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.

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.

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)

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.

• 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 notice that you are feeling victim, then you can be sweet to the part that is feeling victim… none of it has to ultimately land in judgment."

How this affects someone listening: Seeing emotions as parts that need care, rather than flaws that need fixing, rewires the entire healing journey. Small triggers stop being proof that progress is failing and become guidance toward what still needs love. This softens inner criticism, reduces shame and makes deep emotional work sustainable instead of exhausting.

• Topic 3: Psychedelics, Body Wisdom and Becoming Bigger Than Outcome

Timestamp: 14:59 – 27:10 & 34:32 – 35:37

What this unlocks: When the thinking mind is in charge, decisions get stuck in fear, logic loops and "what ifs." Dropping into body wisdom and, for some, working with medicines like MDMA, psilocybin or ayahuasca can help unpack stored pain that blocks intuition. As layers of grief clear, self-trust grows. Life's events still hurt, but they no longer define identity. A person begins to feel bigger than any outcome and capable of leading themselves, instead of endlessly searching for someone else with the answers.

Notable quotes:

• "My body is so brilliant and my brain tries so hard to be in charge… most of the time my body is like, I know this."

• "Psychedelics helped me unpack that pain so that then I could access my own wisdom… now I can lead myself in my life in a way that I could not before."

• "I no longer feel like the world is out to get me… recently I have started doing this thing where it is like, okay, if this thing happens, or if the opposite thing happens, I am the same."

• "I take every emotion that I feel that does not just kind of pass on its own and I journal with my part."

How this affects someone listening: Learning to trust inner guidance over external validation changes how choices are made in love, work and healing. Pain stops being a threat and becomes information. With that shift, risks feel more possible, endings feel less like failure, and it becomes easier to walk toward a bigger, more aligned life without needing guarantees.