
Chrissy’s Corner
From My Desk
Earlier this week I shared on LinkedIn something one of my mentees confided in me: she feels like every slip, typo, or “oops” at work is under a microscope. And it made me pause, how many of us feel like mistakes aren’t allowed in our roles?
Here’s the advice I gave her:
✨ Mistakes don’t define your value, they’re part of learning
👀 If every move is being policed, it probably says more about the culture than your performance
💙 Give yourself grace. EA work is high-stakes, but you’re human first.

I want to pass the same reminder along to all of you. Being an EA doesn’t mean being flawless. What makes you powerful isn’t perfection, it’s the ability to recover, adapt, and keep moving.
If you’ve been feeling the weight of perfection lately, consider this your permission slip: mistakes are allowed here. And you’re still excellent at what you do.
With love and lots of Coffee, ☕
Chrissy
P.S. This week’s “Week in My Life” is brought to you by Offsite, the only reason I’m not crying into my calendar every time someone says, “Can you plan an offsite?” 🫠
Week in My Life: Planning an Offsite
This Week’s Win: Negotiating Power with Offsite
I’m in the thick of planning multiple events right now, and one thing that’s saved my sanity? Partnering with Offsite for end-to-end event planning.
Instead of me juggling every vendor, contract, and back-and-forth negotiation, they’re handling it, and the results speak for themselves. Our initial hotel room rate came in at $299/night. Offsite was able to bring that down to $200/night. That’s nearly $100 back in the budget per person, which means more room for team activities and experiences that actually make the event memorable.
It’s such a breeze knowing they’re behind the scenes working those deals while I focus on the bigger picture.
👉 Next week, I’ll dive into the fun stuff, how I’m using that extra budget to build out team activities that people will actually be excited about.
In-Person Events
🍽️ EAs IRL: Philly Dinner Night
Mark your calendars: on Thursday, October 17th, we’re bringing together Philly’s Executive Assistant community for an evening of connection and conversation. I’ll be teaming up with Mallory Rothstein from More Than an Admin and Kelly Muñoz from EAs to the Rescue to host an intimate dinner designed just for EAs.
This is your chance to step away from the inbox, share stories, and finally meet other assistants from the area in person.
📍 We’ll share location details soon. Seating will be limited, so RSVP now and we’ll follow up with next steps.
Week in My Life: Planning an Offsite
How to Build a Killer Agenda (Without Losing Your Mind)
When it comes to events, the agenda is your backbone.
A messy agenda = a messy event.
Partnering with Offsite has been a game-changer here too, they’ve taken the heavy lifting off my plate so I can focus on what really matters instead of drowning in logistics.
Here are a few of my go-to rules when shaping an agenda that actually works:
Start with Outcomes, Not Hours
Don’t just fill slots, ask, “What do we want people to leave with?” Build backward from that.Balance Work and White Space
Back-to-back sessions look productive on paper, but people retain nothing if they’re fried. Add breaks, buffer time, and at least one real reset (walk, meal, or coffee chat).Anchor the Non-Negotiables
Exec keynote? Customer spotlight? Team alignment session? Lock those first. Then layer the flexible stuff around them.Mix Formats for Energy
Rotate between presentations, discussions, and interactive sessions. Attention spans tank if the agenda is 8 hours of slides.End on a High Note
Don’t close with a dry finance update. Leave them with something inspiring, memorable, or fun, even if it’s a team activity or social event.
The best agendas create a balance: structured enough to keep everyone aligned, flexible enough to leave space for magic. And with Offsite handling the logistics, I finally get to focus on being more strategic about what this event should accomplish.
OOTEA Virtual Events
September Events
🎤 Live Demo + AMA with Offsite
We’re teaming up with the Offsite crew at the end of this month for a live walk-through of their platform, plus an open Q&A. If you’ve ever been voluntold to plan a team retreat, you know the pain of endless RFPs and back-and-forth. Offsite makes the whole process faster, easier, and actually kind of fun.
👉 Come ready with your questions, this is your chance to see how Offsite can save you hours (and your sanity) on event planning.
Workday Anthem
🎶 Song of the Week: “Unstoppable” – Sia
This one’s for every EA who’s carried a week on their shoulders and still showed up with solutions, grace, and a little bit of grit. Unstoppable is the reminder that even when things feel chaotic (hello, back-to-back events and exec fire drills), you’ve got more resilience than you give yourself credit for.
So turn it up, channel that “nothing can break me” energy, and step into the week like the powerhouse you are.
Follow our Spotify playlist for inspo! 🎧