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I've tried probably 40+ AI tools in the last two years.

Most of them? Impressive demos. Forgettable in real life.

But there are 5 that I keep coming back to every single week — not because they're trendy, but because they actually save me time and make my work better.

Today I'm breaking down exactly what each one does, how I use it, and the specific prompt or workflow that makes it worth it.

- ChatGPT — My First Draft Machine

I know, I know. Everyone uses ChatGPT. But most people use it wrong.

They open it up, type "write me an email about X," get a robotic response, and give up.

The difference is how you prompt it. I don't ask ChatGPT to write for me — I ask it to think with me first.

My go-to workflow: Before writing any newsletter issue, I paste in my rough idea and say: "Ask me 5 questions that will help you understand my audience, my angle, and what I want readers to feel after reading this."

That one step alone changes everything. ChatGPT stops guessing and starts actually helping.

Why it works: Most AI output is generic because most prompts are generic. When you force the AI to ask clarifying questions first, the output becomes 10x more specific — and 10x more useful.

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- Claude — My Thinking Partner

Claude is different from ChatGPT in one important way: it pushes back.

Ask ChatGPT if your business idea is good and it'll say yes with a smile. Ask Claude the same thing and it'll say "here's what's strong,



here's what's weak, and here's what you haven't thought about."

That's exactly what I need when I'm planning content strategy or trying to figure out if an idea is actually worth writing about.

My favorite use: I paste a draft newsletter and say "Tell me what's missing, what's confusing, and what you'd cut — be honest." The feedback is sharper than most human editors I've worked with.

Why it works: Claude is trained to reason carefully and not just agree with you. For any task where you need real feedback — not just cheerful output — Claude is the move.

- Perplexity — My Research Assistant

I used to spend 45 minutes going down Google rabbit holes for a single newsletter issue.

Now I spend 5 minutes in Perplexity.

It's a search engine built on top of AI. You ask a question in plain language, it searches the web in real time, and it gives you a summarized answer with sources — so you can verify everything.

How I use it: For any stat, trend, or claim I want to include in a newsletter, I run it through Perplexity first. "What are the latest statistics on AI adoption among small businesses?" — clean answer, real sources, done.

Why it works: Regular AI tools like ChatGPT can make up facts (it's called hallucination). Perplexity solves this because it searches live data. For a newsletter writer, accuracy matters — this tool keeps me honest.

- Notion AI — My Second Brain With a Brain

I already used Notion to organize everything — notes, drafts, content calendar, ideas backlog.

Then they added AI and it became something else entirely.





Now I can highlight a messy brain dump I wrote at 11pm and say "Turn this into a structured newsletter outline." Or I can drop in a long article and say "Summarize the 3 most important takeaways in plain language." It all happens inside the same tool I'm already working in.

Why it works: The best productivity tool is the one you're already using. Notion AI doesn't ask you to change your workflow — it just makes your existing workflow faster. No switching tabs, no copy-pasting between apps.

- ElevenLabs — My Voice (Literally)

This one might surprise you.

ElevenLabs is an AI voice tool. You upload a short clip of your voice, it clones it, and then you can turn any text into audio — in your own voice.

I use it to create audio versions of my newsletter for subscribers who prefer to listen. Takes about 3 minutes after the newsletter is written.

But here's the hidden power most people miss: I also use it to listen back to my own drafts. When you hear your writing read aloud, the awkward sentences become obvious immediately. It's like proofreading on easy mode.

Why it works: Audio content is growing fast, and most newsletter writers aren't doing it. Adding a "listen to this issue" button makes your newsletter stand out and keeps subscribers engaged in a way that plain text can't.

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The Real Pattern Here

None of these tools are magic.

What makes them powerful is using each one for the right job — ChatGPT for first drafts, Claude for honest feedback, Perplexity for research, Notion AI for organization, ElevenLabs for audio.

Most people pick one AI tool and try to force it to do everything. That's like using a hammer for every job in the toolbox.

Pick the right tool for the right task. That's the whole game.

Which one of these are you already using? Hit reply and let me know — I read every response.

📌 These 5 AI tools are most important to me and why (Jun)
🏢 Career OS
📍 Jun