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Jennifer Cook wakes up at five every morning — not because she has to, but because she's wired that way. A fashion buyer for a multi-brand store in Soho, a hot yoga teacher, and the writer behind the Mom Friend Substack, she's built a life in Brooklyn that holds a two-and-a-half-year-old, three jobs, a musician husband, and a self-imposed 8:45pm bedtime. The key, she'll tell you, is knowing which balls you're allowed to let drop.

In this week’s conversation, Jennifer talks about the two hours of quiet she guards every morning before her daughter wakes up, how yoga teacher training was the reset she didn't know she needed, and why she started Mom Friend when she couldn't find anything on the internet that actually resonated.

What We Cover:

• The 5–7am window Jennifer protects every single morning — what she's actually doing in those two hours before her daughter wakes up, and why having time before the rest of the house stirs is non-negotiable
• What prompted her to sign up for yoga teacher training in 2016, and how a twelve-weekend commitment rewired her relationship with herself, her body, and her social life
• What 14 years in fashion wholesale actually taught her, and why a new baby, a move back to the city, and a career pivot to buying all happened at the same time
• The Monday rituals she never skips: reviewing every dollar she spent the week before, cleaning the bathroom after yoga, and why front-loading everything she can makes the rest of her week work
• How she started Mom Friend when she couldn't find content that resonated with her as a working mom — and the unexpected way the Substack has become her primary vehicle for making real adult friends in New York
• What it actually costs to have a night out in Brooklyn (the concert math, the $30-an-hour babysitter, the Uber home) and how that shapes when they choose to leave the house
• The balls she's consciously letting drop right now — and why she's made peace with the laundry pile on the couch, the unanswered texts, and the creative play she'll never quite be good at (same, Jennifer)

Connect with Jennifer:

• Instagram: @jennifersandra
• Substack: Mom Friend
• Website: jennifersandra.com

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Alison Hall doesn't know where her day will take her — and that's the point. As a correspondent for Inside Edition, she might get a call at 7am sending her to Long Island for a court hearing, spend the afternoon at the FaceTime set doing virtual interviews with sources in California, or hop on a flight to London. Her workday ends with show tape between 3 and 5pm, then she bikes home in the same blazer she wore on camera.

In this week’s conversation, Alison shares how her mom's breast cancer diagnosis when she was 14 planted the seed for journalism, how an on-camera interview about Olivia Munn led to her own early-stage breast cancer diagnosis and double mastectomy, and how she protects the rhythms that keep her grounded — 5:30am oat milk lattes, Citi Bike commutes, and the exact same Monday-through-Friday dinner she's eaten for six years.

What We Cover:

• The path from story coordinator to on-camera correspondent at Inside Edition over 12 years
• Her 5:30am mornings, oat milk latte on the couch, and "the brick" — the device that finally got her off Instagram at night
• How interviewing a doctor about Olivia Munn's diagnosis led her to her own early-stage breast cancer (and the double mastectomy that followed)
• Why she bikes to work in a dress and blazer and feels like the 10-year-old version of herself every time
• The exact Monday-through-Friday dinner rotation she and her husband James have eaten unchanged for six years
• Pizza Friday from Gelso & Grand in Little Italy, the wine-shop ritual, and how she completely eliminated FOMO from her life
• The practice of noticing "glimmers" — tiny moments of joy that's reshaped how she moves through New York
• Why Saturday mornings alone in Central Park with her Bernese Mountain Dog are non-negotiable

Connect with Alison:

• Instagram: @alisonhallreporting
• TikTok: @alisonhallreporting
• Substack: Between Headlines with Alison Hall
• Watch: Inside Edition weeknights and weekends

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Episode Music - For Days - Tom Deis via Shutterstock

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Kathryn Humphries turned down a buying position at Bergdorf Goodman to bet on a one-woman PR agency run by someone she'd just met — and that gut instinct shaped everything. From interning in Ralph Lauren's celebrity dressing department to running social media at Gap, she built a career across New York's fashion world before moving home to Houston, meeting her husband, and co-founding All You Need Method with her former boss Carla — a PR membership that teaches small business owners how to land their own press.

In this honest conversation, Kathryn shares what her days look like working from home with a four-year-old in school and an eighteen-month-old with a nanny downstairs, how she structures her work around her circadian rhythms and childcare around her workload, and the weekly routines that keep her family moving.

What We Cover:

• Her morning rhythm: programmed coffee at 6:00am, couch snuggles with both girls fighting over space, and getting a four-year-old dressed and out the door by 7:15
• The daily smoothie she never skips — Kelly LeVeque's protein-fat-fiber-greens formula with "a lot of peanut butter"
• How a Canyon Coffee blog post about circadian rhythms changed the way she structures every workday (mornings for writing, noon to 2:00 for calls, done by 3:00)
• The career path from Ralph Lauren's celebrity dressing department to Teen Vogue to Gap to starting her own PR consultancy in Houston
• A secret love of acting — complete with an agent in Austin, NYU student films, and classes she still takes as a parent
• Her nanny Miss Lucy's game-changing move: cooking dinner during the baby's nap a couple days a week and how she flexes her childcare based on her workload.
• Reading Harry Potter to her four-year-old with some creative editing of the scary parts — and a chamomile tea ritual her daughter now mimics with hot water, honey, and milk
• Sunday mornings at Central Market — the Texas grocery store experience with balloons, fresh fruit, a great playlist, and the whole family strolling the aisles

Connect with Kathryn:

• Instagram: @kathrynwhumphries
• Company: @allyouneedmethod
• Substack: Open Book

Episode Music - For Days - Tom Deis via Shutterstock

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Chassity Evans woke up one morning with a fully formed novel in her head. She hadn’t taken a single writing class, had never planned to write a book, and was about to board a flight to the Bahamas — but by January 6th she was writing chapter one, and a little over a year later, her debut rom-com Pink Sand Summer was finished. Now the Charleston-based content creator (formerly behind Look Linger Love) is balancing a 16-year career in blogging with a brand-new identity as a novelist — all while raising two teenagers and keeping her evenings wide open for whenever they actually want to hang out with mom.

In this honest conversation, Chassity shares what her unstructured days look like as a content creator who deliberately avoids schedules, how she wrote four to five days a week (sometimes eight-hour stretches on Friday nights) while keeping it feeling fun, and why she’s traded evening socializing for the daytime. She also opens up about the surprising shift of parenting older kids — how she went from counting down the days until she wouldn’t need a babysitter to realizing she wants to be home more than ever. I loved hearing from Chassity what her days look like as mom of older kids!

What We Cover:

• How Chassity’s debut novel arrived as a “dream download” one morning — and the year-long writing journey from chapter one to final edits (January 2025 to January 2026)
• Her deliberately unscheduled work routine — and how she keeps everything feeling fun
• The unexpected parenting flip: going from needing babysitters for date nights to wanting to be home in case the kids feel like talking
• Navigating year-round travel lacrosse with her 14-year-old son Fletcher (and watching for signs of burnout)
• How writing changed the way she reads — from “pure candy” to paying attention to the rhythm of every sentence
• Her self-care staples: Peloton strength classes with Callie, walking the treadmill while watching Netflix, and reheating yesterday’s leftovers at 10:30am
• Building Pink Sand Summer into a multi-book universe set on Harbor Island, a place she discovered on Pinterest in 2012

Connect with Chassity:

• Instagram: @chassityevans
• Website: chassityevans.com
• Substack: Chassity Evans
• Book: Pink Sand Summer (out May 12th)

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Rebecca Matchett co-founded Alice and Olivia at 23 with zero fashion experience, now she's building Synchrony, a social platform for neurodivergent adults, and navigating life as a mom of three in downtown Manhattan — including sending her oldest to college in California this fall.

In this honest conversation, Rebecca opens up about the pattern that's defined her career: jumping into industries she knows little about and figuring it out as she goes. She talks about what it's really like to run a startup while managing three kids' travel hockey schedules (they're apart most weekends), why she sets five alarms every morning just to remember to check her calendar, and the bittersweet reality of watching her firstborn choose a school 3,000 miles away.

What We Cover:

• How a dinner with a fellow mom turned into a tech startup addressing the gap in social services for neurodivergent adults
• The Alice and Olivia origin story — and what happens when you make pants out of upholstery fabric (spoiler: they chafe)
• Why Rebecca deliberately chose sports-heavy childhoods to push back against the "Manhattan private school kid" stereotype
• Running a three-founder startup where communication happens across text, Slack, and email at all hours (there is no end time)
• The college application process with a Division I-level hockey player — and why visiting schools changed everything
• Her 13-year nanny who's transitioned from childcare to home management (and why they'll never let her go)
• Using AI to plan a last-minute Portugal trip, review legal documents, and pressure-test business partnerships
• The joy of watching three kids speak fluent Chinese to each other — while their parents have zero idea what they're saying

Connect with Rebecca:

• LinkedIn: Rebecca Matchett
• Website: joinsynchrony.com
• Instagram: @joinsynchrony

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This week, we're sitting down with Hannah Pitner, a professor of Spanish Linguistics in Memphis and co-founder of Lingua Viva, an online language collective she launched with her business partner while juggling a full-time teaching load and a one-and-a-half-year-old son. Hannah shares what it's like to get in movement in between pour over coffee pours at 6am, teach four to five college classes a semester, and build a language curriculum that started on a construction site.

In this conversation, Hannah opens up about the winding path from barely making it into college to earning a PhD in Applied Linguistics, leaving a teaching job during COVID to work as a barista, and the moment she realized she could turn years of freelance language trainings into a real business. We talk about journaling morning pages in silence before her son wakes up, navigating a sudden daycare closure with almost no notice, splitting household duties so she never touches a dish, and why logging her outfits on a private Instagram account for seven years has become her daily creative practice.

What We Cover:

• Why she wakes up at 5:40am to squeeze yoga, journaling, and a pour over into one hour before her son gets up (and why even 10 minutes of quiet alone time changes her entire day)
• The journey from interpreter to barista to PhD candidate—how COVID created the unexpected window to apply, and what it's like teaching four to five college classes while running a business on the side
• How Lingua Viva started when a construction company building an addition to St. Jude needed Spanish safety training, and Hannah found herself in a hard hat creating curriculum for middle-aged men
• Wednesday night at-home date nights where she and her husband JT read one chapter of a book together each week (currently: Hunt Gather Parent) to talk about something other than work and logistics
• How their daycare suddenly closed, the scramble to find a new one, and why a trial week on spring break (and lots of balls) made her son’s transition seamless
• The Curated Closet practice: logging her outfit on a private Instagram account every single day for seven years as a daily creative outlet that takes almost no time
• Why she's finally learning to outsource (starting with marketing after four days of Meta ads nearly ended everything) and let herself ask for help instead of always being the one offering it

Connect with Hannah:

• Instagram: @linguavivacollective
• TikTok: @linguavivaco

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This week, we're sitting down with Kate Strickler, the creator behind Naptime Kitchen, author of "I Just Wish I Had a Bigger Kitchen," and mom of four kids ages 10, 9, 7, and 4 in Charleston, South Carolina. Kate shares what it's like to squeeze an entire content business into a four-hour window while her youngest is in preschool, work on a walking pad because sitting makes her brain "bounce all around," and have anywhere from five to fifteen neighborhood kids cycling through her house on any given afternoon.

In this conversation, Kate opens up about building Naptime Kitchen from the "olden days" of square Instagram posts with Nashville filters, learning that her mom's habit of roasting 12 garlic cloves "just to have" was actually a superpower most people were never taught, and writing a deeply personal book while still showing up online every day. We talk about the collective star chart that's wildly outperforming every chore system they've ever tried, why her husband took over all school communication when she started working more, and why these feel like the golden days with her kids.

What We Cover:

• Why she describes her days as fluctuating, full, and fun, waking up at 5:40am to strength train before the house wakes up, and the bed-making habit she can't skip because she passes through her bedroom 50 times a day
• What it's really like to run a content business in a four-hour window between preschool drop-off and pickup, why she does her best work on a walking pad, and the erratic "chicken with my head cut off" energy she's learned to thrive in
• How advertisements actually work for a content creator, filming for brand deadlines first and then deciding whether to take people along for something random like cleaning shower grout, and why some days look completely different from others
• The surprisingly effective collective star chart for Dude Perfect tickets, where any kid earning a star counts for everyone, and the Saturday morning chore system thats paying out.
• From Nashville-filtered square photos to a published book: how Naptime Kitchen started with long-form captions, and how she decided she was ready to write her book.
• How Mahjong became the protected hobby she didn't know she needed, going from "I will not be there" to spending $500 on tiles, and teaching her kids to play with simplified rules at the kitchen table

Connect with Kate:

• Instagram: @naptimekitchen
• Website: naptimekitchen.com
• Book: I Just Wish I Had a Bigger Kitchen

Episode Music - For Days - Tom Deis via Shutterstock

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From Googling to Building Skills, Markdown Files, and Scheduled Workflows

I uploaded my son's entire baseball schedule into Google Calendar in under two minutes this morning. No manual entry, no typos, no cross-referencing dates. I pasted a link into Claude, hit enter, and 18 games appeared on my calendar. Then I did the same thing with soccer. This is the kind of stuff AI can do for you right now, and in this episode, I'm breaking down exactly how I got here.

In this solo episode, I'm pulling back the curtain on my full AI journey, from treating ChatGPT like a glorified Google search to building reusable skills and markdown files that make Claude work smarter every single time I use it. I'm also sharing your survey results (spoiler: most of you are at about 45% comfort level, and that's totally normal) and walking through exactly how to start, no coding required.

What I Cover:

• How I went from free ChatGPT to paid Claude in about two years (and why I switched)
• The prompting framework I use every time: who you want it to be, what you want it to do, what outcome you need, and any context it should know
• The "if you've told it three times, save it as context" rule for markdown files, and the "if you've asked it three times, build a skill" rule for workflows
• How the /episode-assets skill turns a raw transcript into show notes, an Instagram caption, and an SEO caption in one command
• My full AI tech stack: Claude, Superhuman, Notion AI, Descript, Grammarly, and how each one fits
• The five-minute baseball and soccer calendar hack that saved me 30 minutes (and made me the hero of the mom group text)
• Connectors I'm using right now: Google Calendar, Gmail, Notion, and why I keep everything on "needs permission" mode
• Your survey results: 51% ChatGPT, 32% Claude, 14% Gemini, 3% Copilot, and what that tells us about where everyone's starting from
• Why AI is like learning a new language, and why copying someone's markdown files won't make you fluent

References:

• Am I Just A Text File
• Skills
• Helpful Series to Get Started on Claude Code
• Anthropic Courses
• AI Learning Lounge

Episode Music - For Days - Tom Deis via Shutterstock