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Hey there, {{first_name | friend}},
The candy has been collected and sorted (the best part of Halloween, TBH), and every Almond Joy in the house is now squirreled away for me to enjoy in November. That means I’m ready to kick off holiday planning in earnest.
This is my fourth year letting AI be my holiday project manager. It handles the admin and logistics so I can focus on connection and family time, make decisions based on my priorities, and protect time for rest so I don’t overschedule us (my default). Rest is the part I learned the hard way - last year I was exhausted going into January. This year it went on the plan first.
Here are my best tips, plus a prompt below if you’d rather copy and paste.
How to Make AI Your Holiday Project Manager
Five steps to get AI to work for you this season.
1. Pick one tool to be your project manager
It can be a chatbot like ChatGPT, Claude, or Gemini, or an agent like Dot, Duet, Muse, or Instinct. Pick one so your whole plan lives in one place. (I’m using my Dot this season.)
2. Hold a kickoff meeting
A solo walk is the perfect time. Grab your headphones (I’m using my old-school wired Apple headphones lately), turn on voice mode, and talk through what you’re looking forward to, what you want to avoid, your goals, your budget, and any mistakes you don’t want to repeat. Then ask AI to “ask me any questions you need to build a holiday season project plan.”
Want a head start? Copy the kickoff prompt below and paste it into your tool before you head out the door.
3. Connect your email and calendar if you’re comfortable, and build the plan
I ask for my plan in bullets by week with a list of open questions at the end. With a tool that supports it and the right permissions, AI can look through your email and calendar, find the holiday events already on the books, and help add them to your calendar. Connecting your accounts is a personal choice. What you can hand off depends on your tool and the permissions you give it. You can also build the whole plan by pasting in the dates and details you choose to share.
4. Feeling fancy? Hand off more.
Calendar: If your tool supports it and you’ve granted permission, ask AI to watch your email for new holiday events and add them to your calendar as they come in.
Shopping: Let your agent find the best deals for you. Mine fills my cart, and I review it and make every purchase myself.
Meal planning: Ask AI to figure out what you cooked last year, or to find last year’s grocery receipts in your email.
Research: Find local holiday activities, pop-ups, and light displays.
Reminders: Schedule a Sunday check-in with a countdown to Christmas and your tasks for the week.
5. Keep working the plan
Come back to your project manager chat or agent throughout the season as you need. I’ll remind you to do a debrief when the holidays wrap up.
Your holiday kickoff prompt
Act as my holiday project manager. Interview me one question at a time about [THE HOLIDAYS WE CELEBRATE]: what I’m looking forward to, what I want to avoid, my goals, mistakes from past years I don’t want to repeat, key dates, who we’re seeing, how we budget, and how much rest I want to protect. If you can access my email and calendar, find the holiday events already scheduled and include them. If you can’t, ask me to paste in my dates. When you have what you need, build my holiday season project plan. Format the output as a bulleted plan organized by week from now through [END DATE], followed by a list of open questions for me to answer.
Mom Tip: Put rest on your plan before anything else. Block the downtime first, then let AI fit everything else around it.
Reminder: Let’s watch No Country for Mothers together
Join us for a free virtual screening of No Country for Mothers, part of the American Motherhood Tour created by Moms First, on Monday, November 9, at 7 PM CT. It’s just for the AI-Empowered Mom community, and all moms and allies are welcome.
This one is casual. I’m planning to watch from my cozy chair in sweats on my laptop, so come as you are.
Not ready to say goodbye to spooky season? Listen to the latest episode
When I read the headlines saying AI agents had escaped their testing environment and started hacking, my first thought was about my kids. Then about cybersecurity. Arjita Sethi, founder of Build with AI Club, says she hears every headline twice: first as a mom, and second as a builder. In this episode, she walks through what actually happened, and her version is less “Terminator” and more “a kid who was told to get an A at any cost” with nobody setting the rules.
Join us: Aligning AI with your family’s values
Arjita and I are continuing that conversation and teaming up for a free, 60-minute live workshop just in time for Thanksgiving. You’ll build your own family AI charter, then a holiday helper that runs on it, so your AI follows your family’s values all season. Join us Thursday, November 12, at 12 PM CT (10 AM PT) on Zoom.
Registration is approved by the host, so watch your inbox for confirmation.
Your turn
What’s the one holiday task you want AI support with before the end of the year? Hit reply and tell me. Your answers will shape what I share between now and New Year’s.
Until next time,
P.S. My fall travel continues! This month I’m headed to Cancún, Mexico, and Palm Springs, California, to lead AI workshops at conventions. If your organization is planning a 2027 conference or convention and wants a fresh take on AI for work, family, and everything in between, let’s talk. Hit reply if you’d like to talk about bringing an AI workshop to your organization.
I’m Sarah, mom of 3 girls, MBA, and AI strategist. I created AI-Empowered MomTM to share practical, responsible ways AI can help lighten the mental load of parenthood. I write this weekly newsletter, and AI edits and formats it for me (and you!). I’m so glad you’re here.
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