Pros and Cons of Freelance Work

Variety

One of my favorite things about freelance work is the variety! I’ve written semester-long curriculum for elementary, middle, and high school students, as well as lesson activities from kindergarten through university level. I’ve created online courses, edited videos, and written scripts. I’ve written about topics ranging from college internships, sales onboarding, safety, mental health, and best practices for using AI tools.

Because many freelance projects are short-term and/or part time, I’ve had a chance to work with many different people and organizations. In some cases, I’ve worked as many as four contracts at a time, and – while juggling multiple projects isn’t necessarily a “pro” to freelance work – it does keep the work interesting!

Higher Income (Maybe)

In some cases, freelance work can pay really well. On long term projects, companies may be willing to pay a higher per-hour rate because they don’t also have to pay for benefits. Freelance work also gives you the option to work on multiple contracts, so if you have an available stretch of time, you can look for some work to fill it. 

Freelance work is often paid by the hour. So, the more time you have available, the more you can potentially make. 

Flexibility

Freelance contracts typically establish up front how much time is expected each week and how long the contract will last. So, for example, you may have a contract with 35-40 hours of work each week for six months, or you may have a contract for 5 hours a week for 4 weeks. You can look for contracts that fit the time you want to work. Freelancer websites like Upwork and Fiverr can help connect you to people and companies with projects that fit your available time.  

In many cases, freelance contracts allow you to work remotely and to set your own hours each day, as well. 

Meeting Incredible People!

I have gotten to work with some truly incredible people, from all over the world! I’ve worked with many other freelancers and with designers, writers, artists, engineers, and coaches, to Project Managers and Sales VPs. 

I especially love supporting entrepreneurs who are working on projects they are excited about. I get to learn so much from working with them!

Continual Job Search

Because many freelance contracts are short-term, looking for work becomes a constant process. Freelance websites help make this easier by giving you a place to advertise what you can do, but the job search and application process still take time. It can be frustrating, especially when there are fewer jobs available or when many other people are applying. There’s no guarantee that you’ll have work, even if you’re available. 

Inconsistent Income

Short projects and the continual job search can result in periods of time when your income is less than you need or when you have no income at all. While this may be offset if you earn more per hour when you are working, there are no guarantees. It can be difficult to plan and budget, especially when you are just getting started. 

Lack of Benefits

Contract work typically means there are no benefits: no health insurance, no paid time off, no bonuses, and no retirement plans. Private health insurance, in the U.S., at least, is necessary and can be expensive. Planning ahead for that expense is an important step when deciding to freelance.

When I was first doing contract work years ago and the holidays approached, I had a bit of a panic. I was making really good money at the time, but I realized how much income I would lose by not working Thanksgiving and how much more I’d lose not working Christmas and New Years! I was so used to paid holidays, that it was a bit of a shock to realize that if I didn’t work, I didn’t get paid. 

Taxes

In the U.S., one of the biggest drawbacks of freelance work is that you are responsible for paying more in taxes. As a freelancer, you still pay your regular income tax, but then you also pay additional taxes that an employer would normally cover. This self-employment tax includes both the employer and employee portions of certain taxes. Because you are working for yourself, you end up paying both parts instead of just the employee portion.

This can add up to a significant amount. I may or may not have discovered this years ago and then had a sobbing meltdown in my accountant’s office. If possible, work with an accountant or appropriate tax software so that you can plan ahead. Pay your estimated taxes quarterly so you aren’t penalized for late payment.