Ask Faleskini - The Midlife Crisis Clarity Compass

Are You One Yes Away From Solving Your Midlife Crisis? Jeanne Chung

Peter Faleskini Season 6 Episode 40

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0:00 | 18:21

Most people treat a midlife crisis as an emergency to suppress, but true midlife discontent is rarely solved by superficial fixes. It is resolved when you close the gap between rigid societal expectations and true personal contentedness. 

In this episode of Ask Faleskini, Peter Faleskini sits down with former investment banker, wellness entrepreneur, menopause startup founder, and author Jeanne Chung. Jeanne shares how writing her memoir allowed her to "metabolize" her past—from understanding her father's escape from North Korea and navigating her brother's stroke to repeatedly reinventing her career across Wall Street, international yoga studios, and tech startups. Together, they explore how auditing your past decision points and saying bold new "yeses" can turn midlife uncertainty into a launchpad for your next era. 

Key Takeaways in This Episode:

  • Metabolizing Your Past: Why processing your life story digests both grief and accomplishments, converting past experiences into a solid foundation for your next chapter. 
  • Breaking the "Plan" Trap: How clinging to early-life timelines creates artificial midlife failure, and why letting go of the original plan opens space for authentic direction. 
  • The Power of the Unconventional "Yes": How saying yes to radical pivots—from banking to opening yoga studios in Singapore—builds the internal proof required to trust yourself. 
  • Happiness vs. Contentedness: Why midlife crisis resolution isn't about chasing temporary thrills, but taking stock of what brings deep, sustained contentedness to your life and work. 
  • Pivoting into AI at 58: How Jeanne is stepping into business process optimization and AI tooling, proving that age is never a barrier to learning new industries. 


About Jeanne Chung: Jeanne Chung is a former investment banker (MIT graduate), yoga teacher, wellness entrepreneur, and menopause startup founder. She is an author, speaker, and consultant helping leaders map their major life decisions to step deliberately into their next chapter. 



Connect & Subscribe:

  • Podcast: Ask Faleskini — The Midlife Crisis Clarity Compass 
  • Host: Peter Faleskini 
  • Work with Peter: Send a DM for 1-on-1 coaching, clarity consultations, and executive guidance.


#MidlifeCrisis #CareerPivot #PersonalGrowth #WomenInMidlife #AskFaleskini #JeanneChung #Mindset #ExecutiveCoaching

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Peter's books


The Clarity Compass

Stop Midlife Burnout, Escape the Matrix, and Resolve Faleskini’s Complex


Faleskini’s complex

Diagnosing the Systemic Costs of Midlife Crisis and Advancing Holistic Pathways of Resolution


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