Jen approached the empty nest phenomenon the way many high-functioning, self-aware women approach big life transitions - she saw it coming, read about it, talked about it, worked on it, prepared for it, and tried to get out ahead of it.
And then her son left for college… and the reality sank in.
In this episode of Life: By Design — Going Deeper, I’m joined by my dear friend and client, Jen Liddy, for a conversation about the life transitions we often see coming… and still cannot fully prepare for!
“I really thought I could think my way through this, or learn my way through this, or know my way through this. And it turns out you’ve got to friggin’ FEEL your way through it.” - Jen Liddy
Jen is a brand messaging strategist, a brilliant thinker, a deeply articulate human, and one of the funniest, most honest women I know. And while we could have easily spent this conversation talking about messaging, business, visibility, and the work she does in the world, I wanted flip the script and talk about the parts of being human that do not always get airtime. Being a woman, a mother, a wife… all of the internal conversations and conflicts that are happening when the rest of the world sees grace and professionalism on the surface.
This conversation is about what happens when the roles that once shaped your schedule and priorities begin to dissolve, when motherhood changes form, and when your business stops being the place you pour all of your extra capacity into.
The moments when the old version of success stops satisfying you and is replaced by ease and flow instead. The discovery that it doesn’t feel simple and earned, it feels strangely uncomfortable and guilt-ridden.
Jen speaks with such honesty about the internalized pressure to be useful, productive, available, responsive, and “good at everything.” She shares the way she used to equate doing more with being better, how rest could feel selfish, how ease could feel unearned, and how much work it has taken to surrender and receive the life she has worked so hard to build.
Plus the question underneath so many midlife transitions:
Who am I now, if I am no longer managing everyone and everything around me?
IN THIS EPISODE:
• Why some life transitions cannot be softened by reading, planning, researching, or preparing. The emotional reality of becoming an empty nester, even when you thought you were ready.
• The identity shift that happens when motherhood changes form. The surprising grief and freedom of no longer being needed in the same way.
• The pattern of overworking when more time and space become available. How business can become the place we manage, prove, produce, and avoid feeling.
• Why creating an impact matters more than maximizing your output - and how the guilt around ease can still make it feel uncomfortable, selfish, or unearned.
• And finally, we talk about what actually makes Jen (truly) happy — and how the unwritten rules she grew up with shaped what she believed she was allowed to want.
• Plus, what she’d say to the version of herself who walked into working with The Growth Cycle™ three years ago - and how life looks and feels today.
About Jen Liddy:
Jen Liddy is a brand messaging strategist who helps business owners communicate what they do with clarity, humanity, and the language that actually sounds like them. She has a gift for saying the truest things in a way people can finally hear, and in this conversation, she brings that same gift to the deeply personal world of motherhood, midlife, work, identity, and ease.
Learn more about Jen’s professional world HERE!
About Kate Vanden Bos:
Kate Vanden Bos is an intuitive consultant, coach, and creator of The Growth Cycle™ — a personal evolution framework built on your natural cycles and seasons. Find out more at MyGrowthCycle.com
Going Deeper is a conversation series from Life: By Design where we move beyond polished talking points and into the real terrain of being human. These are conversations about growth, identity, energy, transition, truth, and what it means to create a life that actually fits.
Not a life built by default.
A life grown by design.
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LEARN MORE ABOUT THE GROWTH CYCLE
Everything we talked about in this episode is exactly why I created The Growth Cycle™. It’s a 12-phase map to guide your own evolution - and once you have it, you’ll wonder how you navigated without it.
→ MyGrowthCycle.com
© 2025–present Katherine Vanden Bos. All rights reserved. The Growth Cycle™ is a trademark of Katherine Vanden Bos. No part of this publication may be reproduced or distributed without prior written permission. Content is for informational and educational purposes only and does not constitute professional medical, psychological, legal, or financial advice. This content may not be used to train artificial intelligence or machine learning models.
Life: By Design | katevandenbos.com
