The Goal Digger Podcast | Top Business and Marketing Podcast for Creatives, Entrepreneurs, and Women in Business

919: The Permission to Burn It Down (And Start Over on Your Terms)

October 6, 2025

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  • Trust your instincts when they signal that a part of your business or life no longer brings joy or aligns with who you are becoming, even if the current structure is commercially successful. 
  • Reinvention and evolution are natural parts of a long career, and older entrepreneurs gain wisdom, integrity, and less fear of risk, making their best work ahead of them. 
  • Using work as an overproductive distraction from emotional pain can lead to physical breakdown, necessitating a forced realignment toward sustainability and alignment. 

Segments

Sponsor Readout and Intro
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(00:00:01)
  • Key Takeaway: The episode features sponsors including Mercury, Morgan Stanley, Skims, and Boll & Branch, setting the stage for a discussion on reinvention.
  • Summary: The initial segment is dedicated to sponsor acknowledgments for Mercury, Morgan Stanley, Skims, and Boll & Branch. The host, Jenna Kutcher, introduces the episode’s theme: navigating what happens when a built life or business no longer fits personal evolution. Guest Jen Hatmaker is introduced as an expert on reinvention, focusing on a ‘Midlife Renaissance’ rather than a crisis.
Trusting Intuition on Business Change
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(00:02:01)
  • Key Takeaway: Entrepreneurs must trust instincts signaling a lack of joy or misalignment in current work, even if it means making disruptive changes.
  • Summary: Jen Hatmaker advises listeners to trust instincts when work ceases to bring joy or has run its course due to life changes. While making changes may be disruptive, knowing what feels out of alignment with one’s integrity is crucial. Following this inner wisdom is presented as a reliable guide, even if it requires hard choices and risk.
Reclaiming Inner Authority
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(00:09:53)
  • Key Takeaway: The inability to trust one’s inner knowing often stems from early messaging—such as purity culture or body policing—that taught women to outsource all personal authority.
  • Summary: Jen Hatmaker traces the root cause of muting one’s inner voice back to societal messages that deemed the female body problematic or desires suspect. This led to outsourcing authority to external sources for direction on belief and action. Reversing this learned behavior, where one’s wants are viewed as inherently selfish, is a slow but necessary generational work.
Navigating Post-Crisis Identity
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(00:17:35)
  • Key Takeaway: Emerging from catastrophic life shattering, like divorce, forces an independent re-evaluation of identity, separating the authentic self from the performed public brand.
  • Summary: After a major life collapse, Jen Hatmaker experienced a period where everything was rubble, preventing immediate sorting of identity components. Becoming an independent adult at 46 required a hard look at what mattered, especially concerning public credibility after discussing marriage as a constant. The community’s generous reflection helped anchor her true character while the outer, polished version of her faded.
Aging Gracefully vs. Irrelevance
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(00:28:08)
  • Key Takeaway: The narrative that aging equals irrelevance is a lie used to keep women small; older women possess superior leadership acumen, wisdom, and integrity.
  • Summary: The belief that getting older leads to irrelevance is a significant falsehood, as experience enhances intelligence, wisdom, and leadership capabilities. Viewing the next generation as a threat is small-minded patriarchal thinking, as older leaders’ experience complements the innovation and energy of youth. Women should actively remain at the table, as their best days are ahead of them.
Authenticity and Risk in Sharing
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(00:33:33)
  • Key Takeaway: Writing a deeply personal memoir, especially one detailing divorce, requires prioritizing long-term integrity over immediate reader approval or short-term gain.
  • Summary: Jen Hatmaker found writing Awake scary because it shifted from prescriptive conclusions to vignettes, trusting readers to draw their own meaning. She constantly questioned if she would be proud of including specific memories five years later, which led to deleting content to protect real-life relationships impacted by the story. This process emphasizes that sharing one’s story should be done from a place of settled clarity, not immediate, wounded reaction.
Avoiding Reaction Over Reflection
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(00:47:04)
  • Key Takeaway: The internet encourages immediate reaction without reflection, which often leads to regretted ‘hot takes’ written from a place of being actively wounded.
  • Summary: The digital environment incentivizes rapid reaction rather than thoughtful reflection, often resulting in statements made while still processing trauma. Sharing stories of loss requires giving oneself the benefit of time to process complicity and integrity, leading to wiser writing. Telling one’s story while still actively hurting sacrifices discernment and results in less helpful communication.
Work as Avoidance Mechanism
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(00:49:09)
  • Key Takeaway: Overworking, especially when rewarded, can become an ’eject hatch’ used to avoid processing real pain, a pattern that can lead to severe physical consequences if ignored.
  • Summary: Ambition and overproduction are often rewarded behaviors that can be used to avoid dealing with underlying issues, such as the pain of divorce. Jen Hatmaker overcompensated by controlling work when she could not control her children’s experience of the divorce, leading to catastrophic health issues like high blood pressure and panic attacks. This physical shutdown forced a necessary change in work scope and availability, leading to a life that feels smaller but more expansive and aligned.