Top 10 Mistakes Made by New Freelancers

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This is a guest post by Jen Gordon, a user interface and interaction designer who also teaches how to create landing pages that convert like crazy. When she’s not busy pushing pixels she enjoys writing about design, and many other things that have absolutely nothing to do with a computer.

Now in my 10th year as a freelance designer helping entrepreneurs and marketers, it’s both exciting and horrifying to look back on times in my career where I enjoyed both great success and failure.

Yes, you’re taking advice from someone who has failed not once or twice, but many times. And, even though many of my failures have ironically resulted in very rewarding experiences, my hope is with this post you can avoid a few of my mistakes or validate decisions you are making in your own freelance career.

Think of this article as a quiz. Are you a newbie-freelance-mistake-making-machine? Find out!

Do you trust your gut?

If you get a weird vibe from a potential client – RUN. I can’t get any more specific than that. It’s just a feeling you get when you meet a person for the first time, hear their story, what they’re wanting to accomplish. We all get “a feeling” in situations like this. You know this feeling. And let’s face it – our intuition is an important decision-making tool in business!

Maybe it’s the work itself. It’s not a great fit for your skillset. Or perhaps it’s the client’s personality. Speaking as a graduate of the School of Hard Knocks, every time (and I mean EVERY TIME) I’ve had a bad vibe on a project or a potential client and didn’t trust my gut – I’ve failed ironically gained a valuable experience.

Are you being true to yourself and your talents?

I’ve been the world’s worst when it comes to this! I wanted to be everything to everybody both as a designer and a business person. The truth is I’m not an illustrator. The truth is I’m not a Yale grad. For me, I need a certain level of informality in my client relationships and total transparency around my gifts as a designer.

Whatever you need to be YOU, let it be known! Don’t be afraid to let your personality flow when working with clients. It’s the personal touch (your brand) that keeps them calling you over the fuddy-duddy down the street.

Iceman Forever

Do you back up your data?

The horror of lost data. Ugh! Losing precious work files is like watching Amityville, Carrie, and the Exorcist at the same time.

I’m embarrassed to admit I’ve learned this the hard way – twice! It’s embarrassing because it’s so simple to backup your data. My problem is I don’t think about the techie, networked blah blah side of my business (like many designers) until something blows up in my face and I find myself sprawled on the floor – crying. It’s a pretty awful sight.

When you’re working for yourself, backing up your data is your responsibility and duty to yourself – and your clients. Plain and simple. Make it a priority. Here are some services I’ve either used or am currently researching:

Dropbox – This is my go-to backup plan. I’ve invited some friends to use it and earned around 20GB of free storage as a result. It is reliable and it just works.

Google Drive – Google Drive is an inexpensive option at $4.99/mo for up to 100GB of storage. I’ve used the service and was happy with it, but found the syncing to be slower than Dropbox.

CrashPlan or Carbonite – I’ve recently been researching storage options for large quantities of data. Large like 4TB+ quantity of storage large. Dropbox is perfect for current projects and data that I need to access on a regular basis, but I still have terabytes of data from old clients that I don’t trust staying accessible on the many old hard drives I have lying around.

And for $4/mo for unlimited data you can’t beat the price. CrashPlan also offers a “Seeded Backup” where you to send them your hard drives of data, where they copy that data over so you’re not spending weeks uploading all of your data. Definitely an option to consider if you’re looking for a home for large volumes of data.

Are you working with your ideal client?

When I started my career as a freelance designer, I was eager to work – with anyone! When you’re new on the scene it’s easy to fall in to this thinking. You need work, and income. You rationalize that you just want the experience, and that you really can’t afford to be picky.

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Listen to me carefully. I understand this thinking. I really do. But the sooner you can sort out the type of clients and work that gets you excited about work in the morning, the better.

We each have to learn to work with all types of people. If a potential client doesn’t jive with you *before* the contract is signed, they may not be your ideal client. And, with freelance contracts often being one-time projects, there’s a good chance the the relationship won’t have time to develop and improve over time.

Rarely do you have time to sort out relational issues, unless you sign a long term contract. For short term projects, it’s great if you can choose clients that you can just run with, without the friction of relational conflict that may show itself early on. It was only after I burned out on a couple of “un-clients” that I discovered exactly what I was looking for in my ideal client. You may have to go through this process too.

Do you have a budget for your business?

When you initially go out on your own there is sometimes a sense of urgency to “get everything” you need to run your business. At least for me there was, but I’m a total techno geek / gadget freak. 🙂 Knowing what I know it still pains me to say this, but think Lean Startup and resist this urge.

Believe me, the credit card get bloated and suddenly those shiny new purchases are looking like huge liabilities. Figure out the bare minimum you need to make the business run smoothly, and then write down a wish list of things you’d like to add on in the future. It’s a great motivator to keep plugging along!

Are you marketing yourself as “We” rather than “I”?

If you’re a one-wo/man shop, make sure your clients know this! It’s fine to run your freelance business under a corporate name, but sometimes clients are confused by this, thinking you have an entire staff working on various roles in projects. My advice is to be crystal clear on who you are, what you do, and what you DON’T do.

What happens when you’re not upfront about using a sub-contractor for a piece of the work? The tiniest problem with that contractor’s work is within your sphere of responsibility. If you have a subcontractor that consistently over-performs, you’re set. If not, my recommendation is if you can’t take on all of the project work personally, give the client the option of hiring out that work through another freelancer.

This goes back to defining your ideal client – if they’re looking for a one-stop-shop, they may not be the best fit for your business!

Do you have a signed contract before starting work?

Doesn’t matter how small or big the project, a contract, statement of work and deliverables list is a MUST before you start any project. How else will you and the client agree on expectations and payment terms?

I remember being nervous about asking clients to sign a contract before starting work. Now I look back and realize it was only because I was afraid I wouldn’t get the job. I now know that a client who won’t sign a contract is not my ideal client.


Do you create real value?

You probably do, but aren’t sure what that value is! Ask your current and former clients. Often they can articulate why they would work with you again better than you can yourself.

Want one way to always squash your competition? A way that works every time because almost no one does it? Over the top, outstanding customer service.

Think about it, we live in a customer no-service world. People are absolutely starving for attention from their vendors. So, if you want to stand out & create value – decide what defines great customer service for your clients, and do it!

Are you charging too much, or not enough?

Charging too little is an obvious pitfall. Charging more than the market bears for your talent is also a problem. I was in the market for offloading some design work a few months back and contacted a person who was less than a year out of design school, his portfolio was just so-so and the hourly rate he quoted me was $40. That’s a fine rate if your portfolio says “I do $40/hr work.” But his didn’t. His said “I do $20/hr work.”

So here’s how to sort it out. Take a look at what your peers are charging. And by peers I mean people whose work is of comparable quality. Are these peers getting steady work? There’s a good chance their rate is congruent with the services they are providing. It’s a good place to start.

Do you manage your time well?

Based on your best “work time” figure out a schedule that works for you and stick to it. No matter if you’re most productive at night or early am, establishing a routine for your workday is one way to measure your productivity and manage communication with your clients. For me, my “work/creative time” is in the morning. After lunch I work on tasks that don’t require my creative brain. This fluctuates some throughout the year, and I adjust accordingly.

Check out this technique Neville over at AppSumo uses to manage his days. Pretty cool.

Computer and Desk

What are your newbie freelancing mistakes?

I’m not the only one with freelancing disaster stories – right? 🙂 Leave a comment below and share your own experiences.

Image credits: JD HancockIceman ForeverAnita Cadonau-HusebyFernando Castro

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Hernando Cadet

I know I have a ton of mistakes that I am working to fix, but once I have them all fixed up, I know I will be where I need to be in my life.


Very good advise and tips. I like the first one. This happens quite a lot with clients saying I need this or that but have no sort of plans.


Hey Jen great post!

I have been guilty at one point or another of each of those and most especially the gut feeling on a client one. It’s taking a lot of practice and a certain amount of faith to walk away from work, it’s always a lot harder to do than to say.

Also, on the customer service end of things, I think a good exercise is to sit down and write down your client interaction form beginning to end of a project and beyond. Define those critical junctures in that interaction and make sure that with every client you deliver the same experience.

Thanks again.

Jen Gordon

Thanks @Peter 🙂

Jen Gordon

@BryanG – great point. delivering a consistent experience for all customers is so important! Thanks for adding that nugget of advice 🙂

Gail Joiner

Two problems: Using billable time on nonpaying clients and over delivering.


Thanks for the post. I am just starting out and currently have potential clients in the works, so nothing secured. But this list keeps me in check of things I should and shouldn’t do.

Kristen Hicks

I used to be really uncomfortable pushing for a contract too, and even more uncomfortable asking for an advance.

I figured out over time that a potential client balking at those things serves as a pretty good warning sign. You want to work with people who will behave professionally, appreciate what you’re worth and pay (ideally, on time). Starting off by insisting on these symbols of professionalism helps you weed out some who won’t fit that basic profile.


I’ve been guilty of all of these mistakes, especially in the first year of my business. I had no idea what to charge, and was grateful for any work, so charged only 1/3 of what my peers were charging. I almost burned out completely before I raised my rates.
To my pleasant surprise, I found out that raising my rates to what was comparable for the local market was a great way to weed out bad clients, as my good “first clients” understood and appreciated even more that they got a great deal!
Oh, and the gut feeling… I should have listened to it when a formerly “good client” didn’t like my most recent business improvements! I wish I had settled up with her right away and more assertively.


I think my biggest new freelancer mistake is being too available. I work every day, all hours of the day … so if I client needs something “right now,” they typically get it. I’ve set up some dangerous boundaries. I’ve been successful enough my first year that I haven’t had time to finish my website – both a blessing and a curse, I suppose. I also need to learn how/when to walk away from unclients.

Jen Gordon

@kristin @kay definitely assertiveness and professional is what clients pay more for 🙂

@natosha great point that I didn’t address – accessibility and boundaries! I ran into this all the time when i worked with people on the west coast. i eventually had to tell them that talking to them during my dinnertime wasn’t cool!

Jose Vega

What a great article!

I agree with @Notosha. I work all day and night to get my clients work done. They´re always surprised of my availability. Now I think that makes them perceive me as needed.

I´ve also been a good blogger but suddenly I started receiving a lot of clients through my blog. And ironically, these clients consume my time and I havent published a single post in 3 month!!!

So, now I know say no to clients is really really hard when we are starting a business. Also get our clients to perceive us as real professionals.

Congrats Jen for the post…

Pubudu Gokarella

Very interesting article.Managing time is the hardest part when you are doing freelancing.Treat it as a business so you’ll succeed in it.


My biggest mistake was not getting out and talking to other freelancers, it is amazing how much you can learn and help each other!

Jen Gordon

@bradley @pubudu great points – managing time well and having a community of other freelancers is really helpful – especially on days when you’re questioning how to deal with difficult situations.

Yvette Tripp - Image Outsource

Wow! I feel so much better! I have been doing this for quite some time, and I am embarrassed to admit that I STILL make some of this mistakes. I never thought about the I/WE thing, but you make a very valid point. I will incorporate that knowledge into my website redo this week! (( It’s still flash based.. embarrassing! )) This is great knowledge and I just let myself off the hook a teensy bit… it feels a little better knowing I’m not the only one. Thank you very much.

Kevin Iamburg

These are some really good tips. I’ve learned most of these the hard way, unfortunately, through trials and tribulations :).

It’s one thing to know these concepts, actually implementing them into your daily routine is another. Thanks for sharing.


This is very helpful and as freelance photographer i have been spending most of my times working for clients without agreeing on the terms of payment or signing a contract. It has turned out that in most instances these clients end up not paying and i have a lot of developed unclaimed photographs in my files.

At times when there is a party i get clients who are drunk and they give u there phone numbers so that you take photographs to them and when you call them n the morning to remind them about the whole deal they can barely remember a thing. This article has opened my eyes on the drawing a contract part as i believe this will help me achieve.


Sam Crowe

Watch out for people with AOL addresses. Make sure you are clear about which browsers you support with a web project and don’t get excited when people say they have other business they can refer or know other business owners that they can send your way. Focus on the business at hand if they come through with the referrals later great but in most cases it is an effort to manipulate you to get more than what they are willing to pay for or squeeze more from you. Early talk of referrals almost never pans out.


This is a great article–even for me. I’ve been freelancing/moonlighting on and off for about 10 years now. But, I’ve been freelancing exclusively for almost 3 years now, and my business is JUST starting to gain some speed. So the information is still useful because some of these things didn’t apply until I found some more clients.

For me, the CONTRACT was a huge mistake. I definitely agree that it helps protect the designer in the very beginning. But, what I’ve found over the years is that when you learn to “trust your gut” and run away from the “bad” clients, what you’re also doing is allowing yourself to only work with people that you trust. I’ve also gained my insanely awesome customer service award, so that added to the gut-instinct-factor makes for a great meeting where I discuss, very clearly, how the process goes. I make sure they understand, and if they have any concerns, I work with THEM. That way, we’re pretty much doing it the way they want to do things, and I will walk away from the project if it’s something I don’t like the sound of. For instance, some people don’t mind paying the hourly rate, but some people are scared by it. For those people, I work flat rate so they know what to expect. People who pay hourly put down a deposit, people who pay flat rate pay 100% in advance. Anyway, I’ve noticed that when you actually speak to the clients about the process, they understand and remember it better. Most contracts are lengthy and legal-sounding. Most people just sign without reading it. I think a great middle-ground for newbie freelancers may be to have them sign a contract, but sit and *meet* with them so you can explain it–which would make their customer service rank higher.

As far as mistakes I’ve made in the past: ALWAYS make the client pay something–anything–before you begin. Until I started doing that, I had clients stealing my artwork left and right. Once I implemented that rule, I’ve never had artwork stolen again. It helps you weed out the serious people from the scammers. Those who genuinely want you to design something for them will pay up-front for it. People who are sketchy (e.g., “I don’t want to pay for it first… what if you never do the work”) those people are not good clients. Run away from them, too!


Some sound advice here! I’m glad to say I haven’t had to learn the hard way yet about trusting my gut, it’s gotten me some good clients and luckily I know when to turn down a few.

As for signing the contracts, I remember my first freelance job I didn’t have a contract (smh) but my second one was a much bigger scale and I was nervous but determined about presenting it. What I’ve learned though, is that a lot of small business (3-5 employees) don’t even bother reading it, they just sign it and I think it’s important to try and get them to read over it because I’ve had a few misunderstandings as to why I charged £20 to find a picture even though image sourcing was not included in the contract. Hmm yeah.

Walakira Joseph

I am willing to begin a business but these are very good advices you are availing to me . thax


@Sam Crowe: LOVE that quote: “Early talk of referrals almost never pans out.”

It reminds me to be cautious of anyone who seems to promise the sun, moon, and stars when I first meet them is usually too good to be true.


I have been a freelancer mainly for nearly several years now, and my small business is beginning to get some quickness. Is really great steps you’re getting in my experience. My wish has this particular article you are able to prevent some of my mistakes or examine options you’re making within your freelance profession.

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