The Digital Contrarianâ„¢

Ryan Levesque

Subscribe to the Newsletter

Contrarian insights directly to your inbox.

Subscribe to the Newsletter

Contrarian insights directly to your inbox.
The Digital Contrarianâ„¢

Ryan Levesque

Issue #070

| The Digital Contrarianâ„¢

Seven “Non-Obvious” Email Lessons I’ve Learned Writing This Email Newsletter Each Week.

Seven "Non-Obvious" Email Lessons I've Learned Writing This Weekly Email Newsletter Each Week for the Last 70 Weeks.

Ryan Levesque

13 min read

-

Earlier this week…
 
A black bear got into half of the honeybee hives on our farm…
 
It was a heartbreaking to see the level of death and destruction…
 
(That’s what you’re looking at in that photo above…)
 
And in the spirit of Return to Real…
 
It was an experience that’s personally hit me hard.
* * *
And while the black bear was wreaking havoc on our back forty…
 
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 I’ve learned writing and sending the first seventy (70) issues of this weekly email newsletter – The Digital Contrarian.
 
And while there were a few things on that call I shared that are confidential – strictly for members of the group only…
 
In the spirit of Return to Real
 
There are seven (7) lessons I’ve learned that have been so important (and which I think could be potentially helpful for you) that I wanted to share them with you here in this newsletter today.
 
Beginning with….

Lesson #1: Let Data Drive Decision-Making: Create An AI-Powered Dashboard (ASAP).

Take a look at that screenshot above.
 
(We’ll come back to it in a moment…)
 
Do you see those figures?
 
First, some 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 I’ve been curious to explore…
 
In this process…
 
One thing that’s been most helpful has been an internal “Engagement Score” my team created, that I can use to evaluate the effectiveness of each individual email I write…
 
(For example, see below…)
Now, in case you’re wondering…
 
What does an “Engagement Score” measure, exactly ??
 
I’ll get to that in 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 open rates and click rates…
 
(Both of those metrics can be gamed with clickbait subject lines and ultra short link-only copy and thus provide a misleadingly incomplete story…)
 
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?)
 
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 my team has spent the better part of last year developing – and something we now work with our Return to Real Strategic Content Ecosystem Agency Clients to incorporate into their “Single Source of Truth” emails each week as well…)
 
Now, if you scroll back up and look at the “Engagement Score” screenshot I shared a moment ago…
 
My question for you is this:
 
What do you notice about the RED vs. GREEN boxes??
 
Go ahead and take a look….
 
What you’ll notice is that in the RED box, 4 out of my 5 WORST “Engagement Score” emails (Issues 6, 12, 15, 17) were some of the earliest issues of TDC…
 
In contrast…
 
You’ll notice that in the GREEN box, 4 out of 5 of my BEST “Engagement Score” emails (Issues 65, 66, 67, & 69) were some of my most recent issues of TDC…
 
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 we’ve developed – Email Open Rates – you’ll notice in the figure below, the red trend line goes slightly up and to the right, with recent issues approaching 50% Open Rates after starting in the mid-thirties earlier last year…
 
(see below…)
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 because email lists often get colder and less engaged over time…
 
How can YOU increase your open rates over time?
 
Well, this brings us to…

Lesson #2: The Less I Use AI in My Writing Process = The More Engagement I See.

While I have written every issue of The Digital Contrarian personally myself dating all the way back to [Issue #001] An Embarrassing Confession...
 
In the process of writing each issue…
 
I’ve also often used ChatGPT (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 GPT-5 back in August of this year…
 
I became increasingly disappointed (and frustrated) with the quality of output I was getting back…
 
So approximately six weeks ago, I stopped using ChatGPT 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 I’ve written since, over the last six weeks.
 
(See below…)
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 I Use AI = The More Engagement I See.

Lesson #3: Creative Fecundity = The Key to Success.

 
“Mozart composed more than 600 piece 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.
 
So there is 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 #062] Is the AI Bubble Bursting??
 
It had an unremarkable “Engagement Score” of just 3.57 – below my average score of 3.74.
 
(See below…)
 
 
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 help my channel reach the milestone of 10,000+ YouTube Subscribers.
I don’t know that Van Gogh would’ve guessed posthumously that Starry Night would go on to become his most famous painting…
 
I can tell you with certainty that I never would’ve guessed that [Issue #062] – an otherwise unremarkable middling performer of an email newsletter – would go onto see the success it’s seen on YouTube.
 
You never know which piece is going to pop.
 
This is why creating a consistent volume of work is so critical….
 
This is why Creative Fecundity is such an important Key to Success.

Lesson #4: Keep Your Cutting Room Floor: It Becomes Fodder for Future Issues.

Every week, there is more that I’d like to share 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 of 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 title “[#0XX] Cutting Room Floor” filled with all the “good stuff” that I wasn’t able to fit into that week’s issue…
 
(See below for a couple of examples…)
Sometimes this might be an entire topic I was planning to explore in detail (like the segment slated for [#054] on the left above contrasting the AI work of Mo Gawdat with the AI work of Geoffrey Hinton…)
 
Sometimes this might be a short personal story I ultimately don’t share (like the one on the right earmarked for [#065], when I inexplicably missed wishing my Dad Happy Birthday on his actual birthday – and felt like a terrible human being as a result…)
 
Then, every two months or so…
 
I’ll go back through all my past weeks’ “Cutting Room Floor” files – and will almost always discover “gold in them thar hills”…
 
So if you’re ever wondering what to write about when you’re feeling stuck?
 
Keeping A Cutting Room Floor like this will often serve as Fodder for Future Issues and give you a never-ending well of ideas…

Lesson #5: Habits Are Hard: So Build in a Buffer Day.

When I first started writing The Digital Contrarian seventy weeks ago…
 
I decided to make Fridays my writing day…
 
I did so with the goal of my newsletter going out on Saturday mornings…
 
The only problem?
 
That left me with 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 AM send.
 
This started to put undo stress on me (and on my family…)
 
So earlier this year, I decided to make a slight tweak:
 
I decided to shift our newsletter send day to Sunday mornings.
 
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 to give yourself at least one (or more) buffer days(s) between your writing day and your send day.
 
Which brings us to…

Lesson #6: 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 2-0 at halftime…
 
But we ended up losing the game 4-2.
 
And we lost for one simple reason:
 
Over the half-time break, the other team decided that they were going to win that game.
 
The moment the ref blew the whistle to start the second half…
 
They kicked it into another 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…. What’s this 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…)
 
 
I’ve 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 till three or four in the morning to get this newsletter written (also like a crazy person)
 
 
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 hard.
 
The lesson here is this:
 
Whatever path you choose to follow…
 
Decide to win.
 
And make it non-negotiable.
 
Which brings us to…

Lesson #7: 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.
 
(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.”
 
In the words of Seth Godin, you need to…
 
“Be remarkable – literally worthy of remark.”
 
Or in other words:
 
You need to…
 
Make it GREAT before you make it GROW.
* * *
Okay! So there you have it:
 
Seven (7) email lessons from seventy (70) weeks of writing a weekly email newsletter by hand.
 
And just to give them all to you in one convenient place, here they are one more time:
Lesson 1: Let Data Drive Decision-Making. AI Dashboard FTW.
Lesson 2: The Less I Use AI = The More Engagement I Get.
Lesson 3: Creative Fecundity is The Key (Really).
Lesson 4: Cutting Room Floor: Fodder for Future Issues.
Lesson 5: Habits Are Hard: So Build in a Buffer Day.
Lesson 6: Make it Non-Negotiable: Decide to Win.
Lesson 7: Make it Great Before You Make it Grow.
Now I’m curious…
 
If you had to choose just one of these lessons above…
 
Which one has the biggest impact on YOU??
 
Simply SHOOT ME AN EMAIL to let me know.
 
I’d love to hear from you…
 
In fact, I’ve carved out a bit of time to catch up on email over the next few days, so I’ll leave you with that for now.
 
Shoot me a quick email to let me know…
 
Have a great rest of your weekend…
 
And in the meantime…
 
Remember to hug the ones you love.
 
Until next week,
 
Ryan :-)

Want more insights like these?

Get The Digital Contrarian delivered to your inbox every weekend – before it’s published anywhere else.

Read more newsletters:

Subscribe to the Newsletter

Join over 100K+ readers of The Digital Contrarian getting unconventional business strategies delivered straight to their inbox.

Want more insights like these?

Get The Digital Contrarian delivered to your inbox every weekend – before it’s published anywhere else.

© RL & Associates LLC. All rights reserved.

Privacy Policy | Terms and Conditions | Contact Us

The Great Sea Change

The Great Sea Change diagram from Return to Real