5 common freelance challenges and how I think about them

Introduction

Freelancing is a popular choice right now. But freelancing can be tough. And those challenges can grow infinitely when you’re just starting out.

Here are the 5 most common challenges for freelancers. Nothing scientific here — just the challenges I most often see talked about and can personally relate to.

Here’s how I think about these challenges and a few strategies that have helped me. Hopefully, they can help you too.

Challenge 1: Finding clients

Finding a project is one thing, but finding consistent work to sustain your freelance business is another.

So many factors feed into the amount of work you get as a freelancer. My framing on this: it’s impossible to complete, but it’s easy to improve slowly over time. If you focus on the right things.

See it as a journey — an important part of the process. And understand that a few small improvements can have a big impact.

Factors that affect the work you get are: your reputation, your portfolio, how in-demand your skills are, the size of your network, the relationships you have built to this point in your career and the quality of the work you deliver.

More specifically, the two strategies I think have the most significant impact:

To get new work → Be visible

The more visible you are the more likely you are to get work. People need to know you exist.

To get repeat work → Be easy to work with

I think this is one of the best traits you can strive for. It encompasses many things like being communicative, reliable, adaptable, enthusiastic and more. I actually think being easy to work with is more desirable to clients than producing the highest quality of work.

Challenge 2: Staying productive

Surprisingly, having absolute freedom with your time can be challenging. It can be hard to make good use of that time and feel productive. And it’s pretty easy for bad habits to creep into your routine.

I think it’s helpful to understand what part of the day you’re usually productive. Then build your schedule around this. Play to your natural strengths.

Block out time in your calendars to help focus. I add some recurring blocks to my calendar for specific types of work. I’m not one to block out every 30 mins of my day. But I do find it helpful to protect time for deep work and staying on top of things.

Also important: You don’t need to be productive all day, every day. Don’t beat yourself up.

Challenge 3: Financial stability

Financially, freelancing can be irregular. You’ll have good months and you’ll have bad months. You’ll have months you think this freelancing stuff is easy, and you’ll have months you think you should quit.

Diversifying the work you take on can help with irregularity. As an example if you usually only take on project work. A monthly retainer could complement your project work nicely. And it adds some regularity to your income to level out the peaks and troughs.

Asking for a deposit upfront is great for cash flow and reduces the risk of not getting paid. 50% of the project cost upfront is standard.

Thinking about what you’ll do in low months can be useful too. Do you go all in on finding the next job, spend more time on a side project, or focus on learning something new?

Challenge 4: Loneliness

As a freelancer, you don’t have colleagues like you do in a full-time job. Most of the time it’s just you, your laptop, and the same four walls.

You’ll still work with people, sure. But the dynamic is different.

Connect with other freelancers. They understand what it’s like and that it can get lonely. Having a network of other freelancers is super valuable.

I find a change of scenery can really help my mental health too. I’ll choose to work from a coffee shop or a different space every week or two to mix things up.

Challenge 5: Work-life balance

Usually, freelancers have too much work or not enough work. With no real in-between. Understandably, that can be tough.

I made the mistake of thinking I had 40 hours of availability each week. But of course that doesn’t factor in the time needed to run your business. Things like finding your next job, bookkeeping, and responding to enquiries take a lot of time. So admin builds up, or worse you risk burning yourself out.

Be mindful of your true capacity. Some people recommend leaving 30–50% of your time for general business admin when freelancing.

Conclusion

Freelancing definitely comes with its challenges. But having the right mindset can make a big difference. Hopefully, these tips and strategies can help you too.

Embrace the journey. Move with the landscape. And approach challenges as opportunities.