It's My Plan-iversary 🎉

The Plan just turned one. Today, I'm peeling back the curtain on how it's going, and giving you a sneak peek at the plan for year two. (See what I did there?)

This dumb-looking sheet cake is AI-generated.

A few weeks ago, I stumbled across a Facebook album of my favorite local newspaper celebrating their one-year anniversary. There were drinks! Lots of smiling co-workers! A big sheet cake with their logo!

It was 9PM on a Monday night and I had 16 local event page tabs open on my laptop, putting the final touches on the weekly newsletter for you lovely people.

For a moment, I thought it’d be hilarious to order my own sheet cake from DeCicco’s and take a selfie of me taking a huge bite at my kitchen table in my pajamas. (I probably should have. That AI cake is bleak.)

While I don’t have co-workers to clink a champagne glass with this week, I do have a super supportive husband and kids, a bunch of old friends who have cheered me on, and an armful of new friends and “chosen colleagues” I’ve made this past year just by putting The Plan out into the world.

Friends like NewFriends Social Club founder Melissa Cullens, an old coworker I reconnected with through the magic of the Substack algorithm, and always answers my ‘quick gut-check’ texts with the type of sharp, decisive answer I know I need. Or Kaylin Aarts, the brilliant org. development coach who cold-pitched me last spring and instantly became a chosen colleague & friend. Or entrepreneurs like Vanessa Seide and Lauren Mika who are always sending me great tips (and may be tied for referring the most newsletter subscribers). Or friends like my acting coach friend Katie Willis who helped me feel more comfortable on my Substack Live interviews. Or supporters like Barb Accetta and Kelly Berlin who have been so generous with their time and ideas on where to take this thing next. Or local writers like Chris Vaughn, a huge supporter who always comes through with a great rec from the other side of Westchester.

“Chosen colleagues are the DIY board of directors for the business of you. A portfolio of the best people out there to help you be your best self. And everyone who works independently needs them.” – Leslie Zaikis & Kaylin Aarts, The NewHQ

And I can’t forget all my “local experts” who were more than happy to let me interview them this year about their favorite family-friendly recommendations around town, from beer gardens to flower gardens, great stroller walks to the best kid-friendly spots in Bedford, delicious ramen, and how to do a carnival right. Thank you all.

It’s a little scary to create something, put it out there in the world, call the shots on what to do next, and have no idea whether it’s going to land. But I really love doing it and plan on growing it.

We’re all tired parents and I want us all to win.

Plus, The Plan is a really fun, creative outlet for me. In my 15-year career leading PR for brands ranging from tech startups to massive creative agencies, I was always behind the curtain, ghostwriting and strategizing for the big-shot executives and founders I represented. So it feels a bit weird (and exhilarating!) to have my name out there, attached to my own words.

Looking back on where I started 12 months ago, it seems I’ve turned this little passion project into something semi-legit this year (more on that later). So I want to celebrate by pulling back the curtain for you on how I get it done, how it’s going, and what’s next for The Plan. I love reading this kind of behind-the-scenes content from creators and I have a feeling you do, too.

I’m sharing most of this post with my paid subscribers today as I don’t feel comfortable sharing this kind of thing widely. Some of you are new here and we don’t know each other very well (yet).

Today I’m going to be sharing:

• How do I curate The Plan? And how much time does it really take?

• My favorite subscriber testimonials.

• How much is The Plan making, and what’s the plan for year 2? How many free and paid subscribers do I have? What worked, what didn’t, and what’s next?

To celebrate my Plan-iversary, I’m offering 20% off all annual subscriptions from now until Sunday night at 11:59PM EST. So if you want to support my work, today’s a good day to do so.

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I love writing in the upstairs “speakeasy” at Katonah Reading Room. One time I spotted Jemima Kirke writing on her laptop at the table next to me. She’s lovely.

How do I curate The Plan?

A few months ago, I was having coffee with a friend and the first thing she said when we sat down was this:

“I love The Plan, but I’m worried about you.”

“Worried? Wait, what do you mean?”

“I can’t believe how much work you must put into this. It looks like a lot.”

She’s only half-right.

But if you all think I’m sitting down and writing the weekend event roundup email from scratch each week, you don’t know me very well.

I’m a very systems-oriented person and I have to say, I’m quite proud of The Plan Event Curation System™️ I’ve hacked together this year after much trial-and-error. What I’ve built is a pretty seamless system for:

(1) discovering and quickly adding relevant events to The Plan calendar,
(2) exporting the weekend’s batch of event listings using an iOS Shortcut, and
(3) auto-formatting the event listings using Google Gemini AI to paste into the weekly newsletter.

Here’s how I do it:

I live in Google Calendar.

I’m serious. I started a separate Google calendar in October 2024 called The Plan, and add all my events to that calendar. (Sometimes, I have nightmares where I’ve accidentally deleted this calendar and every event I’ve curated is gone.)

Here’s a video I posted a few weeks ago to get an idea of how The Plan calendar subscription looks in Google Calendar’s “schedule view.” I walk you through how a Premium subscriber might use it to make a weekend plan.

I monitor a ton of online sources.

The weekend roundup you get in your inbox every week is the result of me scanning and evaluating a ton of event listings whenever I get a chance. I actively monitor local organizations’ event pages, local e-newsletters, and Instagram & Facebook accounts every week to surface consistently good, relevant, family-friendly events for all of us. Here’s how:

• I check all the relevant event pages

  If you want to see (and download) a complete list of all my event page bookmarks, here you go. I have my bookmarks organized by town, and every two weeks (or so) I left click on a town folder, open up all the tabs on my browser and go through each page one-by-one to check for any new events to add to The Plan calendar.

  

  If only my actual closet were as organized as my bookmarks.

• I subscribe to local e-newsletters

  I use the Meco app for desktop and iPhone to organize all my newsletters. That way, they don’t clutter up my personal inbox. Every week (usually Sunday night), I just open up my “Local Events” folder, see what’s new, and add any relevant events into The Plan calendar using a Chrome extension called RIP Quick Add.

The Meco app has changed my life.

• I follow Instagram accounts for local organizations

  I only follow relevant local organizations on my @heres_theplan account. If I come across a good event, I’ll just save it to a collection in my Saved Posts. I’ll then add the event to The Plan calendar later that day when I have a minute.

Here’s how my Saved Folder section in Instagram looks.

• I lurk in town Facebook Groups and check Facebook Events

  • Town Facebook groups – I’m a lurker in many of these groups because they’re ripe with great family-friendly events shared by passionate event organizers and neighbors who love to share great events in the comment section. If you’re new here, I strongly recommend you join one. Click here to view every single Facebook Group I track.

  • Facebook Events – Is it just me, or does event discovery on Facebook Events suck? Someone needs to tell Zuck to put the Meta AI team on this problem. (There’s no reason I should see Norwalk High School’s 30th Reunion when I select “events near me this weekend.”) The only good thing about Facebook Events is how easy it is to add events to my calendar. It’s a breeze. See here:

I spot event flyers out in the wild.

I don’t know if I have undiagnosed OCD, but finding and adding every relevant family-friendly event I can find has turned into a game for me.

Around town, you’ll see me snapping photos of the community bulletin boards at places like The Farmer’s Grind in South Salem, the New Canaan and Katonah train stations, and Greenway Market in Vista. I’ll take a photo of event flyers in the window of Planet Pizza or The Toy Chest in Ridgefield. I’ll clock road signs on the way to downtown Katonah or at the intersection near the Pound Ridge Library.

To quickly add these event listings to my calendar, I’ll do one of 3 things:

• Prompt Siri to add an event my calendar – When I drive past a road sign, I’ll immediately say out-loud: “Hey Siri, please add an event to my calendar.” (My kids and husband constantly tease me.)

• Open this IFTTT Applet widget on my iPhone – I enter a quick note like “Sensory Saturday at The Aldrich at 10:30am on Oct 11” and the event is automatically added to my calendar.

• Open my Google Gemini AI app – I’ll snap a photo of a flyer, open it in the Google Gemini app, enter a prompt that says “Add this to my calendar” and it auto-creates a perfect event in Google Calendar for me. It’s insane.

The worst part of this part-time job I’ve created for myself is the awful feeling of completely missing a great event I wish I had told you about. But in the words of Scrooge: “I am a mortal and liable to fall.” So, you know, go easy on me when I inevitably screw up.

“I am a mortal and liable to fall.” – Ebenezer Scrooge (A Christmas Carol, 1843)

I use an iOS Shortcut to export events from my calendar, and Google Gemini to format them perfectly, every time.

If you’re not using Apple Shortcuts on your phone to automate tasks, you’re missing out. Here’s my formula for exporting a batch of weekend events from my calendar:

All the exported events then go into a new Note, and the raw event data looks like this:

Then, I copy all the raw export data, open up Google Gemini, and prompt it to format the event listings exactly how I’ve trained it for publication in the newsletter. See here:

In all, I’d estimate I’d probably spend about -3-4 hours every week scrolling, curating, writing and promoting the weekend roundups on social. I also spend ~3 hours most weeks on work related to my Ask an Expert column. Of course, if it’s a massive project like this volunteer one, it takes a bit longer. These Friday “What’s Coming Up” newsletters take about 1 hour.

But I think my high standards and rigor is worth it. This calendar and newsletter is curated *entirely* by an actual human, and until AI gets better at local event discovery (I’ve tried; it’s terrible) it’s just the way it has to be.

I set out to create a hyper-local, hyper-specific, meticulously curated listing of events (and relevant commentary!) to help us all plan better family weekends in this beautiful little corner of Westchester & Fairfield County. So far, so good.

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My favorite testimonials about The Plan this year

I love an out-of-the-blue DM from a happy subscriber. Or when an old friend says she tells every mom she meets to sign up. Or when a friend reveals that her friend’s husband “is obsessed” with this newsletter. Or when a preschool teacher tells me she’s been mentioning The Plan to every new-to-town family who comes by for a tour.

It all feels great. Here are my favorite testimonials from the last 12 months.

• “I am living for that ‘The Plan’ email. Both weekend days I opened it up to choose something to do. Tell your friend she’s a savior.” – Rebecca, Pound Ridge

• “I feel like it should be a mandatory written law for new families in our area to have to sign up for The Plan.” – Meg, Ridgefield

• “I’ve been dreaming of a local resource like this.” – Phoebe, Bedford

• “The Plan makes parenting sooo much easier.“ – Nancy, South Salem

• “It’s completely changed our weekends and helped manage my mental load.“ – Olivia, North Salem

• “On-point recos, delivered with wit and style to spare!” – Leila, Ridgefield

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How much is The Plan making, and what’s the plan for year 2?

I keep a running Evernote file to jot down potential column topics and ideas on how to make this resource even more useful to all of us. But first, I thought I’d give you an update on some things I tried this year to grow this thing, and how they’re going.

The “Ask an Expert” column is going really well.

It seems you all really love the town-specific posts like Bedford and Georgetown one, so I’ll plan to do a lot more of those in year 2. Fall has been nuts, so bear with me on getting this column going again.

Authenticity is still key.

My plan was always to keep this space as ad-free as I could; relying upon reader support to keep it going. With the exception of Classifieds on Friday, this has remained true. Nobody’s paying me to have their event listed as “Plan of the Week.” Nobody’s paying me to say Grace Farms is gorgeous (it is) or Breads n’ Bakes cinnamon buns are insanely delicious (they are). I didn’t want this to be a brochure; I wanted this to be a helpful weekend guide for all of us.

I used to work in ad tech PR and there was this concept of the “Faustian Bargain” –the question of: “What do you really give up in order to get free content?” We trade our personal data and let advertisers inundate our minds with advertising. And we endure it because the concept of “free” is so enticing. But increasingly, it’s getting harder to discern between what’s sponsored and what’s not, and I’m getting tired of the blurred lines. I wanted to create a reader-supported space where you wouldn’t have to wonder anymore, and I’ll continue to hold true to that.

Classified Ads are catching on.

I launched this last month as a way for relevant, local businesses to get some exposure in the weekly newsletter using real customer testimonials. So far, so good.

Paid subscriptions are going well.

I turned on paid subscriptions pretty early on, and was glad I did. I read somewhere that people want a way to support your work if they love what you’re doing; it makes them feel good. And I must say, it makes me feel good, too. Every time I see a $5 payment notification, it feels like a high five, but also a symbol of accountability to deliver a quality product.

Here’s a breakdown of my free-to-paid subscriber ratio, and my monthly recurring revenue from paid subscriptions: