by Kate Vandeveld

As you may know, the freelance economy is booming these days, with freelancers set to outnumber full-time employees by 2020.

As freelancers ourselves, many of us hear the same question from our networks over and over again: “Do you think I should try it?” The answer might seem simple to other freelancers (yes!), but the truth is…freelancing is not for everyone.

Pros & Cons of Freelancing - via WhyWhisper Collective

As with almost everything, freelancing has its pros and cons. Since we’re familiar with both sides of the story, we’re happy to share our thoughts on the subject. Let’s start with some of the benefits:

All Kinds of Freedom

This one tops the list. With freelancing comes freedom of all kinds. Freelancers have the freedom to create their own schedules, so they can choose to work at the times of day when they’re most effective, rather than forcing themselves to work at pre-determined times. They can go for a walk on a beautiful day, grab a long lunch with a friend, or just take a break when they aren’t feeling particularly productive. When you freelance, not only do you get to choose when you work, but where you work as well. Are you more productive at home? Go for it. Need to be around others? Try a co-working space or a coffee shop. You can develop your own routine, or opt to mix it up. Plus, as a freelancer, you aren’t confined to a limited number of vacation days. Most of the time, freelancers can work from anywhere with a Wifi connection, so you can travel anywhere without disrupting your workflow.

Perhaps even more important than choosing when and where you work is choosing who you work with and for. At WhyWhisper, we prioritize working with the right people and organizations. We choose to work with individuals who are kind, collaborative, and passionate above all else, and with businesses and organizations that are making a positive impact on society. Before setting out on your own, define the types of people, companies, and organizations with whom you feel you would work well.


Uninhibited Growth

As a freelancer, you have the opportunity to grow your career in whatever direction you desire, creating your own opportunities for advancement. In a corporate environment, your career development is often bound by internal structure and protocol. Though you can advocate for a promotion or more responsibility, it’s not always in your control. When you work for yourself, you can choose how much you want to take on and decide how much you want to charge for your services. It’s not always this simple, but generally, the more you put into your work, the more you can get out of it. 

Speaking of rates, freelancers also tend to make more than salaried employees, on average. In fact, the average freelancer makes 45% more than the average full-time employee. Of course, this depends entirely on your skill-set, experience, and the number of projects you are able to take on, and it doesn’t account for benefits, but the possibility of making more is there. 



When you work eight or more hours each day, one of the hardest things to achieve is balance. You’re working on someone else’s schedule, so it can be difficult to incorporate the things that keep you happy and healthy. Because employee satisfaction has such a strong correlation with productivity, many companies have worked to develop corporate wellness programs in recent years. But when you work for yourself, you don’t need corporate wellness programs – you can do yoga at 10am when classes aren’t full, or wake up and go for a jog on a nice morning. When you’re a freelancer, you have the ability to determine what work-life balance means to you, and develop a schedule that achieves it.

Pros & Cons of Freelancing -- via WhyWhisper Collective


Now, let’s take a look at some of the drawbacks, as we see them:


Most would say that one of the biggest cons of freelancing is the lack of reliable cash flow. When your projects vary month-to-month, so does your income, which can be difficult to manage for some, especially at the beginning.

This means that, as a freelancer, you almost always have to be making moves and selling your skillset. It can be fun – you learn a lot, and have the opportunity to meet cool people almost every day, if you’re lucky. But sometimes, it can be exhausting. As a freelancer, you’re a salesperson, and what you’re selling is your own skills. Making the case for yourself repeatedly can be tough, but as you get more confident in your abilities, you’ll likely find that you’re able to speak to your skillsets more readily and your reputation will spread among your network and beyond, solely by word of mouth recommendations.



Remember when there was someone else being paid to manage your benefits? Someone who filed all of your expense receipts for you? As a freelancer, that person is you. And you don’t get paid extra to do it. While it can be empowering to learn about and manage these administrative tasks, it can also get very overwhelming and/or tedious. We’ve talked about how to set yourself up to manage the administrative side of freelancing more easily so you don’t get stuck with hours of paperwork that you don’t understand all at once. The more you prepare yourself, the easier this aspect is.



As much as the ability to create your own work-life balance can be a pro, it can also be a con in some respects. Because you make your own schedule as a freelancer, you also have to set your own limits. While you’re no longer expected to stay at an office from 9 to 5 (and often beyond) each day, you’re also not restricted to any “normal” working hours. This can make it hard to stop and take a break, or move on from work to do other things. And when you do, it can be difficult to shake the guilty feeling that you should keep going, working on your portfolio or seeking out new clients. If you aren’t able to set boundaries for yourself, you could easily burn out.  

So before you decide to take the leap into freelancing, definitely take the time to think it through carefully. Is your personality one that can handle the ebbs and flows of freelancing? Is the freedom worth the uncertainty that comes along with it? We certainly think so, but we know it’s not for everyone.

What do you think are the biggest pros and cons of working for yourself? Share with us! Here’s how: