5 actionable tips to stop second-guessing your copywriting, today

Ever squinted at your latest draft for a client, wondering if it’s brilliant or a wordy train wreck? You’re not alone. Second-guessing is practically the unofficial sport of copywriters. 

Recently, I asked copywriters subscribed to my weekly email about their biggest struggles, and the replies poured in:

• ‘Overcoming perfectionism-based procrastination.’
• ‘Getting started.’
• ‘Confidence that what I’m writing is actually good.’
• ‘Having the right knowledge for the piece of copy I’m writing.’
• ‘Knowing whether or not my copy is actually good enough!’

Sound familiar? 

If you’ve ever stared at your work wondering if it’s bold enough, clear enough, or even English enough, this blog is for you. 

The good news? Doubt doesn’t have to be your co-pilot. 

Here are five actionable ways to kick second-guessing to the curb and take back your writing confidence. 

Ready? Of course you are.

1. Build a pre-writing checklist

Think of a pre-writing checklist as your creative safety net. It’s there to catch you before you dive headfirst into a piece without a plan (and end up spiralling into “Does this even make sense?” territory).

Without a checklist, you risk winging it. And while that might work for Summer day out with kids, it’s not great for copywriting.

Here’s what to include in your checklist:

• Who am I writing for? Your client’s audience isn’t “everyone.” Remind yourself who they are and be specific.
• What’s the goal of this piece? Drive sales? Build trust? Get someone to click a link? Get focused on the outcome before you start to write
• What’s the reader thinking and feeling at the start (Point A), and how do you need them to think and feel by the end (Point B)? 
• What are the 1-2 things the reader must know to move to the next stage of awareness? Hint: It’s not about showing off how clever you are. Identifying key info keeps your focus razor-sharp.

Take two minutes to run through these questions before you write. It’s like plotting your GPS before a road trip—you’ll avoid detours and get to your destination faster.

2. Create an air of collaboration with your client

A lot of copywriters sweat over the first draft they hand to a client, thinking it needs to be absolutely perfect. Cue the overthinking spiral. 

But writing isn’t a solo sport. Sure, it feels like it when you’re typing away in your trackies, but the truth is, great copy happens when you treat it like a team effort.

The key to reducing the amount of second-guessing is creating a collaborative atmosphere from the get-go.

How to make collaboration work:

• Emphasize the importance of their input. From the first discovery call to your kickoff documents, emphasise how their input helps shape the project.
• Float ideas early. If you’re unsure about direction, voice, or concept, float it by the client early. It’s better to jump on a call and adjust course at the idea stage than rewrite an entire draft.
• Normalise revisions. When you send your first draft, set the tone by saying, ‘This is our starting point to shape together. Let me know what resonates and where we can refine further.’ 

Feedback isn’t failure—it’s simply part of the process!

The more your clients understand this, the less likely you’ll stay stuck trying to make a draft “perfect” on your own.

3. Use a writing system (not stream-of-consciousness word vomit)

Here’s a harsh truth: Your brain isn’t as organised as you think it is. If you’re diving into copy without a plan, you’re probably creating more mess than magic (and blowing out your project times in the process).

Instead of relying on “inspiration” (which is notoriously flaky), create a writing system.

A good system isn’t just efficient—it’s calming. It gives you a framework to lean on when your brain wants to spiral into ‘Is this even good?’ territory.

This is something I teach in The Copywriting Inkubator and it’s a game-changer.

• Organise your thoughts first. Begin with a brain dump, then refine it into bullet points, an outline, or a mind map. This isn’t about stifling creativity—it’s about giving it direction.
• Write in timed sprints. Parkinson’s Law states that work expands to fill the time you give it. So, don’t give yourself the whole day to write a single page. Set a timer for 30 minutes to map copy out then 60 mins to get your draft on paper.
• Save editing for later. Writing and editing require two different mindsets. Don’t try to wear both hats at once—it’ll only slow you down.

Remember that deadlines aren’t your enemy—they’re your compass. Even if you’re setting them yourself, treat them like gospel.

4. Find your inner cheerleader

If you’re constantly second-guessing your writing, it’s probably because you’re listening to the wrong voice in your head. (Yes, I know how that sounds, but stay with me.)

Your inner critic is LOUD. It’s the voice saying, “This isn’t good enough. Nobody’s going to read this. Are you even a real copywriter?” But here’s the thing: Your inner critic might be loud, but it’s not the boss of you. 

You just need to turn up the volume on your inner cheerleader.

How to hype yourself up:

• Track your wins. Keep a journal of projects you’re proud of, feedback you’ve nailed, and moments when you pushed through doubt and delivered.
• Save client testimonials. When imposter syndrome hits, re-read kind words from your clients. I call mine my YAH-FILE.
• Find your community. Surround yourself with other copywriters who get it. Share your struggles, swap advice, and cheer each other on.

If you wouldn’t say it to a fellow writer, don’t say it to yourself. (When’s the last time you told a friend their work was “probably trash”? Exactly.)

5. Invest in learning the technical craft of copywriting

Let’s get real: Copywriting confidence doesn’t just show up out of nowhere. It comes from building a solid foundation in your craft. 

Sure, there’s no shortage of blogs, YouTube videos, and Instagram reels promising to make you a pro overnight—but skimming tips won’t cut it if you want to stop second-guessing your work.

The best investment you can make? Stop trying to memorise clever tricks or hacks and start learning the principles, frameworks, and strategies that underpin great copy.

Why investing in your learning is a game-changer:

• It builds unshakeable confidence. When you understand why certain words and structures work (and why others fall flat), you stop second-guessing your choices. You can write with purpose, knowing your copy hits the mark.

• It opens doors. Graduates of programs like The Copywriting Inkubator often find themselves saying yes to higher-paying projects and no to clients who don’t value their worth. They’re able to raise their rates because they’ve raised their skillset.

• It sharpens your strategy. When you understand the craft on a deeper level, you can confidently advise clients on what works—and tactfully explain when their feedback might actually hurt their goals. (We’ve all had those “I think we need bigger  words” conversations.)

Building your expertise doesn’t just change your writing—it changes how you show up in your business. Knowing what to do (and when to do it) can turn the loudest inner critic into a faint whisper.

And there is a lot of excellent copywriting intel at your finger tips. Like this blog for starters! But like most things in life, you’ll either invest time or money. And if you’re ready to level up, a program like The Copywriting Inkubator can give you the foundation to grow.

Final thoughts for you

Doubt is normal, but it doesn’t have to call the shots. 

With these five steps, you’ll move from overthinking every word to writing with clarity, confidence, and—dare I say—swagger.

And if you’re ready to take your skills to the next level, programs like The Copywriting Inkubator can help you turn that confidence into action. Doors open in Jan and Feb!

Out of these five tips, which one are you going to put into practice to boost your copywriting confidence in 2025?

Share your thoughts in the comments or send me a message—I’d love to hear what’s resonating with you and how you’re planning to kick second-guessing to the curb this year!