65: Jenny Child on Grief, Career Transitions, and Presence episode artwork

EPISODE · Jan 20, 2026 · 46 MIN

65: Jenny Child on Grief, Career Transitions, and Presence

from Big F*cking Dreams · host Hannah Kissel

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. 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 #CareerTransitions #GriefRecovery #GriefAndGrowth #WomenInLeadership #ExecutiveLife #CareerChange #Presence #IdentityAndPurpose #HighPerformer   ------- 🚨 Got a career challenge? Submit your questions and frustrations to the Hannah Hotline! Email: [email protected] Gain Access to the free Career Confidence Course: https://www.hannahkissel.com/careerconfidence Follow Hannah Kissel on Instagram: https://www.instagram.com/hannahmaekissel/ Connect with Hannah Kissel on LinkedIn: https://www.linkedin.com/in/hannahkissel/ Visit Hannah's website: www.hannahkissel.com The Truth About Imposter Syndrome:  https://open.spotify.com/episode/129YgMPuJWGLQK5VB9CncR?si=a352646dfec6411a Quiz: Discover Your Career Alignment Score: https://hannahkisselcareerquiz.scoreapp.com  

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65: Jenny Child on Grief, Career Transitions, and Presence

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