Happy Monday!
After two years of writing Cliff Notes, I’m excited to share something I hinted at last week…
We have a new name: AI Playtime.
Over the last 3.5 years of teaching AI, one thing has become incredibly clear:
Getting the weekly “Cliff Notes” on AI is helpful.
But it’s not enough.
The biggest shift I’ve seen, both in this community and in my own journey, is this:
You don’t learn AI by reading about it.
You learn AI by playing with it.
So that’s what this next chapter is about.
AI Playtime isn’t just about keeping you informed.
It’s about helping you get hands-on…to experiment, to explore, and to actually build.
We’ll still bring you:
The most important AI news of the week
The top tools you should know
The same simple, high-signal format you’re used to
But we’re also evolving.
Over the next month, I’ll be introducing new ways for you to learn AI through play…so you’re not just keeping up, you’re actually getting ahead.
Because I truly believe we’ve hit an inflection point:
It’s no longer “Can AI do this?”
It’s “What do I want to build today?”
I’ve never been more excited about where we are right now—and I’m glad you’re on this journey with me.
Let’s play.
PROMPT: Act as a high-level strategic advisor. Analyze the following problem from multiple high-leverage perspectives:
Problem: [Insert problem]
Step 1: Break it down across five lenses
For each lens below, identify:
Core objective (what success actually looks like here)
Key constraints (what’s limiting progress)
Opportunities (where leverage exists)
Friction points (what’s slowing this down)
Lenses:
Strategic — positioning, long-term advantage, and what really matters
Operational — execution, workflows, and process efficiency
Financial — costs, ROI, trade-offs, and resource allocation
Behavioral — human dynamics, incentives, resistance, and adoption
Systemic — interdependencies, second-order effects, and scalability
Step 2: Synthesize
Identify the 2–3 highest-leverage insights across all lenses
Call out any hidden assumptions or blind spots
Highlight where solving one area unlocks others
Step 3: Deliver the solution
Provide a clear, action-oriented plan that:
Is optimized across all five lenses (not just one)
Prioritizes highest ROI moves first
Minimizes friction and increases adoption
Includes specific next steps (what to do this week)
Output format:
Brief executive summary (3–5 bullets)
Key insights by lens
Integrated strategy (the “so what”)
Action plan (prioritized steps)
In Today’s Edition:
🤯 Cliff Notes named changed to AI Playtime
🛠️ 1 new AI tool that you should make time to try this week
😮 New Anthropic model found security problems ‘in every major operating system’
🤖 AI writing assistant inside Microsoft Word
Read time: 4 minutes
🎨 AI ART
📰 AI INDUSTRY NEWS
🛠 NEW AI TOOL OF THE WEEK
📝 Claude for Word — AI writing assistant inside Microsoft Word
🎨View our database of marketing tools mentioned all past newsletters:
P.S. Have a tool you want to submit? Submit it here.
🎓 LEARN
Canva Magic Layers is INSANE! Turn Any Photo Into Editable Layers (No Photoshop)
Learn 80% of Claude Cowork in Under 20 Minutes
📹 TIKTOK OF THE WEEK
🤯 Easy Way To Get Better Responses From AI
@the.rachelwoods Do you edit your messages to clarify what you wanted with AI? If not. Try it! #aioperator #rachelwoods #aioperations #aiops
☕️ THE EXTRAS
One year ago today, I wrote Shopify CEO: No New Hires Without Proof AI Can’t Do The Job
The most clicked link in last week’s newsletter: Claude Code leak exposes a Tamagotchi-style ‘pet’ and an always-on agent
Have a burning AI question?
I read every single question submitted and use it to improve this newsletter. Submit your question below!
That’s it for this time! See you next week.
— Cliff Worley
