Not Boring: One Year In -- Lessons From Building a Newsletter Business
Summary
Packy McCormick's honest retrospective after one year of Not Boring. The core insight: building a newsletter business is "neither as impossible nor easy as it looks." The two most important growth levers were quality and consistency -- just showing up enough for good things to happen. The strategic unlock was finding the intersection of passion and differentiation: serious analysis that doesn't take itself seriously, a voice gap incumbents couldn't fill because they'd already put on their "serious analysis pants."
Key Lessons
- Quality + consistency > tactics: "Show up enough for good things to happen every once in a while." No growth hack replaces this.
- Counter-positioning through voice: Packy found his niche by doing serious analysis with a fun voice -- something incumbents wouldn't copy because it would undermine their existing positioning. A direct application of Hamilton Helmer's 7 Powers.
- Writing can deceive you: "One of the problems with being good at writing is that you can convince people that bad ideas are good. You can even convince yourself." The skill that builds the audience can also lead you astray.
- Trust your gut on bad ideas: When something isn't working, you'll feel it before you can articulate it. Cut bait instead of writing your way out.
- Lean into the intersection: passion x differentiation is the sweet spot. Crowded topics are fine if the voice is unique.
- Make room for hobbies: even a few hours a week prevents burnout and feeds the work
- The muse shows up late: "More often than not, I say there isn't [an idea], whine... and then sit in the basement reading and listening until some idea hits."
Connections
This is the most directly applicable playbook for [[01-projects/newsletter/index|Sanity Check]]. Packy's journey mirrors the revival challenge: finding a unique voice in a crowded space (data/analytics), then committing to consistency.
The "serious analysis without serious pants" insight is essentially what Sanity Check can be for the data world -- making data strategy and analytics culture accessible and engaging, not dry and consultant-voiced.
The quality + consistency finding reinforces [[06-reference/2026-04-03-curiosity-consistency-newsletter-growth|curiosity + consistency as the growth formula]]. Both Packy and that framework converge on the same answer: consistency is the table stakes, quality/curiosity is the differentiator.
The counter-positioning lesson connects to [[06-reference/2026-04-03-part-time-creator-manifesto|part-time creator manifesto]] -- incumbents who've gone full-time and institutional can't easily revert to scrappy, personal, opinionated voice. That's the opening.
The "writing deceives you" warning is relevant to [[01-projects/newsletter/sc-e07-datas-secret-sauce|the Secret Sauce draft]] -- are we writing something that sounds good, or something that's actually good?
See also [[06-reference/2026-04-03-justin-welsh-newsletter-writing-process|Justin Welsh's process]] for the operational complement to Packy's strategic lessons.
Open Questions
- What's the Sanity Check equivalent of "serious analysis without serious pants"? Data strategy with founder energy? Analytics culture with irreverence?
- At what point does consistency matter more than quality? Packy implies they're roughly equal, but in early revival, should we bias toward shipping?
- How do we avoid the "writing yourself into bad ideas" trap when producing content about data strategy?