8 Pros And Cons Of Being A Freelancer

Clare Bochy
min read
May 5th, 2022

As a freelancer, I can honestly say I don't have any plans to go back to a 9 to 5.

This isn’t for everyone, in fact I know people personally who feel a great deal of comfort when they have the stability of a paycheck, insurance, and what have you. As someone who has joined the dark side, there are also bright sides to freelancing that I thought I we could compare. 

But before we begin there is something to keep in mind when diving into this list. I want to remind you that freelancing can vary from different industries. A freelance videographer and a freelance accountant don’t exactly have the same requirements that need to be met in order to be successful but they do share the same blue print of why they might choose to work for themselves verse for someone else. 

So let’s talk about why you might enjoy freelancing.


Handpick who you work with

At some point in time we’ve come across someone whether it was in school, in the grocery story, at an old job, who had rubbed us the wrong way. And I’m talking to the point where you just dreaded interacting with that person again. First, don’t feel bad. We aren’t all made to please one another and it’s even better to acknowledge when the pieces don’t fit for future interactions. As a freelancer, however, you are in far more control and can simply walk away. Sure there are consequences but it’s extremely empowering to not only yourself but your business as well. 

Have the schedule of your dreams - sorta

Do you like to sleep in? Do you like to play before you work? One of the greatest beauties of freelancing is having control of your own schedule. Say your friends invited you out to lunch or you have family in town that want to visit, or like me and have a one year old that needs most of my attention, having a flexible schedule is wonderful for these exact reasons. You can visit friends, plan around teething, and still get a full week of work in. You get to decide. 

More opportunities to increase your income

With that same flexible schedule, you can find other (I won’t necessarily say more) time to explore different means of income. For instance, as a marketing coordinator I also find time to teach yoga and make jewelry. I love being able to grow my jewelry business from my marketing income. This is just one example of how freelancing has been beneficial to me. Maybe you are starting to think of that project you always wanted to begin. Freelancing gives you the opportunity to do that but then also maybe, just maybe, it turns into something more. 

Freedom to pivot and be creative

When you are on your own, there is this grand awakening to the vast world filled with so many creative outlets. It’s easy when you have your blinders on to forget the world around you especially when it comes to taking care of you and your family. That also includes chosen families too. When you get to focus on what you love, your work becomes a passion and YOU get to choose how you want to expose yourself to the variety of opportunities out there. No two days have to be the same and you have a chance to explore many different horizons. 

Ok ok of course there are cons:

Taxes are a BORE

Of course this isn’t any way I can avoid it because it is part of freelancing and one of the many reasons why people avoid it. Whether we like it or not, Uncle Sam wants to know what you are up to and unfortunately we cannot work for free or trade like the good ole days. 

But, it is far easier then it’s made out to be which is probably why it isn’t the most exciting. Programs like Quickbooks Self-Employed make it super easy to integrate your accounts so that pulling numbers for taxes isn't a drag and your accountant know what the heck is going on. 

No “PTO” or Sick days

There might be a flexible schedule but when you are sick, there isn’t anyone covering those days for you and no one to make up that work. PTO does not exist unless you budget it in yourself. That is both money AND time. It is totally possible but definitely challenging especially if you are just starting out. I wouldn’t expect “time off” at least after the first year but with the flexibility mentioned about.... you win some and lose some.

Insurance is a little bit trickier..ok a lot tricker.

Not having insurance can be quite intimidating and a huge factor why people like my husband don't want to take the leap. The healthcare.gov claims “If you're self-employed, you can use the individual Health Insurance Marketplace® to enroll in flexible, high-quality health coverage that works well for people who run their own businesses. You can enroll through the Marketplace if you’re a freelancer, consultant, independent contractor, or other self-employed worker who doesn’t have any employees.” There are some qualifications to enroll in and the chances of the options being more expensive than normal insurance are very likely. These are all things to keep in mind when choosing your career as a freelancer.

Unreliable income

Starting off as a freelancer, there are many quick jobs available that you can pick up to help pay the bills. However, those same jobs aren’t always consistent enough to rely on to start budgeting for future goals or saving for some kind of retirement. The pay can be inconsistent until you find and build relationships with reliable clients. This is an uphill battle at first but there are many relationships waiting out there that will be substantial to the goals you have in mind. 

All-n-all you get to be your own boss. This is both extremely exciting AND intimidating. If you are not one to be on top of your sh*t, then freelancing might not be for you. But if you are looking to explore and have the freedom to work wherever, whenever, and with whomever you want then freelancing is just what you are looking for. 

Here are free resources to get you started!