Freelancing Dreams vs. Freelancing Reality

Whether we want to admit it, or not, most of us started out with some preconceived notions of what freelancing would be like for us.

Sometimes those notions were based on hours of solid research. We read blogs from freelancers. We bought “how-to” books. We connected with freelancers through social media and took careful note of what they had to say. Other times those preconceptions were simply based on our own hopes and dreams of what we hoped freelancing would be like for us.

Both methods have their merits. Hopes and dreams definitely play an important role in helping us to decide whether or not to freelance. Regardless of how you prepared yourself for freelancing, chances are that your current freelancing reality is somewhat different from your early freelancing dreams.

While everyone’s freelancing experience is somewhat different, there are some typical experiences that freelancers rarely talk about. In this post, I’ll contrast some common freelancing dreams with typical freelancing realities.

Six Freelancing Dreams Examined

If you’ve been freelancing for a while, stop to remember what you thought freelancing would be like BEFORE you started your business. Chances are, your freelancing reality is somewhat different than what you expected.

Here are six common freelancing dreams and the typical freelancing reality that corresponds with each:

  1. As a freelancer, I will work fewer hours. It’s easy to believe that freelancers work fewer hours in the day when you’re not actually freelancing. Once you start your freelancing business, however, you may find the reality to be a bit different. The truth is that while you can eliminate the time that you spend commuting to a job from your day, many freelancers work at least as many hours as their non-freelancing counterparts. In part, this is due to the many roles that a freelancer must fill.
  2. As a freelancer, I will take only those projects I like. It’s certainly true that freelancers can pick and choose the projects that they accept. However, if you wish to stay in business and if you’re freelancing full time, then you need to have a steady flow of work coming in. To get that work, from time to time you’re probably going to need to accept some work that’s less than interesting to you. Even your very best clients will sometimes have dull assignments for you. This is particularly true for beginning freelancers.
  3. As a freelancer, I won’t have to deal with difficult people. When you became a freelancer you left those difficult people at the office, right? Well, maybe not. While you can choose which projects you work on and who you work with as a freelancer, there’s an art to learning to manage your customers that can be tricky for a new freelancer to learn. Plus, remember that as a freelancer there’s no boss to appeal to if things get tricky. You must solve your people-problems (dealing with difficult clients) by yourself.
  4. I’ll be able to jump right into freelancing and replace my full-time income immediately. It is very possible to earn a full-time living as a freelancer. Many of our readers will share that they are doing just that. But, it takes time to build a successful freelance business–sometimes a lot of time. Very few freelancers become overnight successes. Building up their business is one reason that many freelancers choose to start out on a part-time basis.
  5. Before you can become a freelancer, you need tons of experience. Many people may be hesitant to take the freelancing plunge until they are an experienced professional, but the truth is that people enter freelancing at all levels of the career. Some freelancers have years of professional experience when they start. Others join the ranks of freelancing right out of school. Regardless of their professional level when they start, most freelancers choose to develop and grow their expertise on-the-job as they freelance.
  6. As a freelancer, I will hire others to do the most difficult tasks for me. It is true that many freelancers outsource work and otherwise delegate work to others, but usually freelancers are only able to afford do this after their freelancing business has been established for some time. In the beginning, you may not have enough projects to keep others busy. Most freelancers start by doing almost everything themselves and then outsource work as their business grows.

Despite facing some of the unexpected challenges of freelancing and dealing with broken dreams, I still utterly refuse to give up on freelancing. In my opinion, freelancing still provides one of the best opportunities around to grow as a professional.

What About You?

After you started freelancing, what was the one thing about it that surprised you the most?

Share your thoughts in the comments.

Image by kretyen


  1. says

    Freelancing is freedom, but a hard one! Fewer hours? it’s the opposite to my opinion. And sadly, difficult clients become a habit. But hey, we love that, aren’t we? We are our boss, we take the decisions, and we take all the credit and the proudness when we succeed! I will never go back to my old job, for sure.

  2. says

    Hi Laura, yeah … ahem …. hmmmm …. hard to say it but my dreams of how it is going to be as a self employed were completely and utterly smashed by reality. On the other hand, that reality turned out to be better than dreams so I guess I did pretty OK.

    But I agree, we tend to have myths about freelance or self employed lifestyle (working fewer hours, the freedom etc.) which do not match the reality. And once you realize that, you’ll be just fine in working for yourself.

    Good post.

  3. says

    Yeah the myth versus reality of freelancing can be a stark check if you have preconceived notions of this type of work. I can relate to number four, I still have a full time job and full time freelance work, but as we all know feast and famine cycles. Not sure how long the full time freelance gigs will continue to develop.

  4. says

    I started Freelancing as a Web Designer two years ago when I left the Insurance Company I had been working for.

    I still work long hours… with lots of difficult people! I still work on boring Projects. The security of money being there in the Bank at the end of every month is non existent.

    What I have gained though is quality of life (I respect my time and make sure other people do), I decided when I wake up and when I go to bed, I have a real challenge everyday (chasing my own income). Most importantly for me I don’t feel like a cog in a big system that doesn’t care how hard I work.

    It’s even improved my health because work is no longer an excuse for not going to the gym!

    I wouldn’t change it for the World. Although It’s definitely not what I thought and I wouldn’t recommend it to everyone. Freelancing does involve sleepless nights when you first start off.

  5. says

    When I started freelancing, I didn’t realise how few holidays I’d end up taking. Of course, I know I can take as many as I like but I don’t get paid for the time I’m away. Also, if clients know you’re away a lot, then they can’t rely on you to there do their work when they need it doing.

  6. says

    The main reason why I decided to switch from daily work + weekend work into freelancing + weekend work is really working a lot…and I mean A LOT. But instead of working for the success of others, I wanted to work for my own success. I think that you can make dreams come true, everything is a question of personal policy. If you see the red flags (hehe ;), you won’t have difficult customers. If you organize yourself, you’ll work fewer hours. If you are professional and have lots of customers, you can choose only the ones you like. Of course, you will gain it with hard work, experience, etc. I myself probably have my weekend job starting September again (higher university lectures) so I feel secure – so maybe that’s why I have a brighter picture of my future. After all, I can pack all my things, take my girlfriend and we’ll go to the UK (sometimes Poland seems to suck sooo much that I won’t have any problems with leaving everything…)

  7. says

    As much as it is glamorized, it is hard work and there are a lot of factors that will make a freelancer succeed or fail. Most freelancers are not good at marketing or sales which makes up for a large portion of the freelance engine to run. It seems freelancing has become the latest trend and false notion that you will become rich fast.

  8. says

    Everything here is true. I recommend wearing multiple hats before you start outsourcing. While it can be frustrating as a designer to manage the business end, you’ll learn a lot and it will be much more rewarding. High risk=high reward, right?

  9. says

    Wype & Pawel @ Self Employed Cafe–For those starting out, the reality can be a real wakeup call. It’s definitely worth it, though.

    Jordan Walker–A full-time job and full-time freelancing? Wow, I’m impressed. You’ve got a lot on your plate.

    The Freelance Geek–I do think that freelancing can lead to an improved quality of life, but it’s up to the individual freelancer to make sure that happens. It sounds like you’ve got a good balance going.

    Freelance FactFile–Sometimes the holidays are my busiest times. It’s as though the client says, “I think I’ll take this time off and get a freelancer to do the work.”

    Sponsi–With freelancing your fate is definitely in your own hands. You benefit from your good decisions and suffer for your bad ones.

    behzad & Dave D–Good points about starting out. The business and marketing aspects are definitely important.

    When I started I bought into a lot of the freelancing myths because I didn’t know any better. Can you guys think of any other misperceptions about freelancing?

  10. says

    @Laura one misconception that freelancers are told is to find their niche. I would strongly recommend once starting to take on as many jobs as you can, it expands your creativity and portfolio as well as job experience working for different sectors of society. Freelancers need to have diverse samples of work. Also not to avoid small clients, remember that small clients could become big clients and small clients might know bigger clients.

  11. says

    I am a new in freelancing {WordPress developer},I see all points are related to me and eventually every point has matched to my present condition :)

    I am full agree with And In point 6 [ Before you can become a freelancer, you need tons of experience ] ,
    NO u may start your freelancing career whenever you want, I started as a freelance as a WordPress developer when I was absolute beginner in WordPress.
    And now I have a good number of clients with their good projects.

    And I am dreaming to be a full time successful freelancer.
    Great !

  12. says


    Great post about the myths many people have about freelancing. I especially think #4 can be a trap. I always recommend that unless someone is laid off, they start freelancing on the side. Better to start building a client base while you still have the security of your regular job. You might decide later to do it full time. Or you might just keep doing the part-time gig for extra income. Or, you might find you actually hate freelancing and just keep your regular job (nothing lost but your time).


  13. says

    Nice post!

    I like the first point. I can’t believe how many people say that they want to be their own boss so they have to work as much. It’s crazy!

    On the topic of taking only the projects you want to it’s difficult when you are starting out. I did however find that when I sat down and figured out what kind of projects I wanted to do and marketed my business to those types of projects I was able to attract more clients who wanted me to do the work that I like to do.

  14. says

    All very good and valid points, reality is such a harsh eye opener, I envy those who just works for themselves and be successful, I’m a dreamer, I dream that one day I will be a part of that freelancing cloud… But until then I will just have to make do of what i have. Thank you for this post. Looking forward to the next one.

  15. says

    This is a very intriguing article, as i’m not freelance myself, i can see the appeal of working from home and choosing your hours, but in reality and after reading lots of articles on the reality of working late and early in the mornings, being freelance has its perks but over all its just as hard if not harder than being employed by a company.

  16. says

    Another great eye-opener. :) Very recommendable to other freelancers, especially those who are just entering the freelance world.

    I always thought that being a freelancer would allow me to work according to my own set hours. I never thought that I’d encounter clients who would ask me to work like an employee (30 hours per week, 40 hours per week). It was surprising for me and several times I’ve agreed to such an arrangement, but after a while I decided it was time to work according to my own work hours.

  17. says

    Number 1 has been a big thing for me. You think you only have to do a few hours of work in the afternoon, and then you’re free to do whatever you want. That is definitely not the case!

  18. says

    Great post!

    I made the switch from working as an editor for a publisher to starting my own freelance editing business this year and I’ve never been happier!

    I do find that I’m surprised at how difficult it is to work from home sometimes though. It feels like I have a lot more free time than I really do, and I find myself wandering to the kitchen to talk with my roommate or spending an hour downloading new music in the middle of editing a project. It’s hard to get back to work after breaking my concentration like that. I’m getting better though!

  19. says

    Number 1 is also a big issue for me. I’m now trying to monitor exactly how much time I‘m spending on articles I write. I mainly use the free service, Slife, to monitor my time. It’s difficult to know how to set your rates when you don’t know how long it takes you complete certain types of projects. Too many times I have accepted a job and underestimated how long it would take me complete it, and thus I end up not making the money per hour that I need to make.

  20. says


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  21. says

    It’s the workload for me, but I’m loving every minute of it. It’s such a thrill to develop your own set of goals and ambitions for how your business will grow. I’m having a lot of fun.

  22. says

    awsome article

    i’ve been building my freelance business for 5 years now while I worked a day job, and have just now decided to go full-time after acquiring a steady income of clients.

  23. says

    I think the main point is, just as you said/wrote, “…freelancing still provides one of the best opportunities around to grow as a professional”

    Great article !

  24. says

    I think when you freelance, you have to be very strict with yourself.
    You do end up working a lot of hours that people in regular jobs do not work, like evenings and weekends. However, there is also the problem that because you manage your own time, you may end up getting distracted, therefore you must be very disciplined. I admit this is something that I struggle with from time to time.

    At the beginning, it is definitely important that you are not too picky with jobs and projects as you probably won’t get too many offers to start with and you need to build up your portfolio.

    At the moment, I am just getting my freelancing career off the ground. i have just left university, so although I have experience in the arty side of things, the business side of things is very new to me. I am learning as I go along and am finding it quite interesting. ^_^

    I also am only doing my freelance illustration part-time whilst I maintain another job, just for a steady income until my freelancing career takes off, which I understand may take years. However, I think persistence and optimism are the keys to become successful. I can’t expect it to happen straight away. =)

    I agree that whilst it has worked for some people, it would be very risky to give up a job and go straight into full-time freelancing.

    There is some great advice in this post. Thanks!

  25. says

    The trouble I found with freelancing is that there was a lot of other business things I had some big weaknesses in. After three years I still found myself accepting rush orders without charging more, or not charging for admin time, struggling with keeping invoicing, and accounting in order and spending time networking. After spending some time in the big business world I have learned to better balance strengths and weaknesses. Using a tool called Freshbooks invoicing and preparing for accounting is easy. Networking is part of my schedule not a once in a while thing, I make sure to “turn on the clock” for heavy admin jobs from clients. Feeling more confident in myself and my abilities made it easier to ask to be compensated and charge for rush or special orders.

  26. says

    Freelancing is a lot harder than I ever thought it would be. I started when i finished university and it was the total opposite to what I expected. You think you’ll have more free time, but your home is your office and you never leave! You sometimes get to the point where you start talking to yourself (never a good thing) and you realise that you actually miss the hustle and bustle of an office life, having people to converse with and share ideas. i recommend freelancing for those starting out as designers, just to build your portfolio, but there’s invaluable experience to be gained by working in a business.


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