My 3 Worst Screw Ups As a Newbie Freelancer

I wish someone had warned me about #2.

No one wants to fail, but when you’re a writer, a new writer, one bad decision can feel detrimental. It doesn’t matter if it’s an unhappy blog reader or an irate client, the smallest hiccup internally registers as a colossal botch.

You become your own worst critic, telling yourself that you know nothing about business and that you’re just not cut out for the job.

The anxiety of a few bad experiences can be so crippling to a novice writer that they’re ready to wave the white flag before they’ve even had a real opportunity to excel.

I know, I’ve been there.

I was ready to give up on freelancing with the first year! While I’d been to college, I had no formal training in the writing industry or business for that matter.

…but you know what?

We’ve all been new at some point in our lives.

We all mess up, we all make mistakes.

During the first couple of years as a freelancer, my blunders were GLARING. Clients would rip me a new one, and I’d spend weeks mulling over how much I sucked.

The thing is, I didn’t suck…I just didn’t know what I was doing, and I had very little mentorship. If you’re reading this, I’m guessing you’re probably in the same boat.

Should this be true, I promise that things aren’t as hopeless as they seem right now. Instead of jumping ship, let me guide your sail in the right direction.

#1 I Underestimated the Workload

Projects that consist of about 800 to 1500 words don’t sound terribly difficult at first glance, but that’s why it’s usually necessary to take a second look.

When I started as an Upwork freelancer, I was beyond excited about the number of invites I was receiving. At the time, I was working multiple jobs and I wanted out of the grinding lifestyle. After a few projects and some stellar reviews, things seemed to be going well…until they weren’t.

I quickly found myself overloaded. Drowning in work that was tedious and time-consuming, I spent hours on projects that only paid $15 to $30 apiece.

The work was no longer enjoyable, and I was never really “off.” At least I could clock out for the day at my 9 to 5; as a freelancer I slept intermittently, surviving on coffee and willpower to get through the endless nights.

How to Fix It: Get selective about your projects!

I know that when you’re just starting, it’s easy to see dollar signs everywhere. You might even feel like you only deserve these low paying jobs because the portfolio isn’t quite there yet.

Your work and your time have value.

Read that again.

If you’re used to working a day job like most of us are, you start to believe that you should have to take on an exorbitant amount of tasks to make anywhere from $9 to $15 an hour. You shouldn’t.

You’re a writer, and you’re doing a job that others can’t. At a minimum, you should be asking for $20 per hour to start with. Charging more will attract higher-paying clients, which means you won’t have to juggle a million projects from folks who want Whole Foods quality with a Dollar Store budget.

If they could do it themselves, they wouldn’t need to hire you.

#2 I Didn’t Know How to Manage Scope Creep

If you’ve never heard the phrase “scope creep,” pump the brakes on all projects immediately. The term refers to constant, uncontrolled changes or lack of control, and it’s usually where writers run into trouble.

A few years ago, one of my clients hired me to write blogs for 3 of their Shopify websites and respond to customer comments on Amazon. After a few weeks went by, they asked if I could do some product fulfillment as well. I didn’t mind, it seemed simple enough to copy and paste an address and check a few boxes. The problem was, I had just agreed to take on more work without asking for more compensation.

Photo by Cytonn Photography on Unsplash

Soon afterward, they’d asked if they could send the product to my home and have me ship it out to unhappy customers, and they had many. This time, I wasn’t comfortable taking on such a task, and I didn’t appreciate the accusatory tone the client was beginning to take. If packages didn’t arrive fast enough, they’d ask if it had been sent out at all.

There was also the comment about “the last girl they’d fired,” which was an underhanded threat to cut ties. Truthfully, I prayed that they would voluntarily end the contract; the whole reason I’d left my job to pursue this endeavor was to gain freedom from the employee-employer dynamic.

The worst part was knowing that I allowed myself to get suckered right back into the “employee” dynamic where the pay did not match the value. This wasn’t my only client, and I could have very easily asked for much more money.

How to Fix It: Stick to the contract, and be assertive.

For many people (including me) it’s tough to claim your power. Remember, you are an “independent contractor,” not an employee. You never have to compromise your worth or your time thanks to the contract.

If your outline looks like this:

  • An 800-word blog billed at 2 hours for $40 per hour
  • 3 scholarly link resources
  • 2 photos
  • 1 round of editing

…but your client asks for a 4th link, or 2 more photos, or excessive editing, you need to start tacking on extra hours. Have you ever heard of a lawyer doing extra administrative work for free?

No, because they have other clients that need their attention, and they have people on their payroll who are still owed a check at the end of the week. Be sure that your project outline is crystal clear, including the time it takes for research, the bulk of the writing, and any post-editing.

Trust me, if you start practicing due diligence now, you’ll save yourself a world of heartache in the future.


I’ll be the first to tell you that missing a deadline BLOWS, dude. It doesn’t matter if it was an error on your part or miscommunication by the client, it’s not fun. You feel like garbage, and the person you’re writing for is somewhere on the spectrum between slightly irritated, and fully pissed.

In the first year or so of freelancing, missing a deadline was usually the direct result of the first 2 screwups.

Think of it as a formula: 1+2=3….If you don’t manage your projects correctly or select the right clients, handing in late projects becomes inevitable. At the time, I didn’t know how to make an honest assessment of how long certain tasks would take because I was still new to the industry. I’d estimate a couple of hours for a 1500 word blog, only to find myself plugging away for another 3 hours, kicking myself the entire way.

How to Correct It

Managing your time is something you sort of have to figure out for yourself. For me, that meant picking a topic I found interesting and timing how long it took me to complete the blog from start to finish.

This is the part where a lot of newbies struggle because it often requires writing without the reward. It means setting up an account on Hubpages or Medium and watching their blogs make little to no money initially. We all started here, so suck it up, Buttercup.

You are not an employee, no one is going to baby you or tell you how much time or effort you should be putting into a project. It’s up to you to spend as much as 20 hours a week honing your craft, or 4.

Introverted animal lover and financial enthusiast.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store