Field Notes with Kerry
Three Weeks Off. Yes, Really!
November is usually a whirlwind, but this year I did something most people thought was impossible for me…I took three full weeks off.
I read five books, soaked in sunshine, ate incredible food, enjoyed great wine, and didn’t work, except for one virtual speaking engagement. That turned into its own adventure. Failovers for Wi-Fi, negotiating one hour of silence with neighbors, and praying the construction crew next door went on break.
When I finally went live, my screen was black on my end, though everyone else could see me perfectly. Talking to a black screen for 45 minutes requires imagination, and thankfully, that’s one skill I’ve mastered over the years.
Takeaway: True rest isn’t doing nothing. It’s letting yourself breathe without guilt.
Ask Kerry Real Questions, Real Conversations
Q: Can leaders really disconnect without everything falling apart?
A: Yes, if you prepare like a pro and trust your team.
Taking time off isn’t a luxury; it’s leadership. It forces you to delegate, strengthen your systems, and build a team that’s empowered even when you’re gone. My break worked because of intentional communication and people who stepped up beautifully.
Takeaway: If you want to test your leadership, try taking a vacation. You’ll learn exactly where your systems need strengthening.
Have a question for next month’s newsletter? Leave a comment below.
From the Creek: Behind the Scenes at Hidden Creek Estates
Holiday Magic (and the Glitter That Never Leaves)
November at Hidden Creek transforms the entire property. We move everything from outdoors back inside, take down the tent for winter, put up the igloos, and decorate until glitter becomes a permanent part of our personalities.
I returned from vacation just as my daughter, now nine months pregnant, needed help at the Estate. So I called in the troops. Friends, staff, and family all came together, and by the end of the day the property was glowing, warm, and ready for guests to make holiday memories.
And here’s what I hope people remember: when you walk into a beautifully decorated place, real people poured hours of care into creating that moment for you. It’s not magic. It’s heart.
Takeaway: Holiday beauty is built. Not by elves but by people who care.
Flight Path Lessons in Leadership & Legacy
Courage Isn’t Confidence
People often confuse courage with confidence, but they’re not the same.
Courage shows up first. It’s the quiet voice that says, “Try again tomorrow.” It’s the willingness to move forward when you’re unsure, unprepared, or afraid.
Confidence comes later after enough repetitions and enough failures that you finally believe you can.
There were many days in my journey when I had courage but absolutely no confidence. And in hindsight, those were the days that shaped me most.
Takeaway: Courage builds confidence. Not the other way around.
Until Next Time
Whether you’re resting, diving, decorating, or chasing your next dream, I hope you find a moment this month to breathe, reset, and support someone else along the way.
Until next month stay curious, stay kind, and keep chasing your own flight path.
With gratitude,
~ Kerry
I needed this blog right now…thanks for the uplifting motivation