Rewritten: Real Talk for Working Moms Who Want It All

Teresa came into this episode happy to receive permission to worry less about the little parenting things. The spark was a recent piece from economist Emily Oster, who makes the case for what she calls deliberate parenting: stop putting enormous pressure on every single interaction with your kids, and put more thought into the choices that shape your family's everyday life. Her shorthand is "obsess less and plan more."

Jess and Teresa start with how the parenting bar got so high in the first place, from a statistic about working moms in 2018 and non-working moms in 1975 to the free dance class that made Jess wonder whether her not-yet-two-year-old was already behind. Then they get specific about the decisions that actually deserve your time and attention: nanny versus daycare, food, where to live, and how you want to show up in the hardest daily moments.

Along the way they get real about what each of them traded to make those calls, including the career decision Jess made so she could show up as a more patient parent.

This one is practical, funny, and a permission slip you didn't know you needed.

In this episode:

•

Why working moms today spend more time with their kids than non-working moms did in 1975, and why it still never feels like enough

•

The free dance class that taught Jess she was comparing herself to the wrong people, and the weekday-schedule clue hiding in plain sight

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Why a stranger's highlight reel makes you feel behind, and the Brooklyn couple earning a million dollars a year with almost nothing saved

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Nanny versus daycare: why the cost is often similar in New York, why Teresa chose daycare, and why Jess reminds parents that hiring a nanny makes you an employer

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Food: giving it to your partner entirely, family meals where everyone eats the same thing, and the division of responsibility (you decide what is served, they decide what and how much to eat)

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Where to live: why Teresa is never leaving the city, why Jess is moving out, and why no housing decision has to be permanent

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How to prepare for the daily hard moments: build a playbook before you need it, pad your schedule, and the sticker chart that got two kids out the door fast

•

The career trade-off Jess made so she could be a calmer, more present parent, and what money can and can't buy for your kids

Stay connected:

Never miss an episode. Sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox: https://reworkit.kit.com/rewritten

Connect with Jess Wass: jesswass.com

Connect with Teresa Sweeney: teresasweeney.com

This is the episode Jess admitted she was low-key dreading. Not because the topic isn't important, but because unlike the workplace dynamics she can talk about all day, friendship has always felt like the one area where she doesn't feel like an expert.

Turns out that made for one of the most honest conversations Jess and Teresa have had. They dig into what happens to female friendships when ambition accelerates and motherhood arrives, the two forces that quietly reshape a friend group more than almost anything else. They talk about the friendships that got better with success, the ones that fell away, the friend who was chronically an hour and fifteen minutes late, and the uncomfortable realization that sometimes you're giving a lot more than you're getting.

They also introduce a concept that's going to stick with you long after the episode ends: the portfolio theory of friendship. Not every friend needs to check every box. And your portfolio is allowed to change as your life does, without that meaning any of it failed.

This one is honest, a little vulnerable, and genuinely useful for anyone who's felt quietly lonely inside a full life.

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The portfolio theory of friendship, and why expecting one person to check every box sets you both up to fail

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The friend who was an hour and fifteen minutes late to a dinner, and what it actually revealed about the friendship

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Why most friendship rifts aren't betrayals, they're expectations that were never actually communicated

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Money, friendship, and the quiet tension of navigating different income levels in the same friend group

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How becoming a mom reshapes who's in your circle, often without anyone deciding it on purpose

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Why Jess believes you can close the door on a friendship without ever locking it

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The one question worth asking about any grudge you're carrying: who does it actually serve?

Resources:

The Friend Math: The number of hours you need to spend to become friends with someone https://news.ku.edu/news/article/2018/03/06/study-reveals-number-hours-it-takes-make-friend

Stay connected:

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox: https://reworkit.kit.com/rewritten

Connect with Jess Wass: www.jesswass.com

Connect with Teresa Sweeney: www.teresasweeney.com

Jess came back from maternity leave to a completely different world. She left before AI exploded into every conversation, every workplace, every corner of the internet, and came back five months later to a landscape she barely recognized. Teresa's journey started earlier and looked different, from a skeptical early ChatGPT experiment gone hilariously wrong (a birthday party venue suggestion that turned out to be an old real estate listing) to now using AI daily across her work in data and technology.

This episode is a practical, honest conversation about what AI is actually good for, both at work and at home. Jess and Teresa talk about the early hallucination problems, how much the models have improved, the exact prompting tricks that make outputs more reliable, and where AI has genuinely changed how they parent, work, and make decisions.

They also get into the bigger question underneath all of it: is AI going to replace people, or replace tasks? Because those are two very different futures, and the answer matters enormously for how you think about your own career right now.

This one is grounded, useful, and refreshingly free of hype.

In this episode:

•

Jess's chaotic reintroduction to AI after five months of maternity leave, and why she felt instantly behind

•

Teresa's early ChatGPT disaster involving a birthday party venue that turned out to be an old real estate listing

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The three prompting tricks Teresa uses to get more reliable, less hallucinated answers every time

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How Jess used AI to help diagnose a middle-of-the-night parenting mystery instead of rushing to the ER

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Why Jess believes there's no such thing as a problem AI can't at least help you think through, and where she still draws the line for human expertise

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The framework that changes everything: replace tasks, not people, and what that means for how you think about your own job

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Teresa's closing challenge: go experiment with something small, but don't forget how good it feels to be a human in the world

Stay connected:

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox: reworkit.kit.com/rewritten

Connect with Jess Wass: jesswass.com

Connect with Teresa Sweeney: teresasweeney.com

Jess's week did not go according to plan. A toddler cousin reunion turned into a stomach bug, days of a sick kid who wouldn't eat solids, and then a husband who woke up unable to get out of bed. And that, as Jess puts it, is just one example of what happens constantly when you have kids.

This episode is about exactly that: what do you do when the plan you built completely falls apart? Jess and Teresa get real about the logistics nobody prepares you for, the systemic gaps that make working parenthood so much harder than it needs to be, and the tools that actually help when everything goes sideways at once.

They talk about building a village before you need one, having an honest conversation with your partner about how sick days get divided, and why so many working parents apologize for something that was never actually the problem in the first place. They also don't let the system off the hook — child care costs, the gap between school hours and work hours, and the structural changes that need to happen so individual families aren't left scrambling to fill hours that simply don't exist.

This one is honest, a little chaotic, and deeply practical.

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The Instagram post that perfectly captured this episode's whole theme, and the working mom's question that started it all: who's covering the hours that don't exist?

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Why building your village before an emergency happens changes everything about how you handle it

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The conversation every partnership needs to have about how sick days and coverage actually get divided

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Why calling out sick for your kid is not what makes people resent you at work, and what actually does

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The framework Jess uses to figure out what has to happen today versus what can be rescheduled

•

Why Jess tracks her kid's sick days, and what the number actually taught her

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The structural gaps in school hours, camp coverage, and childcare costs that no individual family can solve alone, and what's already being done to try

Stay connected:

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox: http://reworkit.kit.com/rewritten

Connect with Jess Wass: jesswass.com

Connect with Teresa Sweeney: http://teresasweeney.com

Additional Links:

WSJ article mentioned: https://www.wsj.com/us-news/cities-losing-families-children-a860a9b1

Moms First organization: https://momsfirst.us/

Money is one of the last real taboos for women, and Jess and Teresa spend this entire episode breaking it open. From their earliest memories with money growing up, to the financial mistakes they've each made along the way, to the exact scripts they use to negotiate compensation today, this episode is a masterclass in financial literacy wrapped inside an honest, personal conversation.

They get into why women are taught to be uncomfortable talking about money, how that discomfort costs real dollars over a career, and what changes the moment you decide information is power instead of something impolite to ask for. From maxing out your 401k to understanding vesting schedules to knowing exactly what to say (and when to stop talking) in a negotiation, this episode is packed with tactical advice you can use immediately.

The through line: financial literacy is not optional, and neither is talking about it. The more women stay quiet about what they make, what they're worth, and what they've learned the hard way, the longer the gap stays exactly where it is.

•

Why money is still a taboo topic for women specifically, and where that discomfort actually comes from

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The compounding interest lesson from a college finance class that changed how both Jess and Teresa save

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Why you should only trust the salary in writing today, never the promise of a raise tomorrow

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The truth about startup equity: vesting schedules, double triggers, and why founders oversell the dream

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How to anchor a salary negotiation at the right number, and why saying too little costs you more than you think

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The negotiation tactic Teresa swears by: state your number, then stop talking

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Why asking your girlfriends what they make is one of the most powerful things you can do for your career

Stay connected:

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox: https://www.reworkit.kit.com/rewritten

Connect with Jess Wass: jesswass.com

Connect with Teresa Sweeney: teresasweeney.com

Every working mom has felt it at some point. You're doing good work. You're showing up. You're delivering. And somehow, the promotion still isn't happening. The recognition still isn't coming. And you can't quite put your finger on why.

In this episode, Jess and Teresa go there. They talk about what actually gets in the way of women advancing their careers and they don't let the system off the hook while doing it. Because yes, there are things you can do as an individual to accelerate your career. And also, there is real, documented gender bias in the workplace that makes it harder for women, and especially mothers, to move up. Both things are true and both deserve airtime.

Jess brings her unconscious bias and managing up expertise to the table. Teresa brings two decades of navigating some of the most old-school institutions in finance. Together they unpack the motherhood penalty, the self-promotion double standard, the difference between a mentor and a sponsor, and why your work does not speak for itself — you do.

This one is practical, honest, and a little uncomfortable in the best way.

In this episode:

•

The real reason women get passed over for promotions — and why it's not just about performance

•

The motherhood penalty: what the research actually says and how it showed up in both Jess and Teresa's careers

•

Why your work does not speak for itself — and what to do instead

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The difference between a mentor and a sponsor, and which one you actually need to move up

•

How promotions really work in most organizations (hint: it's nothing like what you saw on TV)

•

Why switching teams can accelerate your career faster than waiting for your current manager to notice you

•

What working moms in leadership positions can do right now to support the women coming up behind them

Stay connected:

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox:https://reworkit.kit.com/rewritten-waitlist

Connect with Jess Wass:http://www.jesswass.com

Connect with Teresa Sweeney:http://www.teresasweeney.com

Jess and Teresa are back, and before they even hit record they're already deep in it, talking about the school event calendar that somehow has five parent appearances in two weeks, including a bird project presentation that Jess is adamant Teresa doesn’t need to go to.

This episode is about ambition. Not whether working moms still have it after kids (they do), but where it goes, what it gets spent on, and whether the way you're using yours actually lines up with what you care about. Because if you're burning your energy on elaborate birthday party goody bags, international day master chef moments, and showing up to every single classroom event out of guilt rather than desire, you might have a lot going on. But that's not the same thing as being ambitious.

Jess and Teresa talk about how their relationship with ambition has shifted since becoming mothers. It’s moved away from titles and salary benchmarks and toward impact, fulfillment, and a life that actually feels good to be inside. They get into the Yale happiness research, what a house in the Catskills taught Teresa about what she actually needs, and why Jess would move out of New York before she'd give up work she loves.

The through line: becoming a mom doesn't kill your ambition. It strips away the ambition that was never really yours to begin with.

In this episode:

•

The bird project presentation — why Teresa is not going, and why that is the right call

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Why social comparison theory explains the birthday party arms race better than any parenting book

•

The Yale happiness research on money and happiness, and what the data actually says about income and fulfillment

•

How Teresa went from renting a house in the Hamptons to renting a house in the Catskills and realizing that was exactly what she needed

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Jess's framework for time boxing party planning, school event decisions, and anything else that threatens to take more than it's worth

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Why ambition after kids isn't less, it's just finally aimed at the right things

•

What both Jess and Teresa want their daughters to see when they watch them work

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox:https://reworkit.kit.com/rewritten-waitlist

Connect with Jess Wass:http://www.jesswass.com

Connect with Teresa Sweeney:http://www.teresasweeney.com

Resources From the Episode

Dan Martell's Book “Buy Back Your Time” - https://bookshop.org/p/books/buy-back-your-time-get-unstuck-reclaim-your-freedom-and-build-your-empire-dan-martell/528eb346d9aab1fa?ean=9780593422977&next=t

Rachel Feintzeig’s Article in The New York Times - https://www.nytimes.com/2026/04/12/opinion/parenting-kids-burn-out.html?unlocked_article_code=1.elA.-MYD.XlvuHYPSkyax&smid=url-share

Yale Happiness Course - https://online.yale.edu/courses/science-well-being

Ramit Sethi’s Rich Life - https://www.iwillteachyoutoberich.com/how-to-live-a-rich-life/

Jess and Teresa are back for part two of their energy conversation, and this one gets personal fast.

If part one was about fueling your body, part two is about something harder: actually letting yourself stop. Because most high-achieving working moms know, at least intellectually, that they need rest. The problem isn't information. It's permission. The permission to block the lunch hour. To watch four hours of reality TV on a Sunday afternoon without guilt. To build a day off that is actually a day off, not just a chore day in disguise.

Jess and Teresa get specific about what refilling your cup actually looks like for each of them, and why it took longer than it should have to figure that out. They talk sleep, they talk mindset, they talk about the 4am phone call Teresa once got from a partner. And they get into something bigger: the culture that created all of this, what Gen Z is doing about it, and why the women who climbed the ladder have a responsibility not to pull it up behind them.

The through line is simple and a little uncomfortable: rest is not a reward you earn after the work is done. It is part of the work. And until you treat it that way, you will always be running on empty.

In this episode:

•

Why Jess read sleep training books while pregnant — and why she thinks you should too

•

The French concept of "La Pause" and how Teresa used it to get both kids sleeping through the night by five months

•

What happened when Teresa's daughter stopped sleeping and they called the pediatrician in a panic at wit's end

•

Why being sleep deprived is the equivalent of showing up to work drunk — and why we have policies for one but not the other

•

Jess's noon rule: what it is, why she created it, and why it changed how her days off actually feel

•

The athlete analogy that reframes rest as training, not laziness

•

Why Gen Z refusing to grind themselves into the ground is not a generational flaw — it's progress

•

The 4am phone call and what it says about urgency culture

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox:https://reworkit.kit.com/rewritten-waitlist

Connect with Jess Wass:http://www.jesswass.com

Connect with Teresa Sweeney:http://www.teresasweeney.com

Chapters

00:00 Navigating Sleep Challenges as New Parents

12:05 Understanding Sleep Training Methods

17:48 The Importance of Sleep for Parents and Children

23:52 The Impact of Sleep Deprivation on Work Culture

24:50 Systematic Issues in Work Environments

26:13 Finding Balance in Work and Life

26:49 Refilling Your Cup: Self-Care Practices

28:22 Intentionality in Daily Life

33:52 The Importance of Rest and Recovery

37:09 Protecting Your Energy as a Working Parent

39:44 Challenging Traditional Work Norms

45:14 Creating a Better Work Environment

We all know we're supposed to "take care of ourselves." But what does that actually look like when you're a working mom juggling a career, a family, and approximately zero spare time?

In this episode, Jess and Teresa get specific. Not about the ideal morning routine you're never going to do, but about the real, messy, personal journeys that led each of them to finally figure out how to fuel themselves — and what that made possible.

Teresa shares how growing up on a standard American diet of processed food and diet culture fads left her feeling awful in ways she didn't even recognize — until she found a different way. Jess opens up about living with a debilitating digestive disorder for her entire adult life that dictated what she ate, when she ate, who she could go on dates with, and what she packed in her suitcase on work trips to Monaco. And then, unexpectedly, it disappeared. Her explanation for why will make you rethink what your own body might be trying to tell you.

This episode covers the core building blocks of energy, with a focus on food and movement — the next episode dives deeper into sleep and mindset. But the through line is something bigger: learning to listen to yourself instead of pushing through, and noticing what you've tacitly accepted as just "the way things are."

In this episode:

•

Why Teresa went from Fruity Pebbles and Slim-Fast bars to a whole food, plant-forward diet — and what it actually changed beyond her weight

•

The digestive disorder Jess managed (and then lost) — and the surprising reason she thinks it resolved

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Why "picky eater" and "big boned" are more than just labels — and how the stories we tell ourselves keep us stuck

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The four pillars Teresa credits with sustaining her energy: food, movement, sleep, and mindset

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Why Jess's coaching clients are only allowed to work out once a week to start (and why it works)

•

How to structure your calendar around your energy instead of against it

•

The difference between an e-bike up a hill and no gears up a hill — and which one you're choosing right now

Key Questions to Ask Yourself:

•

How do I feel coming out of each work activity?

•

What makes me feel energized, drained?

•

When in the day do I feel most energized?

•

When do I have the best ability to focus?

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox:https://reworkit.kit.com/rewritten-waitlist

Connect with Jess Wass:http://www.jesswass.com

Connect with Teresa Sweeney:http://www.teresasweeney.com

Resources Mentioned

The China Study by Colin Campbell - https://www.amazon.com/China-Study-Comprehensive-Nutrition-Implications/dp/1941631568

Atomic Habits by James Clear - https://www.amazon.com/Atomic-Habits-Proven-Build-Belief/dp/0735211299

Power of Habit by Charles Duhigg - https://www.amazon.com/Power-Habits-What-Life-Business/dp/081298160X

My Body Tutor by Adam Gilbert - https://mybodytutor.com

Peloton (for movement classes) - https://www.onepeloton.com

Pvolve (on-demand workouts) - https://www.pvolve.com/

Chapters

00:00 The Energy Conversation Begins

03:28 Personal Journeys with Food and Health

06:16 The Impact of Diet on Mental and Physical Health

09:13 Listening to Your Body: Recognizing Signals

11:52 The Role of Labels and Identity in Health

14:37 Overcoming Dietary Restrictions and Challenges

17:15 The Connection Between Stress and Physical Health

19:47 Empowerment Through Self-Discovery

22:24 Movement vs. Exercise: A Shift in Mindset

25:08 Generating Energy Through Positive Actions

26:53 Celebrating Small Wins in Fitness

29:07 Finding the Right Exercise for You

32:19 The Importance of Community in Fitness

35:41 Timing Your Workouts for Maximum Energy

48:41 Listening to Your Body and Energy Levels

Jess and Teresa have both built careers that look like success from the outside. But somewhere along the way, each of them started asking a harder question: successful by whose definition?

In this episode, they get honest about how their ideas of success have shifted over the years, what they've had to let go of to make room for what actually matters, and why chasing the next milestone is a game that never ends. The conversation moves from boardrooms to baby schedules, from private equity aspirations to the moment Jess realized she'd move to a small town in the middle of nowhere if it meant keeping the work that lights her up.

In this episode:

•

The senior banker who got to the top and wished he'd spent more time with his kids — and why Teresa never forgot the look on his face

•

Why Jess spent most of her twenties assuming she just wouldn't have kids, and the two things that changed her mind

•

The moment Jess realized she'd move out of Brooklyn to keep doing work that fills her up

•

Why Teresa's definition of success shifted from making partner to something she saw in the women who looked genuinely happy, not haggard

•

The Fair Play Method: what it is, why Jess recommends it to clients, and why her daughter now uses the cards as toys

•

How to tell the difference between fake urgency and real urgency, and why most of what consumes your time is the former

•

The "if I died tomorrow" question Jess uses to make decisions, and why it's more useful than any five-year plan

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox:https://reworkit.kit.com/rewritten-waitlist

Connect with Jess Wass:http://www.jesswass.com

Connect with Teresa Sweeney:http://www.teresasweeney.com

Resources Mentioned In Episode

Fair Play by Eve Rodsky - https://www.fairplaylife.com/

Chapters

00:00 Defining Success on Our Own Terms

09:07 Navigating Work-Life Balance

17:35 The Role of Partnership in Parenting

23:20 Consumerism and Parenting Choices

24:25 Redefining Success and Parenting

26:23 Finding Meaning in Work and Life Choices

29:05 Intentional Living and Making Trade-offs

31:14 The Power of Choice and Future Reflection

32:44 Living in the Present vs. Planning for the Future

37:41 Balancing Urgency and Importance in Daily Life

40:00 Looking Forward and Appreciating the Now

Every conversation has a starting point. For Jess and Teresa, it's a scholarship interview weekend bus ride at Washington University in St. Louis — two women who would go on to build very different careers, end up in very different versions of success, and somehow stay friends for over 20 years through all of it.

This is the origin story. Why they started Rewritten, how they met, and what their paths looked like from a business school hallway in St. Louis to where they are now. Jess built her own coaching and leadership development business after leaving corporate, finally free from asking anyone's permission. Teresa carved her path inside some of the most old-school institutions in finance and corporate life, and figured out how to make it work on her own terms without blowing the whole thing up.

They are not the same person. That's the point. Because there is no one right way to build a career you're proud of, a family that works, and a life that actually feels like yours. And the whole reason this podcast exists is to show you more than one version of what that can look like — and to be honest about the cost, the trade-offs, and the moments where nothing felt figured out at all.

This episode is where it all starts. Pull up a chair.

In this episode:

•

Why two already overscheduled working moms decided to add a podcast to their plates — and what they hope it does for you

•

How Jess and Teresa first met and the generous act Jess forgot about

•

The career trajectories that took them from the same starting point to completely different destinations — and why both worked

•

The moment Teresa stopped waiting for permission and realized her life was hers to create

•

Why Jess left corporate entirely — and what being a Black woman in those environments had to do with that decision

•

The role mentorship and community played in both of their careers, and why they want to pay that forward

•

What Rewritten is really about: not having it all, but having what actually matters to you

•

Never miss an episode — sign up for the Rewritten newsletter to get new episodes, behind-the-scenes updates, and resources delivered straight to your inbox:https://reworkit.kit.com/rewritten-waitlist

Connect with Jess Wass:http://www.jesswass.com

Connect with Teresa Sweeney:http://www.teresasweeney.comhttp://teresasweeney.com

Resources Mentioned in Episode

Bringing Up Bebe by Pamela Druckerman - https://bookshop.org/p/books/bringing-up-b-b-one-american-mother-discovers-the-wisdom-of-french-parenting-pamela-druckerman/5c6559b3e282ff61?ean=9780143122968&next=t

Maven Milk Breastfeeding Support - https://www.mavenclinic.com/maven-milk

Chapters

00:00 Introduction to Rewritten Podcast

03:19 The Motivation Behind Starting a Podcast

06:15 Navigating Career Changes as Women

08:49 The Importance of Mentorship and Community

11:49 Defining Success on Your Own Terms

14:50 The Journey of Self-Discovery in Careers

17:18 Embracing Change and Taking Risks

20:21 Reflecting on Career Paths and Lessons Learned

21:44 Embracing Unique Experiences

23:08 Navigating Motherhood and Work-Life Balance

24:47 Empowerment in Career Choices

27:42 Defining Personal Success

29:01 Creating Family Values and Routines

31:42 The Importance of Self-Care for Parents

34:29 Finding Happiness and Success

37:47 Diverse Paths to Fulfillment