I. Din and Dinner
Several years ago, a dining table discussion with my son turned rather heated. He was in his mid-teens, and making some pretty darn good points about creators’ rights, the First Amendment, criticism as fair use, selective copyright-claiming by YouTube, and the influence of advertising dollars on discriminatory enforcement and bias in the algorithm. (As fellow parents know, there is a strong positive correlation between how cogently your children can argue a point and how passionately they feel about something; this happened to be a topic my son, a creator of digital content, was particularly invested in: interesting study available here).
Our discussion lasted all through dinner, at the end of which my wife and other son wisely retired to leisurely evening pursuits. But us two, we stayed rooted in place and went the distance. Eventually, he grew frustrated with me because I went into full lawyer mode – quite frankly, it took my debating best to stay in the fight. But what I saw as sport, he took as stubbornness, and I fell victim to the parental sin of exasperating my child.
We later talked it out and I explained that I was pulling out all the stops because I was impressed with the quality of his argument, and I wanted to expose him to the kinds of obfuscation and fallacious counter-arguments even (or particularly) serious debaters might resort to. He accepted my apology, but in retrospect, I probably could have held back a bit. Still, our relationship grew a little as a result, and ever since, I’ve considered him my peer or advisor on certain topics which he thinks seriously on. (Many years later, he picked a college and major which offers extensive coursework on these sorts of topics).
II. Measures and Means
Every now and then, my son asks me how Deeply Boring and its new sibling publication, Beyond Boring, are doing. (In point of fact, he asked me a couple of hours ago, and that’s what prompted me to write this). “What are your goals and who is your audience?”, he queries. When I explain my rationale for writing, he reports both good news and bad. The good news, he says, is there aren’t a lot of people writing about this stuff on the Internet. That makes it unique. The bad news, however, is that most people don’t care about it. The content is too heavy-going, leans towards the abstract, is not really relevant to their daily lives, and is not immediately gratifying. Said differently, I make readers work too hard for too little payoff.
Of course, I protest. I write about things I find important; quality of discourse matters; I try not to insult my audience by oversimplifying or glossing things over. “Yup…” is the deeply considered response. Pivoting, he asks about my site traffic and engagement metrics, and, with youthful delicateness, politely observes that maybe they are so bad because I’m not doing what other creators would do to drive traffic and engagement.
He’s right. Here are my five deadly blogging sins.
One. I eschew click-triggering rhetoric such as “Don’t you wish you were X? Here are 7 things you can do to make you more X.” That format is direct and to the point – and if you deliver good content on things people care about, they tend to subscribe and come back for more. My approach is orthogonal to that.
Two. Instead of promissory and direct, my post titles are akin to riddles – nobody quite knows what to expect. Often, they are Easter Eggs dipped in waffly watercolor and dabbed in mystery marker. This makes them easy to pass over, but there is some intentionality as well. I’m trying to draw you in, to arouse your curiosity.
Three. The same criticism could be addressed at my subtitles - which you could say risk cleverness at the expense of clarity. But often, I try to create subtitles that provide a hint at an underlying emotion or conflict that I feel is an essential takeaway of the piece. It often helps to read the subtitle after the essay.
Four. Growing up loving music, I sometimes refer to bands irrelevant to the current generation, and often allude to lyrics from 70s and 80s songs which even people who grew up in that era might not recall. This can seem self-indulgent, but a lot of my younger personal development came through exposure to music, from thinking about the stories and messages I heard. So most of the time, references to songs are an attempt to find commonality, to investigate if you’ve had similar experiences - or to invite you to the same.
Five. Finally, graphics. I go to lengths to pick out images in the hopes that they compel readers to pause and think; they are rarely literal or direct. But I go for aesthetics, and try to find pictures that evoke the message of the writing (the one below, a metaphor for connection, is great).
So if I’m not doing what “works” for others, maybe I shouldn’t be surprised if what I’m doing doesn’t “work” for me.
Right?
III. Reasons and Seasons
So why do this, only to do it poorly? Well, it depends on how you define success. Clearly my approach doesn’t maximize views or drive subscriptions. Even so, it takes effort to conscientiously ignore metrics. Normally I am a big fan of following the data, but not here. In the present circumstances, allowing myself to become preoccupied with metrics risks internalizing the message that my sense of self-worth can be measured in clicks.
Which sort of leads me to the concept of “Thinking Small”. If I chase clicks, then you become clicks, to me. But if I chase you, then you stay you, to me. And at the end of the day, it’s much more important to me to know you for who you are, than to know you as a click. That’s why I try to respond to every comment - occasionally in great detail. That’s also why I appreciate how some readers have connected with me on the phone, on Zoom, and even in person. I never imagined that spending evenings and weekends writing these “silly” articles would yield such rich bounties.
So, whether you work with me at BlackRock, at ICMA or Axiom, or are a former colleague or schoolmate, whether you follow me on Substack or read my newsletter on LinkedIn, or you simply just stumbled onto this, please don’t be a stranger. Take that tiny step, and reach out to someone in the Deeply Boring/Beyond Boring community.
Don't march to the algorithm's beat.
You never know what might come of it.
Grace & peace, J
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Justin, I want to express my deep appreciation for your writings on Substack. Your reflections—on faith, family, and the joy of parenthood—offer a rare blend of intellect and sincerity. You weave the grand questions of existence with the intimate moments of life, reminding us that wisdom is found not just in philosophy but in laughter, love, and the everyday revelations of being present.
Your words are more than insightful; they are therapeutic, stirring thought, sparking curiosity, and creating space for reflection. In a world that often prizes certainty over nuance, your perspectives offer something rare—the freedom to wonder, to doubt, and to marvel.
Know that your voice matters—not just to me, but to many silent minds you awaken along the way. I hope you continue to share your journaling and thoughts, as they enrich more lives than you may actually realize.
With appreciation and solidarity,
Nirmal L.
Really enjoyed this piece Justin. The section on quantifying metrics and measuring success vs. writing for its own sake especially resonated with me. So much of what we do online can make things both on and offline feel like a utilitarian arms race sometimes. It's refreshing to do things for their own sake on occasion.
It reminded me of GB Shaw quote (possibly apocryphal but very much in keeping with the spirit of the man) responding to people querying why he wrote "I write for the same reason that a cow gives milk". The very nature of most artistic and creative endeavours, whilst they may be elevated and crystallised by public recognition, originate in quieter and more personal places. Echoing Nirmal's comments below - Please keep doing what you are doing. Some of us value it for its own sake.
P.S. The above is in no way casting shade on your son's comments or feedback, which I'm sure is valid in its own respect. I would likely provide similar feedback to my dad if he had a Substack/would in any way allow me to provide a legal review of the same. :)
Best,
Ken