The Digital Contrarian

TDC 070: Seven "Non-Obvious" Email Lessons I've Learned Writing This Email Newsletter Each Week.

• Episode 70

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TDC 070: Seven "Non-Obvious" Email Lessons I've Learned Writing This Email Newsletter Each Week.

Episode Summary

In this episode of The Digital Contrarian, host Ryan Levesque reveals the seven most impactful lessons from writing 70 consecutive weekly newsletters by hand.

You'll learn how less AI usage led to higher engagement, why creative volume beats perfectionism, and discover the custom dashboard metrics that actually matter for email success.

Question of the Day 🗣️

Which of these 7 lessons resonates most with you? Drop a comment and let me know!

Key Take-aways

  • Custom AI dashboards beat vanity metrics – track engagement scores, not just opens and clicks
  • Less AI in writing process correlates directly with higher reader engagement scores
  • Creative fecundity is essential – you never know which piece will break through
  • Buffer days between writing and sending prevent newsletter stress and missed deadlines
  • Make it great before you make it grow – optimize for impact, then scale

Timestamped Outline ⏱️

01:26 – Lesson #1: Let data drive decisions (AI dashboard reveal)
05:03 – Lesson #2: Less AI = More engagement (the shocking data)
06:38 – Lesson #3: Creative fecundity is the key to success
08:38 – Lesson #4: Keep your cutting room floor
09:20 – Lesson #5: Build in a buffer day
11:25 – Lesson #6: Make it non-negotiable (decide to win)
13:25 – Lesson #7: Make it great before you make it grow
14:26 – All 7 lessons recap

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Credits

Host: Ryan Levesque
 © 2025 RL & Associates LLC. All rights reserved.

Seven non-obvious email lessons that I've learned writing an email newsletter every single week for the last 70 weeks. So earlier this week a black bear got into half of the honeybee hives on our family farm and it was heartbreaking to see the level of death and destruction. I'm not going to lie, in fact this is what you're looking at on this photo here on the screen. 

Now in the return to real, it was an experience that's personally hit me pretty hard. And while the black bear was wreaking havoc on our back 40, I was in my office delivering a private session for members of my strategic advisory group mastermind over Zoom, revealing some of the biggest non-obvious email lessons that I've learned writing and sending out the first 70 issues of my weekly email newsletter, The Digital Contrarian, which is what you're listening to me read right now. And while there were a few things on that call that I shared that are confidential, strictly for members of the group only, in the spirit of return to real once again, there are seven lessons that I've learned that have been so important and which I think could potentially be really helpful for you that I want to share them with you here in this episode today. 

Beginning with lesson number one, let data drive decision making, create an AI-powered dashboard ASAP. Go ahead, take a look at the screenshot on the screen. We're going to come back to this in just a moment. 

Did you see those figures? Well, first, just a bit of context. Over the last year, using a combination of AI tools, my team has worked incredibly hard to create a custom email dashboard to help me drive decision-making with my writing. For example, I've been able to measure everything from the correlation between email engagement and my email word count, number of links I include, number of images I share, and a whole host of other data points that I've been curious to explore. 

In this process, one thing that's been most helpful has been an internal engagement score that my team created that I can use to evaluate the effectiveness of each individual email that I write. So for example, you can see some of the top performing and bottom performing issues from the last 70 weeks. Now, in case you're wondering, what does an engagement score actually measure exactly? Well, I'll get to that in just a moment. 

But first, when writing a weekly single source of truth piece of content, i.e. like a weekly email newsletter, evaluating how engaging that individual issue is requires looking at more than just your email open rates and email click rates. Both of those metrics can be gamed with clickbait subject lines and ultra short link only copy in the email and thus provide a misleadingly incomplete story. So for example, it's a good idea to also measure things like how many replies an email garners, the number of unsubscribes it gets, as well as the amount of time someone spends reading that individual email relative to its word count, i.e. sure, people might open your email, but do they actually sit down and read it? Now, this is where a comprehensive engagement score can be so valuable, a composite metric that incorporates a number of different data points. 

This is something that my team has spent the better part of the last year developing and something that we now work with our return to real strategic content ecosystem agency clients to incorporate into their single source of truth email strategy each week as well. Now, if you take a look at the engagement score screenshot that I shared just a moment ago, which I'll share once again, my question for you is this, what do you notice about the red versus green boxes? Go ahead and take a look here on the screen. What you'll notice is that in the red box, four out of my five worst engagement score emails, issues number six, number 12, number 15, and number 17, were some of the earliest issues of the digital contrarian. 

In contrast, you'll notice that in the green box, four out of five of my best engagement score emails, issues 65, 66, 67, and 69, were some of my most recent issues of the digital contrarian. Now, this is not an accident. This is what the relentless pursuit of incremental improvement looks like when using data to drive decision-making. 

Everything from what topics to write about, to how many links to include in each email, to how to structure subject lines and preview text. In fact, if you look at just one of the metrics that goes into the engagement score that we've developed, email open rates, you'll notice in the figure on screen, the red trend line goes slightly up and to the right, with recent issues approaching 50% open rates after starting in the mid 30s earlier last year. Now, this is what incremental improvement looks like. 

And most importantly, this is in contrast to most email lists, which typically see a trend line that goes down over time, because email lists often get colder and less engaged over time. So, how can you increase your open rates over time, just like in the chart we looked at a moment ago? Well, this brings us to lesson number two. The less I use AI in my writing process, the more engagement I see.

While I've written every issue of the digital contrarian, personally myself, dating all the way back to issue number one, An Embarrassing Confession, in the process of writing each issue, I've also often used chat GPT and other AI tools to help with things like researching citations, evaluating aspects of the writing for clarity and grammatical errors, and more generally, to serve as a thought partner, to help me think through ideas. But after OpenAI's release of GPT5 back in August of this year, I became increasingly disappointed and frustrated with the quality of output that I was getting back. So, approximately six weeks ago, I stopped using chat GPT in my process of researching and creating this newsletter altogether. 

And interestingly, that one change in my writing process is highly correlated with a significant bump in the engagement score in all but one of the issues that I've written since over the last six weeks. In fact, you can check it out here on the screen. Now, I believe the story here is more complex than implying simple causality, but there is definitely a strong negative correlation between AI usage in my process and engagement score from readers. 

In the simplest of terms, the less AI that I use, the more engagement that I see. Which brings us to lesson number three, creative fecundity is the key to success. As we explored back in issue number 27, How to Design Your Strategic Content Ecosystem, as I wrote, Mozart composed more than 600 pieces of music before his death.

Bach more than 1,000. Picasso produced more than 1,800 paintings and over 12,000 drawings. Einstein contributed over 248 academic papers. 

Edison had over 1,000 patents. And yet for each of these creative geniuses, the number of truly superlative pieces of work they each produced in their lifetime can generally be counted on one hand. This is a passage from Adam Grant's book Originals that we explored in this issue. 

So there's a certain level of creative fecundity and commitment required to produce something that truly lands with your audience and leaves a mark. And the reason for that is you simply don't know which pieces are going to land. For example, last month, I wrote an issue of The Digital Contrarian titled issue number 62. 

Is the AI bubble bursting? It had an unremarkable engagement score of just 3.57, which is below my average score of 3.74. You can check it out here on the screen. But this same piece, after I sat down to film myself reading it out loud, has gone on to generate over 150,000 views on YouTube and helped my tiny little channel reach the milestone of over 10,000 YouTube subscribers. I don't know that Van Gogh would have guessed posthumously that Starry Night would go on to become his most famous painting of all time. 

I can tell you with certainty that I never would have guessed that issue number 62, an otherwise unremarkable middling performer of an email newsletter, would go on to see the success that it's seen on YouTube. You never know which piece is going to pop. And this is why creating a consistent volume of work is so critical. 

This is why creative fecundity is such an important key to success. Which brings us to lesson number four, keep your cutting room floor because it becomes fodder for future issues. Every week, there's more that I'd like to share in my email newsletter than I have space and time to write. 

Like, for example, this week, I was going to open this issue writing about the wild turkeys and migratory ducks and geese that show up in spades on our farm at this time each and every year. That is before the bear decided to wreak havoc on the hives. I decided to cut the turkey segment because it no longer fit.

And every week I go through a similar process. I'm left with an Evernote file, which I titled Issue X Cutting Room Floor, filled with all the good stuff that I wasn't able to fit into that week's issue. And here are a few examples that I'll share with you on the screen. 

Now, sometimes this might be an entire topic that I was planning to explore in detail, like the segment slated for issue number 54, contrasting the AI work of Mo Gadatz and the AI work of Jeffrey Hinton. Sometimes this might be a short personal story that I ultimately don't share, like the one earmarked for issue 65, when I inexplicably missed wishing my dad happy birthday on his actual birthday and felt like a terrible, terrible human being as a result. Then every two months or so, I'll go back through all my past week's cutting room floor files and will almost always discover that there is gold in them there hills. 

So if you're ever wondering what to write about when you're feeling stuck, I'll tell you, keeping a cutting room floor like this will often serve as fodder for future issues and give you a never-ending well of ideas. Which brings us to lesson number five. Habits are hard, so build in a buffer day. 

When I first started writing The Digital Contrarian 70 weeks ago, I decided to make Fridays my writing day. I did so with the goal of my newsletter going out on Saturday mornings, but the only problem with that was this. It left me with literally zero buffer, meaning if there was ever a Friday where I was tied up, whether that meant speaking at a conference or taking advantage of a weather window for a big farm push or being part of a school commitment for one of my kids, I had no choice but to write if I wanted to get my newsletter done in time for a Saturday morning send. 

Now, this started to put undue stress on me and in turn my family. So earlier this year, I decided to make a slight tweet. I decided to shift our newsletter send day to Sunday mornings instead. 

This gave me Saturday as an additional buffer day so that if I couldn't get my newsletter 100% written on Friday, I still had another 24 hours to get it done. And I can't tell you how much of a game changer this one simple move was for me. Pick whatever day you want to write, but make sure that you give yourself at least one or more buffer days between your writing day and your send day. 

Which brings us to lesson number six, make it non-negotiable. Decide to win. Last week when I was coaching my older son's middle school soccer game, our team was up two to nothing at halftime, but we ended up losing the game four to two. 

And we lost for one simple reason. Over the halftime break, the other team simply decided that they were going to win the game. The moment the ref blew the whistle to start the second half, they kicked it into this other gear. 

They played with more heart, more intensity, more desire, and a sense of urgency that seemingly came out of nowhere. In short, they made the decision to win the game. And they did. 

So you might be wondering, well, what's this story got to do with email? Well, sending a weekly email newsletter every single week without missing a single issue is not easy. I've had weekends where I was literally rushed to the emergency room in an ambulance with a head wound, gushing blood, and hustled back home to get this newsletter written like a crazy person. You can see issue number 58, the bombshell week in AI for more details on that one. 

I had weekend long soccer tournaments and all day farm harvests where I couldn't get in front of my computer until close to midnight and stayed up until three or four in the morning to get this newsletter written also like a crazy person. You can see issue number 66, a crazy person's guide to living life for more on that one. But here's the thing, just like with anything in business and life, the secret to success is actually quite simple. 

Whether it's exercising every morning to build your body or writing an email each week to build your business, make it non-negotiable. Get it done no matter what. Hold yourself accountable and stick to the commitment you've made.

As I often remind my two boys, it's hard to become wealthy. It's hard being poor. Choose your heart. 

Now the lesson here is this, whatever path you choose to follow, decide to win and make it non-negotiable. Which brings us to lesson number seven, make it great before you make it grow. On my mastermind call earlier this week, after sharing some of my email stats, a member of our group asked, but Ryan, how much have you grown your email list? And as I explained on the call, I've built massive email lists in the past for context, literally millions of people, but that's not what I'm optimizing for right now. 

Instead, what I'm optimizing for is writing emails that consistently get opened, writing emails that consistently get read, writing emails that have a real impact on people's thinking, writing emails that get shared. I see so many people rush to scale something before it's truly great. And that's a recipe for failure because in the words of Steve Martin, you need to be so good they can't ignore you. 

Or in the words of Seth Godin, you need to be remarkable, literally worthy of remark. In other words, you need to make it great before you make it grow. Okay, so there you have it, seven email lessons from 70 weeks of writing a weekly email newsletter by hand. 

And just to give them to you all in one convenient place, here they are one more time. Lesson number one, let data drive decision-making, AI dashboard for the win. Lesson number two, the less I use AI, the more engagement I get. 

Lesson number three, creative fecundity is the key, really. Lesson number four, cutting room floor, fodder for future issues. Lesson number five, habits are hard, so build in a buffer day. 

Lesson number six, make it non-negotiable, decide to win. Lesson number seven, make it great before you make it grow. Now I'm curious, if you had to choose just one of these lessons, which one has the biggest impact on you? Simply leave a comment to let me know. 

I'd love to hear from you. Okay, with that being said, I'm going to leave you with that for now. Have a great rest of your weekend. 

Remember to hug the ones that you love and I look forward to seeing you on the next episode. Take care. We'll talk soon. 

Goodbye.