Things You Need To Know Before Choosing Life As A Freelancer

Abandoning the office world for life as an independent contractor has its appeal, but there are significant downsides to cutting the corporate cord to make a go of it on your own. The bonuses of breaking free of the standard workweek come at a considerable price.

Black Freelancer breaks some of the cons of a freelance life. If you lack discipline or the ability to motivate yourself, you’ll be at risk of falling short in several areas, including the struggles of setting aside money for taxes, managing your time and working without a boss hovering your shoulder.

A major dealbreaker for anyone considering going their own way is the matter of health insurance. Those with lingering medical issues may find that the costs of buying insurance and keeping up with medical bills can drag down a profitable operation.

Check out the post for more warning signs along the road to being your own boss.

5 Reasons You Don’t Want to be a Freelancer [Black Freelancer]


Edit Your Comment

  1. KyBash says:

    The worst part about working for yourself is that when you call in sick, you know you’re lying.

  2. Tacojelly says:

    Let me put it this way, 60-70% of your job as a freelancer is finding more work.

    Enough said.

  3. TuxthePenguin says:

    This ties back to another post – you better have a HUGE emergency fund to fall back on. The first few years of running my own firm (I’m a CPA) there were many months with so little income that it felt insulting cashing those checks.

    The biggest thing I tell anyone who wants to go on their own – there are no vacations. You will eat, sleep and breath your new job. If you’re not working (and have no employees), you’re not making money. It took about two years before I had enough business to hire someone to help.

    • TuxthePenguin says:

      Also, if you’re going to freelance, make sure you have a good, experienced CPA to help with all the tax situations that come up, not to mention highlight things you can do to help reduce out of pocket expenses. Even I have a CPA that I work with when filing my taxes.

      • Bsamm09 says:

        I 2nd this. You will end up saving more time and money getting it set up right in the beginning. I spend way more time correcting errors and re-classing income/expenses when someone does it their selves than when it is set up right. It more than pays for itself.

        This goes double for partnerships, s-corps and LLCs.

  4. The Happy Homeowner says:

    Too many people are tempted by the allure of being their own boss & jump in too quickly without doing their research. There’s also a misconception that it’s “easier.”

    • KyBash says:

      When you own your own business, you only have to work half a day.

      Either the first twelve hours or the second twelve hours . . .

  5. Ahardy55 says:

    Another reason:

    A company my wife was doing freelance dev work for went under. They owe her $8000 dollars and she is currently getting repaid to the tune of just $250 per month.

    • Velvet Jones says:

      This is a risk in any business. If you’re small it is hard to absorb the loss when people stiff you. For all of the horror stories of bad contractors and shady repair shops you rarely hear about the other side. I’ve known several construction contractor and an auto repair shop that closed up shop many due to people stiffing them constantly. If your a two man enterprise it is tough to handle someone skips out on a $20,000 job. I was amazed at how even large companies deal with this. One of my first jobs out of college was working in a data center. I would print out the past due bills for the company once a month. There would be clients, often local or state governments, that would have bills over a year past due, with balances of $100k+. So much for ethical government.

  6. Fubish says: I don't know anything about it, but it seems to me... says:

    “Freelancing don’t mean you ain’t workin’ – it just means you ain’t eatin’.”

    – P.T. Bridgeport (Paraphrased)

  7. Ahardy55 says:

    Another reason:

    A company my wife was doing freelance dev work for went under. They owe her $8000 dollars and she is currently getting repaid to the tune of just $250 per month.

  8. Hi_Hello says:

    tooo many paper works ….and I’m too lazy to do it.

  9. vliam says:

    1. You don’t need a degree to do it.

    /sorry, computer science graduates

    • Buckus says:

      You don’t need a degree to do most things, but you better know what you’re doing.

      • Cat says:

        Many people *with* a degree don’t know what they’re doing.

        [points at office next door]

        • dolemite says:

          *points to self*

        • Buckus says:

          While I’ll agree with that statement, in general, if you counted up all the people with a degree and those without a degree in any given field where degrees are generally preferred, the people with a degree will have a higher percentage of “knowing what they’re doing” than those without.

  10. BelleSade says:

    You’ll be be broke for the first few years if not always. You probably won’t make as much money as you did before for a long time so budget accordingly and do have back-up money. Your income will not be stable, also, so don’t blow the great money you made one month and then be screwed over next month. Connections mean everything.

    And those are the things I wish my family had done before they all decided to freelance >:-|

    • nishioka says:

      > Your income will not be stable, also, so don’t blow the great money you made one month and then be screwed over next month.


      Some weeks I make $400 or $500 from my freelance stuff (I already have a full time job, this is just a supplement), other weeks I make $25. Always best in an arrangement like this to plan your finances like you don’t have that extra money coming in, then when it does, it’s a bonus.

  11. SporadicBlah says:

    I’ve been freelancing for a year this month. Its TOUGH thats for sure! After loosing my job last year I decided to make a go of it on my own. It has its perks but you really, really, REALLY have to budget to make it work. Did I mention you have to budget? In addition to a really good budget you have to be able to control your spending habits. And budget. :D But I honestly love it and finding the odd part time jobs is really fun. Just last week I met with a lady that runs an apiary looking for a person for 2 days a week. It possibilities are endless! Now I have two college degrees I really don’t need. Wish I had all that time and money back.

  12. goodcow says:

    If Republicans are pro-small business and want to spur entrepreneurship, shouldn’t they adopt national healthcare since it’s such an expensive burden to the small business owner?

    • Cat says:


    • Skyhawk says:

      Or, reduce the tax burden of 40-50%, enforce immigration laws, and means-test any government benefits.
      Then, you wouldn’t need to add a government program on top of the government programs that necessitate it.

      Eliminate federal mandated coverage that jacks up the price of health insurance.

      As a single guy, WHY does the federal government mandate that my insurance covers pregnancy?
      That’s just one of many.

  13. sirwired says:

    I’ll add that you now get to do all the boring administrative tasks yourself that have absolutely nothing to do with your actual job.

    Did you go from Working For The Man to Freelance Web Designer? Congratulations, you are now an accountant, salesman, tech service rep, salesman, benefits manager, salesman, marketer, IT person… oh, and did I mention sales?

    Seriously… lots of people view “working for the man” as: “The Man makes profit off of my hard labor! If I was working for myself, I get to keep that money!” I view it as “In return for this thing called ‘profit’, The Man takes care of all the boring $hit I don’t want to deal with anyway when working in my chosen career.”

    • Cat says:

      In general that’s true – until you reach a point where you ARE the man, and have other people to take care of all that boring shit for you.

      • sirwired says:

        And then you aren’t a freelancer any more. But boy, do you have to go through years of grief, low-pay, and heartache to get to that point.

  14. Apeweek says:

    I’ve freelanced for 25 years. Many people in today’s economy get forced into freelancing – they didn’t choose it.

    It can be the worst of all worlds – extra taxes plus no benefits.

    To make it work, you’ve got to stop thinking of yourself as an employee – you’re a small business. Aggressively pursue tax deductions. Negotiate decent rates for yourself.

  15. Dallas_shopper says:

    My father ran his own business for nearly forty years. I barely saw him during the week when I was a kid.

  16. Dave on bass says:

    This kind of thing is why I freelance on top of having a dayjob. It gives me the feel-good part of being able to do my passion and make a few bucks, but I am not dependent on a steady income from it to feed my family.

    Maybe someday, though, I’ll have enough steady work to at least cut back on the dayjob dependency.

  17. StatusfriedCrustomer says:

    I hated freelancing. I was constantly checking Facebook to make sure I didn’t post anything that would cause me to have to fire myself.

  18. HogwartsProfessor says:

    I did it last year to supplement my income. Now I don’t have a job. I would do it full time if I were married to someone with great health insurance. But because of that, I have to find a full-time job with benefits.

    This whole tying your insurance to your job thing has got to go. If I could work part time and freelance the rest of the time, that would work also but I have GOT to have health insurance.

  19. PortlandBeavers says:

    Just remember to charge enough. Beyond the health insurance is the fact that you have to pay the whole payroll tax, not just the employee part of it.

  20. samandiriel says:

    I’ve been a freelance IT consultant for four years now, and I make a pretty decent living. Thankfully I also live in Canada, so health care premiums aren’t the issue they are for my US counterparts (although I did do my first year freelancing for myself in the states before moving back to Canada). There’s a lot more govt small-business-friendly infrastructure here, which seems very odd given that the US is supposed to be a bastion of capitalism and the little guy, and Canada is often demonized for being a socialist democracy.

    Personally I contract out things like taxes/accountancy, etc. Makes my life much easier, and professionals do it better than I ever could anyway.

    I have to agree that self-discipline is certainly important, and after that the ability to drum up new business. Networking is absolutely key, as regular advertising almost never lands you the nice fat contracts.

  21. jcfiala says:

    As it happens, freelancing went pretty well for me, when I fell into it by accident. However, there are unique factors – I’m highly skilled in a CMS (Drupal) which currently is suffering from a talent shortfall. Between my experienced background and that shortage, I found jobs falling into my lap, often for months at a time, which more than paid my bills. I got lucky, though.

    I’m no longer freelancing due to the insurance problem, however.