About Jessica

Hi, I’m Jessica Wilen and I’m really glad you’re here. My work, and this newsletter, are informed by the multiple hats that I wear, including:

  • Executive coach, specializing in working with high-achieving working parents;

  • Assistant Professor at the Yale Child Study Center;

  • Former higher education administrator. Before coaching full-time, I served as the Director of Professional Standards for the Yale School of Medicine and the Assistant Dean of Students at Washington University in St. Louis;

  • Former psychotherapist and trained mediator;

  • Mom of two kids (the most important qualification of all 😉).

Every Thursday, I publish A Cup of Ambition, a newsletter for working moms (and enlightened dads!) who care about building a meaningful career and being an involved parent.

I’m really glad you’re here and I hope you’ll subscribe and join this amazing community.

Why subscribe?

If the pandemic has made one thing clear, it’s that working parents (and moms in particular) need support. This newsletter is meant to be a thought-provoking and encouraging place for all things related to working parenthood. You can expect interviews, essays, and links covering topics like finding meaning and success at work, how to raise happy and well-rounded kids, and relevant social trends.

I also offer paid subscriptions, which help support the time and resources associated with keeping this newsletter up and running. Paid subscribers have access to regular ask-me-anything posts, community threads, and fun swag as a way to build a stronger community of fellow readers. You can learn more about the benefits here.

So, curl up and enjoy A Cup of Ambition. There’s something for you here… whether your cup runneth over with ambition or you’d rather leave the coffee in the pot and head back to bed. ☕️💪

One last thing…

I want to cover what’s important to YOU.  I welcome reader input in deciding what and who to write about.  Reply to any weekly email to offer your suggestion.

I also offer leadership coaching for high-achieving working parents and organizational consulting centered on building family-friendly organizations (Research shows that supporting parents is good for business!) If you’d like to speak about working together, please email me at drjessicawilen@gmail.com.

Subscribe to A Cup of Ambition

A weekly newsletter for high-achieving moms who value having a meaningful career AND being an involved parent.


Former Yale professor turned executive coach and consultant, mom of two, author of "A Cup of Ambition"