The Dark Side of Freelancing

I’ve been freelancing full-time for almost two years. There are so many things to love about the freelance lifestyle. I can work weird hours and rearrange my schedule on a whim to take advantage of nice weather or have the free time to do something with friends as long as I find the time to complete my client work. I like being able to work from a variety of places: my home office, a coffee shop, a friend’s office, my back porch, a park or almost any other location. I enjoy having the freedom to take on new clients (or not) based on whether the project is (or isn’t) interesting to me. I like having the ultimate level of control over my career.

However, it isn’t all rainbows and unicorns. There are a number of downsides associated with freelancing, which is why I’ve made the decision to go back to a full-time corporate job as a community manager. I’ll still be a web worker, collaborating with people around the world online, but I’ll be doing it as a full-time employee.

Turning Hobbies Into Paying Gigs

When I began freelancing, I was excited that I could turn things that I was passionate about and doing for fun as hobbies into something that people would pay me to do. I could do fun work and earn money! This worked for me for quite a while, and maybe it continues to work for some people over long periods of time. For me, those things that I used to do for fun all became work, and they became less fun as they started to feel like work. I also realized that I really didn’t have hobbies anymore, and I was just spending all of my time working, which left me burned out, tired and grouchy.


On a related note, I used to enjoy speaking at conferences, blogging and attending events when I used to do them mostly out of a passion for the topic, and because they were fun. As a freelancer, these became business development opportunities. I started feeling a big weight on my shoulders and pressure to speak or write only about topics that were directly related to my consulting practice so that I could use them to get more business. Attending events shifted from hanging out with my friends and meeting new people with interesting ideas to meeting people who might need my consulting services. All of these activities became less fun as a freelancer.


Anyone who has ever freelanced full-time knows that the logistics can be complex, painful, time consuming and sometimes expensive. Taxes are much more complicated and time consuming even when you have an accountant do them for you because there are so many things you need to track. Independent health care plans are expensive and not nearly as good as when you get them through your employer. Retirement savings is also more difficult, and you can’t save nearly as much in an IRA as you can with a corporate 401k, especially since most employers match at least a portion of your contribution. I can be very detail-oriented when I need to be, so I was able to manage all of the logistics without any big issues, but it was just one more thing that I didn’t enjoy doing.

Could I have made changes in my working style to make all of this manageable and still be happy while maintaining my sanity at the same time? Maybe. For now, the best choice for me was to go back to working for a company. I’ll still continue blogging and playing with cool technologies, but I’ll go back to doing this evenings and weekends in the hope that they start to feel less like work and more like hobbies again. If not, I’ll just have to find some new hobbies. Bridge, anyone?

What is your least favorite part of freelancing, and how do you overcome the dark side of freelancing?

Photo by Flickr user weeta, licensed under CC BY 2.0.


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