Common Freelancer Fails and How to Avoid Them

The freelancing world is a fierce place to be, and for a newbie freelancer, this is especially true. Competing against the world online can seem like a futile endeavor, which is why most freelancers start off in their hometown or nearby cities working for local business. Usually you have the advantage here–you know them, they know you, and trust is just a side product of that relationship.
I know this topic can be controversial, but this is based on my own experience. If you’ve had a different one, please chime in below and tell me about it. The only way we can all make it is if we view not only our experiences, but other peoples’ experiences as learning opportunities–and not everyone is going to have the same story.
Here are a few of the common freelancer fails–and my advice, which was learned the hard way, on how to avoid them:

1. Overvaluing yourself

When I first started freelancing, I was overvaluing my services given the experience I had at the time–as many do. Straight out of high school, I thought I was the shizz; I knew HTML, had started in PHP, and thought Joomla was my salvation! I was approached by a local heavy machinery company to do a website for their machines, so I set up the initial conversation, and had, what I thought, was a very productive meeting.

They gave me a tour of the facility. It was at the moment when they showed me the machines they wanted pictures of–at that exact moment, I knew I was out of my element. I had no photographer, nor did I know someone who could take decent photos. There was this HUGE machine (that, to this day, I can’t remember the name of) that was about ten feet wide, five feet deep, and about twenty feet tall…how in the world was I going to take a picture of that?! You can’t move it! It’s built in place and stays there for the life of the machine.

Of course, the bold and fearless newbie in me said, “Sure, I can get a photographer to take some pictures of it for the website.” I figured, the internet is full of ’em…right?!

At the end of the meeting came the money talk, which absolutely no one, aside from the freelancer, is interested in. At this point, I barely knew CSS, was nowhere near an expert in HTML, had little PHP experience, and knew nothing about MySQL. So when they asked, “How much would you charge,” my initial response was, “They have money; they can pay just about any figure within reason!”

If there’s any advice I can give a freelancer, first and foremost, it’s that if you think this, you need to check yourself.

Knowing I could do the site in as little as two weeks, I gave them a one month time frame for completion at a $4,000 budget. How was I going to do that? Well, using the Joomla forums, of course–you’ve seen those threads asking, “How do I do this,” “Okay, what about that,” or “Now I have this new thing.” I should’ve learned more beforehand.

And what about a designer? Nah! I’ll just download themes and plugins and spam the forums more when I need help fixing things.

Now, before you say $4,000 is peas and carrots compared to developers today, let me put it into perspective for you. In my town, average wage for high school graduates was, at the time, $5.25-$6.50 an hour. I could only HOPE to make $1,000 a month straight out of high school, so $4,000 was a HUGE pay raise for me.

I literally took what I would like to make monthly, then just multiplied it by four, because why not? They had the money, and I needed it; I figured it would be a win-win if I got the contract. So how do you find the RIGHT figure for you? We’ll get there–don’t worry.

2. Undervaluing yourself

Sometime down the road, years later, I applied to what few web companies we had nearby, and through them, I learned about what used to be oDesk and is now Upwork. After doing some research into how it all worked, I started bidding for jobs. By this point, I had learned the importance of proper estimations and how to make them (or so I’d thought), and I was bidding on jobs while still using my “what I want to make” mental calculator.

To my surprise, considering the pool of jobs available, I was never hired for any of the fifty (or more) applications I had placed in roughly two months. It’s no wonder why–the “winner” in me was a very stupid person at that time, and I made the most idiotic decision I’ve ever made: I bid a job a a whopping $1.00 for, what I thought, was an easy job. I wanted to do anything to get that first review!

If you want something to laugh at, this screenshot is definitely for you. It is FOREVER on my record over at Upwork now, and while yes, I could remove it, I keep it there as a reminder of what NOT to do.

A year or so went by, and of course by that time I had learned my lesson. I had found the sweet spot of getting clients and had started doing jobs for roughly $20/hr. By that time, I was working exclusively with WordPress and had completely rid myself of any Joomla knowledge. Application bots were more prevalent now, and it was getting harder and harder to compete with overseas prices.

$20 for a gallery? I think not!
$20 for a gallery? I think not!

You see jobs like this so much now on freelancing sites. $15 for a landing page, or, oh dear, maybe a whopping $100 for a “simple five page site.”  Perhaps you could cheat and just install WordPress, grab a random theme, set it up, and walk away. If you’re cool with doing that, can you call yourself a developer? What code did you actually write? In doing so, you’d be doing a disservice to yourself and the company you’re working with.

I wanted to win, and I wanted those reviews that I knew would bring me more customers. In doing so, I pretty much set a precedent of how much I was worth to the Upwork community.

Finding the right price!

In order to work, you need to live. In order to live, you need to eat. In order to eat, you need money. So how do you find the right figure for you starting out? While I cannot tell you what YOU are worth–only you can make that determination–I can tell you how I would have calculated my hourly cost if I had the knowledge I have now:

Begin by taking your fundamental monthly expenses–utilities, power, electric, groceries, etc., and add all those up. Now pad that total with a reasonable number (for either your savings account, play money, additional money to go toward debt, whatever), and you should have a general idea of how much you need to make per month. For this example, let’s say that you need $1,250 a month (this number will, of course, vary depending on where you live, how many family members you have, and a variety of other factors that are all deeply individual to you).

Now that you have the total amount you need to make, at minimum, you need to figure out how many hours a month you are willing to work. For me, it was twenty hours a week; I only wanted to work three days a week, and this was the best way to do it. For the month, that means I wanted to work eighty hours total.

You now take the hours per month and divide by the amount per month you need to make, so $1,250 / 80 hrs. equates to roughly $15.63 per hour. Keep in mind–that the hourly cost does not cover the time you will spend hunting for these jobs, nor the time you invest in your own business (if you build your own site, any marketing you do, vetting initial leads, etc.), so you may want to pad that number to account for those time costs that exist as a function of your business, but are not covered when directly interacting with the client.

3. Underestimating Hours

Generally speaking, getting a client that doesn’t give you a time frame for completion will be a stroke of luck. Most, if not all, clients have a deadline in mind when approaching you; sometimes it’s flexible, sometimes it’s not. You have to live with it–or you have to turn it down. You, as a freelancer, have the ability to determine which clients you can and want to take on; you can’t change their terms, but you can determine who you work with and the kinds of projects you work on.

So many times in the early years of freelancing, I failed to properly estimate my hours. One of the most notable projects was when working with CodeIgniter. To this day, I still don’t fully understand how MVC frameworks operate; I get the basics, but there’s some of it that is still a mystery to me. At the time of acquiring this contract, I gave the client a two month time frame, and explained to them that there wouldn’t be a problem because I know what I’m doing. I thought to myself, “It’s just PHP right?” I did educate the client on my inexperience with CI when HE suggested I use it, but forward we went.

However, eight weeks was not nearly enough for learning a completely foreign framework. For those that don’t know CI: It is absolutely NOTHING like WordPress. It’s a framework and not a complete solution. You build what you need–nothing more. In addition to this, the contract did not explicitly dictate what would happen, what the intent was, and left the terms pretty open-ended. It was pretty much “I’m learning this stuff as I go, so you pay me x amount.” Combine this with the fact that the client was feeding me new ideas and shooting them over to me with, “I’ve seen this here–we need to add it!” almost every day, and as you can imagine, it was a development nightmare.

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I knowingly accepted a contract and was completely unprepared for what it entailed. Underestimating a project for which I had no knowledge was possibly one of the worst mistakes I’ve ever made.

NEVER give estimated hours without thoroughly investigating the problem or project. If there is no time to investigate the problem, always significantly pad the hours (minimum 50%) to cover any hiccups or walls you may hit AND to cover Q/A after you may think it is complete.

4. Retainers

As I spoke about in the above sections, money will make or break you in the freelancing business, and it can absolutely wreck you if you’re not careful. Of all of my freelancing clients, I’ve only kept one on a retainer, and that was purely at his request. Sure, the money is great when it’s coming in, but what happens when you hit a dry spell? You have zero control over what people are looking for, unless you are driving the market somehow, and financial inconsistencies will make or break you. At the time, my idea of a retainer was merely having clients host with me–which, honestly, all I did was setup their hosting account for them and managed any updates. This is the MAIN reason I failed as a freelancer.

Retainers should be much more than that. A retainer is a relationship, for better or worse–kind of like a marriage. Unfortunately, with all of my retainers, I was trying to sell hosting, and not update/maintenance services.

I treated retainers purely as a money making tool and tried to get that income, rather than recognizing them as a commitment and an ongoing relationship. This is not to say that the money isn’t important, or that they aren’t a good source of income, but that you’re selling more than you are with a one-off service; there’s a relationship and an expectation that comes with them.

With what I know now, I would offer retainers to all clients at a slightly discounted hourly rate (which gives them some incentive to sign with you–the short term hit for the long term benefit). In addition to hosting, I would also offer things like plugin updates, bug fixes, and small features. Check our peeps over at Maintainn to see what they’re doing for more ideas of what a good retainer and awesome ongoing maintenance support looks like.

5. Time Management

This is perhaps the most discussed item among freelancers–time management! As a freelancer, you have the ability to make your own schedule. Not feeling good? Stay in bed. Want to do something else that day? You can!

While this is technically true, if you’ve done the freelance gig, you know that this isn’t sustainable. In the early stage of my freelance journey, I had the “I do what I want,” mentality. A year or so went by of me getting up at two in the afternoon and searching on oDesk for various jobs. My rule was to spend at least two hours a day looking for work and the rest doing whatever I want. That’s the benefits of being a freelancer…right?


Your ability to find work directly impacts your wallet. I was spending only two hours a day looking for work, which if you’re doing that daily and only using one website, the jobs come in a lot slower. If I found nothing within two hours, I would go play some games or update some code I previously worked on.

"He seems to know what's up but personal reasons seemed to stand in the way of doing things on time." - Don't be me!
Don’t be this guy!

The above screenshot from one of my reviews speaks for itself. Turns out, going to play some games and getting up late negatively affected my client work, and to this date, I regret this review, but I keep it as a reminder. In this phase of my freelance journey, I had no schedule set–only deadlines. Believe me, if you’re a procrastinator, that’s not a good thing to do–and even if you’re not, you NEED a schedule. We can’t all have an awesome project manager to do this for us (although you can use some of their tips to project manage yourself). You absolutely need to sit down and say, “I’m available during X time on Y days of the week,” and stick to it.

Believing that your life as a freelancer will allow you to have a four hour work week with ease, especially at the beginning, is short-sighted. You’ll undercut your skills with your disorganization, and you’ll find that not having a schedule and procrastinating right until up until deadline will prevent your business from growing.


In the freelance world, YOU directly impact how you will survive. It’s a fierce world in the global arena and it’s up to you to stake your claim. I cannot provide a cookie-cutter solution that will make freelancing easy, nor can I predict your successes or failures; I can only detail my peaks and valleys and hope that someone learns from them. Finding work and developing long-term client relationships (through retainers and other ongoing work) should be your primary focus. The best way to do that is to guarantee that you’re available when you say you will be, you’re delivering the service your clients were promised, and setting the right prices for your services.

Your value goes up with experience you gain. Clients aren’t just paying you to push buttons after all; they’re paying you to know what buttons to push and in what order. If you don’t know how to do something, take that as an opportunity to learn, and educate the client on what you know/don’t know and explain to them that this would be an educational task for you. I liked to provide reduced rates for tasks I thought would be a great learning experience, and that, at least for me, seemed to help.

Overall, we’re all human, and we make mistakes which add to our experience. I’m interested in hearing some of your stories as a freelancer and what you learned–whether you’re still freelancing or whether you’ve moved on to something steady.


6 thoughts on “Common Freelancer Fails and How to Avoid Them

  1. Loved this. I am very new to the professional freelancing world. Coming from an agency where I had a steady paycheck and then diving into the super competitive freelancing field is terrifying (yet gratifying). Reading about other people’s honest experiences is so valuable and helps keeps a person grounded.

    1. Thanks so much, freelancing is definitely awesome, but it’s also challenging. I actually went in reverse, freelancing first, then into an actual career.

      This was due to the lack of ‘opportunities’ nearby, there’s hardly any tech here where I live.

  2. Great article! It’s nice to hear a fresh and honest opinion about the world of freelancing. I especially liked the part about undervaluing yourself. That’s easy to do when you’re hungry!

  3. Great article Jay, thanks for sharing your personal experiences. Just wanted to add, when quoting your clients, as a developer, please remember to quote for troubleshooting mobile version of the site including the time it takes you to setup your dev environment, backup/migrate client’s existing files and database. Time to troubleshoot any cross browser issues should also be considered.

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