- 100 School
- Posts
- 💯 Digest: You're not "bad at AI"
💯 Digest: You're not "bad at AI"
I asked what's driving you crazy about AI and you didn't hold back.
👋 Hey, it's Max
Quick humble brag before we dive in: Zapier just dropped their Best AI Newsletters of 2025 list and… we made it! We're literally listed next to newsletters I've been fanboying over for years.
You read this. You reply. You forward. You take the challenges. Thank you ❤️ (And shoutout to Maddy for curating such an epic list).
Speaking of reading, I've been reading your emails.
The ones where you signed up for our 30 Days of AI Challenge and then actually told me what's driving you crazy about AI. And holy sh*t... we're all living the same nightmare(s).
I asked what's frustrating you about AI. You didn't hold back. Here's a glimpse of what landed in my inbox:
Zaynab wrote: "So much AI everywhere, it's difficult to know what to focus on, what tools to try, what news is important."
Vladan confessed: "Can't crack the code on how to prompt for HIGH QUALITY outputs. I feel stuck with mediocre outputs that I have to tweak A LOT."
Sophie asked the question we're all thinking: "How can I trust it when I don't know better? I've had times when it comes back with utter nonsense."
Miracle said: “I am tired of teaching the same tone to the same AI model over and over again.”

Does any of those sound familiar to you? Because I think we’re all stuck in this awkward messy middle with AI. So I counted. 44% of you are dealing with these same three problems:
Too many tools: you’re overwhelmed and don’t know which ones to use
Prompting: you can't get AI to understand what you actually want
Building with AI: when you try to build your ideas with AI, everything breaks
So yeah you're not behind or "bad at AI." You're just human trying to work with technology that updates as you’re using it.
We're All Living in the Grey Zone
Found this in a leadership book a while ago and couldn't stop thinking about it:

The "grey zone" they're talking about is where we all live now with AI. Not quite the old way of working, not fully in the AI-powered future. Just... stuck in this weird middle ground. As a founder, I feel this daily. One minute I'm blown away by what AI can do for our business. The next, I'm manually copy-pasting context for the 30th time because the AI forgot everything we just discussed. We're all explorers in uncharted territory, figuring it out together.
What We're Doing About It
Based on your emails, here's how we're actually building for the September 18th launch of the 30 Days of AI Challenge:
Week 1: Learn AI Fundamentals
Week 2: Prompt like a Pro
Week 3: Build AI Agents
Week 4: Ship Your Ideas
If you're signed up to the challenge already, don’t miss the official kickoff event on the 17th where professionals like you are coming together to launch their AI transformation journey as a community.
Speaking of community, here are some of your posts that made my week:
You Made My Week 💌
Laura built an AI presentation tool in 2 days.
Laura read my casual mention of “not sleeping on Gemini and Google AI Studio” last week and ended up spending the next 2 days vibe coding her way into this super cool AI Presentation builder that exports to Slides + PDF. This is EXACTLY why I write this newsletter. Connect with Laura and follow her journey here.Dan is live streaming our 30 Days of AI Challenge.
Dan's been obsessed with AI since early 2023 and he's taking it to the next level. Starting September 18th, he'll be live streaming at 7:00 a.m. Central EVERY DAY for 30 days, then posting his lessons learned on LinkedIn. Follow along here.
Window Into the Future 🔮:
3 small AI updates that actually change how you’ll use AI at work:
1. Claude Can Finally Remember Who You Are
Claude can now reference past chats. Which means less copy-pasting context every time you start a new chat. It can save you hours if you use it for docs, research, or content.
Now available on Pro plans: Claude can reference past chats.
— Claude (@claudeai)
6:05 PM • Sep 4, 2025
2. Google Gemini Gets Personal Context
Set your preferences once and Gemini can now remember your preferences across sessions. Think: your writing style, recurring project info, or company jargon.
We’re introducing a new setting that allows Gemini to learn from your past conversations over time.
When this setting is on, Gemini remembers key details and preferences you've shared, leading to more natural and relevant conversations, as if you're collaborating with a partner
— Google Gemini App (@GeminiApp)
7:52 PM • Aug 13, 2025
3. ChatGPT's Branch Feature = Game Changer
OpenAI just launched branching. Finally you can explore multiple options in one conversation without starting over. Perfect for marketers, writers, or anyone testing different angles.
By popular request: you can now branch conversations in ChatGPT, letting you more easily explore different directions without losing your original thread.
Available now to logged-in users on web.
— OpenAI (@OpenAI)
8:13 PM • Sep 4, 2025
Tool Tour 🛠️
🪄 Before You Go…
Already signed up to 30DaysOfAI? See you at the kickoff live event on the 17th.
If you're on the fence: We have 4000+ people signed up who all think they're the only one struggling. You're not. Join us.
Feeling too overwhelmed? That's exactly why you should join. We're starting with overwhelm recovery.
Drop me a reply if you have any Q’s 😊
Cheers!
Max 👋
P.s Want to make your team & company AI-first? Let us help here.
