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: reworkit.kit.com/rewritten-waitlist
Connect with Jess Wass: jesswass.com
Connect with Teresa Sweeney: 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
Information
- Show
- FrequencyUpdated Semiweekly
- PublishedJune 23, 2026 at 2:44 PM UTC
- Length44 min
- Season1
- Episode101
- RatingClean
