Self-Employed Vs. Employee: Why I Chose Freelancing Over The 9-5 Life

The traditional job has never been for me. I started freelancing during my third year of university, and eventually ended up doing it full-time once I graduated.

I did have several challenges in my first couple years that made me wish I had taken a traditional 9-5, but freelancing eventually opened my eyes to a whole world of possibilities.

My goal with this post is to cover the various pros and cons to both self-employment and full-time employment, so you can come to your own decision.

Full/Part-Time Employee: Comfort and Security

Most people are familiar with traditional employment- you show up to work, clock in your hours, then collect your check. Some of you may have even started as far back as high school, working at the local movie theater or ice cream shop.

13% of millennials began working at age 20 or older compared to 8.9% of Gen Xers and 6.3% of baby boomers. Click To Tweet

No matter which job you choose, being an employee has certain advantages and tradeoffs. Below are just a few:

Advantages of being an employee

Steady flow of income

The best part about work is that in most cases, you get paid just for showing up. Most entry level jobs pay hourly, with payment sent every two weeks. If you have more experience, a salary is paid out each month, usually enough to cover the cost of living with plenty left over.

In terms of being employed, this is definitely one of the biggest things you’ll miss from having a full-time job. With some clients, payment isn’t promised. It can feel nice knowing you’ll have enough money to get by.

Office/work environment

This might vary depending on the business and industry, but typically having an office or a certain work environment can be a huge plus.

Having a modern open working space, combined with the bustling energy of downtown, can be enough to make you excited to come to work. Even environments like a mall or government building can feel like exciting places to be in.


Work isn’t so bad when it’s with other people. Even though daily responsibilities can feel like a grind, it can actually be fun when you’re sharing the duties with other people. Breaking up the day with casual conversation around the water fountain or coffee machine can really make the difference between a boring job and a fun one.

Occasionally, a full-time job has social events like team-building exercises, company trips, and parties. These special days can the workplace feel like a professional family.

Source: Society For Human Resource Engagement

Health care, taxes and other benefits

Some employers have set up systems to provide basic health care and dental coverage for their employees. In fact, some businesses may be eligible for a tax credit if they have fewer than 25 employees that have an annual income of $500,000 or less.

Other benefits vary depending on the company, from paid parental leave, 401(k), gym memberships and transportation reimbursements. These offerings can make it very attractive to stay with a certain business.

Disadvantages of being an employee

Strict schedule

Whether you work at an hourly gig or a salary 9-5 position, you’re under a certain clock. Whenever you’re late, you might get warnings or even risk being fired.

Hourly positions can be especially problematic- sometimes you are scheduled for hours when your friends or families want to see you, or you might be asked to come in during certain holidays like Christmas or Thanksgiving.

Feeling of inferiority

Working for larger corporations can feel somewhat demoralizing. You always have to take commands from higher authorities, even when they don’t know a lot about what they’re doing.

Lack of freedom

When you work for others, there’s a feeling that you don’t have as much freedom in what you can say or do. Your behavior is usually in check to make sure it falls under the brand’s expectations.

In other words, you’re generally not allowed to speak your mind (if it does not adhere to company standards), you’re not allowed to wear casual clothing, and even when you need to be home, you’ll be asked to stay at work.

Negative associations

It’s an unfortunate phenomenon that we tend to associate what people do for a living with who they are. In other words, “we are where we work.” A person could be a talented artist or skilled in Brazilian jiu-jitsu, but still work at an AMC theater and immediately their other experiences ignored or overlooked.

Sometimes the company may also engage in shady practices- questionable political alliances, propagation of stereotypes, or investment in other reprehensible organizations.

Self-Employment: Carving Your Own Path

Whether you’re a graphic designer, content writer, or web developer, there are countless ways to start on the path of self-employment. I started out my freelancing career doing a mix of content writing, copywriting, and social media work.

Of course, the journey to freelancing is not an easy one. It’s paved by distraction and self-doubt. But the ultimate destination can beat working the traditional jobs in the market.

Advantages of being a freelancer

Flexibility in schedule

The number one perk for many freelancers: flexibility. Forget about that 9-5, you set your own hours. Want to work in the early morning and take the rest of the afternoon off? You can do that. Want to work late at night and sleep during the day? You can do that too.

Best of all, you actually have time to hang out with your friends and family. Ever since freelancing, I’ve had more opportunities to see people I usually would have had to ignore and get to spend more time with my girlfriend. It’s easily one of the best reasons for being self-employed versus the employee life.

Potentially higher profits

You could work a job 40 hours a week, and in some way, you’re still splitting the profits with the rest of the company. Why should you, the person responsible for doing the work and driving the revenue, have to split it with someone above you?

When you’re self-employed, you call the shots. If you run a small business, you decide how much you want to keep and how much others get. If you’re freelancing, you get to set your own rates and keep 100% of it.

Want to learn how to set your rates? Check out this article.

Working from home (or anywhere)

Another added benefit for many freelancers – you can choose where you work. One day I was working from the comfort of my home, the next day at the cafe down the street. Other places I’ve worked: the library, in a car (with a hotspot), at a university, McDonald’s, even at the beach.

All you need is a Wi-Fi connection, but if you have a hotspot, things get even more convenient. Even when I go on vacation to California, I can continue to work while I’m away using just my phone’s LTE connection.

Check out this Wirecutter article about choosing the best hotspot.

Complete autonomy

Once you start freelance work, you start to realize how much more control you actually have. You choose where to work, when to work, how to work- even who to work with. It can be somewhat overwhelming,

But for once, you have total autonomy to decide for yourself. Not having to listen to other people order you around or to follow a strict process can feel extremely liberating.

Disadvantages of being a freelancer

Lack of steady income

In my early freelancing journey, I would struggle to maintain a consistent flow of income. The reality of freelancing is that clients come and go, projects start and finish, and once your work is done there’s no guarantee there will be more.

To combat this, freelancers need to be constantly looking for the next opportunity. Websites like Upwork, Slack communities like Online Geniuses, and job newsletters can provide several opportunities for hungry freelancers.

Feeling of being lost

No one’s going to tell you what to do, if you’re doing it right, or where you should be. You have to do that yourself. And frankly, that can feel pretty overwhelming. There have been a few times where I just didn’t know what on earth I was doing.

That’s natural when you’re self-employed. You could be making thousands, have steadily growing business, and still feel confused with where you’re going. Read our previous article on impostor’s syndrome- what it is, and what to do if you feel you might have it.

Lack of benefits

All of the aforementioned benefits- health care, paid leave, 401(k), get ready to handle that on your own.

Fortunately, there are some plus sides. If you’re setting up your own 401(k), you can set aside more money than traditional businesses require. If you make under a certain amount, you may be eligible for certain federal health care coverage.

Longer work hours

You’ll still have greater flexibility, but expect to work more frequently, and even during the weekends when you don’t want to. There’s always one client asking you for extra work or revisions, or a potential new client you’ll have to court.

To stay efficient, I recommend using a combination of The Pomodoro Technique and Google Calendar to get things done. Productivity is crucial for maintaining and finding more freelance work.

Source: nation1099
33% of freelancers have trouble 'shutting down' at the end of the work day and tend to overwork themselves as a result. Click To Tweet

Choosing between self-employed vs. employee opportunities

As you can see, it’s not an easy choice choosing between the stability of a traditional job and a freelance job. There are certain pros and cons for both sides. Which do you value more: security or freedom?

It’s not as easy as those two choices either. You can feel more secure in a freelance position, and more freedom in a traditional 9-5.

At the end of the day, the question you have to ask yourself is – what is best for you, your family, and your overall happiness? Don’t switch to freelance if you’re not ready or don’t have the resources in place to make the switch. But don’t stay in your regular job if you know you can do so much more.

I knew freelancing would be difficult, but I chose it over a 9-5 anyway. Why? Because I’ve always had a hard time doing work I wasn’t fully invested in.

Freelancing gave me the freedom to live my life according to my own terms.

Want to find out if you have what it takes to be a freelancer? Take this quiz to find out.

Related Posts


Pin It on Pinterest

Share This

Share This

Copy Link to Clipboard