6 Common Freelance Business Challenges to Overcome

Woman climbing up a metal ladder

When I first started my web-writing journey a little more than two years ago, I encountered one obstacle after another.

From racking up countless client rejections, to facing complicated business questions, I was tempted to give up so many times.

Thankfully, with the help of AWAI, I’ve been able to overcome virtually every obstacle I encountered. But, I know first-hand making real progress on the web-writing journey is not always easy.

And, that’s why today I want to focus on the most common freelance challenges writers face in advancing their careers and tips to get past each one.

With these tips, you can get past whatever obstacle you’re currently facing.

Let’s dive in.

#1. Not Knowing Where to Start

Beginning your freelance career is thrilling, but it can be overwhelming, as well. Faced with so much to learn and do, you may not be sure where to start.

To get past this first challenge, the first step is to focus on developing the foundational skills you need to be a freelance copywriter. Doing this will pay off in the long run, even if it takes a few months or more of focused work. You’ll have more confidence and be better positioned to attract well-paying clients.

If you haven’t yet taken a good foundational training program, now may be a good time to do it. Nick Usborne’s classic course Web Copywriting 2.0 laid the foundation for my own web-writing career, setting me up for full-time work as a strategic content marketer in the mobile app world.

One caveat, though. There are so many opportunities to explore, many writers get stuck in the “training” phase. Make the commitment now to learn any skill and then set out to actually get paid for it.

So, ensure you have the foundational skills in place. But, as soon as you’re confident you can offer value to businesses, it’s time to start looking for clients.

#2. Struggling to Get Early Momentum

For many freelancers, the biggest challenge is finding those first few clients. I know this pain well … I got so many rejection notes in the first year of freelancing, I lost count!

There is a ton of excellent advice on Wealthy Web Writer to help you get clients. (Take a look at this, this, and this, for example.)

But, ultimately, the most important strategy is to get your mindset right, so you can stay motivated for the long haul.

How can you adjust your mindset? My personal preference is to keep a victory log.

To do this, simply write down every single positive step in your freelance journey, along with the date, and keep it updated. You can include visuals, if you have them, such as a screenshot of a positive response from a prospective client.

Then, whenever you need a boost, check back in to see your progress. You may even spot patterns as to what activities have led to your biggest successes, which you can then replicate.

Regardless of how you do it, keeping track of your successes, big and small, will help you see the bigger picture of your progress in getting clients and building your business. And, this growth mindset is essential for finding success in the long term.

#3. Not Having Regular Paychecks

Another big challenge for both new and long-term freelancers alike is the that there isn’t a set payday. If your project schedule is irregular, your paychecks will be too.

The first thing to realize is that, most likely, it’s going to take some time to go from launching your business to being able to pay all your bills with your freelance income.

There are exceptions, of course. But, many great freelancers, such as Ed Gandia, have built their businesses while holding down a full-time job.

But, perhaps you’re already counting on freelance work alone to pay your bills … and you’re getting stressed about it.

In this case, it’s ideal to try getting some full- or part-time writing work to supplement your freelance income. Even if the work isn’t as glamorous or lucrative as working for yourself, it will provide some stability. Plus, you’ll get more practice writing and have a chance to keep building your skills.

If you’re a bit further along in your freelance journey and already have a decent-paying client or two, then one of the best ways to turn that income into something more stable is to land what’s called a retainer project.

A retainer project allows you to provide a regular service for a client, such as a weekly blog post or a monthly newsletter. Many freelancers use retainers to avoid the “feast or famine” cycle. If you can convince your clients of the advantages of this arrangement (not just for you, but for them, too), by all means do it!

However you can manage it, finding ways to bring in regular income alongside or as part of your freelance income will make your freelance work much less stressful, and more sustainable in the long run.

#4. Not Having the Structure to Get Things Done

Yet another struggle many freelancers face is the lack of structure they need to help them succeed.

Most of us are used to having highly structured schedules from our work or studies. And, when we go freelance, there’s suddenly no one to answer to.

This freedom is incredibly liberating at first, but it can be quite difficult to maintain discipline day after day.

If you know lack of structure is holding you back, then it’s time to find a way to bring it into your workday.

You can do simple things like start a writers’ group with other freelancers. On Wealthy Web Writer, you can join the Monthly Member Updates, or complete the regular practice assignments to give yourself some clear goals.

Take it a step further by taking live training courses, or even hiring a coach or mentor to keep you moving forward.

The bottom line is this: If you notice you need structure to get work done, then do whatever you can to incorporate it into your workday. Very likely it will pay off, big time.

#5. Feeling Overwhelmed About the “Business Stuff”

In the early days of your freelancing career, the most important thing is to focus on skill building and getting clients.

But, once you need to start sending out invoices, it’s time to establish and maintain a proper business. This step can be intimidating, but it’s manageable, if you take the time to figure out what you need and to do some research to find the tools that best fit your needs.

First of all, educate yourself about what other freelancers do to manage their businesses. I’ve written about Wave, a free software many freelancers use to send invoices and help stay financially organized, but there are many other tools you can use to help you with your business.

Of course, while there’s almost no limit to how much you can educate yourself online, many writers find it’s worth it to pay for professional help managing their legal and tax situations. This is especially true if your situation is particularly complicated.

The “business” aspect of freelancing can become a headache if you let it. So, instead of letting this aspect derail your freelancing success, seek out help as needed, so you can focus on delivering excellent work to your clients.

#6. Struggling to Juggle Your Freelancing with Your Other Responsibilities

The last challenge that comes up again and again for freelancers is simply trying to manage your freelance work alongside your other responsibilities.

If this is you, and you’re feeling completely overwhelmed, then it’s a good time to take a step back and evaluate your situation.

Often when we start our freelancing career, we set sky-high goals for ourselves, perhaps not understanding what it will take to achieve that level of success. Maybe your goal is completely reasonable – but, only if you stretch it out over five years instead of two.

Being rigid with your goals to the point of burnout is never helpful. In fact, it’s natural for your goals to evolve as you learn and grow.

Ultimately, remember that one way or another, you’re freelancing to have a better life. So, make sure your goals are supporting that dream, not undermining it.

What’s your biggest freelance challenge?

Wherever you’re at in your freelance journey, remember you’re not alone in facing your challenges. We’re here for you, and so are the other writers in this community.

Did we cover the challenge you’re currently facing? Share your approach to overcoming it in the comments below.

And, if you’re facing a different challenge, share that, too. The Wealthy Web Writer team will connect you with tips or resources to help.

This article, 6 Common Freelance Business Challenges to Overcome, was originally published by Wealthy Web Writer.

The Professional Writers’ Alliance

The Professional Writers’ Alliance

At last, a professional organization that caters to the needs of direct-response industry writers. Find out how membership can change the course of your career. Learn More »

Click to Rate:
Average: 5.0
Published: October 7, 2020

Guest, Add a Comment
Please Note: Your comments will be seen by all visitors.

You are commenting as a guest. If you’re an AWAI Member, Login to myAWAI for easier commenting, email alerts, and more!

(If you don’t yet have an AWAI Member account, you can create one for free.)

This name will appear next to your comment.

Your email is required but will not be displayed.

Text only. Your comment may be trimmed if it exceeds 500 characters.

Type the Shadowed Word
Too hard to read? See a new image | Listen to the letters

Hint: The letters above appear as shadows and spell a real word. If you have trouble reading it, you can use the links to view a new image or listen to the letters being spoken.

(*all fields required)