Why I Failed at Freelancing

closedThis time around, I have been a pretty successful freelancer if I do say so myself. My bills stay paid, my clients are happy and I’ve never been happier in a career.

Unfortunately, my first attempt at freelancing left me unhappy, in debt and desperate. I took several full-time jobs between my last attempt at freelancing and this one to teach me some valuable lessons and make my way out of debt.

I made many mistakes the first time around and, like any good freelancer, I learned from them and now I am a better, stronger worker. In this post, I’ll share some of the mistakes that caused me to fail as a freelancer the first time around.

Mistakes That Caused Me to Fail

So what were those mistakes that caused me to fail?

  • Too inexperienced. I don’t want to say “young”, because I know there are several successful student freelancers out there, but I was personally too young and inexperienced. At just 21 years old, I was forced out of my job as an animator and illustrator, and I decided to go freelance. Unfortunately, my limited experience and portfolio made it extremely difficult to get work, and client meetings left me looking young, insecure not nearly “expert” enough.
  • No focus. My training was in multimedia, animation and illustration. In my freelance career, I focused on all of those things as well as web design, video editing, drawing portraits and more. Anything that could possibly send a little money my way, I did it. I thought being a jack-of-all-trades would win me clients, but what it really did was ensure that I was a master-of-nothing.
  • Slippery slope” of slow business. When my business got slow, I stopped making demo reels to pass out and business cards to give away. I stopped shipping my illustrations to magazines because postage was too high. This made my slow business get even slower until I wasn’t working at all.
  • No savings. This one is a no-brainer, but my previous job left me in a position of being forced into freelancing before I was financially ready for it. I had to hit the ground running, or actually sprinting, in order to keep my bills paid. My dwindling bank account made me desperate to take any jobs that came my way instead of selecting quality ones.
  • A part-time job. I know many freelancers are only doing it part-time, but this was a balancing act I could never properly handle (maybe I should have read this article). When my business started getting slow, I found a part-time job to help me pay the bills. Unfortunately, it also got in the way of my freelancing. I wasn’t answering client phone calls while at work or replying to emails promptly. I started missing deadlines and just generally being worse at my “core” job of freelancing.
  • Debt. Between slow business, lack of savings and a low-paying part-time job, I racked up plenty of debt in a short amount of time. Debt made me even more desperate to take jobs I shouldn’t have and work more hours at my part-time position, which just spiraled into me doing worse and worse.
  • Client relationships. Because of all of the above, I was miserable at getting and keeping clients, much less getting referrals. I was a guy hard to reach on the phone, slow to reply to emails, desperate for work and without any area of expertise. Why would clients come back or refer me to friends? They wouldn’t, and they didn’t.

After trying and failing for almost three years, I finally recognized that I was not ready for a freelancing career yet and got a full-time job. My job helped get me out of debt and establish a bit of savings for my next attempt, but more importantly, it taught me extremely valuable lessons about life and business that prepared me for a successful freelancing career.

How I Learned from My Mistakes

So what’s different now that I’ve left my full-time job again and have been a successful freelancer for a few years?

  • Experience. After working full-time in the field for almost five years, I am professional, experienced and can speak with authority in my field.
  • Focus. I do web design and development, and that’s all. My clients know what they’re getting into, and I know I’m good at what I do.
  • Savings. Having a bit of money in the bank for the slow times makes me much more confident, secure, and less desperate to take any job, even in the slow times.
  • Great service. I take my relationships with clients very, very seriously. If I am happy with one of my clients, I do whatever I can to make sure they are equally happy with me. Happy clients are returning clients, and business owners know other business owners. This is a cornerstone of my success.

What About You?

I can’t be the only person out there who failed miserably at freelancing only to succeed later in life. What are your stories?

Image by jasoon


  1. says

    This is a really interesting post because I can relate with most of it! The reason it took me so long to get Freelancing working for me was because I wasn’t treating it like a business. I’d take really low paying jobs (and we all know they are the pickiest clients) and I wondered why I was making no money.

  2. says

    Nice post! I started freelancing this year and luckily didn’t encounter any of the “mistakes” you stated. It sure is a good list to remember as I’m moving on. Thanks for this!

  3. says

    Thank you for this post as it’s a learning experience for all of us. I think freelancing after the first year and now going into my 2nd has been the most stressful and most fulfilling job that I’ve ever had as I feel now I’m in control of my own destiny and we get credit for the work that we do. Not someone else getting all the accolades and rewards from our talents.

  4. Koko says

    Hi, i feel I´m looking at the mirror. My bussiness broken 3 years ago, so I started thinking about the reasons. Spent 14 hours woking hard everyday 6 days a week, finally my head crashed. Now, I´m design director of a company, my life it´s great, but I feel I had to try again, becouse, as you comment, now I´ve the experience, not only working, whith everything of my life, my family, my friend… I think many people understand my words, so thanks for the post, It´s nice read something that you can feel like yours.

  5. says

    Great article! It’s hard to tell a young artist that they aren’t ready for the freelance world right from the get-go, but like you, I was one of those starry-eyed illustrators who thought ‘if anyone can do it, I can.’

    I quickly learned that the business strategies they taught me in school don’t necessarily work for someone with no experience, no portfolio, and fledgeling talent. I packed it in after a wandering, unfocused 3-year existence, and got a full-time job in design for the printing industry.

    I quickly learned all the things at my full time job that would have made my freelance career more successful. I learned to price my work fairly and accurately, learned to interact with clients in a more successful way, learned to be busy and schedule my time, and best of all, I got lots of experience in the design field.

    I now have a print & design company of my own, and am doing so much better, thanks to the lessons I learned along the way.

    Hence, my advice for young freelancers: Get a job! Until you’ve worked in the business you want to be in, selling yourself is a very difficult task, and it is far better to get this valuable experience while you are young and can change your home business accordingly.

  6. says

    What doesn’t kill you, make you stronger. Good to see you have made it well the second time. I managed to made it from first try. I was a bit older and still inexperienced but I had no other option and I didn’t believed in second chance.

  7. says

    Fantastic article!

    I constantly want to make the switch to full-time freelance, but am aware of all the pitfalls like the ones mentioned here. So i’m sticking with my full-time job, gaining experience, and building my portfolio. Thanks for re-assuring me to know when the right time to make the switch is.

  8. says

    @Marc, Thanks for your story! I hate having a “real” job as much as anyone, but I do think its incredibly important for everyone to live with one for a few years before pursuing a freelance career.

    @Glenn, It is a very unpopular position, but my 2nd attempt I started out very heavily on job boards. I was smart about it and gained many great clients who I still work with today. My first 6-9 months were extremely difficult, but since then I have been getting many referrals and calls from people who found me on Google. I don’t do the job boards anymore, but I couldn’t have started without them.

  9. says

    @Jordan, Experience in the working world will be invaluable as you pave your own way as a freelancer. Just don’t get too comfortable where you’re at, and make that leap when you feel ready!

  10. says

    This post is so much better than many of the “Pros and Cons of Freelancing” posts out there. More than anything, it makes me admire and respect you for trying again. It’s one thing to say you learned from your mistakes and quite another to prove it by taking a second chance. Congratulations on running a successful business and thanks for sharing your story.

  11. says

    Wow! It seems my situation is not unique. I’m currently working full-time for a marketing firm as web developer (5+ years) but am trying to break into the freelancing world. After my first few projects as a freelancer I was getting new prospects weekly…As it turned out, only about 1 in 20 would eventually turn into an actual client.

    I know that referrals have always been the best way to get new clients so I was willing to charge a lower price for a referred project just to enhance my portfolio. I still haven’t found out if this is working to my benefit or not. I’ve always been prompt when communicating with my freelance clients but where I go wrong is finding which prospects to pursue; after all I do work a full-time job and can’t afford to promise too much to too many people.

    My freelance career has taught me a whole lot real quickly and it’s nice too see that others have gone through some of the same things and learned from their mistakes. Had I read this article many months ago, I definitely would have gone through much less trial and error.

  12. says

    Wow. This is awesome! Very inspiring. :-)

    Its fantabulous that you learned from your mistakes and turned your situation around.

    Congratulations on succeeding – and being honest and humble enough to share the failure you experienced along the way!

  13. says

    I certainly can relate to almost all of this! When I started freelancing years back I just jumped in and failed miserably. I have no regrets though, sometimes you need to dive into the deep-end in order to learn the ropes. Mistakes can sometimes be positive, as long as you learn from them.

  14. says

    I too went back and forth between freelancing and a full-time job. It definitely pays to be “ready” and “prepared” before you take the actual step. I’ve now been back to freelancing since last year and business has never been better :)

  15. says

    Wow man I LOVE YOUR ARTICLE, it’s really good….I’m in the same position as you were on the beginning! So I think I need more experience!

    Right now I’m doing my thesis on PHP and I’ve learned a lot, but I think that I have to push myself more :D

    Have a nice day!

  16. says

    Great story with a happy ending! I too, failed the first time around. Most of it was due to lack of effort and inexperience. I wonder how common it is to fail the first time around in freelancing?

  17. says

    Your experiences pretty much sound like what I’m going through. As a fresh-out-of-the-box college grad, I’ve found it hard to balance my part-time job with freelancing, I find it hard to show enough experience to prospective clients while at the same time I’m finding lots of web design opportunities that don’t pay enough to warrant doing them, which leads to a vicious cycle in some ways.

    I think now that I don’t have classes taking up so much time and money, I’ll be able to correct a lot of my problems that mirror some from your list, but until then… blah. I don’t know.

  18. says

    Thanks for an insightful post, Tim. I wonder if part of the difficulty with the first time is thinking of it as “just freelancing” instead of what it really is, which is “starting a business.” I know it took me awhile to wrap my head around that concept, but once I did, I took things much more seriously.

    Thanks again, and continued success!

  19. David Kaplan says

    Hi Tim,

    Thank you for writing this article. And, thank you, in particular, for wording the title and the article in a way that indicates these are only your personal experiences. I got into an argument with someone here on SM awhile back wrote a similar article but couched it in terms of why “you” (meaning me or others) would fail if you didn’t heed his advice. Drives me nuts when people only share anecdotal evidence as to why there advice is right.

    That said, I don’t think #2 – No Focus, is necessarily a weakness. Certainly, if you’re a web designer you have little place in being an astrophysicist. But, that doesn’t mean you can’t still design logos, etc. If a person puts their energy into different experiences over time, they can become a relative expert in many areas. Additionally, having experience in many different areas can lead to other opportunities – management, perhaps?

    Anyway, great article. Keep writing and keep designing!

    David Kaplan

  20. says

    This is a great article because I can relate.

    When I first started freelancing a year ago, I was horrible with client relations. I was slow to respond, I was never on time and a lot of others that revolve around my maturity. I see myself a year ago being very immature and inexperienced with treating clients properly and knowing my own boundaries.

    Now a year later, I have seen a huge improvement and change within myself. I promptly respond to client emails, I always complete a project before the deadline and I am very professional, but nice to my clients. I see myself as a more mature, young freelancer and more experienced in client relationships.

  21. says

    I just wanted to add a comment here to mention thanks for you very nice ideas. Blogs are troublesome to run and time consuming thus I appreciate when I see well writen material. Your time isn’t going to waste with your posts. Thanks so much and stick with it No doubt you will defintely reach your goals! have a great day!

  22. says

    Great post and points. I’ve been off an on when considering getting a part-time job back, to aid in the slow times myself, and this officially talked me out of it. :) The number one thing I was worried about was indeed what I was going to do when things sped back up again — I’d be tied down with that job and unable to keep up. I’m starting to agree, the better solution for that is to just manage the slower times better by saving up during busy times and living frugally if need be.

  23. says

    Great post. I think the most important point is “No Focus”. Of course, everyone wants to be the “one-stop-shop”, but it’s too distracting. I make that mistake when I first opened Bullsprig. Now we focus on web design and development. We still do a lot of print work, but it’s mostly for our long-time clients… not something we advertise heavily.

  24. says

    Tim thanks for sharing your story, fortunately for me I do not have one to share, but at the same time, I am not freelancing full-time yet either. Most of my freelance work is extra work outside my daily full-time work, reason for this is my current full-time job allows little creativity as I am more of the back-end developer there, whereas my side jobs, I am the developer plus the designer.

    Eventually I’d like to do the freelance work full-time.

  25. says

    It sounds like your first time around you were forced into freelancing. It’s better and more successful to do something on your own terms, so I’m not surprised you struggled in your first attempt.

    Glad to see things are looking up now though.

  26. says

    Very good article, Tim! I’m in the process of building my freelance business and as I read this article I went through and thought about everything to make sure I was on the right track or prepared to not fall into some of the same things you did your first time.

  27. says

    Some interesting points are raised here about Freelancing, and some that are more obvious than others. From reading the comments its clear that Freelancing is a difficult task to balance, especially considering the multiple aspects and skills that are required to keep a good freelancer afloat amongst the ever increasing competition.

    The point given here is that being too young and inexperienced will bring your freelancing business down, as confidence with clients and the ability to handle high pressure situations will make a big difference to your success.

    Another clear aspect of freelancing is that it requires savings as a foundation to your business, otherwise there is no margin for error. I’d be interested to see how freelancers on here react to this article, and any additional comments they may have about starting your own business.

  28. says

    Every single point have a sharp truth! Well done, i also destroyed my freelance full time job 2 years ago because of every single point that you meant here.
    To me the inexperience and the no xpertise on nothing specific was the first stop, but then comes the money issues, complaining from your clients and at the real end i just decide to skip this for a time..

    Now i think i’m really again to rebuild my reputation as a nice freelancer.
    After two years working as a web designer in a international company,lots of books, blogs, and meet some important people during this 2 years (online gurus).


  29. Osvaldo M. says

    I have been a freelancer for a short while but i never liked it, I never planned it to happen but the opportunity sort of showed up and i found myself withouth a proper job but receiving clients who wanted my services.
    Nowadays the internet is full of articles of how to make a living wearing pijamas and staying home, gee, that sounds great if i’m in college or i live 3 hours aways from my office, but maybe it’s just me, but i do not want to stay home all day, check bills, look for clients and then actually work as a web developer. I like getting up early, get ready, get a cup of coffe on my way to work and sit next to my teammates and maybe talk about how’s our soccer team playing or even discussing where are we going to get a bite later in the afternoon.
    For me, a web developer should focus on it’s own thing, that is why there are accountants, administrators and public relations professionals, to keep businesses afloat, check bills and to look for clients or get in touch with them.
    Besides, i have always trusted teamwork above doing it on my own, so why sit all alone in my flat all day when i could be doing better work with other people, and most important, learning from them. Though i acknowledge sometimes our co-workers slow us down or might dont get along, still it’s not the only job around so i could look for another team who would go more with my personality or way of work.
    There is something i’ve found on the net which makes me doubt about the greatness of freelancing, most of the freelances don’t go above 40 years old, and if they do, it’s because they spent something along the lines of 20 years working for corporates or agencies… So i ask myself, do i want to turn 40 and still be looking for clients, sitting all by myself on my house? Frankly, no.
    I have no doubt that freelancing is best for some people, but not for everyone. Nowadays i feel freelancing is such a trend that people are getting into without actually knowing what might happen. I believe, if you are truly learning and improving yourself by freelancing, go for it, but if not, look for a job to learn until you believe it’s ready to take your own path, and frankly, why freelance? go for your agency and surround yourself with the people you’ve met during the years.

  30. Osvaldo M. says

    jeje, i forgot my point during my bitchings about freelancing: great article!, should be read by anyone who is planning to freelance.

  31. says

    This is right on. I would add that not having or working on some kind of passive or recurring revenue stream to be a big mistake. I wish I had started something beyond offering just web, branding and print design skills years back. I didn’t think much about it when I got started way back in 92. I was thrilled to just be in the design field and have done great.

    I would say either work on an eBook, speaking gigs, teaching gigs, or anything to help keep branching out beyond the simple and finite commodity skills. If you don’t pop out, you’ll be passed over and over.

    We have ventured into iPhone development and in addition to offering our own products, we’d like to work with other programmers. I just read today that smartphone sales will overtake PC sales in 2012! That’s something to REALLY think about if you are just focused on PC oriented Web.

    We just got our first app published this week. Hopefully first of many…


  32. says

    Great article, really given me some food for thought. I’ve been thinking about going freelance recently but I’m worried about a few of the things you’ve outlined in your mistakes, especially the getting client aspect of it.

    Also it reassures me that i’m not “too old” to go freelance after i get a good amount of experience.

  33. says

    I think too many freelances, if they have any inclination toward being graphically competent or web-savvy, get involved in web design. Web design could easily be a whole job title unto itself. I personally recommend that any freelancer who wants to offer such services, and in a manner that’s worth while, focus mostly on that (if not entirely). It won’t kill you to do a flyer or business card every now and again. But you’ll be studying nonstop. You have to live and breathe web sites. Especially if you build sites instead of just design them. If you wanna be a developer/programmer, you have to be a bona fide techie. Everything from Apache to Photoshop. One minute it’s designing a header graphic, next it’s brushing up on Perl regular expressions. You gotta run to all bases from knowing good fonts to knowing good PHP login scripts. Just like the “focus” bullet says.

  34. says

    I would like to just add, that all those points I am in agreement with regarding the pitfalls, particular to my first attempt and fail, was preparation in financial terms, and as was mentioned approaching this as a business, and managing your time effectively and constructively.

    One of the biggest mistakes I made was grabbing any work, no matter whether it fitted my remits or particular skill. Sure i could get to grips with DTP or tackle a database here and there, but my knowledge and speed at these jobs was financially prohibitive – I just couldn’t charge the hourly rates i needed to.

    Lastly, the little “jobs” are the worst for wasting time and wanting lots for nothing – I now am confident with my cost requests – that’s how long it will take (with a small margin for unforeseen issues) and that’s how much it will cost – too much? go somewhere else.

    It is not worth your time and perceived value to undercharge, and remember those clients that keep pushing for more are just the same clients that builders and other trades have to deal with – the oh, can you do this while you are…. type – be firm and polite and if it comes to it, remind them that they are hiring your skill, and in this life you get what you pay for most times. Also – please do not feel forced to do work for free – it undervalues and undermines our skills and work – you wouldn’t find a builder or mechanic saying yes, ok then in case he gets referral business – it never happens!

    Good luck everyone, and keep the faith

  35. says

    Nice article. Really motivating despite a rather gloomy first part :)
    I just wonder how long did it take you to pass through the gray and gloomy phase one and get into bright present of your current freelancing career?

  36. says

    Brilliant article. Wish I had read it when I was freelancing, but I probably didn’t have time!
    One thing I’ll add that I don’t think anybody has mentioned (quick scan of the comments) is keeping abreast with new stuff –

    I felt my time working should be justified by if I was being payed or not, so I didn’t research enough to improve my skills or feed my creative mind, learn new techniques, find out smarter ways of doing things. If was to look at design related things I’d have to have a job paying me to do so. I stagnated and really didn’t develop creatively, my skills nor my techniques.
    Now, being in a job, I’ve got boredom to contend with which really stimulates me to search for the interesting and inspiring! Plus I’ve got other creative minds I’m working with and a training budget to boot.

  37. says

    Great Article and Dimitri you are absolutely right, I found myself in those spots as well.

    From experience a lot of clients have no proper knowledge of what it takes for their project. Many will demand too much for too little money. They see commercial from Intuit where they can get a website for $5 per month and now you find yourself explaining why you charge what you charge. I learned that you have charge your rate especially if you feel like you are dealing with a problem client (the ones that are never satisfied, wanting more than they pay for) otherwise you find yourself hating that client and not doing your best. Now these are the things I do

    1. Charge your rate, I no longer take jobs because I used to go by the motto never pass up money. It can cost you more in the long run taking on jobs that you under charge. If they don’t like it, let them move on, it will steer you clear of a headache
    2. Contracts! Outline the project of all the things that you do and what you won’t do, explain out-of-scope and how much it will cost, when it is due. Include your payment schedule. That way you won’t have a misunderstanding on the key part of the job.
    3. Follow your contract, I know we may create personal relationships with some client but once you break the business relationship you just find yourself back at one and sometimes to enforce your contract will create bigger problems.
    4. View yourself as a lawyer, doctor, etc You are a professional, you have skills and experiences that your client wants. Don’t let the client overcrowd you. I have clause in my agreement that states that the client can have the creative input but HOW its done is entirely up to me.

    I stopped freelancing for sometime because I was frustrated with my clients because of their constant haggling about pricing and wanting you to do things for free because if you don’t someone else would. So once I got to the point where I just go myself to say “If they willing to do it free, I would also go with them”. A lot of the same clients would contact me back months later complaining about the free guy.

    Oh one more thing, some clients would also come to me with the sob story that someone else got over on them, screwed them, etc … and their budget is nearly gone because they paid all this money. You are not responsible for their poor decision, stay by your rate and negotiate where you feel comfortable with in case you have to go the extra mile.

  38. says

    What a great post! I can relate oh too well!

    My first attempt at freelancing was 6/7 years ago and I also lasted a gruelling 3 years that ended with me bailing out, with debt in tow and returning to the mundane 9-5 job.

    My main mistake was thinking more of becoming a “design agency”, as oppose to a solo freelancer and, believe it or not, taking on sales reps to go and get me work!
    At that time I wasn’t aware of job boards and subbing your skills to other, already established agencies so, as the various sales reps failed to get new leads, my initial source of work and contacts (that I took from my previous job), soon dried up.

    I’m now in my second attempt and gradually growing once more. I have kept the day job for now, kept myself grounded and realistic and whole heartedly agree with having a safety net of money behind you.

    Soon, it will be time to take the plunge again.

  39. says

    Thanks Tim, for the excellent article. I think people should start freelancing once they have a solid financial backing & should always begin while working full time. som of us are not that fortunate though.

    I’m sure every freelancer can relate in some way to what you are saying & I must say what you have shared is brilliant.

  40. says

    i have freelancers working for me and to be honest there are so many freelancers about these days that there is a good choice. however its very difficult to find a great designer who is willing to go the extra mile, i found one in isreal who is from the UK, a great guy willing to go the extra mile.

  41. says

    Thank you so much for giving everyone such a terrific chance to discover important secrets from this web site. It’s usually so terrific plus jam-packed with a lot of fun for me and my office peers to search your site no less than three times weekly to see the fresh stuff you have got. And indeed, I am also always astounded with your astonishing things you serve. Certain 4 ideas in this posting are easily the most beneficial we have all ever had.


Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>