5 Reasons You’re Failing as a Freelancer (and How to Get Back on Track)

By Sean Ogle •  Updated: 04/27/23 •  8 min read

I spend about 95% of the time being overwhelmingly positive — I don’t like to talk about freelance failure.

My goal is to give you as much advice and information as I can so you can build your online business and go and do more of the things that you like to do in life.

But sometimes, positivity doesn’t work.

People don’t always listen. And sometimes, you need a little kick in the ass.

So today, I’m going to do that. There may be some harsh realities, and you may have to ask yourself some tough questions. But if you want to make it as a freelancer and turn things around, this will help.

I’m giving you five reasons why you’re failing as a freelancer.

If your freelance writing business is not going the way you would like, and you’re feeling like a freelance failure, one of these is probably the reason.

Let’s do this.

Reason #1: If all your existing clients are bad, you might be the bad client

Ouch. Sorry.

But, I’ve found that if you rock as a freelancer, meaning you put together great work, hit deadlines, follow directions, and have few edits, then you’re rarely ever going to have bad clients.

Often, bad clients come from lousy work on the part of the freelancer.

That may mean you’re not:

If your clients are getting frustrated or are tough to work with, take a step back and ask yourself if you’re delivering.

I’ve done it too.

There have been times I’ve thought, ‘Man, this client sucks.’ But then I also have to ask myself, am I being the best client for them?

And there have been times the answer wasn’t always yes. Maybe I turned in something late, didn’t take the time to do extra edits, or knew I started my post with a poor introduction.

Or perhaps, I just wasn’t as committed to the project as I should have been.

So, next time you’re feeling frustrated with a bad client, take a step back and ask yourself if you’re meeting expectations.

Reason #2: You’re not personalizing your outreach

This should come as no surprise to you if you’ve spent any time reading the blog or watching the Location Rebel YouTube channel, but the biggest mistake I see people making is not personalizing their outreach emails.

Creating a template is fine; that’s a great start.

But the keyword here is it’s a start.

Most people skip the next step, and it’s one of the biggest causes of freelance failure.

Instead, they send the same generic email to 100 (or fewer) businesses and get mad when they don’t get any responses — even though it’s super clear to the recipient you’ve sent some version of the same crappy template they get 30 times a day.

generic pitch email - freelance failure


If you don’t bother to personalize your template, you’re lowering your chances of landing a gig or connecting with someone.

So put in the extra effort.

Take five minutes and research who they are, where they’re from, and what their agency, business, or site is about. Then, use that information to add personalization to your email in the first line.

That’s what’s going to help you stand out.

And if you have a template, leave a blank space at the start for your personalization.

When you write your letters of introduction (LOIs), keep them short. Most of them are only 5-6 sentences, so it’s OK to keep that stuff the same.

But use the start of your email to let them know you’ve taken the time to learn about them, highlight how your skills can help them specifically, and show you’re a real person.

It’s the easiest way to stand out, and it takes about five minutes of effort.

A lot of freelancers are lazy, and that’s why they don’t get jobs. So take advantage of the opportunity to stand out.

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Reason #3: You’re too in your head

Your freelance writing business probably isn’t taking off because you’re overthinking everything. You’re thinking about all the things you don’t know yet or other future imaginary scenarios that may or may not come to pass.

So you’re not taking action on the things that will make a difference.

Yes, a website can be important. But if you’re stressing over getting your photos just right, and you’re not sending outreach emails because of it, then you’re not going to get any jobs.

If you’re stressing out over your rates or what happens if you get too many clients before you even have a potential lead, you’re missing the point.

Get out of your head.


Here’s all you need to do to start:

The goal here is to start a conversation and build relationships, which may lead to something down the road.

outreach spreadsheet

That’s it. It’s pretty straightforward, but people make it way too complicated.

So stop overthinking, and take action.

Reason #4: You’re trying to reinvent the wheel

Here’s the thing.

There are thousands of freelancers out there that are making six figures a year. They’re having tons of success, getting work, and knowing how to get clients.

It’s not complicated.

There’s a process I’ve been spending the last ten years of my life walking people through inside Location Rebel Academy.

We give you the exact steps to build a business and get freelance clients. The process isn’t all that hard or complicated. And if you want a sneak peek at it, check out this post on how to become a freelance writer.

It can be hard to stick to it, follow the steps, and trust the people who have gone before you that they know what they’re doing.

So often, I see freelancers that think they know better.

They think they can find shortcuts.

They think, ‘I’m just going to try this my way.’ And they spin their wheels and struggle rather than trying to just learn from somebody who’s already done it.

If you’ve been struggling with this, check out that post. It’s not reinventing the wheel. Instead, it walks you through the basics to get you started. Implement that, and I promise you’ll begin to have success as a freelancer.

And if you want more hand-holding and support, check out Location Rebel Academy. We’ve helped a lot of people build freelance writing businesses.

But, as soon as you start skipping steps, looking for shortcuts, or avoiding stuff like personalizing LOIs because it’s too time-consuming, you’ll start failing.

So just know the plan is out there. Focus on following it.

Reason #5: You’re not making your client’s life easier

Clients hire you for a couple of primary reasons:

It really boils down to that.

So your goal is to focus on delivering those, especially the first one. Your clients are busy. They’re running a lot of stuff and hiring you because they don’t have time to research, write, and edit blog posts.

That’s where you come in.

The fact of the matter is if you focus on making that process as painless as possible for your clients, they will love working with you.

So what does that mean?

Delivering work on time that’s keyword optimized, targeted to the readers, formatted correctly, and doesn’t need edits. A client’s dream is to get a draft from you that they can pop directly into their content or email management system without more than minor tweaks.

If you can give that to them, you’re saving them a ton of time and hassle, and it makes you invaluable to them.

If you blow off those things and deliver sloppy work they need to edit or rework or go through three or four drafts, you aren’t saving them time. Instead, you’re adding to their to-do list.

Clients don’t like that. They aren’t paying you more or referring you to other people. They’re probably out there now trying to find a new writer to replace you.

So keep that in mind as you work with your clients. Put in the extra effort to remove sloppy mistakes and make things easy for your clients.

Make your clients look good and make their jobs easier; they’ll keep you around for a long time.

Ask the hard questions

Freelancing can be an amazingly rewarding career. It’s given me more than I ever imagined. But it’s not always easy, especially if you are stuck in your head feeling like you’re a freelance failure or focusing on the wrong things.

If you’re struggling, it’s important to be honest and ask why. Then, you can start making the changes that can get you back on the right track.



Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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