Turning Pain Into Wisdom, Beauty and Power

In this episode of Life Check Yourself, I sit down with writer and self-healing advocate Alexis Leigh, author of Pain Is a Portal to Beauty: Stunning Discoveries After Loss, Psychedelics and Feeling It All. With roots in Wharton, law school and the corporate world, she shares how a single moment in the woods cracked open a life that looked "perfect" on paper but felt empty inside, and how following that inner voice led through divorce, deep emotional work and psychedelic journeys into a life of authenticity, love and radical self-trust.

 

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About The Guest

Alexis Leigh is a writer and advocate for self-healing through unconventional methods, including psychedelics and deep inner work. She left a successful career in finance and consulting, holds a BS in Economics from Wharton and a JD from Lewis and Clark Law School, and now lives between Oregon and Maui with her partner and three boys. Her memoir, Pain Is a Portal to Beauty, explores how feeling deeply, rather than numbing out, can turn grief and loss into clarity, meaning and beauty.

 

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3 Main Takeaways

1. Answer the inner wake-up call instead of settling for a "good enough" life (01:52)
   
   

2. Use everyday emotions as portals instead of numbing them away (17:11)
   
   

3. Trust body wisdom and courageous tools to turn pain into power and self-leadership (24:26)
   
   

 

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Main Topics, Timestamps, Explanations & Notable Quotes

• Topic 1: When Your Life Looks "Fine" But Feels Like A Tragedy

Timestamp: 01:52 – 11:13

What this unlocks:
Hearing an inner voice that says, "If you die today, your life will have been a tragedy," forces radical honesty. It challenges the belief that gratitude means tolerating loneliness or emptiness. Letting that truth land can be the moment a person finally gives themselves permission to want more love, more meaning and a different life, even when everything looks "fine" from the outside. From there, every pattern, relationship and identity becomes open to being questioned and redesigned.

Notable quotes:

• "I was walking in the woods in the summer of 2020 and I heard a voice that said, 'If you die today, your life will have been a tragedy.'"
  
  

• "I had all of the categories, but I did want more love and more meaning. I just kind of thought you should not want that."
  
  

• "To hear that your life is a tragedy, it is like everything is not working. That is not like your life needs a little tweaking. That is like throw it in the trash."
  
  

How this affects someone listening:
Letting in the possibility that a "have it all" life can still be tragic breaks the spell of settling. It shows that longing for more is not selfish, it is truthful. Once that truth is acknowledged, a person can stop negotiating with their own sadness and start redesigning their foundation instead of endlessly rearranging the furniture on top of it.

 

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• Topic 2: Feeling Feelings Instead Of Numbing – Turning Tiny Triggers Into Portals

Timestamp: 17:11 – 23:32

What this unlocks:
Painful emotions often get buried under food, wine, screens or busyness. Removing those coping habits, even briefly, can stir up anger, panic or irritation. Those first reactions are not proof that something is wrong; they are the doorway. Meeting them with curiosity instead of judgment turns daily annoyances and "overreactions" into chances to release old grief, anger and fear. Over time, this builds emotional muscle and makes it easier to stay present instead of collapsing into victimhood or self-criticism.

Notable quotes:

• "Our bodies protect us from these feelings when we are not ready to look at them… my body dissociated from feeling, numbed me completely when my mom went away when I was young."
  
  

• "It is not about how can I go from not feeling anything to feeling everything. It is about how can I go from not feeling anything to even recognizing what is a feeling."
  
  

• "As soon as you