I am my newsletter's biggest fan (and harshest critic)
Some weeks, I hit publish thinking "this is brilliant." Other weeks, I hit publish thinking "this is trash."
Both weeks, people reply saying it helped them.
After three years and 156 published issues, I've learned something that would have saved me months of agonising: my judgment of my work is entirely unreliable.
The posts I think are throwaway observations become the ones people screenshot and share. The posts I craft carefully sometimes land with a thud.
Confidence vs self-doubt reality
Here's what nobody tells you about consistent publishing: confidence isn't the absence of doubt—it's publishing despite the doubt.
Every successful newsletter writer I know has the same dirty secret: they regularly publish things they're not sure about. Not because they're reckless, but because they've learned that internal certainty is a terrible predictor of external value.
You'll never feel ready. You'll never feel certain. You'll never look at a draft and think "yes, this is exactly what the world needs right now."
That's not a bug in your system—it's a feature. Doubt keeps you honest. Doubt keeps you trying. Doubt keeps you from becoming the kind of writer who thinks every word is gold.
The skill is publishing anyway
The amateur waits for confidence before publishing. The professional publishes to build confidence.
Three years ago, I thought confidence came first, then action. Now I know it's the opposite: action builds confidence, not the other way around.
Every time you publish despite the voice in your head saying "this isn't good enough," you're building the muscle that matters most: the ability to serve others despite your insecurities.
That's the real skill. Not perfect writing. Not flawless insights. The ability to say "this might help someone" and press send.
Your doubt serves your readers
The posts you're most uncertain about are often the ones your readers need most. They're raw, honest, unpolished reflections of real struggles—exactly what people crave in a world of curated perfection.
Your doubt ensures you're sharing something real instead of something performative. Your uncertainty signals that you're grappling with complex problems, not dispensing easy answers.
The moment you wait for certainty to publish is the moment you stop serving your audience and start serving your ego.
Press publish especially when you doubt. That's when your newsletter matters most.
Your readers don't need your confidence—they need your honesty.
Other Posts in The 52 Button Pushes Series
Rick
Post 1: You already know how to write—that's not the problem →
Rick
Post 2: Your newsletter dies the moment you 'find time' to write →
Rick
Post 3: You're not a perfectionist—you're scared →
Rick
Post 5: It's just 52 publish buttons →You can s
These posts give you the mindset. If you want the mechanics, I've built the systems: Ghostwriters for client newsletter management and Newsletter OS for personal publishing. Both templates turn the operational mess into something you can stick with.
Simple Newsletter OS
Newsletters are seen as the new gold with the rapid decline of organic reach in social media. Furthermore, sending out a regular newsletter is also a great way to develop your thinking and writing skills. Besides creating and publishing a newsletter, you also need to consider how you attract new people to your newsletter and promote your current editions; for this, you need some traffic drivers.
Ghostwriter's Zettelkasten Toolkit
The “Ghostwriter’s Toolkit” is a comprehensive Notion template designed to streamline the content creation, enhance note-taking efficiency, and foster continuous idea generation. It seamlessly combines a simple yet powerful content system for planning and executing newsletters with an advanced note-taking system inspired by the Zettelkasten method.