How I write this newsletter: The painful process of a bad writer.


Hey there, I’m Lesley. Welcome to the latest issue of Failing Forward — A weekly newsletter where I share my experience as a bootstrapped founder.

There’s no bravado here. I fear failure, just like you. I write this newsletter to remind us both that failure is not just okay, it’s often the best way forward.


How I write this newsletter: The painful process of a bad writer.

I’ve been writing this newsletter semi-regularly for over a year now. Today I thought to share my approach to writing.

Specifically how painful it is, and how all the magic is in the editing.

I’m a bad writer.

I’m unable to write well with consistency. Some times, I manage to string together some nice-sounding words. On rare occasions, I conjure an original insight, cleverly phrased. But that’s it. My genius is limited.

To me, writing is the act of transcribing thoughts. I don’t know about you, but my brain doesn’t think linearly. Thoughts that appear clear in my head often turn out less than lucid once extracted.

As a result, my writing is like a mind map forced into a linear mould – Full of detours down side paths, inside jokes and non sequiturs.

Editing is when the magic really happens.

I would have written a shorter letter, but I did not have the time.

Blaise Pascal in Lettres Provinciales

I consider myself a bad writer, but a good editor.

Editing lends clarity to my mental mess. Each round of editing makes my writing clearer. I smoothen bumps that slow the flow and detract from the overall point. I do this by deleting ruthlessly or with complete rewrites.

I try to edit from different vantage points. Some times I edit with a microscopic lens, while other times I try to take in the whole picture by editing from afar. This is easier if I have time to step away between edits to change my focal distance.

I begin most posts with a strongly held opinion. Occasionally, a better perspective emerges while editing. I know sunk cost is a fallacy, so I don’t find it difficult to discard the weak for the strong.

I plan most posts with a structure, an angle, and supporting points. Most of these don’t make the final cut. Even when I’ve dutifully mapped everything out on paper, and it all seems logical. By the time I hit publish, the original is barely recognisable from the end product.

Writing is ingredients. Editing is everything that turns ingredients into cake. Most of the posts you didn’t like, thought were too wordy, didn’t have a clear point, or worse, were the result of insufficient or poor editing.

Sorry to interrupt, but if you’re enjoying this post, you’ll likely enjoy next week’s too. Subscribe here so you don’t miss out.

Thanks! See you next week in your inbox.

Twitter helps my writing.

Each week I tweet a summary of my newsletter.

Each week I have to trim sections to fit word limits.

Each week I am reminded how many extraneous words exist in my newsletters.

Consistent writing makes a difference.

Now that I write weekly, I’m forced to get on with it. I can’t be too precious about each newsletter. Something must go out.

Consistent writing means more opportunities to improve. For example, a couple of issues ago, I started paying more attention to the lede. Rather than start a story at the beginning, I start with the key takeaway instead. Or at least I try to.

Writing never stops being hard.

I’ve been writing on the internet for two decades. It’s still hard.

Except for some people. They claim to write in an hour, edit in half, and yet, what emerges is fully formed and brilliant. Either they’re skilled where I am not (this is likely), or they’re lying (also likely).

Editing is therapy.

Editing is a magic tool that uncovers what you really think. If you’re lucky, it also distils and articulates your thoughts. You don’t need therapy if you are a good editor.

I am willing to double down on this opinion if you’ve been writing and editing personal thoughts regularly for more than a decade.

I don’t plan to stop.

Two decades is nothing. Here’s to dozens more!

If you haven’t already, I hope you start.

Writing is hard.

It’s also intimidating, because writing feels like art. And you might not feel like an artist.

Focus instead on getting good at editing. Editing is a skill. Anyone can learn a new skill.

You can too. Just start.


I’m building Newsletter Glue — an email newsletter platform on WordPress with a Gutenberg-first approach.

Here’s what I got up to this week…

🔥 Highlights from this week

Our Pro plugin is live. It’s the pre-launch and the plugin is in closed beta, but this was harrowing.

Crippling fear-aside, I’m glad we pushed to rush this out. Building in the dark is easy, it’s also worthless.

Lots of amazing feedback, love and new collaborations. Here’s one of them.

💔 Lowlights from this week

Everything that could go wrong, did.

Our first customer couldn’t complete his purchase because we hadn’t configured our checkout process correctly.

We also didn’t get as many customers as I would’ve liked.

✅ Completed this week

Well, we launched.

🎯 Goals for next week

A shit ton of bug fixes and UI improvements. I am so grateful for all the feedback given so far.


Worth a thousand words

@tinycactus

Worth your while: Here are my favourite links from this week

Read: Adrianna Tan reflects on life in San Francisco during the pandemic.

“My friends are having brunch and cocktails back home and I know in my bones that would be me, if I was in Singapore right now, too. Because I am bougie like that and I know it.

But I am not at brunch. I am huddled at home, like I have, every night this year. My dog is asleep next to me, farting ceaselessly. I have canceled all holiday plans. We are not going anywhere.”

I read her blog in secondary school, and rediscovered her on Twitter earlier this year. I’m so glad. Her writing remains honest, raw and personal. Read blogpost →

Read: What happened to GeoCities?

A delightful and well-researched article delving into the history of GeoCities. Lots of pictures to make you feel nostalgic. I wish I could remember my GeoCities usernames. What a pity. If you don’t know what GeoCities is, it’s where we all hung out before Neopets. And if you don’t know what Neopets is, well…

Read article →

Read: Solarpunk: Sci-fi that isn’t depressing

“The genre envisions stories set in a future that runs on renewable energy, such as solar or wind, and where race- or gender-based discrimination is more limited than it is today… [It] combines the punk ethic with an optimistic, climate-friendly future. Its aesthetic is solar panels, windmills and leafy high-tech societies.”

Ahhh, for once a vision of the future that doesn’t seem bleak.

Along this vein, I recently finished The Long Way to a Small, Angry Planet. It was character-rich, plot light, and felt like Sesame Street sci-fi. Personally, I loved it. But definitely don’t think it’s for everyone.

Read article →


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