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I wish I would have known: Answers from 11 top freelancers

Today we've got an awesome article for any first time freelancers. I've rounded up a few of the top freelancers out there and had them answer the question "What do you wish you would have known starting out as a freelancer?". Needless to say, this article is full of over 2 thousand words of wisdom. I hope you find use for this article and if you know someone who might benefit from it, I'd love if you shared it with your twitter followers and facebook friends. Thank you :)

Jon Phillips

Twitter | Website
When I got started I used to do everything myself, it worked for a while till I realized that I could outsource a lot of the thing I didn't enjoy doing and then spend time on stuff I enjoy. I wish I had known that when I started out, it would've saved me a lot of time and probably some headaches, too :)

Andy Sowards

Twitter | Website

  • There are only 24 hours in a day. And you are most likely going to need sleep.
  • Taxes Suck.
  • Personal Project time suffers.
  • No income is Guaranteed.
  • When you have a big project to work on, your internet gives you issues.
  • Having said all of that, I still love freelancing :)

Steven Snell

Twitter | Website
I wish I would have known that clients tend to not take a project very seriously if they are paying low rates. When I started out I knew that learning and getting experience was more important than making money at that stage, so I did some very cheap projects. I worked with several people who wanted a website, but it seemed that since they were investing very little into it financially, they just didn't take it seriously and put in the effort on their end that is needed to have a successful web presence. Not only did that make it more difficult for me to do a good job, but it really did a dis-service to their business because their websites weren't as effective as they could have been. I'm not sure exactly what I would have done differently because my services weren't worth a whole lot at that point, but I wish I would have at least understood that people tend to not value or prioritize things that are cheap. I should have done a better job communicated with those clients that if their website is to be successful and useful for their customers/visitors, they must be involved throughout the process.

Sean Baker

Twitter | Website
Things I wish I knew before starting out as a freelancer

Tax Write-Offs
You'd be amazed at the amount of things you can write-off on your taxes being an independent designer. Aside from business expenses like hardware, programs and everyday tools like fonts, there's a whole world of things that may qualify as "research" to your business. For example, your music/MP3, movie, magazine and coffee purchases are creative outlets that may be considered for exemption if they pertain to your business or a particular project. No kidding. I was always skeptical and afraid of potential audits when I did my own taxes, so I sought a local CPA to assist me in the handling of receipts. For a CPA in your neighborhood, check out Save all your receipts and don't be afraid to ask questions come tax season -- you may be pleasantly surprised at how much you can claim!

Strategizing Your Time
You're closing up your meeting with a potential client. Everything went smoothly and you think you're about to land the job. Said client asks for your hourly rate, in which you give and explain. Unless you're underselling your talents greatly, their next question will almost always be: "Great, and how long will it take you?" Suddenly you're in a corner... and you're panicked. You don't want to scare them away, so you feel implied to answer immediately, usually shorting yourself on time simply to appease. Congratulations, you've just pigeonholed this project. From here you'll either be doing some free work or you'll run the client off once they see a higher rate than you originally gave.

It's critical to never give a time estimate without digesting and sleeping on the specs of the project. You need time to unwind and assess the details on your own. If a client asks for a final gauge in your FIRST meeting, cordially advise them that you need time to review in order to give a fair evaluation. Tell them you don't want to jump to conclusions and "over-shoot". They'll respect the fact that you're trying to keep money in their pockets, even if all you're really doing is watching out for yourself. From here, follow up within a few days with a "thank you" and a working estimate/contract.

Amber Weinberg

Twitter | Website
When I first started freelancing, I wish I would have known that it wasn't as insurmountable as everyone makes self-employment out to be. I spent a lot of time at a job I hated to save up enough money for "just-in-case" and once I went out on my own, I spent a lot of sleepless nights the first month and a half, freaking out because I had zero work. After that, it's been a lot of hard work, but it hasn't been nearly as scary as they want you to think. :)

Brian Yerkes

Twitter | Website
I wish I would have known (and been prepared for the fact that) not every client is going to like your designs / concepts / ideas. I've been freelancing for over 4 years now, and I still struggle with hearing "We don't like it.".

The problem is that when it comes to being a freelancer, you tend to put a serious amount of effort and personal pride into your work, and every time you complete a concept or idea for a client, you are confident that it is the the correct one. When a client says that they don't like it, you have to understand a few things.

1. That the client is not always right. Seriously. They just aren't. If I was having a house built I might ask my builder to use Play-Doh. Obviously, this would not be a good idea, and as the customer, I would be terribly wrong! The builder needs to step in and tell me what correct option is. That's why the builder is a builder and I'm not. He/She is the expert at what they do. So, sometimes when the client says that they don't like your work, you may want to consider having the cojones to discuss the reasons why they are wrong. Often, a professional client will appreciate your confidence and your dedication to the success of their project, but unfortunately there are times when a client will just get even more upset with you and continue to tell you that you are wrong. It just takes some good judgment on what way to respond to each situation.

2. Sometimes your work just doesn't hit the mark for what the client is looking for and what is needed for the project. This can happen for many reasons, but the important thing is to recognize it, understand the value of it, and move forward to developing better concepts. Decent clients are able to tell you why your concept doesn't work, and why they don't like, and this may give you an even clearer brief from which you can work from for the next concept. Rome wasn't built in a day, and clients need to understand this.

and finally

3. You have to ensure that you don't take it personally, ever. This is the biggest thing that I personally struggle with. When a client emails to tell me that they aren't happy with a design, it puts me in a bad mood for a few hours. It's the number one thing that I try to deal with better every time it happens. Fortunately, 99% of the time, my clients are happy with my work, but you can never win them all.

So, to sum up, I wish I would have known that not every client is going to love your work. If I had known that, it would be a lot easier to deal with it internally when it happens!

Chris Spooner

Twitter | Website
I wish I had known how to put across my 'professional' opinion as a designer. In my early days if a client wanted a change or didn't like a particular element. I'd simply cave in and agree, then I'd not feel as happy with the final design. Nowadays I don't think twice about offering my opinion in return, and explaining how I think my solution would work better. Often a client will agree once they hear the underlying reasons behind a particular element. At the end of the day the client has a better end product and I'm happy and satisfied with the outcome.

Brian Hoff

Twitter | Website
Having started freelancing I wish I would have known and planned out better organization and maintaining a structured work flow. Its something that I still struggle with from time to time being a one-man-show. Often when you start freelancing you only thing of how to organize your actual design work that comes through, not details such as a better system for replying and saving emails, making it easier and more efficient to get contracts/proposals out the door, saving client information that show interest in your work, as opposed to those you only work with, in additional to other areas such as schedule time to market online using Twitter, Facebook, commenting on blogs, starting a blog or writing guest articles, etc — the aspects that you overlook many of times when it comes to online marketing, but can go a long way. I actually detailed a full article on some of the ways I organize my business that has helped in recent years, titled How to effectively organize, manage and maintain your freelance design business.

Sneh Roy

Twitter | Website
Things I wish I knew when I started freelancing.

  1. Thou shall always create a logo in vector format
  2. Thou shall not jump through hoops for a client.
  3. Thou shall not be afraid to say "No".
  4. Thou shall not crumble, falter and surrender to your client’s whims and fancies.
  5. Thou shall set a wide, comfortable time line for project completion.
  6. Thou shall not have a life, or evening off, or proper eating hours in the first few months.
  7. Thou shall never let someone else present your work.
  8. Thou shall never bow down to corporate red tape.
  9. Thou shall not be afraid to increase your hourly rates.
  10. Thou shall not succumb to "Just make this one change, I promise that is the last one!"

Rob E. Bowen

Twitter | Website
I wish I had known before I started freelancing that there was such a rich and active community that existed online waiting to be engaged. A community ready to help with learning and invaluable advice. Collaborations and varying degrees of other opportunities woven within this expansive base of people all a part of a larger whole. It was really cool, and a little unexpected. The community made the entire undertaking more approachable and not as maddening as I had anticipated.

The community has played a large part in my freelancing growth and success, and I think that the trepidation that slowed my entrance into this forum would have been eased considerably had I known how inviting and welcoming the waters were. So much so, that the community actually altered my initial mission that I entered with. I initially got into freelancing for the opportunity to work for myself, and I found instead, that I am working for the community. Now what I mean by that is, that I found a purpose that fit and served me better. Not that it was like the community demanded it.

So I began to focus more on working to give back to that community, and along the way, ventured in directions that I thought followed in suit with those desires, but that actually were only in that vein on the surface. So I would have to re-adjust my course from time to time, always trying to be aware of what could best serve and give back to this amazing online collective. And allowing myself to evolve and be as fluid and dynamic as the community itself. This is something I never thought would happen before I started freelancing.

I never saw this job, evolving and changing me in ways. Becoming a career of communal collaboration and inspiration. And that inspiration reaching beyond the 'job' part and into my creative personal work and life as well. I never knew that freelancing was more of a way of life than simply another job where the boss wasn't as much of an asshole as I was accustomed to.


Twitter | Website
I don't take on many "freelance" projects, but I wish I would've known that even with a signed contract, you still have to go through the court system and pay all kinds of fees to get the ball rolling if something terrible happens... like say a client cancels a check. After $160 in court/paper costs or so and no response from a loser client, I also wish I would've trusted my instincts. Which leads me to this: Don't be afraid to say "no" to a project. If I could only pass along one small piece of advice to kids starting out, and even to those who've been at it for a while, that's it. Sometimes it's really not worth it... in more ways than one. Have a bad feeling about a client? Trust your gut and walk away.

One more thing: Sometimes the most important and best projects are the ones you do for yourself, including working on your portfolio and re-branding yourself. The devil is in the details... get out your pitchforks.

What do you wish you would have known?

Let us know in the comments if there's things you've learned along the way that you can pass along to the first time freelancers who may be reading this post. I know we can always learn something new - new freelancer or old, knowledge never stops.

Additional Reading: Computer Arts has an awesome article, asking 11 freelancers (freaky, huh?) what their freelance secrets are. It's really in depth and worth checking out. Read it here

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  1. Nice article Mike, some excellent points. Some that stand out for me is the outsourcing of tasks and the tax right-offs.

  2. Cookie says:

    Wish I had known I didn’t have to be so afraid. Freelancing always came across as this arduous walk through the valley of death, a struggle to make a living where you needed sharp elbows and a fearlessness I just didn’t think I had. Then my well thought out life crumbled, the M.Sc. never happened, couldn’t get a job – and things just seemed to happen. Suddenly I was a freelancer and my life is so much easier than before. I still don’t have very sharp elbows, but I’m not as afraid anymore. :)

    And yeah, get someone else to do your bookkeeping and taxes – but never surrender control over your finances and financial planning!

    • Mike Smith says:

      wow Cookie, thanks for that. It’s inspiring to read. I’m glad everything worked out for you and don’t worry, I’m sure you’ll sharpen your elbows along the way :)

  3. Brian Yerkes says:

    Nice post Mike, and thanks for the inclusion.

    Interesting to see Chris and I both gave the same sort of answer. “Don’t be afraid to voice your opinion when the client says “No” to an idea/design.”

    If you just rollover and make every terrible change that the client wants , you’re nothing more than a pixel monkey, and you’ll end up not liking the project at all.

    • Gist Studio says:

      One technique I’ve found useful with some clients is to “interview” them about their product or brief. This may bring up things they haven’t considered and has often altered or clarified weak briefs.

      You’re right about not taking things personally too. Some people have appalling taste or are just ignorant of the implications of their request and don’t listen to reason. Unfortunately for them, I’ve often been proven right in the end but it’s an expensive lesson for them to learn when they need to reprint or the design doesn’t appeal to their target market.

      Also have had account managers accepting terrible client requests because they’re frightened of blowing the budget. I pointed out that if the job looks bad in the end then they probably won’t get repeat business. Your reputation is only as good as the last job seen by the public eye.

  4. Alan Dowling says:

    Excellent suggestions. The tip about trusting your gut concerning potentially sketchy clients is key. Oh, and keeping all your receipts. Writing off expenses always feels like I’m pulling off some sort of weird tax magic trick.

  5. Rob Bowen says:

    Thanks for including me on the list, Mike, seeing all the others that you feel I am in the company of is truly humbling. So many great answers and so much great advice, I am happy to be a part of this post.

  6. Kayla says:

    I wish I would have taken my freelancing more seriously as a business when just starting out. Granted I’m better about it now, in my first few months I bought my way into a lot of debt by not taking my finances or taxes seriously enough. After my first credit card scare though, I started tracking my finances like a hawk, and also got more serious about what to charge my clients fairly, and secured my projects/finances with contracts. I also upped my marketing plan so I’d be sure to have a more regular flow of work.

  7. I have freelanced on and off for the last 5 years while maintaing a full-time job. While I may not do it full time, I can agree and say I have experienced almost every one of these points in this article. The hardest for me ahs always been trying to argue with a client why they may be wrong…. As the post says above, WE are the experts here!


  8. zainab sule says:

    I wish I’d have started freelancing earlier. And Blogging too. And twitter. And Facebook.

    I wish i’d have known that there were people who were willing to help you learn thru all the means stated above.

  9. Dan says:

    I’m currently getting more into freelance now and I know that I’m already guilty of a lot of the above mentioned. Great article though. This really gave me a lot of confidence of how I should be doing things. I’ll refer back to it again I’m sure.

  10. Alan says:

    Good article there, and its certainly good for anyone just starting out.

    I found alot of the above things out in my first 18 months of employment.

  11. Kostandinos says:

    Great idea, Mike! I love that you opened this up to a bunch of us. It’s great to have insight from so many in the field when it comes to things like this.

    I’d like to hear more of what Amber has to say about starting out, and anyone else who’d like to chime in. I’m actually considering starting a new career that would have nothing to do with design, but I think the freelancing/starting out knowledge would still be helpful.


  12. There is so much wonderful advice here! The one that really hit home with me was Sean Baker’s advice to take your time and sleep on it when it comes to estimating hours for a job. I’ve been caught in that trap many times — rushing to come up with a number, only to find end up selling myself short.

    I’d also add in, “Don’t let yourself be bullied.” Potential clients can be pushy, and even threatening, trying to bully you into lowering your prices or shortening your timeline. They’ll throw things out like, “I spoke with someone else who said that they could design my site for X dollars,” or “If you can’t finish by X date, I’m going to have to go elsewhere.”

    Those types of clients are always the most troublesome — sometimes stringing you on for weeks or months and then not wanting to pay. The post on Guerrilla Freelancing earlier this week “5 Dreaded buzz kill phrases every freelancer should avoid” should be required reading for every new freelancer. Don’t give into people who try to push you around or threaten you — stand strong in your estimates, and if they can’t handle it, let them go elsewhere.

  13. I’ve freelancing a bit here and there on the side now and I must say that all these advises seem very good and applicable!

    In a couple of months I’ll be graduating so I’m trying to really get my freelancing going now.

    Thanks for the good advice!!

  14. Mahmoud says:

    Interesting read!
    For me, I wish I started reading blogs – like this one – earlier, it is a must (I personally think!).

    *Note: The link for Sneh Roy’s Twitter profile is broken!
    Just thought of letting you know so you can update it. :)

  15. Kim Smith says:

    I totally agree Jon Phillips. When you’re solo and a perfectionist it’s hard to let others in and help you. I am realizing now after 2 years that there are only 24 hours in a day and as things get busier and you get more clients, you suddenly start to realize your limits. You should do the tasks you enjoy doing to outsource those that you can or don’t enjoy.
    Also, Brian Yerkes’ and Chris Spooner’s comments ring true. A client hires you because you are an expert in your field, therefore, you should always voice your opinion professionally. If after you’ve done this and the client still doesn’t like your design, then at least you can feel good that you’ve offered your best advice.

  16. Great post, it’s neat to see advice from people that have been at this for a while. I completely agree that you can’t be afraid to tell a client their idea sucks. They don’t always know best, and they are paying for your expertise, even if they forget that sometimes 😉 Good luck to all freelancers out there!

  17. Sid says:

    A very motivationg Article and i m sure it will be help me in freelancing but also my daily stuff .. :)

  18. Ravi. S says:

    This article will help me a lot…created a kind of confidence in me! Esp : Brian Yerkes’s.

  19. Jenny says:


    I learned a lot form this post, especially about “trusting ones gut” I wish I’d had this piece of advice a couple times a year ago when I first started freelancing.

    Outsourcing is a great piece of advice, but something a little farther down the road when you have a few steady clients.

    That’s been the most difficult part in my neck of the woods…steady clients. Clients leave loving the work, and I may get another job from them, but getting the idea of good design across has been difficult.

    Thanks again!

  20. Jon Bergan says:

    I always love these types of articles because they always remind you of things you either need to do or lessons learnt. I couldn’t agree more with Jon Phillips though. Its amazing how much you try and tackle in the beginning only to realise that half of it can be outsourced for next to nothing.

    Great post. Keep up the awesome work man!


  21. Leigh Hunter says:

    I wish I had known that the value of being the master of your own time, and therefore life, outweighs any kind of financial security I thought I had. I waited too long to start my own thing, purely out of fear for not having “job security”.

    Now my business is thriving and I couldn’t be happier, but in all honesty, I’d take less money over someone else owning my days any time.

    That, and, like everyone else said: Get someone else to do your taxes… lol

  22. And they say your hard work will never pay off. Well, thanks for this. I happen to be just starting out in the freelance world, so this will give me a leg up!

  23. Mike Smith says:

    WOW. Thanks for the comments everyone. I really appreciate it and am happy to see your “wish you would have known’s” in the comments.

  24. Sean says:

    I have one I will add that I recently discovered – don’t ever take a project based solely on percentage of sales especially if it’s a startup without building in a base rate for the project.

  25. Andy Sowards says:

    Great idea for a post Mike (As usual) :)

    Totally honored to be listed here with these great and extremely talented people!

    Love hearing their end of the story – I hope to see many more posts with these guys in it, and many more years freelancing around their inspiration :)

    Keep up the good work!

  26. Marnie B says:

    Brian Yerkes’ comments struck a chord with me – I still really struggle when a client hates the design I’ve presented. More often than not, I’ve found the client isn’t necessarily right and with a good talking to they come around, but I’ve also had to learn to recognise when I haven’t come up with the best design for them too.

  27. Skum says:

    Great article. The one thing that really stans out for me is the outsourcing of tasks. I find that i might be inclined to say no to a project simply because i’m not sure i can take on a certain aspect of the project, and you’re not entirely sure if the outsourced task will measure up to your own standards. But it is a great point, and a great way to grow your business.

  28. Vladimir Dj. says:

    I have question for Big-Head-Top-Freelancers as a freelancer, guy-to-a-guy, co-worker to a bodss :). Question is – “Where do you go for vacation?”

    • Jon Bergan says:

      Well, I try and get away every twelve months. I believe I have to in order to stay sane! 😉 As freelancers, we spend a LOT of time working. So, we need to get away from time to time to keep a clear head.

      This year I went to the UK and Italy with my life. Last year I went to Melbourne, Australia for a week. Next year I’ll be going to Fiji. Anywhere where I can experience history/culture or simply relax is a good place for me. I need to switch off every once in awhile.


    • Mike Smith says:

      I have yet to take a formal vacation. I do try to take a few days off here and there, just to recharge. I think personally for me, this works better than just taking one week off every year. 2-3 days of no work every month keeps me sane.

  29. Jon Bergan says:

    I actually also take most weekends off and one extra day off a month (generally the first Friday of the month). I work hard every day that I work though so I need to recharge. The last thing I want to do is burn myself out as thats a hard place to get out of. :)

    I think as freelancers/business owners, we need that time off to recharge and to regroup.


    • Mike Smith says:

      Yeah, definitely. The burnt out stage is definitely one that will suck the life out of you if you’re not careful.

      I’m kind of jealous you take weekends off :)

  30. Charles says:

    Outsourcing is a big one. As a wise man once said, delegate everything that is not genius. Most web designers don’t like to fool around with code, so why do it. Your genius as a web designer is DESIGN! So design and leave the code to the professionals. Cozality, for example, has taken the usual route as a proprietary CMS for non profits of collaborating with freelance web designers. Want to provide a solid, feature rich, socially integrated website for a non profit organization? You design. Cozality will apply the “power”. You keep your clients. Everybody wins.

  31. Sean Baker says:

    Big shout out to Mike for reaching out! This is such an important article to newcomers; deciding when to go solo is probably one of the scariest things for designers. It’s a dangerous plunge, but the results are extremely rewarding. Be humble and never stop pressing for work.

  32. FoxTopper says:

    Good article and excellent points! :) And yes, I agree taxes do suck 😛 Haha

    Here’s a feature that might be helpful to freelancer out there as well :—the-free-32-page-e-book-from-freelance-advisor.aspx

  33. Lisa Raymond says:

    When I started freelancing, I wish I would have known it’s not okay to chase the money; in other words, it’s not okay to pursue an opportunity merely because I needed the money. By doing this you may pick up a client you’ll wish you hadn’t. Don’t be afraid to “fire” a client.

  34. Great Stuff
    thanks for the share

  35. Adam says:

    Great article and comments!

    It’s amazing how much we learn as our careers progress and develop.

    For me, I wish I had known that micro-business (aka small business owners) owners were not necessarily the best demographic to go after. Often, they’ve never worked with a freelancer or agency before, under-value the amount of skill required to complete “the easiest of websites” and don’t have the resolve to put in the effort it takes on their end to ensure that their site gets traffic and is effective.

    I definitely would have started with bigger clients, projects and a better mindset.

    Tied for first is also that it’s necessary, mandatory and surely advised to be gentle with yourself. You will make mistakes and beating yourself up only leads to potentially destructive behaviour.


  36. April says:

    I really enjoyed reading this article. I started my freelance graphic/web design business in January ’10, after being in school for my AS Degree for only 3 months. I’m about to graduate this fall, and here I am with clients, PAYING clients, and it feels great! I’m glad I wasn’t afraid to get started while I’m in school. I think my rates are very competitive, and most clients tend to be very patient with me, as they understand that I’m still a student and still learning.
    Also, I am not afraid to try things that are unfamiliar. I recently designed a flash site using, which I had never used before, and it turned out phenomenally! The client was very pleased, and I did a much better job than I probably would have done had I tried to design the site from scratch in Dreamweaver.
    I know I’m rambling, but the things I’m most interested in taking away from this article is learning how to outsource and build a team I can count on, in addition to getting creative when it comes to tax time. In this economy, it’s been hard trying to find a “job”, but I may not need one if I continue to build my business! I love the freedom of being a freelancer, and I wish all of you much success in your endeavors!

  37. I love your column, and I’m putting a link on my blog/website, It’s so helpful to hear other people’s experiences. I’ve been at this for many years, and there is still always something new to learn! Thanks for sharing some whimsy and wisdom through the eyes of these talented freelancers.
    LisaBeth Weber

  38. Brandon says:

    One important component is understanding time allocation. Break down the components of your project by what you’re positive you can deliver on time, and then get creative. You’ll save yourself a lot of energy and sanity by sacrificing “great” for “good” for the sake of meeting your deadline.

  39. Doug C. says:

    ROFL … Sneh’s list busted me up. How true! Everyone one of them.

  40. Doug C. says:

    “I wish I had known before I started freelancing that there was such a rich and active community that existed online waiting to be engaged. A community ready to help with learning and invaluable advice.”

    Rob, that sounds awesome. Where is it?

  41. Andrea says:

    I wish I would have known how important it is to have a contract that encompasses the entirety of each project down to every last detail. Costs. Ownership. Amount of changes that can be made. Etcetera. It is helpful to begin a client experience with clear goals and budgeting.

  42. Katie says:

    I’m relieved to see that some folks responding or commenting know that it’s just plain bad grammar to say “I wish I would have known”. It should be “I wish I had known” . Period. This usage is not evidence of linguistic change, it’s evidence of not knowing any better.

  43. Denim Geek says:

    Great read, a few tips to pick up in there! Wish I had read it earlier as unfortunately I some of this the hard way.

  44. Ben Shape says:

    I wish I had known that sometimes, there are simply ‘bad clients’

    Every article will attempt to tell you otherwise, but after 10 years in the game, I can confirm that it’s true =)

  45. Lisa says:

    This is some wonderful advice. Especially for those of us just starting out. While all helpful, the ‘thou shall nots’ are my favorits.

  46. Rhonda B says:

    What a good read! I can totally relate to many of the things talked about. I have learned that as a freelancer you have to stand your ground and stick to your policies (and in the first place establish some). I will definitely keep this article bookmarked for future reference. The comments are interesting also.

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