Freelance writing is incredibly accessible.

Every single week, I get testimonials and reports from writers who are hitting significant milestones in their journeys, enjoying successful careers, and building profitable businesses.

That said, not everyone is succeeding in this space. Part of the accessibility means there are a lot of people who give freelance writing a try… and fail.

Over the years, I’ve observed that five things in particular seem to derail freelance writers more than almost anything else.

In today’s episode of Write Bites, I’ll take you through these five common pitfalls and show you exactly how to avoid them on your journey.

This episode of Write Bites is sponsored by Copy.AI, a toolkit that helps writers, marketers, and freelancers harness the power of GPT-3 to quickly create first draft copy for their businesses and clients. Click here to try Copy.AI free for 30 days.

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What are the things that are most likely to prevent you from succeeding as a freelance writer?

In today’s episode, I’m going to break down the five things that I most commonly see derail freelance writers…

And we’re going to be explaining how to prevent those things from derailing you on your journey.

Today’s episode is sponsored by CopyAI, a toolkit that helps writers and marketers and freelancers skip writer’s block and quickly create first draft copy for themselves and their clients.

If you’d like to get a free 30 day trial head on over to

Freelance writing is incredibly accessible.

Every single week, I get testimonials and reports from other freelance writers that are hitting significant milestones in their journeys, enjoying successful careers, and building profitable businesses.

That said, not everyone is succeeding in this space.

Freelance writing is accessible. And that means that a lot of people come into this space and try their hand at freelance writing ultimately won’t end up succeeding.

Over the years, I’ve observed that five things in particular seem to derail freelance writers more than almost anything else.

#1: Negative Beliefs

The first one is to be honest, a little bit surprising.

So many freelance writers come into this field with the assumption that they can’t do something.

Sometimes it’s as broad as “I can’t succeed as a freelance writer” (which becomes a self-fulfilling prophecy), but more frequently, it’s specific things.

For instance, when they look at people who they consider successful and they see things that those writers are doing, they think “Oh, I couldn’t do that”.

Maybe it’s that they noticed that a writer has a byline on Forbes or that so-and-so is working with a Fortune 500 client. Whatever the reason, they feel like they can’t compare.

The ironic thing about this is that there’s really no pre-qualifications for doing almost anything in the online space.

If you want to do something, achieve something, accomplish something in the writing space…

The biggest differentiator between people who have done it and people who haven’t is whether they’ve tried it.

When you see someone who has a byline on a big publication, 9 times out of 10, it’s just because they happen to send a good pitch at the right time.

If you were to send a good pitch at the right time right now with your current skillset, you could get that same byline.

Now, that said, maybe you give it a try. Maybe you send the pitch and it turns out you just don’t actually have the writing chops yet to get published on a particular publication.

That’s great news! That gives you a specific target to aim for: increasing your mastery and hitting the goal that previously was just this vague “Oh, I can’t do this” – now, it’s “oh, I need to develop this specific skill set and I can do it”.

That’s ultimately what building any career is all about: figuring out what are those specific things that you need to do in order to move up the ladder or move forward in terms of growing your revenue, uh, or just hitting that next stage in your business journey.

The takeaway here is never assume you can’t do something.

Approach everything with the mentality that you’re going to try it first.

Don’t start with asking questions.

Don’t start with trying to find a mentor to help you do it.

Just try it and see what happens.

Go through the experience yourself of making an attempt.

In some cases you’ll hit it right off the bat, and you’ll be shocked that you could have been doing that the whole time.

Never assume you can’t do something.

Always try at first and then go from there.

#2: Refusing To Sell

So the next big thing that tends to derail freelancers is that they just refuse to sell.

This is pretty understandable.

If you’re coming from an employment background,  you probably didn’t have to sell every single day.

Your job probably had a pretty specific hierarchy where you just informed the person below you of what they needed to do. And the person above you did the same and everyone did what they were told.

Or maybe the skill set you had wasn’t even interacting with people. There was no persuasion required. It was just straightforward doing the work.

As a freelancer, everything you do is sales.

You have to sell yourself in order to get work.

Once you get the work, you have to sell your ideas to the client.

And then once you’re actually doing the writing, you’re often selling an idea on behalf of the client to their target audience.

Everything is sales. And if you want to be successful as a freelance writer, you have to embrace that.

You can only fight it for so long before it’s going to derail your career.

Even if you do manage to extend your career by several years without really embracing sales…

You’re going to be making a lot less money than your colleagues and associates who have embraced the fact that being a freelancer is all about selling yourself, your ideas, and your copy.

It’s all sales. So embrace it and succeed.

That brings us to number three…

#3: Trying To Do Too Much

The next big challenge that tends to derail freelance writing careers is  -in my opinion – the most tragic one. So many freelance writers just try to do too much.

Freelance writers have a wide array of sources and influences telling them how to run their business. And the result of this is often that they’re trying too many things and they’re trying things that aren’t even the right fit for their stage of business.

Some of this just comes from the personal ignorance that a lot of people bring into freelancing and entrepreneurship: where they think that stuff like getting a professional logo designed, setting up a really great website, starting an LLC or any of these things is gonna make a big difference to them succeeding in business.

Some of it is also coming from trainers and coaches (like myself) having different philosophies on what you need to be doing to grow your business. So a lot of people will say stuff like “Hey, you absolutely have to isolate a specific niche right off the bat”.

Or that you need to create a blog, use content marketing, SEO or whatever else.

Everything I just mentioned can potentially benefit you in a big way at some point in your business.

But the reality is that if you’re just getting started or you’re only a few years into your freelance career, it’s probably not the priority.

The truth is there’s really only two things that are going to move the needle for your business within the first few years…

And those two things make up our final two points.

#4: Not Writing Enough

The next big thing that derails people’s freelance writing careers is simply that they don’t write enough.

For people who have been reading and writing their entire lives for fun, this doesn’t really apply.

The last one that we’ll mention is going to apply to you, but for a lot of other people, they come into freelance writing without reading blogs, without reading books, without writing as a personal habit.

They just see it as an accessible career and expect that they’re going to become good copywriters overnight

Copywriting is a simple form of writing, but it’s not an easy form of writing.

If you aren’t coming in with a relatively strong writing baseline, you’re going to have to do quite a bit of work to actually become a good copywriter.

Even talented writers usually take a good six months before they’re writing copy that’s even passable.

It really blows my mind how much many writers come into this space expecting to just make a lot of money without actually becoming good writers.

The only way to become a better writer is to write a lot of content, to write a lot of copy, to do a lot of writing period.

If you’ve done a lot of writing in your background, great! You probably can just focus on specific projects.

But if you’re coming in without a long history of writing, you need to be writing every single week.

Even if you haven’t landed any clients, yet you should be pre-writing blog posts or pieces of copy as practice or as potential pre-made assets to shop around and sell.

I don’t care. Even if it’s just journaling, you need to be writing every single week.

That’s something that I probably haven’t emphasized enough in the past.

For me, it always just went without saying, but I’ve noticed more and more that it needs to be said.

If you aren’t writing every week, you’re going to struggle to succeed as a freelance writer.

And this brings us to number five, which is both the second thing that’s going to really move the needle on your business and the final entry in our list of things that tend to derail freelance writing careers, and that’s simply…

#5: Not Getting Your Brand In Front Of Enough People

While I typically emphasize pitching here, networking can and should play just as big a role in how you get your brand out there.

You need to be constantly meeting new people in your space, your industry and any niches that you’ve chosen.

Other writers, editors, business owners: the more people you can meet, the more people you can connect with, the further your brand’s going to go.

When you’re connecting with people, when you’re meeting people, when you’re talking to people you already know, you need to be letting them know that you do writing.

You need to be letting them know that you have a skillset.

You don’t have to sell them on it, but you need to be letting them know that you have it.

That’s going to give them the opportunity to engage further with you around that context, hire you directly, or to refer you to someone else that they meet who potentially needs your services.

For a lot of freelance writers (myself included), our first ever gig came from simply talking with a friend, mentioning that we did writing and then suddenly discovering there was a fit there and they needed something we could do.

Boom: first project in the books, payment in the books and potential setup for more referrals down the road.

In my case, it was only a $50 or $100 gig, something like that. I don’t even remember the exact number. But it can be a lot bigger than that.

I have a lot of students who land four-figure projects, just talking with people in their warm network.

I even had one student who landed a $14,000 gig just by reaching out to people they knew and saying “Hey, I’m doing freelance writing”.

So regardless of how you reach out – pitch, network, whatever – you need to just constantly be getting your brand in front of other people. In front of other brands. In front of other business owners. In front of other employees, people, it doesn’t matter who.

The more people who know about what you’re doing – know about your service and your brand – the more people are going to hire you. It’s as simple as that.


So to quickly recap:

  1. Never assume you can’t do something. Always try it first and then go from there.
  2. You absolutely have to embrace sales. Whether it’s selling your services, selling your ideas, or writing copy, that’s sales. If you’re a freelance writer, you are in the sales game and you have to embrace that.
  3. Don’t try to do too many things at once.
  4. Write more.
  5. Pitch and network more.

It’s that simple.

Anyway, I hope this was helpful. And I’ll catch you in the next episode.

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Share Your Thoughts

I hope this was helpful, and I’d love to hear your thoughts on this topic.

Do you agree? Do you disagree with the fierce heat of a thousand suns?

Let me know in the comments below.

Plus, if you have a question you want answered on a future Write Bites episode, ask in the comments or shoot me an email, and I’ll add it to the schedule.

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