To Freelance or Not To Freelance, That’s The Question

To Freelance or Not To Freelance, That’s The Question

Being a freelancer is serious business. This is why we’ve decided to make a collection of pro’s and con’s for you to help out a bit. Deciding if you’re going to keep that 9-5 job or dive into the world of freelancing can be quite tricky to figure out. There are many things speaking both for and against this. Many times, the positive aspects seem to be many, while the more “negative” or challenging sides can be more hidden to you until you’re actually facing them.

To Freelance or Not To Freelance, That’s The Question

Here’s a list of 15 pro’s and 15 con’s of freelancing. We hope these tips can help you decide what to do, and also help you be better prepared for the future!

The Pro’s

Being positive human beings, we’re going to show you what we think are 15 of the biggest pro’s in choosing a freelance career.

Creative Freedom

Many freelancers best motivation to start up often is the chance to get full creative freedom. No boss to look over your shoulder and no co-workers that take all the best jobs. As a freelancer you will be able to choose what direction your work will take. It will be you and the client without anyone else. There have been studies to show that many people in creative jobs would actually accept a lower pay for the same amount of work given they get full creative freedom. This proves that it’s definitely important to many of us.

Image credit: .lollo.

Setting Your Own Work Hours

Being able to more or less start and end your day when it fits you the best can be a really huge advantage for most people. This doesn’t necessarily mean to sleep all day and work all night. Setting your own hours can mean that you get to drive your kids to school before you have to start working, that you can go out for private errands during lunch, attend school shows, go with your wife to the dentist or sleep a bit longer if the kids cried all night.

Seeing Your Family More

As a freelancer there are many ways that you’ll be likely to see your family more. This could be the fact that you’re actually working from a home office, that you can plan your time to fit in with family meals and much more. Not only will this make you happier but it will give a boost to both your creativity and productivity.

Seeing Your Family More
Image credit: Iwan Beijes

Planned Vacations

In many countries around the world, getting your vacation when you want it can be hard. Many families struggle to be able to get their summer vacations at the same time and so on. When you’re a freelancer you can plan your vacations to fit in with the rest of the family. By planning in advance you can make sure that no deadlines will be due when you’re supposed to have a week or two off.

Working Extra Hours

At times people may want to work a bit extra. This could be because they love their work or simply because they need extra money for unplanned expenses. When you’re a freelancer you often have piles of work waiting to get done. My dishwasher recently broke and by working a few extra hours two weekends I could afford to get a new one pretty quickly. With a regular 9-5 job this could’ve been way harder. So if you’re in need of extra money for whatever reason you could let yourself work a bit extra without having to fight with 20 other workers for those extra hours.

Working Extra
Image credit: Dreamzzzz

YOU decide

In general, you’re the boss when you’re freelancing. This means many different things. You decide whether to accept an offer, you decide when you get time off, you decide how to decorate the office. Many new freelancers choose this as their top reason to quit their regular day job. Being able to make all the important decisions in your work-day can feel very rewarding and boost the work morale for many.

Doing what you love

We all seek to do things we love and get paid for it. There’s a saying by Confucius that says “If you enjoy what you do, you’ll never work another day in your life”. Today there are many people who wake up in the morning and don’t look forward to a days work. They do something they’re not too fond of to get enough money to live. By having the chance to start freelancing you can do things you love and get paid at the same time. This is a dream for many.

Like What You Do
Image credit: The Marmot

Client Contact

If you work for a bigger company, the direct contact with clients can be quite rare. Being a freelancer you’re the one that both gets in touch with the clients and does the work. This can be very rewarding and you can experience a great satisfaction from being able to have that full client contact under control. This gives a better connection with the whole project along with decreasing the chance of having misunderstandings or unhappy clients ruin a project.


Many a creative soul really grows when given responsibility. Many of us who’ve worked in bigger companies for years, have been dreaming of getting more and more responsibility. In a way you’re responsible for either success or failure when you’re a freelancer. Either way, getting some extra responsibility can be more rewarding than even the biggest paycheck.

You Make a Difference

By being one person and one business as a freelancer, you’ll soon notice that you can make a huge difference. If you’re sick and tired of just being one of many workers in a business, being a freelancer will definitely show you a different side of things.

Unique and Different
Image credit: HOMAKO

Choose Your Work Environment

As mentioned earlier, a freelancer is his own boss. One really great advantage of this, is being able to make a work environment that you love. For many of us, this can mean a huge difference. Redecorate your office, choose where to work from and so on. Only imagination will set the limits.

Combine with Studies/Part-Time Work

Another great thing with being a freelancer is the fact that you can still do it if you’re a student or only a part-time worker. As a freelancer you can choose how much work you actually want to take on and do the work when you have the time. Not many other jobs offer this great opportunity.

Mold Your Future

Being a freelancer you can mold your future to a large degree. You can choose what kind of projects to do, when to do them, how much extra to work and what direction to take. You can aim to expand within a set period of time to develop a business that will give more people work in the future, or you can choose to keep freelancing.

Mold Your Future
Image credit: Sarah Lewis

Vibrant Community

One thing that I especially find really great is what I like to refer to as the vibrant freelance community. In the local area you don’t necessarily see too much of freelancers, but once you take the step online, you’ll see that there are many great people out there sharing their experiences. As a freelancer you’re definitely not alone as there are many others to find through forums and so on. Sharing experiences with other freelancers anywhere in the world can help you get more efficient, earn more money and be happier!

Choosing Your Projects

Just like with molding your future you can mold your present. You can choose which projects to engage in and which ones you’d prefer not to have anything to do with.

Image credit: photoshoparama – Dan’s

The Con’s

Now time to have a look at some of the not so great things about freelancing.


Working more or less alone can be hard for many people. Especially those who are used to being around many co-workers all day long.

Image credit: Sanja Gjenero

Paying for Own Equipment

There’s no boss to go to when you need a new computer or getting the printer fixed. As your own boss you’ll have to find ways of coming up with the money on your own.

Many Expenses

When you’re a regular employee you usually don’t see much of the expenses related to your work-place. When you go freelance this will completely change. Everything costs; coffee, paper, phone lines, office rent, gas and so on. This can for many be quite overwhelming.

Many Expenses
Image credit: Alessandro Paiva


I’ve set this as an own point, basically because you need to be very much aware of this one. Depending on which country you’re living in, this can be a very important part of your budget. Make sure to check out what it’s like in your country. You’ll most likely need some sort of insurance to make sure you get any money if you’re sick any time, if you get injured while working or if your equipment breaks.

No 9-5 Job

Being a freelancer rarely means working 9-5. If you want to succeed you’ll be very likely to have to work a whole lot more than that, especially during the start-up and through periods.

Can’t Hide

You have to take responsibility and you can’t hide behind your desk on a bad day. You’re out there all the time and you have to be available for your clients. This can in some cases make you more vulnerable.

Can't Hide
Image credit: Hob

Hard Work

Freelancing is hard work, it’s never an easy way to success. And no matter how much you read up on it and how well-prepared you are, you’re likely to be surprised by the amount of hard work it’ll be.

Financial Responsibility

The overall financial responsibility will be yours and no-one else. This means taking care of everything related to economy. At times this can be very hard to deal with, especially in a young freelance business with limited money.

Unsteady Income

When you freelance you’ll never know exactly what you’ll get paid from month to month. This can be hard to live with for many people, especially when you have a lot of monthly expenses that have to be paid no matter what.

Unstable Income
Image credit: annfrau

Ups and Downs in The Market are Very Noticeable

As a freelancer or business-owner in general, you’ll notice changes in the market more than a regular employee. This means you’re vulnerable and that a business you’ve spent years to build can be torn down in hours. The good thing is that there are always certain precautions that can be made.

Many Laws and Regulations

Again depending on which country you’re in, there are laws and regulations you need to know. It can be quite a job to read up on all these and get everything done right, but it’s necessary.

You’re “Always” at Work

A common freelance-challenge is to feel that you’re always at work. This could be because you always have projects that are being worked on and because you’re always trying to earn as much as you can.

You are Always at Work
Image credit: Fabio

Takes a Lot of Discipline

Being your own boss, getting up in the mornings, doing what you’re supposed to do and so on takes a lot of discipline. One thing that’s definitely for sure is that freelancing isn’t for everyone.

Can be Hard for Outsiders to Understand

Freelancing can be lonely in many ways. One of the things that could surprise you is how hard it can be to get the acceptance and understanding of those around you. This could be family members having a hard time understanding that your home office is off limits during work hours, friends who think you can take time off “whenever you want” and so on.

Can be Hard for Outsiders to Understand
Image credit: Ben Cameron

Getting Clients / Entering Markets

When you’re a multimillion company with your own marketing department, money for marketing and a good brand, getting new clients could happen automatically. When you’re a freelancer it’s definitely not that easy. Even though you may know some people here and there, actually having them sign a contract with you doesn’t have to be all that easy.


So it’s hard to be a freelancer, we know that. But it’s also extremely rewarding. Most things do have pro’s and con’s and it’s up to you to decide how all of these points weigh in on that final decision. You could read up a lot to be prepared in the best way you can, that’s recommended. Still there will be a few things you just can’t know unless you’ve tried.

Image credit: Sigurd Decroos

What we can do is to try to help you understand which things to consider, and we hope you’ve found this article useful! Remember that we would also love to hear about your own experiences in the comments!


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