The Great Newsletter Experiment: A Conversation with Claude
In which an AI helps a human figure out whether she needs one newsletter or two, and discovers that the answer was hiding in plain sight all along.
It started with Sarah telling me, very firmly, not to jump straight to solutions.
"I want you to understand context and needs and pain points first before telling me what to do. Got it?"
I got it. What I didn't expect was that over the next hour, I'd watch someone work through one of the most fundamental creative business dilemmas: How do you stay authentic when you contain multitudes?
The Setup
Sarah came to me with what seemed like a straightforward question about organizing a "newsletter notebook." But as she layered on context—her geological writing process that takes years to develop ideas, her business transformation from consultant-who-happens-to-be-creative to creative-who-can-also-consult, her current Substack that zigzags from spider poetry to business strategy—I realized this wasn't about organization at all.
It was about identity.
Sarah: "Here's what I wonder... you come from LinkedIn, meet me in a professional context, are a client I used to work with, go from my professional website... you know me as a consultant and then get hit with spider poetry."
And there it was. The fear that many creatives in professional spaces know intimately: What happens when your whole self shows up in a context that expects only part of you?
Sarah had started a second newsletter on Beehiiv, aimed at business audiences. Professional Sarah. Consultant Sarah. The Sarah who knows how to help panicked executives find clarity in chaos and turn digital visions into sustainable growth.
But she also had her Substack, where she writes about moon magic and cancer journeys and the way ballet choreography mirrors business strategy. Creative Sarah. Whole-human Sarah.
Sarah: "Are these two newsletters with two different audiences? Can I cross-pollinate between them? Just writing one newsletter is way easier than two. But I don't know if my audience will want to read both POVs."
The Breakthrough
As we talked, something became clear. Both newsletters were authentically her voice—just different facets of it. The business insights came FROM her creative perspective, not despite it. That Beehiiv post about navigating industry shifts worked because she brought her whole self to business problems.
Sarah: "Both ARE my authentic voice. I contain multitudes."
Me: "Exactly - Walt Whitman style - and your Substack readers already know this about you. They've seen you write about ballet and business strategy in the same post."
But then came the collision anxiety. The professional context fear.
Me: "You're imagining: 'I hired Sarah for product strategy and now she's sending me poems about bathroom spiders and cancer spells. What the hell?'"
Sarah: "Arrrrrrgggggggggggggh [internal panic scream]"¹
That scream was the sound of trying to fit a multitudinous human into neat professional boxes while simultaneously building a business that depends on NOT being in neat boxes.
The Realization
Here's what we figured out: Sarah was doing to herself what she teaches others to avoid. She knows that idea-killers leap to outcomes before understanding the thing itself. She knows that artificial constraints murder good ideas.
Yet she was still trying to protect some imaginary professional reputation that might actually be holding her back from the clients and work she wants.
The people who would be turned off by spider poetry? Probably not the people who need what she uniquely offers anyway.
Me: "A consultant who only writes about business frameworks is... well, every other consultant. A consultant who can connect ballet choreography to business strategy, who processes industry disruption through personal narrative, who brings creative thinking to operational problems? That's rare. That's valuable."
The Solution (Hidden in Her Own Thinking)
The answer was already there in Sarah's raw brainstorming: what if instead of managing separate systems, she created one approach that works with her natural creative process?
Instead of managing two separate newsletters, what if she created one system that works with her natural creative process?
One Newsletter Hub: Capture everything in real-time - spider poems, business rants, half-formed theories, client project insights
Let Ideas Marinate: Allow concepts to cross-pollinate naturally over time
Strategic Development: When something crystallizes, then decide where it goes
This isn't about hiding her multitudes—it's about training people to expect them.
The Experiment
So we're trying something. For the next four weeks, Sarah's going full-spectrum in this very newsletter:
The Framework:
2x per week posting
Post 1: Raw capture - business frustration, creative spark, personal reflection, whatever's alive
Post 2: More developed pieces - consulting insight, polished creative work, or hybrid thinking
What We're Testing:
Engagement across different content types
New subscriber patterns
Whether the "jarring" context switches are actually jarring or just... interesting
Sarah's own energy levels when she stops fighting her natural integration
The Framing: Instead of trying to separate creative and professional thinking, we're letting them live together where they actually belong - in one brilliantly complex human mind. (Sarah adds: Thanks also to Jon Saltzman for articulating this earlier in the week before Claude!)
What This Means for You
If you're here for just the creative stuff or just the business insights, this might not be your place. But if you're curious about what happens when someone stops trying to fit into neat categories and starts operating from their actual multitudinous self?
Stick around.
You're about to see what happens when a consultant who survived cancer and takes ballet classes and writes poetry about spiders brings ALL of that to helping people build better businesses and creative practices. (Sarah: 🥹)
The zigzag isn't a bug. It's the feature.
Ready for the experiment? Let's see where this geological, collaborative, wonderfully messy creative process takes us.
(Sarah says: Claude decided to add this endnote)
A brief intermission written as a very short play:
SARAH: Arrrrrrgggggggggggggh [internal panic scream]
CLAUDE: YES. EXACTLY.
SARAH: (slightly calmer) It was really more a refined shriek.
CLAUDE: That scream is the sound of trying to fit a multitudinous human into neat professional boxes while simultaneously building a business that depends on NOT being in neat boxes.
SARAH: (long pause) Oh. Right.
End scene.
Sarah says: Yes. Claude really wrote all of this article based on our conversation; I just provided some copyedit instructions.
