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The Dark Side of Freelancing

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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.

21 Responses to “The Dark Side of Freelancing”

  1. Wow! All my freelancing pet peeves written in such details. Great post Dawn. To answer your question, what I love about freelancing is the freedom to work anytime and anywhere I wish ( without silly dress codes or overbearing bosses ). I guess, I’m a social animal and I hate the isolation that freelancing brings. Thanks for the tips!

  2. I’m not a freelancer but I sure love buying their time for my company projects. I have hired people from all over the world and love having an on-demand work force.

    I would say the most challenging thing about my relationships with my many freelancers is time change and communication. Learn how to “be around” for your employers and learn the English language really well so communication is not an issue.

    Under promising and over delivering certainly is a great thing as well, do that and you will have me coming back for more again and again.

  3. you know what kills me? the late payment aspect. with freelancing we are always cutting everything so close and having to convince people to pay you for work that was already done and on time… just cuts deeply into the bottom line.

    i so feel your pain. the health care issue though is the bottom line for me pursuing a “normal job” after 6 yrs…


    ps are you attending SXSW?

    • Yes, late payment can be very stressful. But on the flipside, at least freelancers can set up multiple income streams for security. If you’re working for a company, you only have one, and they won’t give you any warning before they fire you/they go belly up.

      Healthcare would be a biggie for me too in the US, especially if I had a family. Here in the UK it’s not such an issue.

    • I was fortunate to have spoken with a friend’s wife that has been freelancing for years. I copied a lot of good info from her bid sheet and invoice that outlines payment. I used it on my last bid and they didn’t even blink. They are a large company that has an employee (accountant) dedicated to A/R and A/P so hopefully it won’t be an issue on this job :)

  4. I’ve been reading these comments with both horror and fascination. With the economy in such “fine” shape, I started planning my freelance gig as Plan B. Good thing. In December I was called in and told that, “due to the recent downturn in our industry, your position has been effected.” Twenty minutes later I was walking through the parking lot with my new office in a box. I really like what I do as a copywriter/tech writer, but now I not only have to do the work – I have to generate it as well. Granted, my hourly rate went way up – but now I find myself in the company of like minded folks looking for health insurance.
    The majority of work I’ve been picking up are writing projects I like, but I have to fill in the gaps with jobs I don’t like. As far as trading job security for job happiness – there is a balance and it’s different for us all. I’ve freelanced on the side for a long time, knowing that steady paycheck was always there for me.
    In that vein, if you are here trying to glean some info and decide if freelancing is for you – my advice would be this: while you still have the corporate sugar daddy paying your way, update your hardware/home office now. That was the smartest move I made and didn’t even realize it. When I got laid off, I was actually OK because I had virtually no start up costs. I got my first 250 business card for free online.
    I think I do have you all beat in one respect – I am currently working from the back of a thirty foot camper that we are now living in – but only til the 1st of April.
    Great site. I look forward to hanging out with you folks.

  5. Melanie A.

    My least favorite aspect of freelancing here in the USA is obtaining medical care. I’ve bought individual health insurance, which, paradoxically, I’m afraid to use very often out of a not-unrealistic fear that the for-profit company which insures me will raise my premium. It’s a testament to the American “can do” spirit that we persist as freelancers despite the world’s most irrational health care system.

  6. Luckily there is a way to prevent yourself from going mental at home and that is Coworking ! Google for coworking (or Jelly) and your nearest city and the odds are that there is a coworking community or place out there. If not…. start one. :)
    In Prague TheWorks is organizing casual Coworking events (so-called Jellies) and they are attended by a growing group of freelance workers. There are future plans to establish a more permanent space. Lemme know if I can help setting up a community or Jellies.

  7. great post. // freelancing most certainly has ups && downs. // the lack of community is what sometimes gets to me, that’s why i recently start’d // it’s a place for people who work on the net ((’rs )) to get together && swap stories, tips, etc. // i’m hoping to get the community in a position where it super useful for design’rs && coders // you can check it out @

    keep up the great work && good luck back in the corporate world !!

  8. If I could bring all my friends together for the upcoming party?
    WOWOOOWOOOOOWOOOOOOOW! And, not one single hangover afterwards!

    The event evolved into collaborative byob/g-style, AmJAX-laden, reciprocally-inverted eigen-vernacular of Market-Objectified PR:

    razorwashed, plasma-distilled, holographically-mastered HypHens!

  9. A lot depends on your expectations when you begin your career as a freelancer. It’s not for everyone, and it is a lot of work. It’s no different than any other job, except you are responsible for your own success or failure. There is no glamorous side. It’s damned difficult to manage.

    Some things are better off as hobbies than as careers. You don’t know until you try it, so kudos to you for realizing freelancing was not the right choice for you. Good luck!

  10. One of the big hazards of working from home is psychological an emotional. It’s imperative to leave the house on a regular basis, and to have some sort of structure. Otherwise, you may start developing bad habits.

    After working from home for over a year, I started skin picking again. Chronic skin picking, in particular, is a pretty recent diagnosis and is related to trichotillomania (aka hair pulling).

  11. Freelancing is a YMMV (your mileage may vary) thing, and lots of people who think they can do it really can’t because they find out it’s way more than just doing work. My tip after years of doing it? Do what you do best, farm out the rest when practical. And don’t get discouraged.

    After all, someone has to start to the businesses, or else there’s nowhere for the drones to work ;) but I hope the author has a new respect for the boss and what challenges they actually face.

    That said, I believe the future of working is in the independent contractor model, like it or not, it’s here to stay. The jobs I see coming back are not the kind with retirements or heavy benefits, because companies have learned that they simply can’t promise it – look at the collapse of GM and others.

    People more and more are going to have to run themselves like businesses because that’s the reality. I don’t necessarily blame the individuals – school teaches you to be good at school. Large swaths of our culture are in shock and don’t understand or comprehend the new way of work. My significant other just got off the phone with relatives who don’t understand that she actually “pounds at that computer” for a living.

    I realized awhile ago it’s better to just embrace it and make the change instead of complaining about it. This is the new reality, how do we deal with it?

  12. I’m sorry but the writer just comes off and a whiner. Its not the work that was the problem its your lacks of overall discipline if balancing your personal time and your freelance projects for clients. Some people just aren’t cut out for freelancing but once a whiner usually always a whiner. I’m sure being a worker drone will be very rewarding for you. Not. What a waste of a post. Two whole years. How long will you last at Intel. Yawn city! Oh, and I’ve been successfully freelancing since 1991, so I know of what I speak.

    • At the risk of feeding the troll; Shane, you’re an idiot.

      Dawn’s reason’s for switching back to full-time employment are all valid and, more importantly, her own.

      Freelancing isn’t the only way of working to achieve a good work-life balance; if you don’t have the mental capacity and social skills to realise this then it’s no wonder that you have been freelancing since 1991 – I doubt many people would suffer your attitude in their office.

      The happiest people are ones who can adapt easily within their environemnt to their short-term needs without having to sacrifice their long-term goals. Sometimes this means working for the man, but if that doesn’t bother you I don’t see why it’s anyone else’s business.

      The fact that Dawn has taken the time to share this is not a waste of a post either; as these comments reflect, freelancing is not for all and some people who have gone from permanent to freelance and are struggling may not see a viable way back – Dawn illustrates that there clearly is.

      Thanks for sharing Dawn, good luck with the job.

      • Well stated Steven. Thanks for your input Dawn and keep up the good work. I joined this forum because of the (mostly) professional posts from other freelancers.
        The negative post above only demonstrates a serious lack of professionalism.
        Dawn, I think a lot of folks, including me, are looking forward to more of your work.