When AI Automation Collides with Chaos
How To Go From Messy Beginnings to AI-Driven Flow
Before you can automate a system, you have to prove you have one.
We all love the idea of hands-free automation. A system that just works.
But too often, we chase that fantasy without doing the boring work first—getting clear on what we're actually trying to automate.
I’ve seen it (and felt it) firsthand: the tools are powerful, the ambition is high, but the process underneath is a mess.
And when your foundation is fuzzy, no amount of automation will save you.
The Pain That Sparked a System
One of my own sticking points was writing this very newsletter.
Each issue started as a tangle of voice memos, half-formed notes, and title ideas that didn’t match the actual content.
Some weeks I’d get stuck polishing a section too early.
Other weeks I’d build a distribution system before I even knew what I was saying.
The result: sprawl, stalls, and a creative process that felt more like a maze than a path.
So I did what I now always do when the friction gets loud enough—I turned it into a system.
I built a Newsletter Issue Generator recently in Plumb, using AI to help shape early drafts based on voice memos.
But I didn’t start with automation. I started by mapping the process and spotting the handoff points where AI could help without replacing my judgment.
This issue walks you through that experiment (at a high level)—not just what I built, but why it worked.
Mapping the Path Before You Build
True automation doesn’t start with the tool—it starts with clarity. Before you ever write a prompt or wire up a trigger, ask yourself:
What’s the goal? In my case: share practical lessons on AI, productivity, and SaaS with fellow consultants.
What are the pillars? Define your core themes and subtopics so each issue builds toward something intentional.
What’s the sequence? Content first → then draft → then title → then imagery → then distribution. When you name the steps, you give your automation something solid to plug into.
This one shift—documenting my creative steps—turned vague ambition into a process I could actually improve.
Inviting AI In, Gently
With the workflow mapped, I began exploring where AI could add real leverage—not replace me, but assist me.
Capture raw ideas. I start with a voice memo and just talk. No filters, no perfection—just the raw clay.
Transcribe and refine. I feed the transcript into ChatGPT or Claude to get a rough first draft. It’s not precious—it’s a starting point.
Shape the voice. I compare the AI’s output to my style, refine the prompts, and build up a library of things that sound like me.
Human final edit. The AI gets me to 80%. I finish the last 20%—for tone, story arc, rhythm. That’s where the writing really comes alive.
The AI becomes a creative partner—not a ghostwriter, not a gimmick.
It gives me momentum and structure.
I bring the judgment and voice.
From Partnership to Pipeline
Once you nail the handoff points—where AI stops and you begin—you can start wiring it all together in a no-code automation platform like Plumb:
Trigger: Email a new voice memo from my iPhone.
Action: Transcribe and feed into AI draft template.
Action: Send draft to your preferred editor or inbox.
Human-in-the-loop: You revise, approve, and schedule distribution.
Suddenly, your newsletter (or any repeatable deliverable) becomes a predictable system instead of a gauntlet of guesswork and sporadic energy.
Automation isn’t magic—it’s method.
Get crystal on your goal, document your normal steps, then layer AI in exactly where it multiplies your impact.
Treat it as collaboration, not a shortcut.
Start messy, refine relentlessly, and you’ll build a flow that lasts.
Scraps Worth Saving
There were a number of topics in my voice memo that didn’t make the cut!
If you’re interested in hearing me talk about any of these topics, all I need is for you to leave me a comment comment with the text in bold.
Title Tinkering - Debate about whether to craft titles before or after drafting content.
Image Sourcing - Pros and cons of using AI-generated images versus manual selection.
Social Sharing - Ideas around automating social posts after the newsletter is written.
Prompt Library - Storing and reusing effective AI prompts for consistency.
Insights Summary
Clarity Before Automation - Automation only works when built on a clearly defined process—not on vague intentions or messy workflows.
Map the Sequence - Outlining the steps of your creative process gives structure for both your work and any supporting tools.
AI as Collaborator - AI adds the most value when it assists specific stages of your process rather than replacing your judgment or voice.
Systematize the Handoffs - Identifying where humans and AI each contribute enables smoother automation and better creative control.
Build from Friction - The pain points in your workflow are signals—use them as opportunities to design systems that actually work.
Plumb gives you the tools to not only build solid automations, but to share them—at scale. Turn your best workflows into subscription-based products your clients (or audience) can use without custom setup every time.
If that’s interesting, come join us 👉 Plumb
What’s New With Me (and Plumb)
AI Builders Club (Podcast Update)
We’re launching the AI Builders Club podcast in a few weeks! We’re talking about how to use AI in your day to day (not just news!) and I’ve been wondering…
Do you have a workflow idea you’re wrestling with—or wondering if it’s even worth building?
Aaron Dignan and I are breaking these down, and we’d love to riff on yours.
Hit me up on Twitter (or leave a comment here) and we’ll see if we can get it into the lineup.
Collab with Boring Marketing
Our team has been doing weekly workshops and we recently did a collab with Boring Marketing about how to Build a LinkedIn Content Agent in 30 Minutes:
If you use LinkedIn and you’d like to try this out, you can subscribe to it in Plumb!
That’s it for this week, if you can do me a favor, I’d love to hear from you about what you’re interested in, so leave a comment!
From the space between spark and structure,
Chase ✨🤘
