Failed at Freelance Writing? Do these 5 things to Revive Your Business

By Sean Ogle •  Updated: 10/23/23 •  10 min read

Be honest.

Have you felt like a total failure lately? You tried freelance writing, and you haven’t landed a client or made enough money to support yourself. So now you’re thinking there’s got to be a better way.

Here’s the good news: there probably is a better way.

What you need to do is clear the decks and hit the reset button to help revive your freelance writing business.

And it’s not as hard as you think.

So I’m going to cover five ways to help get you out of the ditch and start over.

Here’s how to restart your freelance writing business.

Let’s do this!

Step 1). Do a Post-Mortem and a Hard Reset

The very first thing you need to do is a port-mortem and a hard reset.

What’s a post-mortem?

Not to get morbid, but it’s basically an autopsy. You know your freelance writing business has failed (so far). So you want to go back to your actions and experiences and take a hard look at the causes and where you went wrong.

The key to this is to be brutally honest with yourself.

Take away all the fluff and the excuses you gave yourself, and think really hard about why it didn’t work.

Ask yourself some of these questions:

These are just a few of the questions you can start with, but I want to reiterate again you need to be honest. Because the answers you have here are what you’re going to use to help you move forward.

You’re going to take the parts you can learn from and change…and forget the rest.

That’s right. We’re doing a hard mental reset.

This is a new clean slate. You have not been a failure. You’re tossing out all that mental baggage you’ve been carrying around with you.

Instead, you have a bunch of new knowledge (the answers to these questions) that you can use to help kickstart this new career.

And you’re going to treat it like it’s the first time you’re using it, so you stop beating yourself up over the past.

Sound good?

Step 2). Don’t Reinvent the Wheel

I know you’re smart, and you have the brains to succeed. You wouldn’t be reading this if it weren’t true.

But here’s the idea: thousands of freelance writers out there are making a good living freelancing full-time. And the vast majority of them used the same approach to get there.

So you don’t need to start from scratch and reinvent the wheel here. You don’t need to try and do all sorts of out-of-the-box super creative stuff that no one’s done before, especially at the start.

Just look for what’s worked and follow the path that’s been laid out.

It’s all out there.

We show you the path inside Location Rebel Academy.

One of my favorite stories is from a member named Colin.

He joined LRA years ago to start freelancing, travel the world, and all that good stuff.

For two years, he didn’t really follow what was laid out in LRA. It seemed boring and not fun to send out tons of LOIs. So he did it his own way.

You can probably guess what happened.

Not much. He spun his wheels and got frustrated.

He finally came back to me, admitted defeat, and decided to just follow the steps laid out in the LRA to a tee. Eight months later, he quit his job as a bartender and moved to Southeast Asia, working full-time as a digital nomad. And now he’s working for himself as a social media pro doing something he absolutely loves.

So the moral of the story is to follow the steps.

You don’t need the extra headache and stress of trying to come up with some new way to do it when the process of becoming a freelance writer is pretty straightforward.

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Step 3). Find a Mentor

Something else I’d do?

Go out and find a mentor. Maybe it’s someone you know offline who is also a freelancer and can help point you in the right direction.

Maybe it’s someone like me who has a proven online course that helps people and knows what they’re doing. And even if it’s not LRA, if you go with someone who has a course, make sure they’ve actually made money freelancing first.

Either way, whichever you choose, listen to this person. Recognize they know how to do this and follow what they’re doing.

That can really help you avoid a lot of the pitfalls of building a freelance business. There are tons of successful freelancers online who spend a lot of time on their site or social media sharing the mistakes they’ve made and things to avoid.

Listen to them and follow that advice!

I’ve been where you are before. And the reason I’m still here 14 years later is I had a few mentors that I listened to and adjusted accordingly.

One last thing on mentors. It doesn’t have to be a formal thing. And a lot of people don’t have the bandwidth to mentor 1 on 1. But if you can get into some freelance writing circles and network with other freelancers, you can find people in your community who are doing the things you want to do.

And connecting with them can be as easy as building a relationship and hopping on Zoom to chat for 20 minutes.

Step 4). Set a Schedule

This is the most tactical step here. When you’re building a freelance writing business for yourself, it’s common to treat it like a side hustle.

But the reality?

It’s not your hobby. It’s your business.

So you have to treat it like your business and build your schedule around it. Even if you only have an hour a day to work on it.

However much time you do have, you need to block off that time to be focused work time. This is just like any other job. You know exactly when you have to be at the office or have that weekly team call with your group. It’s on your calendar.

This needs to be the same thing.

You need to set a schedule and stick to it. Make it consistent. It has to be sacred hours; it’s not something that’s put on the back burner or pushed because you don’t feel like doing it.

Building a freelance writing business is a commitment you’re making to yourself right now for your future.

So the first part is setting a schedule. The next part is listing out exactly what you’re doing during your scheduled time.

That’s going to help you avoid wasting time or procrastinating because you don’t know what you should do, or don’t feel like marketing, or are overwhelmed. You want no ambiguity, so when you sit down to work, you know exactly what you’re doing.

So on Sundays, spend 20 minutes laying out your schedule for the week.

Put it in the calendar. I’m doing x, on Monday, y on Tuesday, z on Wednesday, and so on.

It may seem like a small thing. But having that schedule and getting into the habit of sticking to it is one of the best things you can do. And I’m willing to bet that part of the reason you may have failed previously is because you have a defined schedule or know exactly what you should be doing every day.

Step 5). Adopt the Milestone Mindset

I can bet pretty much everyone who struggled to build a freelance writing business falls into the trap where they set goals that are way too big and overwhelming.

It’s easy to watch a million YouTube videos or read blog posts or see social media posts talking about how it’s so easy to make tons of money freelance writing.

You know what I’m talking about, the make $1ok in a month people.

You probably have realized by now that’s not going to happen. Eventually? Sure. But right away? Nope.

What you need to do is get rid of the zero versus one mentality.

This is a goal like I’ll make $10k a month in six months. Depending on a million factors you may hit that goal, or you may not.

But what happens is when you have this mentality that you’re a failure until you reach this big audacious goal you’ve set is that you’re always failing — there’s always a big fat zero on the scoreboard.

So rather than seeing six months in, you’ve made a ton of progress (like maybe making $5k a month) and have learned a lot, you’re only focused on the big goal.

And that’s when people start feeling like failures.

But the reality is you’re not a failure! You’ve made money! You’ve learned a ton of new skills.

Instead, you need to set much smaller milestone goals (that help you get to the big goal) and celebrate every one of those wins along the way.

That’s the milestone mindset. It’s building momentum and celebrating all the stuff you accomplish along the way.

If you want to make $10k a month, that’s great.

But break that big goal down into a ton of smaller goals (and remove the time frame).

What are the direct actions you can take to help you get clients and make more money?

So that may be things like:

Each of these are small things. So small that most people ignore them and only focus on the big dollar sign.

Every time you do one of these, celebrate.

You bought a URL? Celebrate.

You wrote a sample? Celebrate.

You sent one LOI? Celebrate.

It’s a chance to build positive momentum and feel good about yourself as opposed to feeling like crap because you haven’t gotten where you want to be yet.

When you start feeling better, that’s what helps you get over that hump when things get hard.

Hit the Reset Button

So if you’ve spent the last few weeks (or months) really struggling?

It’s time to start over.

Doing these five things allows you to regain the competence to build your business and actually start having some fun with it.

And once you start feeling good about it instead of bad all the time, some pretty amazing things can happen.

If you’re ready to revive your freelance writing business, this is how to get the ball rolling again.

You can do it!

Looking for More Freelance Writing Help?

Try these posts:

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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