I’ve done this a hundred times before

🤠 Howdy ya’ll!

Welcome to the very first Wednesday issue. This is where we’re going to get into all things AI, automation, and how to simplify the already chaotic, never-ending to-do list that comes with this role. 😵‍💫

Because if we’re being honest, a lot of what we do runs on patterns. And even now, I still catch myself stuck in old ones, operating like the only option is to just do the work.

This week I got one of those requests. Not hard, just painfully tedious! 🫠 The kind that makes you stare at your screen for a second and think this is about to eat up my entire day (and normally, it would have).

But something 💡 clicked.

Instead of opening a blank sheet and starting from scratch, I paused and thought, wait… Why am I doing this? So I handed it off to Claude, told it exactly what I needed, and let it run in the background.

Just like that, I was working on the things that actually required me while it handled the rest. I’m not exaggerating when I say it felt like I finally had an EA.

And that’s when it hit me… If this is happening to me, it’s probably happening to you too.

So let’s get into it.

I’ve done this a hundred times before

I realized this wasn’t new work.

It just felt new because the inputs were different. Different event, different city, different names, but the output was almost always the same. A structured sheet, a clean list, something organized enough to actually use.

And once I saw it, I couldn’t unsee it.

The same workflows, rebuilt over and over again without thinking twice about it.

That’s when the shift happened. Not in the tool I was using, but in how I was seeing the work in front of me.

Stop typing what you could say in 10 seconds.

Wispr Flow turns your voice into clean, professional text inside any app. Emails, Slack, client updates — speak once, send without editing. 4x faster than typing.

It wasn’t about saving time

At first, it feels like a small win. You save a few minutes, maybe avoid some manual work, and move on.

But that’s not actually what’s happening.

Because once you notice it, you start seeing it everywhere. The same workflows, the same outputs, the same structure, just rebuilt over and over again.

And the question changes.

Not what’s the fastest way to do this, but why am I doing this at all.

I’ll show you exactly what that looked like

This is the part most people miss.

The moment you stop treating these as tasks, you realize they’re systems. And systems can run without you.

Pulling together a conference agenda, building out flight options, organizing messy information into something usable, none of that is new work. It just looks new because the inputs change.

Most people stop at using AI to help them do the work faster. But the real shift is using it to build something once so you don’t have to do it again.

And it’s not theoretical. I did this this week with something I’ve done a hundred times before, and it completely changed how I approached it.

I’ll show you exactly what I did. 👇

Stop rebuilding the same work

Once you start looking for it, you’ll realize how much of your work follows the same pattern. The inputs change, but the output doesn’t. Different event, same structured sheet. Different executive, same type of brief. Different vendor, same comparison table. And that’s the opportunity.

Example 1: Conference agenda → structured sheet

This is the one that made it click for me. Instead of manually pulling sessions, speakers, and times into a Google Sheet, I gave AI the source and told it exactly what I needed.

I used Claude Co-Work for this, but honestly any of the tools can do this, ChatGPT, Codex, whatever you’re using.

Prompt:
Take this conference agenda [link] and extract all sessions, speakers, and times into a table with columns for Session Title, Speaker, Time, and Location. Format it so it can be pasted directly into Google Sheets.

It actually generated the Google Sheet for me. I downloaded it, made a few small adjustments, and it was ready to go.

What normally takes 20–30 minutes came back in seconds, clean, structured, and usable! No formatting, no cleanup, no second pass (although I did anyway, it’s a personal choice 😉 ).

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Unlock The Operating System

The rest of Wednesday's issue includes 3 more workflows with the exact prompts (flight options, meeting prep, vendor research), the framework for turning any repetitive task into a system, and what to try this week so you can start spotting it in your own work. This isn't about one-off tasks. It's about building systems that run every week without you. 💪

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