12 Reasons You Shouldn’t Freelance

[tweetmeme]Going into business for the wrong reasons can bring ruin into both your financial and professional life. While freelancing comes with many perks, it’s important not to base your self-employment decision solely on those perks, as you may run yourself out of business.

What are some of these perks of freelancing?

  • You can choose your own hours
  • You can choose your own clients
  • You can choose the type of work you do
  • You can choose your rates

We’ve discussed great reasons to start freelancing, but we haven’t really talked about why you shouldn’t start freelancing. Let’s take a look at some of the worst reasons to go into business for yourself.

Reason 1: To Sleep in All Day and Leave Work Early

It’s true that as a freelancer, you can set the hours you work. However, if you think that means you can sleep in all day and get off early, you’ll be sadly disappointed.

Clients still expect you to keep some normal business hours. While it’s ok to shift your schedule to times where you’re most productive, you’ll still have clients who request to speak to you by phone during nine to five hours. Limiting your work hours to starting at midnight and ending at 3 a.m. will cause you to lose a lot of potential business.

Reason 2: Freelancing Will Make You Rich

If you want to start freelancing, you shouldn’t do it solely for the money. While you’re free to set your rates, chances are you’ll have little or no money when starting out. Making tons of cash, even if you’re a seasoned professional, is pretty unlikely.

Reason 3: You Hate Working with People

Sorry to burst your bubble, but even if you plan on working by yourself, you still have to work with people. You may have to work with clients, agencies or other freelancers.

Reason 4: To Spend the Day with Your Kids

Unless you’re planning on only working part-time, expecting to be able to spend ample amounts of time with your kids is a huge potential pitfall. Once you get your business going, you’ll rarely have time for lunch and bathroom breaks; much less to change diapers, have playtime and offer help with homework.

Plus, if you’re not careful, staying at home with your kids can be a huge distraction and prevent you from getting any work done. Especially with younger kids, the temptation to spend time with them can often throw a productive day out the door.

This isn’t to say freelancing isn’t a good option for stay-at-home parents. You just have to be realistic in your goal settings and realize you’re not going to be able to be as productive, busy or profitable as a regular freelancer.

Reason 5: You Can Charge Whatever You Want

Related to Reason 2 above, you can’t simply charge any amount of money for your work and expect anyone to hire you. Your rates have to fall into what the market can bear and take into account your quality of work and experience you offer.

Of course, the busier and more well known you become the more you can charge to “fit” in those clients or schedule them in months ahead of time.

Reason 6: Freelancing Is An Easy Job

Freelancing is one of the hardest jobs out there. It’s one of the few careers where you’re truly alone, in the sense that you’re responsible for everything. This includes finding the work, doing the work, billing for it, tracking down late payments and taking care of the books and taxes. That’s a lot of work for one person!

Reason 7: To Keep Up with the Household Chores

It drives me nuts to wake up to a kitchen full of dishes or stuff where it shouldn’t be. However, I often have to hold back this urge until lunchtime or after work. Just like kids, it can be tempting to take just a “few” minutes to pick up the house and promise yourself you’ll get “right” back to work. Before you know it, half the day is gone and you haven’t done any work…paid work that is.

Personally, I try to have the dishes from the night before finished that night so I don’t wake up with them in the sink. I try to pick up as I go throughout the day so there isn’t a mess, or I wait until my lunch break to clean up what’s needed.

Reason 8: Work Will Just Come to You

It takes a lot of work to freelance before you even start “working”. Just sitting at your computer everyday and staring at your screen won’t get you clients.

Reason 9: No Boss!

Without having someone behind you to make sure you’re staying productive, it can be tough to stay motivated and on target. You have to make sure you have enough drive to push yourself to make it through the boring everyday tasks of freelancing.

Reason 10: You’ll Save Lots of Money

While it’s true you’ll no longer have to fight morning or evening traffic, that doesn’t mean you can sell the car and save lots of money. It gets lonely in your own office so you’ll want to work remotely a few times a week.

Often, you’ll find yourself going to your local bookstore, cafe, or restaurant to work for a few hours and you’ll probably end up spending some money there as well. After you factor in this spending money and gas, plus the extra money you’ll spend on electricity and water now that you’re home more often, freelancing can easily add up to be more expensive than a nine to five job.

I once spent a ton of money at Target when I had no money coming in because I was “bored” from being at home all the time. Don’t make the same mistake!

Reason 11: You’ll Have More Free Time

When you’re a freelancer, you’ll actually have a lot less free time than when you were working a regular nine to five job, even if you keep the same or less hours than before.

Why? The biggest reasons are overscheduling and procrastinating. It’ll take some time to properly schedule your work, but even then it’s impossible to predict if a client is going to have last minute changes or a rush project. You may even end up working nights and weekends.

Reason 12: Your Family Will Respect You More

Most non-web people don’t understand what we do at all. They understand even less what we do as freelancers. You’ll probably have some difficulty getting your family members to understand that you’re really working, even if you’re at home. They may not understand you’re running a real business and trying to make some real money.

To this day, my mom still doesn’t understand that I can’t just drop everything I’m doing in the middle of the day to do something with her. Just because I set my own hours, doesn’t mean I can make myself free whenever I want to, as I still have to take care of my clients.

If you’re married, or living with a significant other, it’s easier for them to see you’re doing real work if bills are getting paid, but sometimes they forget and may try to talk to you or ask you to do things around the house. The best thing to do is to try and talk to them and explain that you need to be left alone, as if you’re working at a regular job, during your office hours. You may need to close and/or lock the office door while you’re working to prevent interruptions.

Freelancing Is the Best Job Ever

But, it’s also the hardest and most demanding job ever. It can be frustrating because you have no one else to share the business duties with. People, including clients, misunderstand what you do and may not think you’re a real business who charges real rates for real work.

That being said, I do believe it’s the best job ever. Really, I wouldn’t go back to a full-time job, even if they offered me a six figure salary. Like everything else, it has it’s drawbacks but it also has lots of good perks.

The important thing is to make sure you really like working independently and you have the drive to do this all by yourself. The freedom and satisfaction from being able to control your own career is reward in itself.

What About You?

What were some of the reasons you started freelancing? Where they good or bad reasons? Did they work out? Please share you experiences!

Image by joeyparsons


  1. says

    Great article, thanks. I started freelancing three years ago so I could stay home with my then three year-old daughter. Totally agree with your points, especially those about spending time with kids. I purposely work part-time so I can pickup my daughter after school, host playdates and help with homework. My workload sometimes requires a full time effort, and when that happens I hire a babysitter. Freelancing is the best job ever, but it takes a lot of work.

  2. says

    Good stuff, Amber! While I agree that most of us aren’t rolling in cash when we start out, I disagree with reason #2. I truly believe that you CAN earn much more as a freelancer than you could as an employee in the same profession — if you’re smart about how you position and market yourself…and how you run your business.

    I’ve met too many people who are doing much better financially (myself included) on their own to know that this is true. It does take hard work, strategic planning and smart decisions.

    Also, I guess it all depends on what one considers “making tons of cash.” That definition will vary from person to person. But if you’re earning $50k as an employee and you’d like to double that income, it many freelance fields, you can totally do that. No, it won’t happen overnight. And it won’t happen on its own. But it’s very doable. My own income has increased by more than 50% since I went solo 3.5 years ago.

    One last point: I fully agree that no one should become a freelancer for the money alone. In fact, I don’t think you should ever do anything just for the money. They money will get old at some point (even if you’re rolling in it). So you have to enjoy the craft.

  3. says

    It worried me when I read the title of this article in my RSS feed as someone who has just gone freelance, but after reading the full article I am reassured that I am doing this completely for the right reasons.. and I thank you for reaffirming this in me!!

  4. says


    Very well written and resoundingly true. When I freelanced full time, I was fortunate to have a family that supported — and understood — my unorthodox schedule. I’ve been able to educate friends and colleagues who seek to make the leap into freelance work come to terms with the reality awaiting them.

    At http://tinyurl.com/taftat, I offer a succinct bit of advice for anyone considering a leap from the corporate world into the teacup of freelance. Your post today is
    a fantastic reality check for anyone entertaining — or newly — navigating the waters.

    Keep writing!

  5. says

    Hmm, my take:

    To Sleep in All Day and Leave Work Early: You can probably get away with one OR the other but not both. What I am saying is that you can follow your own circadian rhythms when freelancing. I work very very very well between 8p and 12p. I “sleep in” til 8ish. That’s sleeping in compared to a day job of up at 6a to shower and commute.

    You’ll Have More Free Time: Well, just by virtue of quitting work at 3 most days, I have that “extra” two hours from 3-5. Which I tend to fill up with my kids.

    You’ll Save Lots of Money: Yes,you will. Do you know how much women’s work clothes cost!?!? And gas, if you’re in a driving state? whew! and getting rid of after school childcare alone saved me $400 per month!

    I think I pretty much agree with the rest of your points though.

  6. says

    OMG! I was so cracking up! There have been so many times when I am so busy I forget to eat or use the bathroom. Reason Three – Hate Working with People – I work with more people now than ever before.

    Great post!

  7. says

    All valid points. It takes determination and a true passion to take the office to the home. That being said, never quit your day job and IMHO always ensure whatever you are doing you are doing it for the FUN and FREEDOM.. not the money~! @mattylynch

  8. says

    Good post Amber!

    While I love freelancing and would never give it up, it’s not an easy path to fame and fortune like some people assume it is.

    There’s a television commercial that used to air in my area (maybe it still does, I don’t know) that shows a man floating in a pool in front of a huge home. The man says something to the effect of “I work at home and earn ten times what I did before.” Then viewers are directed to call a toll-free number so they can purchase whatever freelancing product the commercial happens to be selling.

    The implication is that it is possible to earn lots of money without doing any real work.

    That’s not the reality for most freelancers, though. Occasionally I can take a day off and lounge in the pool (or go shopping during the week), but if I did it all the time I wouldn’t earn anything.

    As Ed points out, it’s very possible to earn a good living a freelancer. Some freelancers may even become rich. But, there is effort involved before that success can be obtained.

    This is a good, realistic post that balances the good with the bad. Freelancing is one of those things where everyone’s experience a little bit different. I think you did a good job of balancing the pros of freelancing with the cons.

  9. says

    @Ed I didn’t mean to state that you’re not likely to make more money than your previous job – I certainly make a whole lot more than my lsat full-time job – but many people are under the illusion that it’s a quick and easy way to make a lot of money (like $200k +) You’re not going to make a lot of money as a freelancer for a while after you start.

    @Allena You’re right. I tend to not get out of bed until 9 am, but that means I work until 6-7 most days. I certainly work a whole lot more hours than I did with a normal 9-5 job, because if a client has an emergency or rush job – it’s up to you, not your boss, to put the hours in.

  10. says

    Great article Amber. Some good points that people should read when debating going freelance.

    I freelanced for about 3 years and loved it. It was rough and I feel you on family members not understanding when your always at home. I started freelance directly after high school, so didn’t have a 9-5 job or the money from one to compare it to. Still freelancing a be a great choice for those able to motivate themselves to work without having a boss over them.

    I agree with you on working more hours normally. I have had a 8-5 design/development job now for just over a year and I used to work a lot more hours freelancing then I do now. Of course a lot of it has to do with how you handle your booking of projects and making sure you don’t over book, the money is nice, but gotta be able to schedule projects/clients. I look forward to getting back to freelancing in a year or two.

  11. says

    I’m actually stopping freelancing due to the income being so unsteady. I cannot stand companies not paying me on time and just the ups and downs. Too much stress! Other than that, I enjoyed other aspects for sure.

  12. says

    I have been working full time and freelancing as a web developer and all around rent-a-geek for quite a few years. I will definitely be working fewer hours when I go full time freelance this summer. I think the long hours and hard work have been a good primer to getting started on my own.

    @Kate – I understand what you are saying about getting paid. One thing I have been doing for larger projects is a phased payment plan. I get paid 1/3 up front, 1/3 at a specified milestone and 1/3 after sign off. That helps solve the cash flow issue and helps keep the customer focused on the project since they already have money invested.

  13. says

    I should just state the it’s articles like these that begin enforcing my decision to start working for a firm/company rather than aim head straight into freelancing out of college. I’m not saying that’s a bad thing, but because of where I am in my life right now, I would much rather prefer the consistency of a weekly/bi-weekly pay check rather than the stresses of freelancing. I’ve experienced enough (part time) to know that I think I’m set in my decision and later down the road decide whether or not it’s a worthwhile endeavor to get into.

    Great article!

  14. says

    All valid points, however I think freelancing *can* work for people who want to stay home/ be more accessible for their kids. I freelance out of my home and I have a 5 year old and a 7 year old. While they are at times a distraction, by in large they understand that I’m at work if I’m in front of the computer. I try to be reasonable, if it is nice out and they are dying for some extra attention I’ll take the day off, but I realize that I’ll have to make it up later. I wouldn’t trade those occasional lazy days for the world and the only reason I can do it is because I freelance.

  15. says

    Great post Amber!!

    I actually have a question about payment. Do any of your freelancers accept payment by Paypal? Do you find that this method is used by your clients? I was wondering if it would be a way to get payed faster.


  16. says

    @Kristina Of course – my point was that you shouldn’t expect to be able to have all day free for your kids – or you’ll certainly get no work done.

    @Ashley Yes, I only deal with Paypal payments and my clients love it. I don’t outsource often but normall pay by paypal or check. If a client insists on paying by check, that’s fine as well (as I don’t have to pay a fee to cash it)

  17. says

    Since I’ve been focusing on my freelance career fulltime over the last 8 months, I’ve been guilty of every single item on that list that’s not kid-related. Though substitute dog for kid and I guess I’m guilty of those too! LOL

    I never liked working in an office. I never liked the office politics, people got on my nerves, and I had to put on headphones the last couple of years to cut out the incessant white noise of office chatter. So I don’t miss the office environment at all. But working at home every day DOES get lonely and monotonous. I’m so sick of my apartment some days I could scream. (Of course, not getting a single ray of sunshine in here EVER has something to do with it. Stupid first-floor back-of-the-building apartment!)

    But I also find I don’t get hardly any work done if I move outside of my apartment. Libraries, Starbucks, anywhere…the people watching is too much of a distraction. At least at home I have the power to turn off the internet, Twitter, Facebook, etc. Outside I have no control over the people walking by. So I do most of my work at home. And I use my dog walks to get outside a bit and see the world for 15 minutes or so. Then it’s back to the cave. :)

    That outlook may look dark and gloomy to some, but I wouldn’t trade it for the world. It’s mine and I’m in control. Freelancing is tough (I work a helluva lot more, and far longer hours, than I ever did in an office), but it was the best move I ever made.

  18. says

    I’ve worked as an independent business reporter and editor for most of the past 15 years and based on that, have to disagree with your point that freelancing isn’t lucrative. The first full year I worked as a freelance writer I made more than my salary as a daily newspaper staff writer, and I worked at one of the top 25 papers in the country. Within five years I was making more than I ever would have if I’d stayed in newspapers, especially if I still worked in papers today. I took some time off for family reasons, which affected my income, as did the recession last year. But over all, I’d have to say freelancing can be quite lucrative. You just have to approach it as the business that it is, as you put it so eloquently in the rest of your post.

    Michelle Rafter
    WordCount: Freelancing in the Digital Age

  19. says

    I am working as a Freelance from last 4 years and well known with every aspects from the field . . yet Its not preferble to work as a freelanace in Pakistan cause PAY PAL don’t work well here

    Yet good things have to come .. those who are willing to work as a freelance from Pakistan have them self ready set go

    Set Your own Goals .. No Boss .. that’s the charm

  20. says

    Very good article. I like your approach – it’s almost more like “Bad Reasons to Freelance” than reasons you shouldn’t freelance. Reasons 1 and 11 kind of tie together and are the most common ones that I come across.

    I think it’s just true across the board that anything worth having is worth working for, and the work isn’t optional ;)

  21. says

    @Amber thanks for these points. True, As a computer science graduate I am working with website development for 4 long years. But I feel like I am not succesful aciving the goal as a freelancer. I faced lots of ups and downs in my way. Even for 1 long year I had to changed my field to Textile business. Another problem I am facing at the moment is different enveronment. My origin is Bangladesh where you can find lots of website developer but they can not improve their point of view to international level because of lack of resources. I was quite succesfull there as a freelancer, because within my limited resource I was better in that small enveronment. But when I here in UK for my masters, with lots of dream and sense that “I can do better in place of unlimited oppertunity”, I was really upset. I had start from very beginning and compete with lots of international talented designers. Things started getting getting tough for me but now I am coping up with these issues. I am trying my best to improve myself still. Freelancing surely is not easy, I know by going through hard way.

  22. says

    Most of the issues presented here have been a problem for me too, as a fulltime freelancer. Since getting back to the “normal” job wasn’t a possibility for me, I took the freelancing “train” with all strength and energy I could. It’s not easy. I work A LOT, it’s stressful, I have to schedule everything and be organized. Contrary to others’ belief I do make MORE money then before. Let’s say that after 6 months of work I have tripled my “wage”. I still have small rates and am increasing progressively. This way I’ll be able to earn even more. Once you get accustomed to the schedule and the realities of this business, it’s getting easier.

  23. says

    Well, earning depends on the location also. I am from Serbia, and I worked for IT company from Canada (they have offices in Serbia), and I was paid $5 (yes 5) dollars for hour, and that’s considered here to be a lot. As a freelancer I can form much realistic work prices, and I am earning 5 or 6 times more as a freelancer than as employee in Canadian company.

    Also, being smart about finding long term clients is very good idea. From my regular clients I get about half of my income. And after years of working as freelancer, I have found enough time to start my own business that I hope to replace freelancing work.

  24. says

    Great read . . . even if now I feel a little guilty :( – especially @ number 8. I keep waiting for the editor at TIME to call me with a cool project “only I can do”!

    Alas, haven’t had the call yet.

    (TIME editors reading this? Call me!! Please)

  25. says

    Great article, so many points spoke to me… as a “work at home freelancer” many of my friends think its the easy life, forgetting that as a freelancer youa re ervything, accounts department, marketing, customer services, sales and design! It can be a real juggling act and if you have no people skills you are best of forgetting it!

  26. David Kaplan says

    Good article. I disagree with #2, though. I believe that if you think of yourself less as a “freelancer” and more as an “entrepreneur”, that frees you from the notion that you’re a one-person, one-product business.

    Investing time in developing a few products (SaaS products, themes, etc) that bring in passive income in addition to your regular design jobs can significantly increase your revenue. Additionally, gaining larger jobs and hiring other freelancers or contractors (and marking-up, of course) can lead to even more income, as well as, larger clients and a healthier network of colleagues. Finally, investing time in growing your skills and knowledge in emerging tech or a specific area (while risky) can allow you to charge more for specialization and/or novelty.

    It never hurts to think big and to strive toward, one day, growing from a single freelancer to a substantial design/dev firm.

  27. Tina Louise says

    This was a great read!! I’ll be quitting a job I hate this summer to start freelancing, and I’m not scared at all. After reading this I’m even more confident than before that I’m doing the right thing. Thanks!

  28. says

    Freelancing would be better for me if I rented out a small studio with other freelancers. That way I would be distracted by all my toys at home. LOL Yes, it’s tough but also fun and more comfortable.

  29. says

    Great post. I have been trying and struggling on how to start off with becoming a web designer. I always have had a passion and aptitude for learning and coding simple websites with HTML.

    Last year, I decided to learn more and understanding more about standards for HTML and CSS, programming client side, Javascript, and server side.

    I already have a 9 to 5 job but its in a field I feel that doesn’t utilize my talent. I feel much more with myself as a creative but the pure amount of learning is a bit overwhelming. I like to make some friends with developers and designers.

    Thanks for the tips though.


  30. Kendra says

    Great article, but re “tons of money,” it’s all relative. My current full time job (the one that’s sucking the life right out of me) pays $11/hr. So for those of you making $30k a year freelancing, to me, that IS a ton of money!

  31. says

    All that is real!

    1- you must keep an office schedule,
    2- hardly you will become rich, even we have big jobs with big pays that ones don´t come every day,
    3- Some client are harsh to deal with, worst when you are a freelance,
    4- have no kids, but if my dog take so much time of me no doubt a son of mine will take more time from me,
    5- Almost all my clients don’t wanna pay my rates they say “you are a freelancer you “”MUST”” charge me less”,
    6- Example, today I cannot do nothing!! meeting with a client take all morning, and all afternoon doing paperwork to get paid in the offeces of another client,
    7- for a big project I don’t have to wash dishes becouse I have not eaten all day, just dinner (made by Mom, she wash the dishes),
    8- to have regular clients you must work a lot, and expend some money, how can you sell yourself as a web designer with no web site of your own (a real one not one at bloggspot!), how can you offer to design some brochure if you don’t have examples of the ones you do, I was both employee and part time freelancer 5 years before turn to full freelancing, when a have a real portfolio of clients,
    9- you don’t have a boss! every client is your boss! at less all they think that,
    10- I have to spend lots of money in stationary, equipment, blank cd’s and stuff, some big bucks in the “legalization” of the bussines so I can access bigger clients that don’t take you seriously as a lone individual,
    11- In the office I use to work if I need something, ink cartriges, paper, cd’s, equipment I just have to ask and magically they come, now I must go seek and find that things by myself, it takes too much time,
    12-My mom don’t understand why I get paid until last month that some of my work was published in the national newspapers and she see it in his office and later says to me “looks like what you are doing yesterday” and I said “yes mom, I did it!”

    Is trully demanding right now is 9:20 pm here in El Salvador while I was writing this comment the client from this morning call me to give me some more instructions, office hours ends at 5:00pm, all of us have our own examples but at the end we all share the same misfortune, but I can tell you freelancing makes me happy!

  32. Coyote says

    I’m also going to nth what a few people already commented on — I absolutely disagree that freelancing can’t be lucrative. I finished my first year and made a little over my previous full-time job. It is harder the first year (leaning the ropes), but it is only going on direction after that. I’m increasing my rates, have quite a few clients and am specializing even more.

    Aim high, not “I’m going to earn less money…or “earn less $ for several years”, etc.

    It is also not as time consuming, although there are a few evening or weekend crunches but I did that by procrastinating or deciding to take an assignment.

  33. says

    One good reason not to freelance is no group health insurance!

    My out of pocket costs for heath care will be over $10,000 this year not including a few thousand dollars in dental work and not including an extra $15,000 for a medical procedure (taking place out of the US). If you have a chronic medication, you’re screwed unless you’re married to someone with a “real job”

  34. says

    You’ve put me off freelancing, for now that is anyway. I have done a little freelancing in the past just as a supplement to my income and that was a good challenge but freelancing full time doesn’t look that enticing.

  35. says

    One good reason not to freelance is no group health insurance!

    My out of pocket costs for heath care will be over $10,000 this year not including a few thousand dollars in dental work and not including an extra $15,000 for a medical procedure (taking place out of the US). If you have a chronic medication, you’re screwed unless you’re married to someone with a “real job”

  36. says

    I think that “No boss!” is wrong really. I feel like I have a whole bunch of bosses, none of which realise I’m working for the others as well. So you get pulled in all directions at the same time. But I wouldn’t go back, mainly because I would earn less, but also because I enjoy doing what I do how I do it.

    Anyone who gets into freelancing thinking it’s going to be easy has a nasty shock coming, that’s for sure.

  37. says

    @Carla. Sorry to hear about your health costs! As a subject of HRH the Queen, it’s a little different for freelancers on this side of the pond, but certainly a valid point for the USA crowd!

  38. John says

    I love this article. I’ve been a freelance consultant for 9 years, and have experienced every single one of those items. And while I make more now than I ever could have working full-time in my industry, it was a long road to get there. And I work many more hours and days than I would if I were salaried sitting in a cubefarm.

    Carla, my advice to you on insurance (having gone through the exact same thing) is to look at your local Chamber of Commerce. Quite often, in exchange for your annual $200-400 in dues, you can get in on a pretty cheap group plan. The $400 per year I spend on CoC membership saves me thousands in premiums per year.

  39. says

    Great article. But I disagree with #1 and #10. #1—it all depends on the industry and the type of jobs you are going after. There are actually freelancing jobs where you really do get to set your own hours. #10—again, it all depends, in this case where you live. I’m based in NY. I spend $300 a month to commute. That does NOT include my car bills (gas, insurance, maintenance). Staying at home *will* save me considerable amount of money. Even if I spend the whole day at a coffee shop to save money on electricity and heating bills, I’ll still come out ahead if I spend $6 a day on coffee.

    At least to me, it seems that the best advice can be summarized in “Unless you have kids or for some reason badly need to work at home, freelance part-time and keep your day job…until you get established.”

  40. Tom says

    Carla is right. It seems as if you missed some of the chief reasons not to freelance.

    1. Health insurance. Unless you are freelancing from outside the US, you will suddenly find yourself picking up 100% of your insurance costs. (Employers typically pay 75%.) If you have a pre-existing condition, you are SOL on the individual market. Your only hope is to set up a group plan, perhaps with your spouse as the second employee. In any case , it is expensive and time-consuming.

    2. Retirement savings. When you go to work for a company, they typically contribute a certain percent of your paycheck to a retirement plan from day one. When you freelance, you are responsible for this – a daunting task for new (often unprofitable) businesses.

    3. IT costs. When you go to work for yourself, there are no IT people to drop by your office and fix your system. You either have to learn this yourself – very time-consuming. Or you have to fork out needed cash for IT support.

    4. Legal fees and liability insurance. See number 3. At the very least, this is a hassle. But it can also be expensive. Companies foot this bill for us when we are employees.

    Bottom line – when one sets out on his/her own, many bills come due that the company paid before. And when/if business dries up, there is no fixed salary to fall back on.

  41. says

    @Tom I didn’t mention these bc they aren’t normally drawbacks:

    1) my Heath insurance is $60 a month for an HSA plan
    2) none of my old employers had retirement plans.
    3) IT costs are only paying for monthly Internet – which I did even when I had a job
    4) legal fees and liability issues – this may depend on what kind of business you are – I’ve been in business 5 years and have never had either of these.

    Of course this is all my personal experience and these might be different from yours :)

  42. says

    All of this is well and good. But, for some of us (over 60), it’s simply a matter of survival. Having been an entrepreneur for over 25 years I find that, after 3 serious attempts to work for others, that I’m no longer suited for the employer/employee relationship.

  43. Travis Warlick says

    A strangely large number of web-people (and particularly Software Engineers) have Attention Deficit “Disorder”. Myself included. I’m not talking about the childhood “rambunctious kid” ADD. This is the adult, “my brain won’t stop flipping channels on me” ADD. (note: quotes around “disorder”: while there are very bad symptoms, there are also very good symptoms — “absent minded professor” syndrome)

    If you’re in this ADD boat with me, please pay close attention to #7 and #12, and don’t neglect your mental health. We switch tasks to household chores and talking with our partners and family members because we love them, irrespective to the damage it does to our work and our relationships (and yes, it does do damage to our relationships when we become irritable or angry when we loose our concentration). Pay attention to yourself, set rules, and do consider seeing a doctor. It will help.

    “gnothi seauton” — “nosce te ipsum” — “Know Thyself”

  44. says

    “That being said, I do believe it’s the best job ever. Really, I wouldn’t go back to a full-time job, even if they offered me a six figure salary.”

    Tell you what–when you get that offer, send it my way. After more than 20 years of freelancing, paying for my own health insurance, dealing with clueless editors, and waiting for the checks that are always late, I’d take it in a heartbeat.

  45. says

    This is a really great piece. Kind of nice to know that I’m not the only one who feels the same way about these things.

    a few things i think should be added:

    re #2: One of the hardest things for me freelancing is not having a steady paycheck. Even though I am making more money than I was working full-time, I occasionally have to go up to 5 weeks without a paycheck. Make sure you’re good at saving if you’re going to do this – a second income, from a spouse or partner helps too.

    re #9: This is the biggest thing I could say. No matter what you do – you now do everything. You’re the project manager, the account manager, the sales, the accounts payable, accounts receivable, the intern, and the boss. This can add up.

    re #11: I’ve found that if I’m upfront and honest with my clients ahead of time, they are understanding of my work hours. One of the reasons that I left my last position was because of a boss that expected 50 hours a week at the office and another 25 at home. That’s too much – it’s not fair to your family or yourself. By setting time restrictions (I’ve available 8:30 to 6:30) daily or after that only if it’s absolutely urgent, I’ve found that it helps keep myself in control.

  46. says

    Here are some of my related comments:

    -IT costs .. can really be mitigated when you run your own shop. I’m 100% Linux and Open Source. Open Office, Firefox, Inkscape, Gimp, GanttProject, Engineering software. Clients all use MSOffice and etc and I trade documents and data with them fine.

    -Have a spouse with healthcare ; )

    -Global automotive consulting .. means conference calls and meetings from 7am to Midnight, but there are breaks during the day.

    -Keep your household expenses light so you can weather the income ups-and-downs.

    -Your spouse will complain ‘you’re working all the time… when are you not working?.. and so on”. You need to have a spouse that understands what you are doing, and why.

  47. henry says

    freelancing sucks. I mean… I have clients on the side of my 9-5, but it is such a chore to get them to PAY ON TIME! I don’t know what I would do if my primary source of income wasn’t as stable as it is now.

    Yeah, it sucks having a boss, and yeah it sucks working on stuff that you don’t like to work on, but its not like your clients will be any better! In most cases your clients will be EVEN MORE misguided than anyone in your office. At least at a 9-5 you have a staff of people that will stand behind the quality of your work.

  48. says

    I would also guess that it’s pretty difficult getting approved for a mortgage in a tightening credit market when most of your income is based on short term projects. Bankers love those W2s and pay stubs!

  49. Tom says


    Good points all around.

    1. HSAs are great for the young and the healthy. Hell, if you are young and healthy you can get COMPREHENSIVE insurance for $300-400 a month. Things change drastically, you will hopefully never see, when one has a pre-existing condition. Or when one is old. A freelancer going the HSA route has to (or should) save up a pile of cash (depending on how high the deductible is), to ensure against financial ruin should a medical emergency or accident arise. (Most insurance plans cover $1 million in lifetime expenses. Do most freelancers have this kind of cash sitting around?)

    2. Same thing here on retirement. In either case – stingy employer or freelancing – you have to save a pretty hefty sum if you don’t want to work until you are 85. It’s incredible how many successful freelancers fail to do this and end up living their golden years on the edge. The benefit of being an employee (at most companies) is the retirement benefit that is above and beyond your salary.

    3. IT costs are just an internet connection? What about your computer? Most employers provide them free of charge. Also, computers break. You might have the skills to fix your own system, but freelancers in other sectors have to hire that out or learn – costing precious money or time.

    4. Re: legal fees and liability. Companies should probably hold liability insurance, in case they are ever sued. It’s not expensive unless you are a doctor, lawyer, or accountant. Lawyers fees are usually unnecessary, although most companies have law firms on retainer (or even an in-house team). As your company gets more successful, it is something you may have to deal with.

    Bottom line – one can run a small company on the cheap if nothing goes wrong. But ALL the financial risk is now shifted to the freelancer/entrepreneur/owner. Risk is a fickle thing – most freelancers make it out alright. Some do quite well. And others end up in financial ruin. The risk is what draws many of us to it. But it is also what scares us off when we have dependents counting on us or when we (or our dependents) start having health issues.

  50. says

    I strongly disagree!
    Granted, freelancing isn’t easy, but it sure pays off!
    I think you missed a major point, and that is Quality of Life. Without a doubt, if you learn (and strive) to organize your time, you will live better and happier than you would having the boss and the card punching 9 to 5.
    Good article though; its good to get some perspective from time to time…

  51. says

    @Tom Of course I don’t want to be argumentative, but here’s my .02 again, all this coming from my own experiences of course:

    1) I have several preexisting conditions and a major family history of cancer and my insurance is only $66 a month, and I only have to pay a $2500 deductible and the insurance pays 100% after that. It depends on the state you live in, if you’re located in TN I suggest checking out my company, TRH Health plans, they use Blue Cross Blue Shield through Farm Bureau and have been the cheapest plan so far

    2) If you’re good with money it’s not to hard to put away 20% for savings for retirement. Although if you’re not disciplined you certainly can get stuck freelancing till your 100. ;)

    3) Most people have a computer even if they have a full-time job..so this isn’t an added cost, it’s a normal cost to most households, if one breaks down. If my laptop blew up when I had a full-time job, I’d still need to replace it, so I don’t consider it an added cost to freelancing..same with the internet. I’d have it either way.

    4) If you have a strong contract, a one-person freelancing company should never have to deal with this. You can be sued by anyone, but that doesn’t mean they’ll win.

    @Alberto Of course it pays off! The point of my article wasn’t to talk bad about freelancing or discourage people, but it was to try and set realistic expectations, as many people come into freelancing thinking it’s going to be an easy ride.

  52. says

    About the health an retirement issues it depends of where you live, here in El Salvador we have AFP Administradoras de Fondos de Pensiones (Pension Fund Administrations) you can take the service as an individual an have an account with monthly payments depending of your “official” income and have a pension at 60 years of age.

    And about the health care here the Sistema Nacional de Salud (National Health System) is free to everybody, you can be treated of any disease or medical problem and have medical procedures from simple teeth extractions to brain surgery for free, but with downsides like long wait to the procedures and lack of some equipment, we also have the ISSS Instiruto Salvadoreño del Seguro Social (Salvadorian Institute of Social Security) is the obligatory health service for all the employees, pay by the employer and the employee, as freelancers if I team up with someone else we can suscribe as a bussiness and have the service is real cheap when I was an employee I just paid $7.29 a month for the service, and if you have a relative with an established business a shop or something they can put you in the ISSS coverage paying him/her the employeers fee for your subscription, better than the national service and all the prescriptions are free, and if you are laid off of your work you still have coverage in health services an emergencys for 6 month since the day you are laid off.

    Here freelances have not much concerns about that issues

  53. Ruud says

    When I told my mother back in 1993 i would start as a freelancer she replied “good, nobody will be able to fire you.” I became freelancer because I don’t get along to well with people telling me what to do.
    I didn’t freelance to get rich. I didn’t want a 9 to 5 job, but I didn’t want to get into business either.
    Lazy as I am, I haven’t been out of work since. I have a small pool of people who know to find me when they need someone for the things they need. It works both ways. They don’t have the hassle employing me. I don’t get bossed around.
    OTH. No social security, I was lucky in having money at hand just in case and not getting ill too much or getting sued. No problem to motivate myself, I’m to much into fulfilling a given promiss
    But the main thing is you learn to live your life, you learn to depend on yourself and see things coming and prepare for, not taking anything for granted. But also to respect other peoples efforts, because you know how easy it is to screw up and take the flak because you’re responsible for what you do.

  54. Alejandro says

    Interesting article.
    I get up at around 12 midday, and work all the way to 4 or 5 am, thats when i have lots of work, i choose freelancing after over 10 years in corporate enviroment, and i can say im doing good, after just 3 months i am making more money than what i was earning, and more projects come rolling in, i think im going have to hire someone out to help me! oh no, too much work, i should stop looking at my monitor so work doesn’t come :P
    Amber, i enjoyed the article very much, but i believe that most of the people that commit those infringements are not cut out to be freelancers. Just my opinion.

  55. says

    I wish I didn’t have to freelance, but most of the web development jobs (I am a ColdFusion Developer) are freelance jobs. Some of them I work from home, some I go to an office and work. I started my consulting company during the dotcom burst when i was sending resumes out and not getting any results. Sees we are back to that as I have been unemployed since August. I have a few project in the works, but they are on hold as the company can’t get the funding to go ahead with them. I would much rather have a permanent gig with benefits.

  56. says


    I wish we had that here in the US. I am 41 and unless things change, I will have nothing when I get to retirement age. Luckily my heath care is covered by the Veteran’s Administration since I am a disabled Veteran, but every time I seem to get things going with a 401k (which is our “pension” plan here in the US), I end up having to cash it out to pay bills when I start experiencing long term unemployment. The other thing that is going to kill me is taxes. I had a gig that was corp to corp this summer and I was unable to put the money aside for taxes as I needed it for bills and food. That was the last gig I worked, so i am going to end up taking a serious hit when I file taxes and not be able to pay…then deal with the harassment from the government and their hired collectors when I can’t pay it.

  57. Aaron says

    I have nine years of experience working in freelance. I don’t agree with hardly any of this. I don’t think you can drop a template on people like this. I work in a handful of niche industries, I never put in more than 30 hours a week, and I pull down $250,000+ per year after taxes and expenses.

  58. says

    @Aaron Everyone has different experiences and this was not supposed to ne a “template”. This post was meant to set realistic expectations for the common freelancer. Most are not going to make much money the first couple months they start out, and unfortunately I’ve heard all of these “perks” from several people who thought this was what freelancing was about – and then had to go back to a full-time job when they couldn’t make it. So there are certainly lots of people in the mindset that it’s easy to make lots of money and lie in bed all day.

  59. Ron says

    I’ve been a career web dev freelancer for 10 years – meaning I’ve NEVER held a fulltime job in the time I’ve been doing the work.

    I 100% agree with everything you say. After a decade and a one of the worst years I’ve ever encountered I’m about ready to give it up. Things have really turned ugly and I dream of the security and 9 to 5 aspect of a fulltime job.

    When your income is dependent on the time you work and it bleeds into your personal life it can have disastrously stressful effects, especially when the quality and quantity of work drops off….

  60. says

    Great post. Freelancing can be horrible just because client work in general can be so horrible. It can be very difficult dealing with client demands, especially when they render your work useless from a portfolio perspective. I made the decision to stop doing client work and focus on my own projects and it has served me well, at least from a sanity standpoint.

  61. davidbaer says

    Experts have talked about this before. How many times have you read about the importance of ‘adding value’ for your audience? How many times have you read about ‘building trust’ with your readers/prospects?
    Many, many times. You know it well. Every marketing guru has spoken about this topic. I’m sick of hearing it. But it STILL bears repeating.


  62. Tom says


    Excellent points all around! Your “can-do” attitude demonstrates, I think, why you are a successful freelancer.

    1. I did, however, take a quick look at the TRH HSA Plan, and found the HSA $2,500 deductible plan you were talking about. As you mentioned, it costs $70 for a “preferred member” (much more for higher cost/risk patients), but it also only provides 80% insurance after $2,500 (60% for out-of-network providers…which one needs when he/she gets very sick.) This means that after paying full price for all medical services up to $2,500, you would have to pay 20% (or 40%) of all bills after that. As long as you stay in your network, which is sometimes impossible, TRH guarantees an “out-of-pocket” limit of $3,750, which means you will pay $6,250 – each year – before TRH will kick in with 100% coverage. If you leave your network for specialist treatment, there is no out-of-pocket limit, meaning you could be stuck with 40% of all your medical bills. 2-4 hospital stays can easily run you over $100,000. Do you have $40,000 sitting around, each year, to pay for treatment for a complicated condition that sends you out-of-state for treatment?

    Sorry to be negative, but HSAs aren’t insurance. They are “partial insurance,” which means they aren’t tenable for people who have dependents who are really sick.

    On a positive note, HIPPA-certified group policies are a better bet for free-lancers with sick or high risk/cost family members. They are affordable, very heavily regulated by the federal government, and can be started with a minimum of only 2 employees.

    On a realistic note, when a free-lancer first sets out with $2 in his/her pocket, he/she will probably be better off signing up for Medicaid. It’s hard to start a company when you can’t afford your asthma medicine.


    Disclaimer: My comments come from my experience free-lancing in a number of countries. It is much easier to free-lance – especially as a beginner – outside the US, where societies see health care as a public service like the police and fire departments.

    2. Your point about saving 20% for retirement is valid, but one has to take into account that a freelancer is no longer receiving an IRA match from his/her employer.

    3. Your point about IT costs and computers is valid if, in your case, your employer did not provide you with a laptop AND you would have a personal laptop anyway. Most mid and high-level executives receive a laptop and cellphone/blackberry. They are not expected to pay for them out of their salary, and most do not buy expensive ones for personal use. (Some don’t buy any for personal use. One would be surprised at how many CEOs live very humbly, and don’t spend a penny they can’t expense to their company.)

    Summary: I agree with you completely that it is very possible to be very successful freelancing. But you can’t look at your salary at a company that provides a 7.5% IRA match, a 7% Social Security match, a 75% HIPAA health care subsidy, pays your office rent and electricity bills, provides you with software-laden laptop, cellphone, and blackberry…..and compare that to your free-lancing salary. Especially if, as an employee, and you live in a small, modest apartment with no scanner, fax machine, a the only computer you have is a 10-pound Toshiba laptop running Windows 2000.

    If you live very humbly in your personal life and make $80,000 at your company, you would have to bring in at LEAST $90,000-$100,000 freelancing to come out even. (You probably have to make more like $110,000-120,000).

    It all depends on your willingness to bear risk…

  63. says

    I freelanced with increasing success for 12 years, then realized that since the business was ME, I wasn’t gaining equity in anything with all my hard work. I found a partner and started a “real” business, and as a result increased my income. I’m also building a business I can actually sell someday, in addition to the fact that because I have employees, I can take a vacation and the work will continue without me.

    I don’t like the commute and the decreased freedom, but I feel the trade was worth it. I actually love the increase in social activity and all the things I learn from my employees.

  64. says

    I freelanced with increasing success for 12 years, then realized that since the business was ME, I wasn’t gaining equity in anything with all my hard work. I found a partner and started a “real” business, and as a result increased my income. I’m also building a business I can actually sell someday, in addition to the fact that because I have employees, I can take a vacation and the work will continue without me.

  65. says

    Amber, i would agree with the latter part of the article… however, on the first part to which you mentioned that making money online is hard… well, i guess for starters who still don’t understands the business that they are into, but you have discussed this anyway and cleared yourself in one of the comments… but yes! a lot of times you’re more busy than ever and a lot of people do not understand that you are running a business and you’re totally busy with a lot of workloads on schedule. Despite the tiring hours… I still won’t trade the business that I am now into with the money that i make now compared to my past corporate jobs…

    Freelancing is meant for the brave men and women who has leadership and management skills and not a follower… coz if one’s mindset is to have a “very balanced lifestyle” this kind of business won’t work for them and leave them frustrated.

  66. says

    I had work as a seo freelancer for more than 3 years, I got some success, if you do not like to have any boss you can work as a freelancer, but I think the market of outsource now may be saturated, thanks

  67. says

    I’ve been freelancing and setting up companies for the last 10 years and there’s nothing like it for empowering you and putting you in charge of your own destiny!!

  68. says

    As usual I feel it’s a double edged sword. There are huge benefits in terms of time and pay/salary, however there is less job security and stress due to responsibility. It depends which side of the line you personally feel more comfortable on…

  69. says

    As with most things there are pros and cons…if job security is important to you then stay clear. If flexibility of time is important and you are happy to put the hours in, just when you would prefer to, then it could be for you.

    Don’t be under any illusion that it’s a get rich quick scheme! It’s harder work, but more fulfilling.

  70. says

    Yes, going into freelancing for an easy life would be a big mistake! It can be a great life but it’s for people that want to get out there and make the most of life and not those who prefer a regular routine, a desk for 50 years and then retirement!

  71. says

    Working for yourself is the best. I know we all have highs and lows of work, but isn’t it great controling your own destiny? if you want to work hard and get on, take the odd risk, then working for yourself is for you. On the otherhand if you want to plod along, take pointless instructions and go home bang on time evry night, thenn work for a company!

  72. says

    All the above is true. It comes down to the fact you will always occupy that space between your ears. If you can’t be your own boss, someone else eventually will.

    Even worse is the ‘limbo state’ – just getting by, working long hours, not putting retirement money away….. etc.

  73. says

    For freelancers to be successful, they have to be highly disciplined and self-motivated. Working alone at home can sometimes cause boredom or laziness. Freelancing is a business and each freelancer must remain as professional as possible, even when doing client calls in pajamas.

  74. says

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  75. says

    12 Reasons You Shouldn’t Freelance | FreelanceFolder I was suggested this website by my cousin. I’m not sure whether this post is written by him as nobody else know such detailed about my difficulty. You are incredible! Thanks! your article about 12 Reasons You Shouldn’t Freelance | FreelanceFolderBest Regards Yoder

  76. says

    This is getting a bit more subjective, but I much prefer the Zune Marketplace. The interface is colorful, has more flair, and some cool features like ‘Mixview’ that let you quickly see related albums, songs, or other users related to what you’re listening to. Clicking on one of those will center on that item, and another set of “neighbors” will come into view, allowing you to navigate around exploring by similar artists, songs, or users. Speaking of users, the Zune “Social” is also great fun, letting you find others with shared tastes and becoming friends with them. You then can listen to a playlist created based on an amalgamation of what all your friends are listening to, which is also enjoyable. Those concerned with privacy will be relieved to know you can prevent the public from seeing your personal listening habits if you so choose.

  77. says

    Write more, thats all I have to say. Literally, it seems as though you relied on the video to make your point. You definitely know what youre talking about, why throw away your intelligence on just posting videos to your weblog when you could be giving us something enlightening to read?

  78. says

    Personally, I have found it’s more luck than anything else. Some people seem to hit the jackpot without too much hard work. Others have to work day and night just to survive.

  79. says

    I left catering many years ago because I was tired of the long hours. As freelancing I am doing just as many hours – however I think there is a different feel to working as freelance and yes it is more enjoyable

  80. says

    Wow, fantastic blog layout! How long have you been blogging for? you made blogging look easy. The overall look of your web site is wonderful, let alone the content!. Thanks For Your article about 12 Reasons You Shouldn’t Freelance | FreelanceFolder .

  81. says

    Unfortunately I went freelancing about 9 Years ago and its always been tough out there. However, I do get so much satisfaction in controlling my hours and getting the work in.

    Its nice to read something like this that really does give the ups and downs for advice. Freelancing is not for the faint hearted.

    Great post and true advice!

  82. says

    I am still classed as freelance although working for a client full time on a consultancy basis.

    I like the freedom and could never work for a big company!

  83. says

    I completely agree with all 12 reasons. You can earn more cash with full time employment but I don’t think it’s as exciting or challenging.

  84. says

    If you haven’t tried freelancing and have the opportunity I would highly recommend at least trying this. Some people take to freelancing like a duck to water, others struggle preferring the security of secure employment. Depending upon circumstances its well worth trying

  85. says

    All the things you listed are true. Freelancing might be the best career change I’ve done so far but there’s nothing easy about it. A lot of my friends tend to envy me because of my work sched flexibility and they even tried to sign up in Odesk. They keep on asking me how I did it. I told them that they should leave their office jobs and go full time in freelancing but they have a hard time digesting the fact that in order for someone to succeed in the freelance world, one should know how to take risks and learn how to be self-reliant.

  86. says

    We started our small business blog to really help people in every warp of life, and we definitely think freelancing can be brilliant. But as the blog shows there are high and lows – and do it at your own risk.

  87. says

    Wow, after literally just starting our new internet marketing business, after reading this blog post perhaps working from home will effect my homelife? Divorce, unhappiness and no joking, d’oh!!

  88. says

    I’m afraid as with many things in this world there is no gain without pain. Don’t be put off freelancing, but the intial period could be a bit painful. Work could be slow and chasing payment is another subject. Once you get over the initial set up period and settle into a regular work pattern that suit’s you and your customers there is no going back. Stick with it, be focussed as to what service / product you offer and go for it. Afterall, you only get one life, unless you are a cat!

  89. says

    Really not sure whether we are put off from freelancing or want to continue to look, but supposedly this is every business dilemma. But really this is all a learning exercise for all of us, work for someone in a office and you tend to get more done for all the people around you, but work from home and sometimes if your not determined you could or can fall into the lazy trap.

  90. says

    Freelancing is the best! If you work hard you will get rewarded, but if you end somewhere you do not like you can easily move on to the next project. Take some personal responsibility and work for yourself. No job is ever guaranteed for life so why not give this a go? It’s better to have tried something and failed than to never have tried and regretted this.

    • Ryan Domm-Thomas says

      I agree wholeheartedly! It can be difficult at times, but like you said, if you work hard you’ll be rewarded!

  91. says

    Freelance is taking a bit of a risk – being self employed. I have been doing it for 16 years and not only do I see it that I am my own boss in charge of my own time and destiny, the rewards I get are exactly what Im worth, Like Rehan says – make sure you set goals!


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