failing as a freelance writer

You’ve been trying to get into freelance writing for a while now.

You read blogs, buy books, and attend webinars.

You’re doing everything right.

(Or at least you think you are.)

But you’re getting nowhere fast.

All the while, you see story after story online of freelance writers growing their business, yet that just hasn’t happened for you.

And you’re frustrated.

Pissed off.

Right on the verge of giving up on your freelance writing dream completely.

Don’t give up just yet, my friend.

Because you might be making a simple mistake that’s easy to fix.

You could be one good decision away from the freelance writing business you’ve been trying to build for a while now.

And if that’s the case, I want to help.

So let’s talk about the most common reasons freelance writers fail.

I’ve also got a video on the topic below – watch it to learn even more about why online businesses fail:

And by the end of this post, you should have some insight on why your business isn’t growing quite as quickly as you’d like it to.

You analyze to the point of never taking action.

I’ll be honest with you.

If you’re risk-averse to the point where you stand on the edge without actually ever jumping off, freelance writing probably isn’t for you.

I’ve seen freelancer after freelancer say stuff like:

I’m just not sure which niche to pick yet.

I don’t really know how to set up a freelance writer website.

I don’t have any writing samples.

You know what I think?

Those are all excuses.

For example, if you don’t know which niche to pick, make an educated guess and start marketing yourself.

I mean, you might as well, right?

Think about it like this:

You can pick a niche today, get a niche website up and running by tomorrow, write some niche samples by the end of the week, and start marketing right after that.

If you try your best to land clients in that niche for a while but find that it wasn’t what you expected, guess what?

You now know one thing that doesn’t work.

That means you’re one step closer to finding a niche that DOES work for you.

Otherwise, what were you going to do?

Probably just sit and wait around for something to happen to you.

So it’s not like failing is a waste of time.

You weren’t going to do anything else anyway, you know?

What I’m getting at is this:

It just takes some trial and error sometimes.

You have to be willing to fail fast and bounce back from your failures.

That approach works a LOT better than waiting for the “perfect” time or niche or website (which doesn’t exist!).

You give up too easily.

So, above I talked about moving quickly to pick your niche, set up your site, and go after clients.

Where a lot of freelancers go wrong is the “go after clients” phase.

They send 20 cold emails that get ignored and then give up.

They ask 2 people for referrals and get discouraged when neither person can help.

They spend a week on their social media strategy and decide it’s not worth it when they don’t get immediate results.

I’ve seen freelancers with TONS of talent and potential do these things.

And I just want to shake them and say:

“You CAN do this – it just takes patience and hard work!”


You need to experiment.

You can’t expect success overnight.

I mean, I might’ve scaled my freelance biz to $5K/mo in 4 months, but do you really think everything was smooth sailing that whole time?

If you DO think it was easy, well…

*laughs hysterically*

I changed niches, re-designed my site, wasted time trying marketing methods that didn’t work well for me.

All kinds of things went wrong.

But one of the reasons I ended up being successful is because I didn’t give up.

I looked failure in the face and said:

This isn’t the end. It just means I need to try a new approach.

And that’s the attitude you need to have too if you want to grow your freelance writing business.

You’re broke as fuck.

Okay, so before I go to deep into this, I want to say that you DON’T need a ton of money to start freelance writing.

But you do need to be ready to invest in basic things like a website theme, hosting for your site, etc.

Otherwise, you have no business starting a business.

I’ve seen so many freelancers talk about how they don’t want to spend money until they’re making a ton of money, and man…

It blows my fucking mind.

You’re literally starting a business.

…What business can you start (and more importantly, scale quickly) with a budget of $0?

*crickets chirping*

Now, I understand that some of you reading this might not have a dime to spend on your business.

I’ve been there.

At one point in my life, I slept on people’s couches for months in a row and had basically nothing.

My car almost got repossessed. I was barely getting by and rationing one can of Lays Stax for multiple meals.

And when I started my freelance writing business, I wasn’t exactly financially stable either.

I had just been fired, and I had pretty much no savings.

I didn’t have family to fall back on financially. My husband’s work contract has just ended.

But I was willing to do whatever it took to get my business off the ground. I had no choice.

Sure, I could’ve let fear take hold and bid on shitty Upwork gigs and put up with clients who wanted to pay $10 for 1000 words.

But I didn’t do that.

I wasn’t going to let fear control my decisions.

I invested in myself. I made a professional website. I bought leads so I could start cold emailing.

Even though it was a risk.

Whatever it took, I was ready to do it.

Speaking of that…

You don’t want it enough.

I remember having a conversation with my husband when I started my freelance writing business.

I told him I’d literally take on any shitty part time job I had to take on and work 12-hour days outside of it if it meant I’d be able to grow my business in a few months.

Do you want to make freelance writing work that badly?

Are you willing to sell some of your shit, drive for Lyft, take on a part-time job for a while, or do whatever else you need to do?

I can tell you one thing for sure:

If you are, you’re about 1000x (super scientific and exact, obviously) more likely to succeed at freelance writing.

In my case, I never had to take on a separate job or sell a lot of my stuff. I busted my ass to get my business going, and it scaled quickly as a result.

If you want the same thing for your business, you’re going to have to ask yourself how much you want it.

Oh, and one more thing:

If you have a backup plan (someone who will pay your bills for you, a job you love and aren’t really motivated to leave), you’re a lot less likely to succeed.

Because nothing lights a fire under your ass like having no other choice but to succeed.

That’s just the facts, jack.

You haven’t niched down.

I get a lot of emails asking for advice.

Probably the #1 piece of advice I give is to niche down.

And, more importantly, market the shit out of your niche.

Because picking a niche won’t do you any good if you aren’t marketing your expertise on your website, in your portfolio, and on social media.

High-paying clients want to work with someone who has expertise in their industry – not a generalist who might be able to get the job done right.

You’ve picked a clientele that isn’t profitable.

When you choose your niche, you also choose who to market to.

For example, I write B2B blog posts about marketing/tech for SaaS companies. So, my clientele is mostly SaaS companies.

And I know from experience that SaaS companies value the kind of work I do + have the budget to pay me well for it.

But let’s say you specialize in something else…

Writing about relationships.

You might market your services to small blogs about relationships.

But the thing is, if your clientele is mostly small blogs run by one person or a very small team, those probably aren’t going to pay well for content, and then it’s not going to be easy to scale your business quickly.

On the other hand, maybe you could write for and similar large businesses/apps all about dating and relationships.

In that case, you’d probably have a lot more luck finding consistent, high-paying gigs because those are bigger companies that likely understand the value of content marketing + have the budget/desire to pay good money for good content.

(By the way, don’t be afraid to pitch bigger businesses – even if you’re just starting out and don’t have some massive portfolio. You’d be surprised how much just marketing your niche expertise can make you stand out + make clients want to work with you!)

See what I mean, though?

The same niche can have both high-paying and low-paying clients in it.

You just have to learn the difference (which takes trial and error sometimes!) and make sure you’re pitching your services to the right clientele.

You know the “what” but not the “how.”

In other words, you understand what you need to do, but you’ve taken a wrong step or two while executing.

For example, you might understand that you need to use SEO on your freelance writer website.

But if you use SEO the wrong way and/or optimize for the wrong keyword, you’re not going to see any payoff.

Another example:

You know that you need to send a lot of cold emails if you want to win more clients as a newbie freelance writer.

But you just blast out a ton of cold emails with no real strategy.

So, you don’t get any results.

Bottom line:

It isn’t enough to know the “what.”

You need to know how to implement the best strategies for your freelance writing business too.

Related reading: How Cold Emailing Grew These 6 Freelance Writing Businesses

You don’t set goals and work backward from there.

When I plan out the year for my business. I don’t start with the first week and go from there.

First, I look at the big picture.

What do I want to accomplish by the end of the year?

And I’m not talking vague goals like “post on social media more” here. I’m talking super-specific stuff like:

  • Reaching 30,000 email subscribers
  • Reaching 100,000 monthly pageviews for my blog
  • Reaching a monthly income of $15K

Once you set these kinds of goals, you work backward from there so you can reach them.

When I set a goal of reaching 30K email subscribers by the end of the year, for example, that means I need to start planning for the previous months based on that end-of-year goal.

I need to do things like:

  • Create more gated content for my audience
  • Promote my gated content
  • Gain more relevant blog traffic

And then these mini-goals can be broken down into even more specific steps, which I go in and set deadlines for.

Sounds like a lot of work and a lot of planning, right?

It is.

But it is WORTH IT.

And that’s coming from someone who is NOT a planner or organized person at all.

Once I started approaching my business from the perspective of setting “big picture” goals and working backwards from there, things totally changed for the better.

So get a planner (I use a Mead Cambridge planner like this one. #BasicBitch), get some sticky notes, and plan out your year – or even just the next quarter – for your business.

As nice as taking things day-to-day is, it’s just not a realistic approach if you’re looking to grow a freelance writing clientele, a blog, or really any kind of business.

You’re experiencing information overload.

This goes hand-in-hand with “analysis paralysis.”

You read books, bookmark blog posts, take courses…

But you never act on what you learn.

You’re too fucking scared.

Well, here’s some encouragement: all freelancers are scared of something.

Scared of forgetting about a deadline or meeting because of how scatterbrained they are (*raises hand slowly*).

Scared of suddenly losing all their clients and not being able to pay bills.

Scared of putting themselves out there (because what if people say mean things!? *throws hand over forehead dramatically*).

You have to feel the fear and do it anyway.


Fear is almost always part of the reason for freelance writing failure.

Sure, some just don’t have the motivation or writing skills to make it happen, while others end up deciding they’re better suited for a 9-to-5 gig.

But mostly, fear is to blame for failure.

Now, I realize that this post is a little more of an ass-kicking than most of what I write here.

But I don’t want you to feel bad if you recognize yourself making the mistakes I’ve mentioned in this post.

I’m telling you this stuff because I want you to grow your freelance writing business if that’s what you really want to do.

You just have to get good at calling yourself out on your own bullshit, really.

So make it your goal to become more self-aware.

Get REAL about why you’re failing at freelance writing.

But don’t dwell on the fact that you’re failing or let yourself get in a negative mindset.

Just look at the problem, figure out how to fix it, and get to work.

I’ve made tons of mistakes over the course of my career.

And I’ve learned that sulking, ranting, and wallowing in negativity doesn’t help anything.

What DOES help is being self-aware, taking action to solve problems, and being resilient enough to keep going.

Do you feel like you’re failing as a freelance writer? Need some helpful advice? Throw a comment down below!

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