No Benefits

While I don’t miss being a banker, I sure do miss those incredible benefits. As a freelance writer, you don’t get the perks of having health insurance or a 401k match like other jobs. So, if you are single and don’t have a spouse who can add you to their health insurance plan, you will need to pay for it out of your pocket—which can get costly.

As far as retirement, you will need to set up your own plan and allocate a specific amount of your income towards it.

Responsible for Taxes

This is a big con in my book because it’s so much easier to have an employer deduct your taxes from your salary rather than having to save and pay them yourself. How much you will need to sock back will depend on your tax bracket, but Jackson Hewitt Tax Services recommends putting away about 30% of your income the first year as a full-time freelancer.

This sounds steep, but it’s to help cover self-employment and income tax. Plus, it’s better to save it than have a hefty bill due when tax time rolls around.

Fatal Freelance Writing Mistakes To Avoid

Okay, this sounds a bit dramatic, but there are some massive mistakes that can sabotage or even kill your career as a freelance writer. Trust me, I’ve made some big ones and had to dig myself out of the trenches on more than one occasion.

So, here are the main fatal mistakes you need to avoid to prevent setbacks and become a successful writer.

Starting a Job With No Contract or Agreement in Place

When you finally have the opportunity to see your name in print, it’s easy to get carried away and start solely on a conversation you had with a potential client. However, this leaves you open to not being paid the agreed amount, expectations not being met by you or the client, and even getting ripped off. The worst thing you can do is pump out several articles only to be ghosted and not paid for your time.

You don’t have a leg to stand on if you don’t have something in writing. So, avoid this fatal freelancing mistake and ensure everything is worked up in writing via email or even have a contract in place.

Not Having Insurance

Something that drives me nuts is that almost every “How to be a writer” article doesn’t discuss one of the most vital things you need to start. As a writer, you are responsible for the content you create, and that means you need to have insurance policies in place to protect yourself and your business. This is even true for starting your own blog.

The two types of insurance policies you need are General Liability and Professional Indemnity insurance. These insurance policies protect you from various claims like personal injury, copyright infringement, and plagiarism. Having the proper insurance is critical when it comes to building a thriving freelance writing business.

Jumping in Without a Business Plan or Clients

Although I started freelance writing as a side hustle, there was a time when I jumped ship from a full-time job to try freelancing instead. However, I did this without a plan and with one client who didn’t offer consistent work. Talk about taking the leap!

Personally, I don’t recommend doing this unless you have enough emergency savings to cover you for the first few months that it can take you to find work—then it’s still pretty risky. Because let’s face it the almighty dollar doesn’t stretch nearly as far as it used to.

So, rather than diving in without a life jacket, I recommend creating a plan, starting your writing career as a side hustle, and then growing it into a full-time career.

Not Accounting for Start-up Costs and Expenses

Freelance writing can be one of those side hustles with sneaky start-up costs that you don’t think about until you begin. For example, you will need to purchase your insurance policies, invest in software programs such as Grammarly Premium, and possibly launch a website. These costs can add up fast, and they are recurring expenses.

You can opt to pay some start-up costs by the month rather than the annual amount, but it ends up costing more if you pay for things in installments. Just keep that in mind when starting out. So, your wallet is going to take a hit from expenses you need to pay to get going before you will begin boosting your bank account from your writing.

How To Start Freelance Writing

Now that you know the pros and cons of freelance writing and what mistakes to avoid, are you still in love with the thought of being a writer? Hopefully you are, because getting paid to write is extremely cool.

So, if you’re ready to learn how to start freelance writing, follow these key steps to make your dream a reality.

Learn the Ropes or Take an Online Course

Unfortunately, there is much more to writing than writing. While the digital world has opened up many more opportunities to those who want to write for a living, it also means knowing more than just writing a good story. For instance, knowing how to pitch publications and stand out from the other thousands of writers is a vital skill.

Knowing SEO aka search engine optimization is a common desired skill that many companies search for in a writer. Now this isn’t a must have skill but it can definitely help you land more gigs if you learn about it. There is a lot to learn when it comes to freelancing and taking the time to tap into the right resources can help you tremendously.

You can start learning the ropes by reading various blogs and articles about freelance writing. I started out this way, but then I invested in online courses, where I learned everything I needed to know to land more clients and earn more money.

There are many types of online courses and resources to pick from, so choose the method that works best for you and your budget to begin with and go from there.

Get the Proper Insurance in Place

Before you begin writing for companies and clients or even launching your own blog, you need to obtain the proper insurance first. Remember that having General Liability and Professional Indemnity Insurance is a must for being a freelance writer.

In fact, I write for large publications, and some of them actually require you to have these insurance policies to freelance for them. So, check this off your to-do list first thing.

Open a Separate Bank Account

When starting a side hustle or business, you should keep your finances straight by opening a separate bank account to track your income and expenses. Most banks will allow you to open several types of accounts for free in your name.

I advise opening a free checking and savings account that doesn’t have fees or minimum balance requirements. That way, you can pay for your business expenses out of the checking account and use the savings account to save money you will owe for taxes.

Choose Your Niche

Once you have the legal stuff out of the way, you get to choose what you are going to write about. This is also known as your “niche,” which is an area you specialize in. For instance, my niche when I began writing was finance because I had extensive personal finance knowledge from my background in banking. I leveraged this to land gigs writing for financial blogs, like this amazing site.

While some say to stick with one niche, I decided to branch out and become a “Lifestyle Writer.” That’s when you write about various topics rather than just one thing.

Now, Tim Denning, one of the most prosperous personal development and entrepreneurship writers on the web, says you should pick two topics—one you are knowledgeable about and one you enjoy.

So, you can try out two to begin with, then dabble in other areas as you go if that’s what you want to do.

Create a Portfolio of Writing Samples

After you choose your niche, you need to write samples to show off your writing style to future employers and publications. You should have at least three articles on the topic you choose to provide when applying for jobs. Having a website can make you look more professional. However, you can utilize a site like Medium instead to use as a portfolio if you don’t want to pay for a website yet.

Medium is a fantastic platform that only costs $5 a month to use. Depending on your location, you can also participate in their partner program to earn money for your stories. Honestly, I would start with this platform if you’re interested in blogging as well because it’s easier to earn money with it than a traditional blog, and you can get paid for the samples you create.

Create a Contract Template

Some companies will have their own contracts, but there are clients who won’t. Rather than writing a contract from scratch every time, it’s best to create a contract template so you can simply fill in the information as it changes with each client. You can use Google Docs or Canva to make a custom contract easily.

Pitch Publications and Potential Clients

Whew, that seems like a lot, but after you knock out these tasks, it’s time to find work! Here is an insider tip from a fellow writer to help increase your chances of getting published and landing clients: Do your research before pitching.

You want to make sure your article idea hasn’t already been done on their blog or site, and you also need to find the appropriate editor to pitch to. Emailing the right editor can drastically increase your chances of a response.

The same goes for applying for writing gigs. Try to find out the name of the person reviewing pitches or applications so you can address them personally when you pitch. This shows you took the time to care about who to contact and that you did your homework about the company.

Network To Find Clients

There are various ways to find writing jobs and clients, and networking can boost your odds of getting work. One of the easiest ways to network is by setting up a LinkedIn profile to connect with other writers and editors, and you can update your status when you are open for work.

Depending on the type of writing services you offer, you can also contact local businesses in your area. I’ve even reached out to existing clients to see if they knew of anyone who was searching for freelance writers. Start networking to find new clients and build your business faster.

Use These Tips To Have a Successful Side Hustle or Career as a Freelance Writer!

Freelancing isn’t for everyone, but I consider it one of the best side hustles or careers to choose from. It’s lucrative, flexible, and you can get paid to do something you actually like. Plus, being able to work anywhere with a Wi-Fi connection means you could make money traveling the world or from the comfort of your own home.

So, why not explore the incredible pool of opportunities available in freelance writing and turn your words into wealth?