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What is the most difficult part about being a freelancer?

Nov 26, 2020
(updated: Feb 14, 2023)
Max 5 min read

Being a freelancer is rewarding and comes with a plethora of benefits. You set your own schedule, choose which projects to take on, and work from wherever you want. You may also have more freedom to take days off or go on vacation and you can work as much or as little as you want or need. 

But freelancing is not without its drawbacks.

For example, freelancing can be challenging because, oftentimes, you need to build up your portfolio for working with bigger clients. Also, if you’re not extremely disciplined, you might have a hard time organizing your time. Being a freelancer also means you have to undertake a wide range of tasks that might not be your forte, from marketing yourself, maintaining client relations, and invoicing.

In short, it’s not always a walk in the park.

If you’re thinking about working for yourself but haven’t yet taken the plunge, keep reading to learn about the most challenging aspects of freelancing.

Setting a schedule

This can often be one of the biggest challenges for freelancers. You’re no longer at a nine-to-five job so you have to figure out organization of your time. There are deadlines and overlapping client jobs to coordinate, so you really have to be wise about how you work and spend your time. What’s more, freelancers often see work ebbs and flows: sometimes you’re overwhelmed with assignments and other times you might not have anything on your schedule, but that’s the perfect time for outreach and looking for more gigs. The bottom line is that it takes a dedicated and organized person to be successful as a full time freelancer.

Finding work

Freelancing is an excellent work-from-home job, but it can get very competitive when it comes to finding jobs. Whether you use platforms like Guru, Upwork, Fiverr, 99designs, LinkedIn or others, there are a lot of people vying for those jobs and you really need to stand out. Ideally you will build up a portfolio of clients and get new jobs through referrals, but that takes time. Even established freelancers can hit a drought every once in a while, so you really need to establish a stable group of clients, ideally on a retainer, to offset any decrease in workflow.

Balancing budgets

No matter how great a freelancer you are, payments don’t always run like clockwork. For example, some clients will pay right on time, others may pay quarterly, and others may make you chase them down to get your hard-earned money. Freelancers may struggle to bring in a stable income. What’s more, one month you might make great money and the next month you might make a fraction of that amount.

Creative blocks

Getting into a rut in a creative project happens to even the best freelancers, and it can derail an otherwise productive day or week. When a freelancer has a busy schedule, creative blocks can be a real setback. You really need to develop the skills to overcome these situations, and the best freelancers know what to do, and which tools to use, to help them get back on track and complete and deliver quality work consistently for their clients.

Work/life balance when you work at home

Many freelancers will say that this is one of the most challenging aspects of working for yourself. The idea of working from home is appealing and may seem like it’s easier to achieve a better work/life balance, but this isn’t always the case. While you might be available to do things like pick up the kids from school, you might also find yourself working late into the night and skipping family time to meet deadlines.


Freelancers may have great disdain for this civic duty. In most cases, they’re considered independent contractors and are responsible for reporting their income, which means that they must keep track of every monetary interaction between themselves and every client, which takes time away from the work they should be doing. Freelancers, especially new ones, are also walking the tightrope between paying too much or too little in quarterly taxes. If they pay too much, they won’t see that money until they get their tax returns back, but they will get a devastating tax bill at tax time if they pay too little.

Social isolation

Working from home, on your own, can definitely be lonely, especially when most interactions happen through email and messaging apps. You can always go to a café or the library, but you’re still by yourself. Freelancers should have a sound support system and some human interaction to offset the fact that they spend most of their day in isolation staring at a computer screen.

Lack of benefits

Just like freelancers are 100% responsible for their taxes, they typically don’t have other benefits that come with working a full-time job outside of the home. Freelancers have to find their own health care and retirement plans, which are always more expensive than employer plans. Even if you can pay for these plans, it can be time-consuming and stressful figuring it all out.

The learning curve

When questions come up over the course of a project, there’s no manager or co-worker on hand to ask for help. There are many situations where clients ask freelancers to use a program or app that they’ve never used and they must familiarize themselves with new software relatively quickly. This takes time, though learning something new is also a great investment. New freelancers may also spend a lot of time to find programs that make their work, and lives, easier.

Conducting sales

A big part of being a freelancer is being a salesperson, and this can be stressful if sales aren’t your strong suit. In many cases, freelancers must pitch clients without knowing their budget, so they are trying to walk the line between making as much money as possible and being passed over for a less expensive worker. Freelancers also have to be their own accounts receivable department and may need to send invoices and remind clients about payment.

Ready to freelance full-time?

There are lots of challenges that come with being a freelancer, and you will have to decide if you think you can make it work. There’s a lot to learn before you take a leap of faith but with the right work ethic, tools, skills, mindset and attitude, anyone can triumph as a freelancer.

Get started today!

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