In this episode, we explore the idea that meaning often comes after action. Inspired by a lyric from Robyn’s new album Sexistential, we unpack the difference between therapy, philosophy, poetry, and relationships — and why artists, rappers, writers, and improvisers often don’t fully understand what they’re creating until after it’s made.

We discuss why overthinking can block transformation, how freestyle rap reveals unconscious truth, and why some of life’s deepest insights can only be discovered through participation rather than analysis.

Topics include:

• Therapy vs existential suffering
• Why philosophy answers different questions than psychology
• Freestyling, flow states, and unconscious creativity
• Carl Jung, Sartre, Kierkegaard, and existentialism
• Why meaning is often retrospective
• The danger of waiting for certainty before taking action
• Relationships as the ultimate test of self-awareness
• “You live your way into new thoughts”

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

Gambling Addiction: 1-800-GAMBLER

In this episode, we explore why mystery isn’t something to eliminate from life — it may be the very thing that keeps us moving, connecting, hoping, and growing. Beginning with a two-year mystery involving peanut shells appearing outside a house, the conversation expands into relationships, neuroscience, detective stories, fear, curiosity, and the courage to enter the unknown.

Topics include:

• Why humans are drawn to mysteries, whodunits, crosswords, and haunted houses
• The psychology of curiosity and how uncertainty activates the brain
• Why new relationships feel electric and emotionally alive
• The difference between healthy mystery and painful uncertainty
• How “let’s find out” can become a philosophy for living
• Why certainty can sometimes lead to boredom, paralysis, or emotional deadness
• Reflections on rejection, risk-taking, creativity, science, and wonder
• The idea that hope only exists when the future remains unwritten

Mysteries

(Listen) Mistletoe Murders: https://shorturl.at/qftcN

(Read) Fresh Water For Flowers: https://shorturl.at/mcjtL

(Watch) Chestnut Man: https://shorturl.at/R5qxK

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

How do we cope with the mental, emotional and physical pain? Survivors of lightning strikes and electrical shocks have lessons for us.

Key coping mechanisms:

• salt packets
• sauna
• massage
• group therapy
• mindset shift

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

Gambling Addiction: 1-800-GAMBLER

What if feeling trapped isn’t about having a bad life—but about having a life that leaves no room for you? Using Odysseus and The Odyssey, I explore the idea that sometimes we can have love, security, success, and comfort while still feeling profoundly disconnected from ourselves.

• Why Odysseus rejects Calypso’s version of paradise
• How your greatest strengths can become sources of suffering
• The difference between wanting your life to end and wanting your current life to change
• Why boredom, burnout, and entrapment can be signs of lost agency
• How asking “Where do I get to be myself?” can become a first step toward finding a way forward

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

Gambling Addiction: 1-800-GAMBLER

When a boss’s email, meeting request, or tone of feedback feels disproportionately intense, it may not be about the present moment alone. For many people, workplace dynamics can quietly reactivate older emotional patterns tied to childhood experiences of criticism, invisibility, powerlessness, or conditional approval. This episode explores how that happens—and how to recognize when the nervous system is responding to the past, not just the job.

In this episode:

• Why authority figures at work can unconsciously resemble early caregivers
• How simple workplace feedback can trigger shame, fear, or collapse
• The role of childhood experiences in shaping adult stress responses
• Why “professionalism” can sometimes override emotional self-protection
• How to tell the difference between present-day feedback and old emotional memory
• What it means to stay grounded when the body reacts before the mind can interpret

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

When intrusive thoughts feel like a war zone, the goal isn’t to defeat every thought—it’s to establish a ceasefire. Just as peace agreements are more likely to hold when neutral third parties monitor them, our mental peace is more sustainable when therapists, friends, journals, or mindfulness practices help us observe thoughts without escalating them.

Key Takeaways:

• Intrusive thoughts can feel like repeated violations of an internal ceasefire.
• A neutral third party helps monitor, interpret, and de-escalate mental conflict.
• Therapists, trusted friends, journaling, and meditation can serve as peacekeepers.
• The goal is not to eliminate thoughts, but to prevent them from triggering emotional retaliation.
• Healing comes from creating distance between the thought and the response.

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

Hope is often mistaken for a feeling of optimism, but for many people it looks much quieter: the decision to stay alive and keep going even when nothing feels certain. In this episode, we explore how hope is less about feeling inspired and more about choosing, day after day, to remain open to the possibility that life can change. Sometimes the most meaningful act is not thriving—it’s surviving.

Key Takeaways

• Hope is not a mood; it is a decision.
• You do not need certainty to keep going.
• Survival is a meaningful achievement.
• Choosing “one more day” is an act of courage.
• Staying alive preserves the possibility of connection, healing, and purpose.
• Quiet hope often sounds like: “I’m not done yet.”

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

Why do some men spend an afternoon talking about sports, parenting, and work, only to drive home listening to The National or James Blake and cry a little? In this episode, we explore the hidden loneliness of “good” conversations and why being around people isn’t always the same as feeling seen.

In this episode, we discuss:

• Why men can feel lonely even after spending time with friends
• The difference between proximity and true emotional intimacy
• Why tears often show up in the privacy of the car
• How masculine social norms keep conversations safe but shallow
• The grief of almost feeling connected
• Small ways to make friendships 10% more honest and meaningful
• Why authentic connection is one of the strongest protective factors against suicide 

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

What happens after you finish the thing that gave your life structure and meaning? Whether it's writing a book, raising kids, winning a championship, or completing a major goal, the end of one chapter often leaves us feeling empty. In this episode, I explore why that emptiness isn't a sign that something is wrong, but a signal that you're ready to be challenged by life in a new way.

In this episode, I discuss:

• Why achievement often leads to a surprising sense of emptiness
• The difference between rest, recovery, and restlessness
• The psychology of the “arrival fallacy”
• Why the brain thrives on pursuit more than possession
• How purpose gives shape to our discomfort
• Why misery is trying to recreate the past
• How to become “unhappy in a whole new way”

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.

In this episode, I explore a simple but powerful idea: most of us aren’t actually chasing happiness — we’re trying to feel less miserable. When happiness becomes the goal, we overthink, compare, and pressure ourselves to feel a certain way. But when we shift the focus to reducing unnecessary suffering, life becomes more manageable, grounded, and sustainable.

Instead of asking “How do I feel amazing?” we ask, “What’s making life heavier than it needs to be?”

Key takeaways:

• Why pursuing happiness can increase rumination and pressure
• How high emotional expectations make normal days feel like failures
• The difference between happiness (a spike) and contentment (a baseline)
• How reducing cognitive load lowers day-to-day misery
• Turning rumination into small, actionable movement
• Focusing on 1–3 priorities instead of overwhelming to-do lists
• Choosing meaningful connection over constant self-optimization
• Lowering the goal from “feel great” to “feel manageable”

This episode isn’t about forced positivity. It’s about relief, proportion, and creating a life that feels lighter — not perfect.

Thrive With Leo Coaching: 

If you want to reduce your psychological pain, regain your purpose and forge your own path, go to www.thrivewithleo.com to begin your journey.

If you or anyone you know is considering suicide or self-harm, or is anxious, depressed, upset, or needs to talk, there are people who want to help:

In the US: 

Crisis Text Line: Text CRISIS to 741741 for free, confidential crisis counseling. 

The National Suicide Prevention Lifeline: 1-800-273-8255 or 988

The Trevor Project: 1-866-488-7386

Outside the US:

International Association for Suicide Prevention lists a number of suicide hotlines by country. Click here to find them.