Issue #40
Hey there, I’m Lesley. Welcome to the latest issue of Failing Forward — A weekly newsletter sharing my experience as a bootstrapped co-founder.
There’s no bravado here. I fear failure, just like you. I write this newsletter to remind us both that failure is not only okay, it’s often the best way forward.
A new look and listening to feedback
New look
As you can see, this week’s newsletter looks slightly different. I had some incredible feedback on the newsletter from Taylor and Colin this week. And what you’re looking at is the result of those suggestions.
Most importantly, they both highlighted that I should provide more context, and create headlines that better explain what the section is about, and why a reader should care.
I hope I’ve achieved that. Thanks for the feedback, guys.
If you’re reading this and have opinions on the new format, please don’t hold back. As you can see, I love getting feedback and will actually take action.
Listening to feedback
Speaking of feedback, I’ve noticed with interest how tentative some people have been about sharing feedback for Newsletter Glue (the WordPress plugin I’m building).
One person began with, “I had an idea, forgive me if it’s not part of the roadmap!“
While another ended an email with, “I realize that my advice is unsolicited. I don’t mean any offense by it.“
I don’t know if this tentativeness is due to their lack of familiarity with me (which is totally reasonable, I am a stranger on the internet), or if they’ve had some negative encounters in the past. Likely, the answer is both.
But for the purposes of this post, let’s focus on the latter bit.
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
- Newsletter Glue can now be used for custom post types. This lets users use Newsletter Glue across their entire website, rather than just for blog posts.
The first time I heard this feature request, I didn’t react. But then I heard it twice more in quick succession, and implemented it asap. Such is the value of a steady stream of feedback! 😉
💔 Lowlights from this week
- Noticed some plugin conflicts causing Newsletter Glue to break some sites. It’s always stressful to hear this, but it’s super common inside WordPress. 35% of the internet is on WordPress, which means there are millions of different WordPress configurations and it’s impossible to account for all of them.
I spoke to a bunch of super experienced WordPress plugin and theme owners, and they said the best thing I can do is fix things as they come, test for those conflicts in the future now that I know about them, and try not to stress out too much. Sound advice!
✅ Completed this week
- Made huge strides on our Newsletter block manager
- Moved to newsletterglue.com for emails, website, support and more. This was super mundane work, so I’m glad it’s mostly done now.
🎯 Goals for next week
- Continue to build premium newsletter blocks that give people more features for creating newsletters inside the Gutenberg block editor.
- Start building out the newsletterglue.com website.
Worth a thousand words

Worth your time: Sharing my favourite links from this week with you
Watch: Andy Miller recounts how he once accidentally stole his boss, Steve Jobs’, laptop.
Andy Miller is now the Chairman and co-owner of NRG e-sports, but he used to be VP of Mobile Advertising at Apple. In this video, he tells the story of how he was booted from Steve Job’s office and, in his panic and hurry, he accidentally took his boss’ laptop. Eep! Watch video →
What happens when you follow data at all cost
Excellent article on the dangers of an over-reliance on data. Measuring the wrong thing, wrong attribution, and a perversion of incentives are just some things covered.
“When Spotify opts you in by default to noisy push notifications (“the Beatles are now on Spotify!”), they might increase some engagement score, but they also annoy their users. That annoyance may not show up in any dashboard: maybe users keep using the service exactly as much, but when some PR fiasco blows up the following year, they’re less inclined to take Spotify’s side.” Read article →
Aphantasia: How It Feels To Be Blind In Your Mind
Aphantasia is a mental condition that prevents a person from picturing things in their mind. In this post, writer Blake Ross explains his experience with it and how he came to realise this wasn’t normal.
I first came across this post some years ago, but am sharing it again because it remains the best way to show how we’re all wired differently and that one can never be sure of what’s going on in each other’s minds. Read article →
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