🤖 AI Isn’t Taking My Job, It’s Taking My Scheduling Headaches

✔ This Week’s Agenda

Last week was my birthday 🎊 , and like most birthdays, it had me reflecting. What am I doing? Where am I headed? What do I want more of in this next chapter?

Somewhere between that internal monologue and a slice of cake 🎂 , I started thinking about all the things I’m genuinely grateful for, and this community is high on that list. 💗

It brings me so much joy to know that what I write resonates with so many of you. The whole purpose of this newsletter has always been to be your work bestie: the one who lets you vent it all out… and then builds a master plan to remind everyone just how good you are at what you do.

So thank YOU. Truly! 🫶 Everything I build, I build with you in mind.

Now that we’ve had our feelings moment… let’s get into what’s actually keeping me up at night, and no, it’s not aging. It’s the little tasks that steal your time, the calendar flipping, the “let me just double-check,” the mental gymnastics of matching someone’s availability to your own.

Let’s get into it. 👇

With love, and lots of coffee ☕

Chrissy

^{Heads up: This issue may contain affiliate links. If you click through and make a purchase, I might earn a small commission—at no extra cost to you. It helps keep the coffee flowing and the newsletter going. ☕}💌 ^{I appreciate your support!}

It’s 4:52 PM on a Friday of all days. I’m tired, I’m hangry, and I’ve got one last email before muting the entire internet. Then it lands:

And like clockwork, I’m bouncing from my inbox to my calendar, scanning for times and trying to make it work.

Naturally, I wonder why scheduling still feels this painful.

But this time, I finally tested something I’d been meaning to try: Vimcal EA’s AI Free Time Finder feature.

I took a screenshot of the message, dragged it into my calendar, and it automatically highlighted those exact times against my real availability. Just like that, 1 to 6pm next Thursday and 9am to 12pm next Friday were highlighted on my calendar.

Even Calendly links (which usually send me down a rabbit hole of tabs and checking their available times against my calendar 😩) are copy-paste friendly 🤯. Drop one in, and Vimcal EA shows me the overlap right inside my calendar. 

No toggling, no guesswork, no “let me get back to you.”  (Bless.)

It’s not just convenient, It’s the kind of quiet brilliance that makes you wonder why we’ve been doing this the hard way for so long.

Get your 14-day free trial here!

Here’s the truth: AI is going to change our profession. And honestly? That’s not a threat… It’s a relief.

Because the more we can automate the repeatable stuff, the scheduling spirals, the calendar Tetris, the “who’s free when” madness, the more time we free up for the real work:

✨ Strategic support
✨ Planning and execution
✨ Thinking three steps ahead instead of drowning in logistics

Embracing AI and productivity tools doesn’t make you replaceable, it makes you even more essential.

Imagine offloading things like:

🧾 Drafting follow-up emails
📅 Comparing 6 execs’ calendars
🔁 Weekly task updates and reminders
📦 Tracking down delivery confirmations
📊 Turning meeting notes into action items
🧠 Even prepping agendas with AI-generated context (yes, that’s a thing now)

The point isn’t to do less, it’s to do more of what matters, the part of your role that only 🫵 you can do.

We talk a lot about redefining what it means to be an Executive Assistant, and this post by Scot (with one T 😉) says it all. He’s challenging outdated gender assumptions in our field and reminding us that being an EA isn’t about fitting a stereotype, it’s about showing up with strategy, precision, and purpose. A must-read perspective from someone who’s built an intentional, powerful career in this role. 👇

If you’re gonna say “hi,” please say the rest of your sentence too. I’m not emotionally prepared to wait. 👀

Quick hits, upcoming events, and news from inside the EA world, straight from my desk to yours.