I Made a Mom Cry (With Joy)
"My friend is moving here and was so concerned this was a 'sleepy' area. I sent her your newsletter and she literally cried."
I get messages all the time from OG subscribers. These are the parents who encourage me to keep going. The ones who tell me they tell everyone they know about The Plan. The ones who are dropping it in the group chats, mentioning it at story-times and after-school pickup lines, and telling their partners to “stop asking me what’s going on this weekend and get on the list already.”
My friend Meg in Ridgefield recently messaged me with the best one of all.
As a parent of two little kids, I dreamed of one local go-to resource here in Northern Westchester and Fairfield County that would just tell me what’s going on that weekend, and whether it was worth my time, money & parenting energy.
It didn’t exist, so 8 months ago, I decided to create it. Yesterday, I reached 500 subscribers and a consistent 75% email open rate (a rarity for e-newsletters).
To celebrate, I’m having a 20% off sale for annual subscriptions. That’s just $40 for a year’s access to the entire archive of my curated family-friendly events and things to do in our area + subscriber access to The Plan calendar.
A subscription unlocks everything in the archive, including posts like these that you can refer to again and again as you plan your weekends:
The problem I’m trying to solve
Rewind to two years ago. Too often, I was having that Thursday afternoon panic when looking at our family calendar.
“Shit. We’ve got nothing planned this weekend. And I literally have no idea what’s going on around town.”
I’d frantically start checking everywhere: Facebook events, all the nearby town pages and library event calendars, my e-newsletter subscriptions, local influencers’ Instagrams, my saved Instagrams, screenshots in my Photos app, and my Local Things to Do note on my phone.
I’d inevitably find a handful of ideas, pitch them to my family, and we’d have a loose weekend plan.
But the process was exhausting, and I knew we needed a better system.
So I just tried something one day. I started saving weekend events around town to a “Local Events” calendar in my Google Calendar. I was relentless. I asked Siri to save events I noticed on library bulletin boards and roadside signs. I took snapshots of flyers and had Google Gemini auto-create calendar events for me. I subscribed to every local venue’s e-mail newsletter, calendar and Eventbrite page I could find.
Last summer, I started sharing my calendar masterpiece with friends. Then one night last September, I caught a post in a local moms Facebook group.
“In need of suggestions! I'm trying to plan the ultimate CT fall weekend for October 4-7. Our close friends are visiting and they're interested in moving to the area, but they've only been to CT once and we're trying to show them that it's wonderful here! I would so appreciate any ideas or recs. They have a 2-year old and a 7-mo old, too. I've searched the group for fall events this year, but didn't see many! So I'd love any tips if you don't mind!” - Meg, Ridgefield
Me:
I exported my calendar’s weekend’s events using an Apple Shortcut, and pasted my perfectly-formatted weekend event list in the comments. She was thrilled.
Soon after, Meg and I started messaging each other on Facebook and she convinced me to start something. I took a few weeks to nail my calendar curation system, opened a Substack account, and curated my first post. Her feedback was invaluable, as were the suggestions from my brilliant copywriter friend, Corrie Jackson.
I sent my first newsletter in October 2024 to 5 subscribers and by November I had 100. Just 8 months later and I’ve got 500 subscribers and it’s growing every day.
How are YOU using this thing?
While I’m over here talking to Siri and Google Gemini in libraries and coffee shops, I’m always so curious to hear how you all are using The Plan. Here’s what I’ve heard:
Ideas for stepping outside your comfort zone – One mom I spoke to uses The Plan for ideas on new places to explore with her son.
Last-minute plans – One mom told me she opens up the calendar every Saturday and Sunday morning to see what they can squeeze into the day’s schedule, and then toggles it off when they’ve made a plan.
Weeks-ahead planning – Personally, I continue to use The Plan on Google Calendar (on “schedule view”) to plan out our family weekends, weeks ahead.
A reason to meet up with friends – I’ve talked about this before, but The Plan is my go-to resource when proposing a play-date or a weekend hang with friends.
Evaluating family-friendly events – One dad told me he loves to read my take on whether an event will really be worth the time and parenting effort.
A way to help out – One mom told me her friend sends The Plan to other parents and caregivers to help them lessen the mental load of weekend planning.
How are you using The Plan? Let me know in the comments, send me a message, or take this 2-minute survey. I love hearing from subscribers.
The 6 Most Requested Features for The Plan
And my thoughts on each.
In-person meetups for The Plan subscribers – This idea has been rattling around my head for a while. Stay tuned. 😉
Add-to-calendar button – I considered this and decided not to. Here’s why:
The Plan calendar subscription appears right in your Google or Apple Calendar. If you see an event you like, you can just copy it to your personal cal in 1 second. It’s literally the same idea as an “Add to Calendar” button.
Event categories by age – I decided against this, too. To me, every parent parents differently. For example, we don’t bring our kids to late-night events (they’ve still never seen fireworks), but I know plenty of cooler parents who have trained their kids to not turn into a pumpkin when the clock strikes 8PM. I wouldn’t dare tell you what not to bring your kid to. But I will always tell you in the event description if there’s an age limit.
A printed monthly calendar – If someone has an AI hack for this, let me know. I have spoken with some folks at a few calendar-management software companies and like what I see, but so far nobody offers exactly what I’m looking for.
Partnerships or discounts with kid-friendly places & events – I have been thinking about this and haven’t yet landed on an answer. Ideas welcome!
A “what’s coming up” email to plan ahead – I just started sending these every Friday to paid subscribers. Let me know what you think.