freelance writing tips

I get a lot of emails from freelance writers.

Some ask me for advice. Some just want to say hi.

And some of them tell me all about how their fear is holding them back.

…The fear that they “aren’t good enough” or “don’t know enough” or “don’t have enough experience” to make it as a freelance writer.

Know what it often comes down to?

A fear of failure.

Yep – and it’s something I’ve struggled with in the past too.

I’m pretty sure every freelance writer has dealt with it at some point.

If you can relate, I’ve got some tough news for you:

You’re going to fucking fail at some point. Hard.

Seriously. I don’t care how Type-A you are or how much you think you have your shit together. It’ll happen.

And I’m not talking about a cute little “Whoopsie – I woke up 10 minutes late! Darn that silly ol’ alarm clock!” kind of fail.

I’m talking a “Steve Harvey announcing the wrong winner of the Miss Universe pageant” kind of fail here.

(…Okay, maybe not that bad.)

But it’ll be something that’s going to freak you out and make you question your decision to start your own freelance writing business.

How do I know this?

Because my freelance writing career has been full of failures.

Don’t get me wrong – I wouldn’t trade being a freelance writer and blogger for any salary. And I’ve done some good things for my freelance writing business too (like avoiding content mills and bidding sites like Upwork at all costs).

But I have, at times, been a MASSIVE fuck-up.

So guess what?

Today, I’m going to let you in on some of the biggest mistakes I’ve made in my freelance writing career. Along the way, I’ll also tell you what I learned from each situation.

Before we get started, keep this in mind:

The whole point of this blog post isn’t to scare you or make you question your decision to become a freelance writer.

It’s to help you realize that you will fuck up at some point no matter what, so you just have to take action anyway and do your best!

Let’s start with one of the dumbest things I did. 🙂

1.     I let all my projects stack up right before a major holiday.

My husband and I go to his family’s house every year on Christmas Eve.

Then, we wake up early on Christmas day to spend time with each other. And after that, we drive to my mom’s house a couple hours away.

Well. Last year in December, I had to write five 2000-word blog posts for my biggest client.

And guess when they were due?

The 25th of the month.

That’s right. Christmas Day.

And of course, I didn’t start on the blog posts until a couple days before they were due.

Know what I ended up doing?

Working on Christmas Eve AND getting up super early to finish the blog posts on Christmas Day.

So the time I was supposed to spend enjoying time with family was instead spent frantically trying to finish up 5 massive blog posts.

I barely slept in those few days, and I was a cranky, stressed out mess. Yuck.

Not only did I miss out on a much-needed holiday break – I lost the first chance I’d had in a while to spend some quality time with my husband and enjoy the fact that he was off work.


What I Did to Fix It:

Now, I never (I mean NEVER) allow myself to push projects until the end of the month.

If I have a client who wants a lot of stuff done by the end of the month, I give myself my own deadlines for the work.

In fact, I just started working with a client who wants 4 long, in-depth posts by the end of every month.

And you better believe that I’ve already tasked myself with writing one per week! Because I know that putting them all off until the end of the month would result in a huge clusterfuck.

So if you ever have a client who wants a lot of different blog posts by a specific date, plan to work on those posts a little at a time.

Trust me on this one – planning out your work ahead of time in chunks makes everything a lot more manageable and saves you from a ton of stress. Totally worth it.

2.     I worked so hard that I got sick.

Let’s face it – being a freelance writer is tough sometimes. You have to deal with deadlines, manage clients, send invoices, market yourself, and still manage to write your little heart out on a daily basis.

So basically, you’re doing the job of multiple people. All by your damn self.

Add a way-too-heavy workload into that mix, and every day starts to feel like a gigantic shitstorm that you’ll never be able to escape from.

Not only have I gotten super stressed and tense from working too hard – I’ve actually gotten physically ill as a result of the stress.

Ridiculous, right?

What I Did to Fix It: 

For one thing, I stopped overworking myself. Seems like common sense, but if you’re anything like me, you know it’s much easier said than done.

I mean, I still work hard, but I try to be a lot more intentional about the work I take on. I’m pickier.

I also make time to de-stress during the week.

Like, I go on walks during the day without thinking about my workload the entire time. I take 30-minute video game breaks. I schedule lunches with people to get myself out of the house.

Because you know what?

You don’t have to hustle 24/7 to maintain a successful freelance writing business.

And you sure as hell don’t have to keep taking on more work if your workload is already insane.

Now, if you’re just starting out, then yeah – you need to expect to have some long days and get ready to frontload a lot of hard work.

But it has to level off at some point, or you’ll end up burnt out and too stressed to get anything done. And that’s no fun.

3.     I missed a deadline for one of my biggest clients.

I’m pretty good with deadlines.

Don’t get me wrong – I’m not super organized or good with time management (quite the opposite, actually!). But I do have a system in place that works for me.

In fact, it works so well that I didn’t miss a freelance writing deadline for an entire year! (That’s probably not that big of a deal to most people, but since I’m pretty scatterbrained and disorganized, it feels like a trophy-worthy accomplishment. 🙂 )

But not too long ago, I did miss a deadline.

Know why?

Because I failed to use the system I had in place.

I hadn’t even added the task to my task list, so I was pretty much clueless about it being due.


What I Did to Fix It:

First, I apologized to the client and worked extra hours to get it done quickly.

Then, I reminded myself of my process and made a point to stick to it moving forward. No matter what.

Here’s what that process looks like:

Step 1: A client tells me to write something.

Step 2: I IMMEDIATELY (!!!) open Basecamp and create a task with the due date and details.

Step 3: I get shit done on time.

So simple, right?

But with the deadline I missed, I had skipped that second step.

Instead of assigning the task to myself immediately, I got caught up in other work and probably just told myself I’d assign the task once that work was done.

Yeah. That clearly didn’t work out.

So if you struggle with deadlines or if you’re forgetful like I am, create a process that works for you and make sure you use it every damn time you take on new freelance writing work.

Because a freelance writer who consistently hits deadlines is one who is more likely to consistently win work from clients.

Related reading: How I Built a $5K/mo Freelance Writing Biz in 4 Months (Month-by-month Breakdown!)

4.     I made a phone call SUPER awkward.

Ever have one of those days where every social interaction you take part in feels like a disaster?

Well, I had one of those days early in my freelance writing career – big time.

And I had a client phone call scheduled the same day.

Now, normally I do OK on the phone with clients.

But I was particularly nervous about this call because the person who referred me to the client pretty much gave me no information about the client or the writing work that they needed help with.

They just set up a call for me to go over the details with the client.

So, I wasn’t able to prepare my pitch or note important things to mention on the call because I was in the dark about what I was getting myself into.

And that call was so. damn. awkward.

Seriously – I don’t think I’ve ever sounded less confident in my life. I stumbled over my words. I didn’t know what to say half the time, so there were lots of awkward silences. And I sure as hell didn’t do a good job explaining how I could help the client with his business.

And to make matters worse, the client was traveling in a loud vehicle, so I could barely hear/understand him. I must’ve asked him to repeat himself at least 5 times.


I couldn’t get off that phone call fast enough.

What I did to fix it:

Not gonna lie – at first, I was pretty upset with myself for screwing up the opportunity so badly.

But then I had to remind myself that everyone makes mistakes and goes through awkward social situations sometimes.

I mean, one bad phone call (out of the dozens I had done overall, most of which went well) wasn’t really that bad.

It just meant I needed to change a few things about my client onboarding process, like:

– Getting at least SOME information before I hop on a call. I try to check out the client’s website and make sure I understand what kind of content they need help with.

– Scheduling phone calls for times I know I’ll be alert and at my best. 8AM? No thanks.

– Doing a pre-call ritual that helps me feel more confident. Sounds dumb, but it works. I pump up some upbeat music, read positive feedback I’ve received from past clients, and look over my client notes so I feel prepared. If I’m feeling particularly awkward or uncertain, I’ll have a beer before the call. One of the many benefits of working from home, right? 🙂

Another thing I learned is to re-schedule the call for a later time if I’m struggling to hear the client because they’re in the car or whatever. Because there’s no sense in staying on a phone call where you have to go “I’m sorry – what did you say?” every 5 seconds!

5.     I took on a project that was a disaster in every way.

I took on my first ever major freelance writing project while I was still at my 9-to-5.

And let me tell ya… it was a HUGE project that involved writing over 30 pages of website copy.

Here’s what I did wrong:

– Let the client set an unrealistic deadline. I think I had about a week to get everything done. Since I was still working full time, that meant I would work from 8:30AM to 5:30PM every day, take a short break, and then work again from 7:00PM to 1:00AM… It was unhealthy and certainly didn’t allow me to do my best work because I was so exhausted and overwhelmed.

– Failed to get clear on the scope of work upfront. The client kept adding tasks to the project and telling me to make changes. I was a newbie so I really didn’t know how to handle that or understand that I should’ve set the right expectations from the start.

– WAY undercharged. Looking back, all that work wasn’t worth the money. Not even close. I didn’t know what to charge, so I just ended up asking another writer what to do (that writer was actually undercharging too!).

Really, I should’ve known better than to take on the client in the first place. There were so many red flags that I just overlooked because I was a newbie who wanted to make some quick cash.

What I did to fix it:

Now, I NEVER take on any project I have a bad gut feeling about.

No exceptions. Because I’ve learned to recognize red flags, and I trust myself to determine whether or not a client is going to be a good fit for me.

I also:

– Set realistic deadlines. Sometimes, I tell clients I can get something to them in 2 or 3 weeks because it gives me plenty of time to plan ahead and get all my other work done too. This allows me to turn work in early on occasion, which clients seem to really appreciate (underpromise and over deliver, right?).

– Set clear expectations before I write a single word. I don’t use contracts (for no reason really other than I’ve just never taken the time to do it!), but I definitely outline the scope of work in an email before I start anything. That includes payment terms, expected deliverables, deadlines, and anything else that I need to clear up to avoid misunderstandings in the future.

–Charge what I’m worth. I know what my work is worth, I know the value I bring to clients, and I know how long certain projects take. So I charge based on all those things and negotiate for better pay when necessary.

If you only remember one thing from this blog post, let it be this:

You’re going to fuck up. Take action anyway.

And when you DO fuck up, FIX THE PROBLEM, learn from the situation, and move forward.

No excuses.

I still fuck up on a regular basis. I take on more work that I actually need, I procrastinate, I screw up awesome opportunities, I waste time, and sometimes I have off days where I just can’t freaking write.

But I keep going anyway. And you should too.

Because being a freelance writer isn’t about waiting until things are “perfect” to get started. And it sure as hell isn’t about rolling over and giving up when you’re down.

It’s about being resilient. Looking failure straight in its big, ugly face and saying:

“Fuck you. I’m going to do better next time.”

Wanna share a time when you failed as a freelance writer (+ what you learned from it)? Let’s talk in the comments section!

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