Case Study: My #1 Lesson Learned About Newsletters After Launching 8 Weeks Ago
This newsletter, like everything I’ve done for the last 8 years, is meta.
I learn, then teach others to learn faster and better.
I learn mental models, then share them in the Mental Model Club.
I study writing, then create a year-long course on it.
And now the same is happening with newsletters and video clips.
I focus on the meta level for several reasons:
Motivation. Learning stuff that I’m naturally drawn toward and that I can apply to my life is extremely motivating. Even if I never published an article, I would still be happy with everything I’ve learned.
Stress-Testing. Applying stuff to my own life stress-tests and improves the ideas I share.
Learning. When I share what I learn, I learn it more deeply (see Explanation Effect).
Thought Leadership. Writing helps me impact others, build relationships, make money, and become a recognized expert.
Compounding Via Consistency. While my small curiosities are constantly changing, my core passion for learning, ideating, and writing has only gotten stronger. This consistency gives me the confidence to invest more deeply in learning and teaching these skills, because I can see myself exercising these for the rest of my life.
This is why a mentor once told me that the money is in the meta.
In that spirit, I wanted to be transparent about how I make the decisions in this newsletter so that you can learn from my thinking process and the results that come from it…
The Posting Schedule Of Your Newsletter Determines Everything Else
The posting schedule is a lever that determines many, many critical things about your newsletter and life:
The format of your posts
How readers make a habit of consuming your content
The quality of your posts
How much time you devote to your newsletter
Your lifestyle / work-life balance
Your balance between quantity & quality
Your stress levels
Etc
Therefore, it’s worth taking a little time to think about the right frequency for you.
Over the last 8 weeks, I’ve gone through four schedule changes. Below is why I made each one and what I learned…
The Evolution Of My Posting Schedule
Schedule #1: Mon, Tue, Wed, Thu, and Fri at 5:00 am EST
When I started the newsletter on July 11, I committed to a daily posting schedule for one primary reason: to help readers build a habit of consuming my content.
I was convinced to do this by the rationale of paid newsletter pioneer Ben Thompson:
Source: The Logan Bartlett Show
I’ve also gotten signals from other places. For example, below is a comment I received today:
The info you've been presenting in this newsletter - especially the paid version - is EXCELLENT.
In terms of making it 'better' - the only thing I have to suggest is having the email arrive at Noon. This way we have the AM to focus on our top 80/20 - and it's not coming late in the day - after my energy is spent. The other thing 'might' be that the making sure the newsletter arrives on the day's it's expected - it would help me (us?) build a routine around it.
These are minor 'issues' - but it would be keep up with and absorb the valuable info you're producing. Keep up the excellent work!
The way I think about it now is that I envision the old days when physical newspapers were delivered to people’s homes at the same time every morning so that they could read them in the morning over breakfast and coffee. The newspaper was tightly woven into a specific part and place in people’s day. In other words, it wasn’t read at random times. And, if it was shipped at 10:00 am instead of 5:00 am, the experience with it would completely change.
One caveat is that Thompson specifically recommends that you:
Focus on quality first with your first article, so you can make an incredible first impression
Focus on quality second through your next several articles, so you can gain a fan for life
Focus on quantity third once you have the skills, so you can become an important and regular part of people’s lives.
I write about this model in Quality-Quality-Quantity: How To Succeed Online According To The Highest Paid Writer On The Internet (Ben Thompson).
Immediately, I found that the daily deadline pushed me to focus all of my attention on meeting it. This was good, as it got me to put all my energy into producing the newsletter rather than filling up my free time with something else. This is important because I believe that the amount of time you put into a newsletter is correlated with its success. More specifically, the amount of time you put into actually creating content is the most important way to spend the time.
But, by the end of the first week, I realized that the daily schedule was unrealistic, so I updated it…
Schedule #2: Mon, Tue, Wed, and Thu, and Fri at 5:00 am EST
The 4x per week schedule was a definite improvement.
But, a few weeks into this new schedule, I noticed that I was consistently late on the Thursday post, so I changed things up again. I moved the Thursday post to Friday so that I would have another day of buffer.
Schedule #3: Mon, Tue, Wed, and Fri at 5:00 am EST
This schedule worked better than the first two, but then things started to evolve in unexpected directions:
I noticed I was drawn toward longer posts that connect many ideas and video clips, rather than just sharing one video clip per post like my initial plan. I think that this is due to the fact that I’ve spent thousands of hours researching and ideating in my courses and programs already. So, I’m sitting on a lot of ideas that I’ve tested and am passionate about that I’ve never shared publicly. If this wasn’t the case, I think I would’ve still stayed at the one video per post format. Furthermore, I’m not against sharing one video only if the video is comprehensive enough.
I was getting feedback via paid subscriptions that people valued these longer posts as well. At first, I was getting a handful of paid subscriptions per post. Now, I’m getting 10-15.
As a result of increasing the scope per post, the articles have been taking twice as long. Rather than taking 6 hours per post, the average post started taking more like 12 hours. Suddenly, I was working nights and weekends. Even then, I was still behind and feeling stressed about it.
On the one hand, I’ve really liked pushing myself harder than I ever have as a writer to stick to the schedule. I’ve shipped more high-quality content than I ever have in my writing career. I’ve written 35 posts that probably average roughly 2,500 words per post.
Part of me wants to keep pushing hard. I still have the energy, and there is a thrill to pushing myself. The newsletter is now at 280 subscribers, and, if I kept the same pace, it would likely be at 2,000 on the anniversary of the newsletter.
On the other hand, it has been unsustainable on multiple levels:
My wife and I got into an argument last week because she’s picking up my slack at home.
I’ve been incurring operational debt in the business as we push off everything not related to researching, ideating, and writing Substack posts.
While I’ve been shipping out quality articles, I could definitely increase the quality of each post in a way that makes up for the lost quantity.
While I’m improving my efficiency, I’m not improving on the quality of each post, because I’m not putting time into really challenging the quality holes in the writing process and finding ways to improve it.
I haven’t been consistently meeting my commitment to readers on the posting schedule, which makes it harder for readers to create a habit around the posts.
There have been days when I was writing a post at 10 pm, and I’m completely tired and feeling overwhelmed. If I continued at this pace for many more months, I’d risk burning out.
I haven’t been able to create a backlog of content, which means that if something happens (i.e., I get sick, I fall behind on a post), then the post is delivered late.
Bottom line: I find that I feel like Indiana Jones every day—adventurous on the one hand, but unsustainable on the other…
I didn’t change the schedule earlier, because I had hoped that the constraint would force me to pioneer a format that took less time, but kept the same level of quality and would allow me to be consistent. I spent at least 8 hours brainstorming different formats, but I haven’t found that format yet.
With that said, I am now officially changing the posting schedule to this...
Schedule #4: Mon, Wed, and Fri at 5:00 am EST
I’m excited about the shift, and I think it will be the best for me, the content, and for you, my beloved reader.
I appreciate your patience as I figure things out.
The good news is that you get to learn from me so that when you create your own newsletter, you’ll be aware of the challenges and have the scaffolding to make better decisions for yourself.
At the end of the day, my #1 lesson from my 8-week sprint is this…