Reasons to Become a Freelancer

For me personally becoming a freelancer was one of the best ideas I’ve ever had. Being a freelancer beats all jobs I have had in the past and maybe more that 99% of all potential jobs I could realistically expect to have. And I certainly can’t complain of lack of lucrative offers, even now, when I am off the market for hired power.

For me the main reason to become a freelancer was the fact that I already had too much experience to be an ordinary staffer and some bitter experience as a manager of bunches of idiots, so becoming a manager again wasn’t exactly the thing I dreamed of. Starting my own company was also an option but basically I decided to play the lonely wolf and go on my own rather than deal with all the administrative chores around a company of my own and all the staffing pains that I have already had while working for somebody else.

While my reasons are hardly rare, there are also many more that drive people into freelancing. I will try to present a summary of the main reasons that motivate a person to become a freelancer. However, be warned that none of the reasons (i.e. more money, better work-personal life balance, etc.) are to be taken for granted. On the contrary, if you don’t know how to arrange your freelancing business or simply if you are out of luck, all the benefits of freelancing can turn into huge disadvantages.

1. No Boss

The most obvious reason to become a freelancer is the desire to be one’s own boss. However, being one’s own boss isn’t easier! In many cases it is even much harder, especially if you have no managerial and sales skills. Well, if you have had the pleasure to have mainly idiots for bosses, it is very hard to perform worse than them but if you have had the privilege to work with top-notch managers, as I did in one or two cases, you will always compare yourself to them and you might feel you will never reach their level.

Basically, if you have no managerial skills, you will learn the hard way that technical skills alone, even if they are superb, won’t take you far. In this case freelancing might be your worst disappointment. This was the case with some friends of mine who are technically better than me but who just lack any sales/managerial skills and for them freelancing was almost a suicidal idea.

2. No Coworkers and Subordinates

When your boss is an idiot, this is very nasty. But when your coworkers and subordinates are unreliable, this is worse than a malicious boss. When you are in a team, you depend on other people and if they fail you, you drop. It is especially bad when you have subordinates who are not worth a penny but due to various reasons you are forced to work with them.

In one of the cases when I was in a managerial position, the so called “team” was just a group of losers who were close to the bigger boss and who didn’t work at all. I was between a rock and a hard place – having a team that is totally useless and being responsible for other people’s failures. To add insult to injury, some of the team members were paid more than me simply because they had been longer with the company! But in fact this was good – it took me a very short time to decide that I don’t belong to this group of losers and to move on.

3. More Freedom

In theory, when you are a freelancer, you have more freedom. You decide which projects to take. You pick what you like.

In practice, this isn’t exactly so because very often, due to various reasons, you pick not what you like but what is available, which is quite different. Still, all equal, as a freelancer you have more freedom to make decisions and if you decide to make a compromise, you know it is your decision, not that you are again sacrificing yourself because of other people’s wrong decisions.

4. More Money

In my opinion, more money is a major reason why people become freelancers. Unfortunately, very often this is the biggest disappointment, too.

On one hand, if you are really good, for the same amount of work, you can make more money than what you will be getting at a company, unless of course you aren’t among the privileged few, who don’t work but get more money than the workhorses. As a workhorse under your own management, you will have more than under a poor management – this is for sure.

Additionally, if you freelance from home, your expenses might be lower – you won’t be paying for gas, for eating out, etc., which could easily be $500 a month or more. If you manage to negotiate good rates on your projects, it might turn out that you are making more in a day or two as a freelancer than you would make in a full-time job for a week.

However, when money is concerned, you need to consider your increased spendings, too. Taxes, equipment (hardware, software), office rent (if you have to rent an office) are all expenses that go out of your freelancer’s pocket and if you don’t budget well, you can end with a net income much lower than what a 9 to 5 job pays.

5. No Wasted Time to Commute

Time is money! Probably this is what you are thinking every day on the 2+ hour journey to and from work. When you freelance from home (or your office is a block away), you don’t waste time to commute. If commute takes 1 ½ in each direction, this is 3 hours a day lost on the road. If your hourly rate is $20, 3 hours a day lost to commute are $60 a day, or $300 a week!

6. A Better Work-Life Balance

For everybody in a demanding job work-personal life balance is a tough issue. In theory, when you are a freelancer and you decide when to work, it must be much easier to find this balance. The benefits of working from home are especially tangible for people with kids and above all for single parents because this allows them to spend more time at home and saves quite a lot on daycare.

However, it is not always easy to make your kids behave as if you were not at home and kids can easily turn into a huge distraction. A (male) acquaintance of mine got so pissed off by having his family around him at all times that he rented an office nearby, where as I joke he is hiding from his loved ones, so that he can work at least a little.

7. No Other Options

Finally, one not so romantic reason to become a freelancer is the lack of other options. About 2 years before I decided to go freelance full-time, I was unemployed for quite a lot of time. I did get lots of offers but they were so bad in terms of career prospects, money, technologies used, management, company culture, etc. that I was joking I could accept them only if I were under the influence or out of my mind.

While I was looking for permanent jobs, I found some freelance opportunities that I regarded as a temporary solution till I found something better. These opportunities weren’t something out of this world but they brought some money and saved me from the necessity to sell myself – i.e. to accept one of those bad offers.

When I finally found a job that wasn’t as bad as most of what was available, I quit freelancing but after this job too turned pretty nasty in about a month or so, I stayed there for 3 months only and again went freelance.

After that I had a couple of more other full-time jobs, each of which went nasty in a different way. This was what convinced me that when you are not your boss, even a job that looks decent can quickly go bad and you have either to leave, or put up with all sorts of idiotisms. I guess I have gathered enough experience and wisdom to decide that I am much better off as my own boss and that it makes no sense to put up with the consequences of other people’s mistakes.


As you see, there are many reasons behind the decision to become a freelancer. Not all these reasons are valid for everybody and it will be interesting to hear what your reasons to become a freelancer were and if you regret your decision.

All Images: Set of Funny Business Cartoons via Shutterstock


  • Piet

    having been a freelancer for some years there are a few misconceptions with some of the points you mention, namely:

    – more money: you forget that when working for someone, there most like was a person or team taking care of sales, meaning you were always coding/designing away. When you become a freelancer, some of your time you need to dedicate to sales, otherwise you will soon have way too much time on your hands.

    – better work-life balance: I would say it’s more like to be completely the opposite! Once you are working from home, you will be glued to your computer and there is hardly any incentive not to work. Having “a quick peek” before going to bed results more often than not in being stuck in the office for many extra hours.

    just my two cents 

  • There is nothing better then take your career and destiny in your hands, that’s challenge and you can test your skills and how much you really worth. If you love to compete, learn, prosper there is nothing to think about, otherwise just skip it and look for good company, also it is recommended to ensure support from family and friends before switching to freelancer.

  • Aaron Chancey

    I am interested in becoming a freelancer.  How did you get your start?  How did you find projects to work on?  Isn’t some of freelancing have good contacts?

  • Henry Veldman

    This was written by a person who’s career seemed to been dominated by having been surrounded by incompetencies or just plain losers. To me, that is the exception.
     Agree with Piet (Dutch?) that there is little incentive “not to work” and you end up working many more hours.
     What I miss most is the “learning by osmosis”. The conversations in the next cube that would spark my interest. I would discover a whole new subject, method, whatever that I did not know about.
     I find that I get better in the subjects that I was good at but I find it difficult to enter a complete new subject (translate to “computer language”) or techniques.
     That said, I love what I call “FeeLancing”

  • chad

    i’ve been a freelancer since 6 months (fresh), and i chose this path for the following reasons:
    – Being my own boss: I am a leader type, i like to take my own decisions
    – More creativity: i am a creative person and i find working for a boss kills creativity, because you will be “fixing” stuff most of the time and not “creating” stuff. Your creative skills become more automated scripts
    – No corporate politics and scam: no need for meetings everyday  (that serve for nthg other than complicating stuff for no reason). No need to “Fake” smile and do all kind of modern lifestyle folklore’s (i have never done them before anyway)..etc..
    – Better quality of life: I can eat healthy meals i cook when i am working from home. I can go to the gym whenever my brain gets stuck. Also it might be beneficial for when getting married as it is possible to spend more time with the wife and kids.
    – Last but not least, the need for feel “free” is the main drive behind this choice. Each person has a unique talent: some are meant to work for a boss and live all kind of modern living work folklore’s, while others operate better when they choose their own destiny and create their own projects( i am one of them)

    I believe in a famous quote for “Steve wozniak”: “Most inventors and engineers I’ve met are like me — they’re shy and they
    live in their heads. They’re almost like artists. In fact, the very
    best of them are artists. And artists work best alone —
    best outside of corporate environments, best where they can control an
    invention’s design without a lot of other people designing it for
    marketing or some other committee. I don’t believe anything really
    revolutionary has ever been invented by committee… I’m going to give you
    some advice that might be hard to take. That advice is:
    –>Work alone… Not
    on a committee. Not on a team.”

  • adaivanoff

    @ Piet: Well, maybe as much as I try to generalize, I can’t escape from my own background. I am not purely tech, I do have a sound business/sales/marketing background and for me this part of the process is the easy one. It does take time, though but I don’t put it in the Work category at all. But some of my friends, who are purely techies, have really hard times with this. Some of them even try to get me to become their sales agent because for them all these talks with clients are a nightmare.
    As for the long hours, it’s what you to do yourself. :) I must admit that for most of the time I am in the long hours category but it was the same while I was working for various companies. 

    @Henry: “This was written by a person who’s career seemed to been dominated by
    having been surrounded by incompetencies or just plain losers.” You hit the nail on the head! I do consider the majority of my former bosses, coworkers, and subordinates incompetent or just plain losers. And I have worked for huge corporations, mid-sized companies, and small companies, most of which were among the leaders on their market! I definitely don’t miss this because when you are surrounded by losers you soon become one of them. I’ve lost a couple of friends this way. After a couple of years in a corporate environment they became such idiots in terms of personality and expertise that we just had to part ways. :( As for contacts, don’t online forums give the same feeling? I usually don’t have the time for this but when I do, I find quite a lot of interesting things there, including by people I know personally.

    @Aaron: I think the safest is to start part-time while still working full-time and see how it goes. I am a bit skeptical towards sites such as Guru or Elance but I know many people who started as freelancers thanks to such sites. Personal contacts always help – sometimes you can land projects solely by personal contacts.

    @Bojan: Exactly, as a freelancer you see how much you are worth. You don’t have the security of the corporate job but you have freedom. And yes, support from family and friends is really paramount.

  • Terry

    This is my 27th year freelancing. I have been able to keep this “job” through lean times because I have a husband with a good job. If I had to be the breadwinner, I dare say I would have been looking for full time employment. I could have worked harder at it, but I was raising two kids and keeping the house going. Now that my nest is about to become empty, I am SO happy I kept at it. I can now dive in harder to make a different set of dreams come true.

    Advice…work hard, be flexible, stay current, be willing to give up some of the awards and accolades for peace and quiet. Build a great space for yourself, and be the master of your domain!

  • Me

    Thanks for taking the time to write this article, and thanks for the comments from everybody. For someone like me who is mulling the idea of jumping away from the “idiotisms”(!) of working for a historic company and going freelance i’ve read loads on the subject hoping to find something that frees me from the crippling fear of actually doing it! I think that being a developer in a non-technical organisation brings a LOT of what you say into reality, so much so that being a freelancer seems like the only way you can get in control of what you are doing instead of having what you do dictated to by people that use websites so must be experts.

  • Steve Naidamast

    Up here in New York, it is somewhat difficult to become a successful freelancer in the IT profession but it is being done.  As a result, I have opted for that in-between role of a senior consultant with an agency.

    After my time in “Corporate America”,  which is quite a bit, I agree that most of the business situations I have worked in are fairly bad even if I had great colleagues.  As a result, I am no longer interested in being an employee for anyone.  If I am “on the bench” for a while until I get my next assignment so be it…

  • Mike L.

     Have been a freelancer for 30 years. Love it. But freelancing is not for the insecure. No company health plan. No company pension plan. No paid vacations. No paid sick-days. No paid holidays. No corporate perks. Higher tax rates ….

  • Redquicksilver

    I’ve been a ‘freelance’ software developer for 12 years now and find the article a little patronising if not just plain wrong in my experience.  The reasons to go ‘contracting’ are to earn a lot more money and having more time off.  A few years ago, due to the economy and downturn in this industry, I opted to take a permanent position for a reputable company for a very healthy salary, (around £90,000 per annum, that is UK Sterling so probably around the $145,000 in USA) but the tax killed me, and the lack of holidays – the company only allowed its staff to take up to 2 consecutive weeks off a year.

    After 1 year of doing this, and earning a miserly £3,500 a month after tax I went back into contracting which is where I should have stayed.  I am now back to earning a take-home salary of around £6,000 a month, (which is just short of US $10,000 a month) and in full-time employment terms equates to around £180,000 per annum, (or $300,000 a year).  Now you tell me that you can earn that sort of money working for a company!

    Not only that, but I choose to work around 40 weeks a year and generally take off July and August each year to enjoy the summer holidays with my wife and children.  There are not many, (any) employers who would be fine with me taking 2 straight months off every year, (as well as time off througout the year at Christmas, Easter, etc…)

  • adaivanoff

     Freedom comes at a price and life is not a bad of roses but what I’d recommend is try some freelance while still at a job and see how it works for you.

  • adaivanoff

    A consultant’s position is also an option. If the agency finds the projects and you get a fair share of the profit, this is also better than being a nameless employee in some huge corp. The typically unsteady cashflow is a big problem when you live in an expensive area as NY is, or when you are the breadwinner in the family.

  • adaivanoff

    I already said it that freedom comes at a price. :) Despite everything, for me the perks of freelancing beat the insecurity.

  • adaivanoff

    You prove again and again that you can make more money when you work for yourself rather than for somebody else. Not everybody can achieve this, so you can’t say that when you are a freelancer this always translates to more $$$$$ and months on the beach but the chance for it is much higher when you are your boss. :) 

  • adaivanoff

    Thanks for the input, I loved the quote from Steve Wozniak and I agree 100% with all your reasons to love freelancing. I though I was a rare animal because none of my freelance friends considers the healthy eating benefits option a perk of freelancing – some of them eat pizzas and burgers all the time and they can’t understand what’s so cool about cooked meals, for instance. The fact that you make your schedule is really a huge perk. :) As for ‘fixing’ vs ‘creating’ I again totally agree – the ‘creating’ is the bait to get you onboard a company, then you go ‘fixing’ till you get familiar with the products and all of a sudden it turns out you are so good at it (and nobody else is willing to do it) that you will be fixing the unfixable till the day you retire. :D

  • adaivanoff

    Great advice, especially for women. One of my closest friends who is a really talented designer almost gave up her career while raising her kids. She just didn’t want to work freelance (or to work at all, to be honest) and planned on very extended motherhood (like till the kids get in their 30s :))) but her husband kicked her back to fulltime work, which only did her good because she didn’t have the time to forget everything. Otherwise, she would have been done with design, if she decided to return to it 10 years from now. One needs to balance life and work and freelancing is really suitable. It gets a bit harder when both of you are freelancers, as was the case with me and an ex-boyfriend of mine but in our case the real problem were our disastrous cashflow management skills. :) We didn’t starve (or at least not literally) but it would have been useful to happen for a couple of weeks because it would have taught us to manage our expenses and receivables in a more responsible way. :)

  • Tyler Lesperance

    Henry makes a good point which I am working on right now in the earlier stages of my design career.  My goal is to one day freelance and by my own boss but right now I find it more valuable to work at a company where I can learn from those around me.  I find it incredibly useful to be able to ask someone in my office a question when I am stuck.  Being able to work with people and learn through osmosis, observing, or discussing is something that will help anyone with their own designing/coding/creating/whatevering career.

  • Harmony

    Great article, thank you :) I love freelancing for all those reasons and plenty of others, like being able to take lunch as late in the day as I need to, sometimes going for a really long walk to give myself some headspace and not worrying about a boss back at the office watching the clock to see when I walk back in. I especially love being able to work without the constant interruptions so typical in a normal 9-5 job (team mates, bosses, phones, meetings etc).

    But you’re right, it’s not easy, and it’s not for the faint-of-heart. It’s hard, it’s scary, it requires very long hours and tough decisions, it’s something you have to fight for nearly every day. But it’s so so worth it.

  • Agreed on the work life balance, all my friends think that since I work for myself I can take the day off whenever I want, when in reality I just feel more pressure to work on weekends (aka now as I’m writing this instead of being outside enjoying the sunshine).

  • Chad

    “ the BAIT …”, veryyy true! as for healthy eating, you are on the right way. There is nothing like good quality food and exercising to boost your body and brain with energy and good visions. You become sharper, healthier, faster and more pragmatic. Don’t blame your friends, the concept of nutrition is underrated worldwide because no body understands how there is a direct connection between your mood/morale and what you eat and exercise! check this quote by “Thomas edison” :”The doctor of the future will no longer treat the human frame with
    drugs, but rather will cure and prevent disease with nutrition.” Keep it up, you are on the right track, they should follow you.

  • Neo

    This comment was written by a person who might not have experience “real FreeLancing”. You see, sometimes freelancers work in a team rather than just working alone. And at that point, there is no “cube” or “cage”, they all stay in one room and invest time discussing with each other, innovating new stuffs…  Freelancers have more independence to use the Internet and harvest all kind of information (unlike in a previous company where I worked, I was not allowed to access many websites and information sources). The “learning by osmosis” process, I believe, works better in such circumstances :)

    That said, I love what I call “FreeLancing” :) :) I FeeLanced before, but somehow I think the restrictions, the low salary, the scary boss and the political environment was not allowing me to grow as much rapidly as I expected. Guess I was lucky to find my own dream team at the right time and quit my job.