Pros and Cons of Freelancing vs. Employment When Chronically Ill

When it comes to working remotely you have plenty of options. You can choose to work full-time, part-time or you can do freelance work. If you’ve always been an employee, the world of freelance may seem like a daunting undertaking—but you might find, once you know the ropes, that taking on multiple clients instead of working for one company is a better option for helping you to manage your workload.

Let’s talk a little bit about the difference between a job and a freelance “gig.”


Jobs are a paid position of regular employment. I’m sure you knew that. Taking a job means becoming a W-2 employee. With a job, you’ll be applicable for benefits including options like health insurance, vision and dental insurance, a 401-K, and paid time off. It’s important to note that not all jobs will include these. Generally jobs require a 40 hour a week minimum. You may be eligible to work overtime and earn more money. Your company will deduct taxes from your paycheck and come tax season, you’ll have a simple form to submit to your accountant which will list all of your income.

Freelance Gigs

As a freelancer, you can take on multiple roles at once with different companies. You’ll be a 1099 contractor, which means that you’ll have to pull money out of every paycheck and save it in a separate account for when you have to pay your taxes. Gigs are not full-time jobs. They can be based instead on productivity. So, if you’re a writer, you may take on a story assignment for a proposed fee. Sometimes companies will have a dedicated budget which you can choose to accept or decline. Sometimes you can evaluate the project and come up with your cost proposal—which the company will have to choose whether to accept or decline.

What are the benefits of having a (remote) job when you are chronically ill or disabled?

  • Once you sign a contract and are fully employed, you’ll have a steady paycheck each pay period.
  • Your company may offer benefits like insurance, paid time off, or a 401-K.
  • You may be able to take paid time off.
  • Your company will be required to help make your job duties accessible to your disability.
  • Since you’ll work for one company, you won’t have to constantly be searching for new income opportunities.
  • You may have a chance to get promoted and earn a higher salary over time.
  • If you become pregnant you may get maternity leave.
  • If you become further disabled (to the point where you can not work at all) you may be eligible for short or long term disability benefits.
  • If you are fired, you may get a severance package to support you until you can find another full-time job.
  • In general, you may find you have more financial security working at a job.

What are the cons of having a job as someone who is chronically ill or disabled?

  • You may not be able to choose your own hours, so you may struggle to be able to make doctors appointments during the week.
  • You may not be able to rest or deal with flares as you’ll be expected to perform your duties throughout the day.
  • You may have to deal with social issues in the office and questions about your condition that you may not want to discuss.
  • You may not be well enough to go on business trips or travel, which may impact your value as an employee.
  • You will have a definitive salary that you may not be able to adjust even if your healthcare costs become more expensive.
  • Your team will be dependent on you—and you may encounter stress if your illness gets in the way of productivity.

What are the benefits of being a freelancer and taking on gigs as someone who is chronically ill or disabled?

  • You get to choose your own hours and set your own schedule.
  • You can depend on multiple companies and clients for income and if you’re fired from one gig—you have others to fall back on.
  • You don’t have to deal with office politics.
  • You can change your fee structure at any time.
  • You can stop working if you need rest or time off.
  • You get to work with different companies and on different projects instead of the same work every day.



What are the cons of being a freelancer and taking on gigs as someone who is chronically ill?

  • You may not have an even workload. Some weeks you may have less than 40 hours of work, some weeks you may have more.
  • You will have no benefits like health insurance, paid time off or a 401-K.
  • You will have to invoice clients and follow up to make sure they send payment on time.
  • If you’re fired from a client you won’t receive any severance—and possibly any notice.
  • You will have to pay for your own materials and overhead—things like your cell phone bill, internet, software or office supplies.
  • You may need to hire your own accountant or bookkeeper, depending on how much business you do.
  • You will be working alone most of the time, meaning you’ll have to be self-motivated and able to complete your work without a team to guide you.

What’s the best pro and worst con of your job/freelance career?

Leave a Reply

Your email address will not be published. Required fields are marked *