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Why Freelancing Sucks

March 26th, 2008 by Bob Bly

GM, a reader of this blog, posed a question to me recently.

“Bob, you say that the freelance life has a large number of pros ? and probably an equal number of cons. What would you say is the #1 drawback of being a freelance writer?”

I think there are as many answers to that question as there are freelance writers on the planet.

I talk with a LOT of freelancers. Among their most common complaints are clients who: don?t like your copy ? ask for endless revisions ? haggle over fees ? rewrite everything ? want copy written overnight ? never return calls ? or don?t pay their bills on time.

For me, the biggest drawback to self-employmentn is the outrageous expense of paying for private health insurance. The annual premiums for our family are now equal to the annual salary I earned in my first writing job out of college, as incredible as that sounds.

Every month I write that huge premium check, and it makes me sick. Then, when we file medical bills for reimbursement, they send them back again and again for verification or more information — improving their cash flow by delaying our check.

The freelance life isn’t all beers and skittles. What bugs YOU about being a freelancer? What’s YOUR biggest headache in your freelance writing business? I’d love to know!


This entry was posted on Wednesday, March 26th, 2008 at 11:44 am and is filed under General. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.

70 responses about “Why Freelancing Sucks”

  1. Matt Johnson said:

    I agree with Bob. All those other things that freelancers complain about can be fixed or at least managed. And the fact is they happen with any service related business whether you are in corporate America or on your own.

    What drove me out of freelancing was the fact I couldn’t get healthcare for my wife and probably couldn’t have afforded it if I could.


  2. Paul said:

    I gotta ask.

    Why do people nowadays feel that health insurance is an absolute necessity.

    We’ve come to think that good health is a right, not a privilege, and certainly not a responsibility of our own, so we’ll hand it off to the powers that be, and wonder why they charge so much for it.

    With some obvious exceptions, if you add up many major medical expenses, the price of paying for the procedure outright in cash (most hospitals give a cash discount), is often less than a years worth of premiums.

    My wife and I found that out with the birth of our first child that included complications for both her and our son.

    Anyway, sorry for my rant, but I wish health insurance were my biggest problem.

  3. SA said:

    I’m not a freelancer but I have a huge problem with freelancers because they never have time to meet friends, GM being a case in point.

    health insurance in India is btw not a complete necessity. and the healthcare is fantastic.

  4. Bob Bly said:

    Paul, SA: health insurance in the USA IS a necessity because of the outrageous cost of health care. If you get a serious illness requiring surgery (cancer, heart attack), the bill can easily run to $100,000 or more.

  5. Brandon W said:

    My main reason for supporting a universal health care system in the U.S. is that I believe the corporate-supported system is a hindrance to entrepreneurialism. That, in turn, is contributing to the destruction of our economy. The other reason I support one is due to a long piece I wrote about 5 years ago about U.S. health care. The overhead in our “free market” system is over 20%. That is, over 20% of the money that is paid into the system evaporates in administrative costs. The universal systems run around 4-5%. They’re simply a more efficient use of resources. And isn’t THAT supposed to be what economics is about?

  6. SpongeBob Fan said:

    I wish I could buy a catastrophic policy covering the HUGE problems like cancer and/or getting hit by a bus (with months in intensive care).

    Unfortunately, here in Massachusetts, the policy I have to have covers things I will never use — including chiropractic and maternity.

    From what I hear, they’re also thinking about adding complusory coverage for stomach-stapling and sex-change operations!

    Being forced to pay for things I will never use – that’s what breaks my heart! (But not my spirit. Who is John Galt?)

  7. Dina at said:

    Hi, Bob,

    I would have to say that this month, non-paying clients are getting my goat.

    I almost never have to go chasing after payment. I like to think that’s because I have a sixth sense for knowing what clients might be a risk, and avoiding those.

    I have two people on my Hit List this week and in my head there are revenge plots brewing.

    What makes it even crazier is that they’re both small business owners. You would think that someone who is in the same business as you are would have more respect for others’ hard work.


    Have a nice day, Bob.

  8. Craig Hysell said:

    Three reasons why freelancing sucks (for me):

    1. Keeping a consistent base of work when just starting out.

    2. Clients that change copy thereby, in essence, telling me I don’t know what I’m doing and insulting me. Upon which I must take more time out of my day to prove to them to leave it they way I had it so that the message we want to get across remains clear. (Which I guess is alright at the moment since my work is inconsistent.) This happens almost every time. And every time, once I explain it, they leave it the way it was.

    3. Clients that string out that final payment or get mad when the bill increases after my “up to two rewrite rule” is put into effect (which is clearly stated in the contract that was signed by said client.)

    My problems with the health care system in this country (U.S.) cannot possibly be summed up here. Suffice to say that I still enjoy working for myself more than anyone else.

    If only it were a bit more consistent… :p

  9. Bill Hilton said:

    Although it’s a lot less than perfect, we have the National Health Service over here, so healthcare is lower down the priority list.

    The big downer for me is only being paid for the hours I work. If I take seven days off for a holiday, I lose about ten days pay (the days away, plus three days wrapping up beforehand and sorting out the inbox when I get back).

  10. Bob Bly said:

    Bill: That’s why I started a second business selling information products online. On my last week-long vacation, I earned zero dollars from my copywriting business. But I made $5,743 on the Internet even though I never even went online!

  11. Kristi Holl said:

    The ongoing hardest part of freelancing for nearly 30 years and raising kids has been the cash flow issues. Feast or famine! I am a great budgeter and very frugal, making an advance last 6-9 months if necessary, but delayed advances, pokey royalty statements, late payments by magazine publishers, etc. have caused the most headaches. Family health insurance was #2.

  12. Bob Bly said:

    Kristi: The best financial advice I ever heard for freelance writers was at a writer’s conference, where a panelist said: “Live below your means.” It sounds like you do that, which is wise. I used to do it (I am a tightwad), but then I got married, and have a family that likes to spend money, which I don’t.

  13. Jodi Kaplan said:

    Health insurance! If this helps, there’s been an extended discussion on this subject in the NY Times Shifting Careers blog. It also lists several helpful resources.

  14. Geoff said:

    After leaving the 9-5 ranks I wrestled with a couple of “individual group healthcare plans” that only seemed good at continually raising premiums. A few months ago I joined NASE (Nat’l Association for the Self-Employed).

    They carry a plan underwritten by MEGA that is a very good 70/30 PPO package. In addition, the kids get blanket coverage through California’s Healthy Family program.

    It’s mostly catastrophic, which I prefer anyway. Plus, with the return of premium rider, I get every cent back tax free in 20 years minus any claims.

    I have to say, I’m pleased all things being equal.

    So finally, health insurance isn’t my #1 issue.


  15. Jim Kirk said:

    The biggest problem is clients who don’t pay, or who don’t pay within anything resembling a reasonable time frame. You can’t budget anything since you don’t know if the client is going to pay , is going out of business, or is going to require you to go to court to get your few hundred dollars!

  16. Melanie said:

    Thanks to having a spouse with a “regular” job, healthcare is not my peeve. I am a happy freelancer with a diversified palate of writing and editing and project management. So, at the risk of making everyone groan, my problem is time–and the fact that few people seem to respect mine.

    Some people think I’m sitting around doing little to nothing and can therefore be waiting by the phone to answer their calls, or babysit their children, or run their errands.

    So, yeah, it could be a lot worse. After working in offices and for myself, I’d have to say that–all things considered–freelancing doesn’t suck for me. Except when I have to do taxes. I hate taxes.

  17. SpongeBob Fan said:

    Melanie –

    All I can say is … get an accountant! It took me YEARS to convince my husband and now he would never go back to doing ours himself! NEVER! It probably costs less than you think … and it’s worth 10x every penny! March & April are happy months now … well, except for the p-a-y-i-n-g the taxes.

    My best friend works for a big mutual fund co. and they have astonishing benefits, plus the fact that her dept/job is very much 9-5, so it’s not like she’s there night & day. And she’s right in the middle of the big city every day. I miss that, and I would love the benefits she gets. But she wishes she had my job – writing from home. So, it’s probably one of those greener-grass things, impossible to ever really sort out.

  18. Stephen Kimball said:

    Man, I must be spoiled. I love being a freelance writer! Best decison I ever made. Insurance? I hate paying ALL insurance. But good clients make it an easy payment.

  19. Dianna Huff said:

    Melanie — I second SpongeBob. I haven’t done my taxes in years. It is worth *every* dollar to have the accountant do it. He does my corporate and our personal taxes.

    Second, tell all callers, door knockers, and emailers that are not clients that you are not “at home” but at work. Sometimes you have to be plain out rude but once people “get” that you’re working and not eating bon bons, they leave you alone.

    Jim — Get a 50% deposit before beginning any job. And do you get signed contracts? Another copywriter I know gives a 2% discount if the client pays in full up front.

  20. SpongeBob Fan said:

    Melanie – I second Diana with the interruptions. The phone has to be the easiest – get Caller ID and screen. With the others, tell ’em you’re on deadline and tell them when you can help, if that’s what you want to do. (P.S. Make sure you’re not your own worst enemy here … have you set firm “office hours” in your own mind?)

    And Jim, Diana’s right on the money too. Any client who won’t give you 1/3rd to 1/2 up-front is probably trouble anyway!

  21. Lou Wasser said:

    If you think that freelance writing is anything less than a noble profession in this difficult time, try this on for size:

  22. Ed Gandia at The Profitable Freelancer said:

    I have a great accountant. I have great clients who are reasonable and pay their bills on time. I’m even happy with my self-employed health insurance, believe it or not (that’s another post).

    But what I can’t stand is how bad Uncle Sam stabs you in the back when you’re self-employed. You get hit with the full 15.3% payroll tax (here in the U.S., your employer pays half of that when you’re an employee…but you pay it all when you’re on your own).

    You then have massive federal taxes. And I also have to deal with state taxes. Thankfully, I don’t city taxes to deal with, like many of my peers in the northeast!

    But really, guys. We have our priorities backwards in this country. Our tax system is a disaster. We abuse the little guy, the small-business owner who provides most of the jobs in this country.

    We take progressively more from you as you become more successful (thanks to our progressive tax system), and we don’t even say “thanks.”

    I would love to expand my busienss and hire people. I’m that busy. But I’ll never do it. Too many regulations. Too many taxes.

    I mean..why should I continue to bust my hump when the government is taking half of the revenue I generate? That’s right, folks. Don’t fool yourselves. If you make about $80k or more, you ARE paying about half of your gross earnings in taxes (fed, state, local, sales tax, property, etc.)

    Let’s not forget that no great nation has ever taxed itself to prosperity. Ever.

    Wow! Glad to have that off my chest!

  23. SpongeBob Fan said:

    Uncle Sam gets the employees too – employers aren’t paying “their” half out of the goodness of their hearts! Or at all!

  24. Dianna Huff said:

    Ed, I’m with you. One reason I have not hired employees is due to taxes and regulations. And paying that monthly payroll tax bill every month hurts. Thankfully I’m able to mitigage it with my self-employed 401k. Every freelancer should have one. If you don’t think so, go read, Automatic Millionaire by David Bach.

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  26. Bounce House said:

    I hate the most the clients who believe they know how to do this and that and tell me how to do my job. And the worse part is that, if they are experts already, why do they need me anymore?
    Did they ever consider that maybe they don’t know a thing and they just like to look smarter than they are? easier not to ask themselves that.That is my problem as a freelancer…”smart” client knowing it all

  27. Sheri Cyprus said:

    I’m a bit late for this post, but I enjoyed reading the other responses. I’m Canadian so freelancers do get what they say is health insurance, except dental is not included. Teeth are a part of physical health so I don’t get why it’s not included. I cannot have any sort of dental plan and my dental health suffers greatly for it.

    The equally bad thing about freelancing for me is the lack of consistency in work. I’m self-supporting so my housing costs and bills are all up to me and while sometimes I make $50 an hour, if I don’t get enough work it may dip down to an average of $10 which is difficult to live on.

    If I could just get about 10 good paying, regular clients I’d be so so happy! 🙂

  28. Sheri Cyprus said:

    I just want to add that, ironically, clients generally rave about my copy and don’t ask for revisions!!!! It’s just that they only need my services every few months and I need steadier work. sigh.

  29. Jessica said:

    My biggest complaint is that the freelance writers who leave me multiple e-mails when I log off. Don’t they realize I have a life too? And then NOTHING I ever do is the right way for two of my clients (one who fired me and one who I finally dropped). So yeah not exactly happy. Thinking about tossing in the towel.

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