5 Big Freelancing Headaches (and How to Solve Them)

Freelancing can be a double-edged sword. Some freelancers really crush it making six figures (or more), while others seem to struggle to find work and make ends meet.

So what’s the difference between a freelancer whose business is successfully moving forward and a freelancer who lives month-to-month, unsure of what the future will bring?

Successful freelancers know how to overcome the biggest and most common headaches in the industry.

So today, I’ll share what I’ve learned after 10+ years working closely with freelancers to identify some of the biggest freelancing headaches you’ll come across—along with solutions for overcoming them.

Here are some of the biggest headaches freelancers deal with:

1. Not knowing where their next job is coming from (or when)

One of the most common issues I’ve seen with freelancers is they don’t know when or where they’ll get their next job.

According to a study in 2019, word-of-mouth marketing continues to be the number one reported source of new business for independent workers.

The problem is that word-of-mouth is highly unpredictable and can leave freelancers unsure when or how their next job will come their way.

The Solution

The best way to erase the anxiety and nervousness you feel as a freelancer who doesn’t know where their next job is coming from is simple:

Be proactive.

Build a sales process you can regularly use to reach out to prospective clients. Optimize your Fiverr gigs for more exposure and higher conversions.

Successful freelancers don’t wait for business to come to them. They go out and get it for themselves.

2. Battling the feast/famine revenue cycle

Hand-in-hand with not knowing where your next job is coming from comes the ever-persistent issue of the feast/famine cycle.

Essentially, the feast/famine headache is this: You have plenty of work and revenue this month, so things are going nicely.

Then next month hits, and you can’t seem to bring in any new work. Your revenue drops, you briefly consider getting a “real job” and stress about making ends meet.

The Solution

Fixing the feast-famine cycle in your freelance business comes down to discipline.

The solution? Always be selling.

Constantly be selling yourself—even when you have a lot of work on your plate (perhaps especially then). Never stop promoting your Fiverr profile or putting yourself out there on Linkedin.

The biggest mistake you can make when times are “good” is to rest on your laurels, stop worrying about sales, and line yourself up for a nice “famine” next month.

3. Struggling with burnout and work fatigue

For anyone growing a business—and perhaps especially freelancers who are growing something on their own—burnout and fatigue are genuine issues.

Sometimes, it’s easy to put blinders on, convincing ourselves and our loved ones that the most important thing in the world is to keep our business afloat.

Unfortunately, it often comes at the cost of personal burnout, work fatigue, and damaged relationships outside of work.

The Solution

Here’s the biggest problem with feeling burned out. If it were just a matter of slowing down and doing less, no one would be burned out.

Whether you’re going 100% solo or trying to build an agency, there are many hats to wear. In most cases, it feels like your entire business may be riding on what you can accomplish in a singular day.

You’re not alone on this.

The best solution I’ve found is to automate and hire.

Start by using technology to automate tasks you don’t actually have to do yourself.

If there are still too many tasks, ask yourself if you’d benefit from hiring another freelancer to help you get some of your client work done and free up some of your time.

4. Not getting paid by clients

Not getting paid as a freelancer can be one of the biggest headaches there are.

Your livelihood depends on getting paid every time you complete a project or hit a milestone. Yet time after time, clients either forget to pay or completely avoid payment as long as they can.

The Solution

There are a few solutions to help you get paid what you’re worth and on time.

First: understand the most common reason clients don’t pay on time.

Next, if this is a persistent problem, take upfront payment or use a site like Fiverr that protects you and your client in the event of a dispute.

Finally, leverage software like AND.CO to automate follow-up emails on unpaid invoices.

5. Feeling lonely or isolated

Finally, it’s not uncommon for freelancers to deal with loneliness. Some feel it on a small level, while others become debilitated by it.

Feeling lonely is completely understandable if you’re working alone most days. This is particularly true if you’re emailing/calling your clients instead of meeting with them face-to-face.

The Solution

If you’re feeling an overwhelming sense of loneliness, there are a few ways to address it.

Consider joining a coworking space where other entrepreneurs and small businesses actually come into the office and interact with other people throughout the day. This is a great way to make friends and a nice way to network and build your book of business.

You can also create or join a local Fiverr meetup group to hang out with fellow Fiverr freelancers and learn from them.

What's next?

Here are a few parting thoughts to consider if you’re facing any of these common freelancing headaches.

Remember:

1. You’re not alone. Freelancers everywhere are figuring it out just like you.
2. There’s a lot of upside. People who work desk jobs have their own issues. There’s a lot of positive upside to working for yourself.
3. Headaches can be solved. No headache is so terrible that it can’t be solved with the same ingenuity you use to work on your business daily.