0004: Lenny’s Newsletter
On Learning from the best.
My Substack categories are:
Art & Illustration | Business.
At time of writing In art and illustration I rank between the top 55-65, I’m aiming for top 10. I’m not ranked in the business category, but it would be nice to get to the top double digits.
Could I write the no.1 ranked newsletter in the business category?
The number 1 Newsletter in Business is called Lenny’s Newsletter, it talks about building products.
Today
dropped a Free Newsletter about time management that actually works, and it gave me the feels because I felt, I could have written that! Obviously I recognise this as the Dunning-Kruger effect.1
I’m generally aware of the time management ideas and the books and authors mentioned, I even use 9/10 of the ideas suggested in some degree, but could I really write a newsletter like that?
I’ll humbly say no.
What is the no.1 newsletter in the Business Category doing that I’m not.
So now I can ask what does the number 1 newsletter in the business category do, that I don’t?
This issue of Lenny’s Newsletter is a ten point article, so I asked Claude to compare it with one of my own 10 point articles, then make a checklist of what I could improve. This is the checklist:
Checklist for Newsletter Improvement
## 1. Visual Formatting
- [ ] Add a clear, engaging title at the top of the newsletter
- [ ] Include your name and the date of publication
- [ ] Use bold, larger font for main section headings
- [ ] Incorporate relevant images or screenshots to illustrate key points
- [ ] Use block quotes for emphasizing important statements or quotes
## 2. Structure
- [ ] Add a brief introduction summarizing the newsletter's content
- [ ] Use consistent numbering or bullet points for lists
- [ ] Create clear subsections with descriptive headings
- [ ] Add a conclusion that summarizes key takeaways
- [ ] Include a footer with additional information (e.g., about you, how to subscribe)
## 3. Content Enhancement
- [ ] Add brief explanations or examples for each of your 10 steps
- [ ] Incorporate relevant statistics or data to support your points
- [ ] Include quotes from industry experts or successful illustrators
- [ ] Provide links to additional resources mentioned in the newsletter
## 4. Engagement and Call-to-Action
- [ ] Add a clear call-to-action for newsletter subscription
- [ ] Encourage reader engagement with a specific question or prompt
- [ ] Include social media links for readers to connect with you
- [ ] Mention any upcoming events, courses, or offerings
## 5. Professional Polish
- [ ] Create a consistent color scheme for headings and highlights
- [ ] Use a professional, easy-to-read font
- [ ] Ensure consistent spacing between sections
- [ ] Proofread for any grammatical or spelling errors
## 6. Value Proposition
- [ ] Clearly state the benefit of reading this newsletter issue
- [ ] Tease upcoming content to encourage continued readership
- [ ] Consider adding a 'Quick Summary' section for skimmers
## 7. Personalization
- [ ] Include a personal anecdote related to the topic
- [ ] Add your photo or a custom illustration to make it more personal
- [ ] Sign off with a personal note or signature
## 8. SEO and Discoverability
- [ ] Include relevant keywords in your title and headings
- [ ] Add alt text to any images you include
- [ ] Create a shareable snippet or quote from the newsletter
What did I learn?
There is a huge gap between my best work, and a regular free Wednesdays newsletter.
What excites me is that this gap in not in the knowledge category, rather it’s in the Ugly Work category.
What makes Lenny’s Work so great is the amount of Ugly work that has gone into it. The kind ow work that anyone could do if they bothered to.
I was sitting at a local Chinese coffee shop today, and my wife remarked on the lack of hospitality on the face of the owner. And I argued that the place was actually very hospitable, it was extremely well lit and ventilated, it was playing classical music by modern orchestras, each of the individual vendors had clear descriptions about what was on sale in all their variations.
Maybe the owner was tense trying to make sure all he plates were spinning correctly.
The ugly work of making a newsletter is a kind of hospitality. The only way to justify the categoric work of making a newsletter as hospitable as possible is if you had a large audience to make all the effort worthwhile.
But you can’t get a large audience if you’re not first hospitable.
Next Steps for me.
Implement the changes suggested by Claude
Make my own list of improvements beyond that and implement those.
Write a blog post on each of the time management tactics suggested by Lenny
If you’re looking for a time management tips that work, do check out Lenny’s newsletter:
And here’s a specific tip I saw on X to help with email overwhelm.
So, could I get to number 1 in a category?
Am I willing to do the ugly work to get there?
Will I be able to Master the time management skills it takes to do the ugly work effectively?
Did you get anything out of this blog?
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