What started out as a random idea post Covid (have a few entrepreneurs at my house for a CEO week) has become a beloved tradition for both myself and my clients.

CEO Week 2025 was my fourth event of this type, and though much has changed, the core idea has remained the same: Hang out together in the woods at my house in Connecticut to rest, reset, and work.

Nothing was recorded or transcribed so everything I’m about to share is from memory.

A few contextual details about how CEO week is set up:

• There were 26 of us.
• We sprawled out in my house and worked/talked/masterminded all day and evening.
• We had lively table chats, quiet headphones on workstations in the basement.
• Several clients (the ones not bothered by the heat) sat outside on the two porches.
• I have one small room I use for prayer and therapy, and we had a “reservation list” for people who needed a fully private room.
• I had sign ups for private hotseats with me, and then we had signups for afternoon “group” hotseats.
• All in all, I either did or facilitated 24 hotseats.
• Everyone showed up between 8:30-9:00am.
• I catered three lunches: Sandwiches, make your own salad bar, and New Haven style pizza.
• Dinner on night one my husband and I hosted. He cooked all of us some of his Colombian favorites.
• Dinner on night two was at a seafood grille by the beach.
• Dinner on night three was Thai takeout at my house.
• My gym was open for workouts.
• My animals (chickens included) were open for cuddles.
• We had whiteboards, laptops, snacks, a drink fridge, a coffee/tea station, and plenty of wild animals and birds.
• Sara even spotted our resident Bobcat during a happy hour walk!

Here are the four most important business and mindset takeaways from the week:

#1 Rest isn’t a reward for work. It’s the other side of the coin of productivity.

This idea really has taken hold in my mastermind this year, and our May Mastermind started with one full day of rest & reflection. So it’s no surprise this theme continued into CEO week. Abby Springmann brought up a great point from the book Rest. She said that a wave can’t crest without a trough. The low part of the wave is a critical part of the cycle. Rest isn’t what you get when you finish. It’s a necessary part of productivity.

This tracks in nature and science and with God. There’s nothing in our natural world or spiritual world that doesn’t work on a rest/work cycle.

#2 AI isn’t the future. It’s right now. And it’s intense.

We had so many discussions about AI. About using it for copy, making clones for coaching, and how it is going to upset marketing, ads, and all knowledge work. A few videos were shared by Stephanie Blake… I’ll link below.

Brittany Long also talked about her Coaching Clone in her coaching business. She helped us all reframe how these AI clones could unlock new levels of coaching without making yourself feel irrelevant.

She’s using Delphi and building out coaching clones and it’s fascinating!

• AI in Context – We’re Not Ready for SuperIntelligence
• Liam Ottley – This AI Technology Will Replace Millions (and how to prepare)

#3 The weekly webinar is the clarity engine every entrepreneur needs.

We had lots of discussions about the power of the weekly live webinar. It’s doing so much to help business owners clarify their offer, create revenue every week, get in front of customers, practice sales skills, etc. But it’s also an art.

There was a lot of moaning about the process itself. It’s not the easiest thing in the world to do. You need a coach. A system for optimization. And most importantly, patience!

If you’d like to learn my method for weekly webinars, two ways to do so. Reach out to me personally [email protected] or sign up for our Launch Gorgeous Accelerator and get a copy of our coaching curriculum that teaches this process.

#4 Learn how to conquer overcomplicating, overthinking, and over functioning tendencies by first understanding the difference between the three.

We had a lively discussion about the three “overs” that many heart centered entrepreneurs face: Overcomplicating tasks, overthinking, and over functioning. The interesting part was noting the differences between the three and what it says about what you’re really avoiding or afraid of.

Over Complicating: The question to ask yourself is “What are you avoiding?” Most people who over complicate things are looking to control every outcome. They don’t want to be pigeon holed or trapped. They cling to freedom. The work is to learn how to simplify, but also get comfortable with “constraint”. Not to trap you, but in the same way a weighted blanket regulates a nervous system, less options create peace.

Over Thinking: The question to ask yourself is “What are you afraid of?” Most people who over think are looking to avoid fear or rejection or failure of some kind. Where as over complication shows up as doing a LOT but spinning in circles, over thinking often is accompanied with paralysis and procrastination. The work is to learn to trust in intuitive action. To build confidence in done vs perfect.

Over Functioning: The question to ask yourself is “What are you trying to prove?” Most people who over function are trying to perform or prove something about themselves. It can be based on status or fear of safety. The work is to learn boundaries, rest, and contentment.

CEO week is quickly becoming one of my most favorite weeks of the year.

If it sounds like something you need to do, I encourage you to reach out to me. Digital Insiders Mastermind (where you can get access to CEO week) is one of the longest running, reputable business masterminds and coaching programs for entrepreneurs trying to scale to $1,000,000 a year.

I hope you consider it!