Tired of Free Advice That Goes Nowhere? Here’s How Real Coaching Can Fast-Track Your Freelance Biz

You’ve downloaded the freebies. You’ve attended the webinars. You’ve watched the reels, saved the tips, followed the “experts,” and maybe even tried to put together your own roadmap to freelance writing success.

And yet… you’re still stuck.

You keep asking: Why isn’t this working? Why is it taking so long? What am I missing?

So, what’s the issue? You’re trying to build a business off advice meant for the masses. There’s nothing wrong with free content. We love a good tip or tool around here. But when it comes to building a sustainable freelance writing business, free advice usually hits a wall.

You need a plan, and someone in your corner who actually knows what they’re doing. You need coaching, a real strategy, and personal accountability. That’s where The Pajama Writer steps in. 

Not quite convinced? Completely understand. But, don’t let hesitation stop you from taking the next step. 

Let’s Talk About the Free Advice Trap

Before we get into what coaching actually does, let’s call out the elephant in the room: free advice is everywhere. Going down a Google rabbit hole of advice can be overwhelming and leave you more confused than when you started. It’s like trying to learn how to swim by reading 72 blogs, all while standing on the shore. At some point, you just need to get in the water. And with someone who knows how to keep you from drowning.

Here’s why free advice can sometimes feel like a dead end:

• Motivation without direction: It’s all “just keep going!” with no map of where you’re supposed to go.

• Conflicting strategies: One expert swears by building an email list before you even think about getting clients. Another says you don’t need a list at all, just start posting on LinkedIn. You end up doing nothing out of sheer confusion.

• No feedback loop: You can try a strategy, but when it flops, who do you ask for help? You’re left guessing.

• Wasted time: The hours spent piecing it all together could be used to build an actual client base. Remember, we don’t get paid unless we are writing. 

What Happens When You Trade “Figure It Out” for “Let’s Do This Together”

Getting a coach might feel like a big move when you’re just starting, but truthfully? It’s a way to stop second-guessing everything and finally start making real progress.

1. You Get Clear Direction

• Stop the guessing game. You get a real strategy that fits your goals and is personalized to what you envision your business to be.

• You learn how to market yourself, set your rates, pitch clients, and build systems that work for you.

2. You Move Faster

• A coach helps you skip the detours and dead ends, and really hone in on what’s important.

• They’ll get you writing, and in turn, making money.

3. You Get Unstuck (For Real This Time)

• When imposter syndrome shows up or your brain goes full “what’s the point,” a coach helps you stay grounded and move forward.

• You get actual tools to handle setbacks and keep showing up.

4. You Start to Feel Like a Pro

• You stop saying, “I think I want to be a writer” and start owning the fact that you are a writer.

• Your voice gets stronger. Your confidence grows because you’re doing it, not just talking about it.

What to Look For in a Writing Coach (So You Don’t Waste Time or Money)

Not all coaches are created equal. A good coach helps you dig in. They get to know your business and your goals. Before you sign up for anything, make sure they offer:

• Real structure: You should be getting more than just encouragement. Look for someone who teaches systems, strategy, and execution.

• Experience with freelancers: Not just writers, freelance writers. Someone who knows the business side as much as the creative side.

• Client wins: Are they helping people actually get results, or just growing their own brand?

How Coaching Changes the Game (Let’s Get Specific)

When you have a coach that guides you, here’s what starts happening:

• You know how to talk about what you do with ease.

• You pitch clients with confidence and actually hear back.

• You build packages that pay your bills.

• You finally stop looking at what everyone else is doing and start focusing on what you can offer potential clients.

Let’s Talk About What Coaching Might Look Like

There are different coaching formats out there depending on how much support you want, how you like to learn, and how quickly you’re trying to grow. No matter the format, the goal is the same and that’s to help you move forward faster, with less guesswork and more confidence.

Here are a few common coaching packages:

• One-off sessions: Think of these like a power hour. You get direct help on one thing, maybe pricing, pitching, or planning out your services, and walk away with ways to move forward.

• Group programs: A great option if you want guidance, structure, and a bit of community energy. You get lessons, live calls, feedback, and the chance to learn alongside other freelancers figuring it out too.

• 1:1 coaching: This is the most hands-on, personalized support. It’s built around your specific goals, challenges, and style. 

• Self-paced courses with coaching elements: Some programs include training videos or templates you can work through on your own time, plus access to a coach for questions or feedback along the way.

You Don’t Have to Wait Until You’re “Ready”

A lot of new freelancers think they have to reach some invisible milestone before they can work with a coach. Like, “once I land a few clients” or “once I make X amount per month.”

But, coaching isn’t the reward. It’s the tool that gets you to the reward. If you want real direction, plus a writing business that pays, you don’t need to wait. You just need someone to show you how.

The Pajama Writer Is Here to Help

If you’ve been nodding through this entire post, I see you. You’re ready. And the support you need is right here.

The Pajama Writer coaching programs are built for writers who are ready to do things differently. We teach you the business and the mindset, with support that’s approachable and intentional.

Want to stop trying to piece it all together and finally start building something sustainable? Let’s talk. Book a call. Let’s figure out your next move and start building the freelance writing business you’ve been dreaming of, all in your coziest sweatpants.