Jenny Child on Grief, Career Transitions, and Presence

By
Hannah Kissel
January 21, 2026
65
min
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About the episode

In this deeply human conversation, Hannah sits down with former Oroton CEO, Jenny Child, to explore what happens after the title, the success, and the carefully built career identity. Jenny shares her experience navigating grief, leadership, and major career transitions, and how learning to slow down, let go, and be present reshaped not just her work — but her sense of self. Together, they unpack what it means to lead through uncertainty, to grieve versions of ourselves we've outgrown, and to build a life that isn't driven solely by achievement.

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Superscript

Subscript

This episode is for anyone who's:

  • Stepping away from a high-level role
  • Moving through grief or loss (personal or professional)
  • Questioning who they are beyond their job title
  • Learning how to be present in seasons of change

A powerful reminder that growth doesn't always look like striving — sometimes it looks like listening, resting, and allowing space for what's next.


Key Takeaways:

  • Grief isn't only about loss — it often shows up during career transitions
  • Leadership roles can deeply shape identity, making transitions emotionally complex
  • Presence becomes essential when control and certainty fall away
  • Stepping back doesn't mean failure — it can mean integration
  • True success evolves as we evolve
  • Slowing down can reveal what achievement alone never could


Timestamps:

00:00 – Introduction & Jenny's career background
02:10 – Identity beyond leadership and success
05:00 – Grief as a teacher during life transitions
08:30 – Leaving a role that once defined you
12:15 – The emotional cost of high-performance culture
16:00 – Learning presence when certainty disappears
20:10 – Letting go of urgency and external validation
24:45 – Redefining success after loss and change
29:30 – Advice for leaders navigating transitions
33:00 – What it really means to trust yourself again

Hi there, I'm Hannah

Executive Coach, podcaster, speaker, writer, and builder of big f*cking Dreams. My mission? To help ambitious professionals build self-acceptance, self-trust in their careers.

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