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.

In this episode, I reflect on James Baldwin’s powerful insight that “a human being can only be saved by another human being,” and why 4 a.m. can be one of the most dangerous times to be alone with our thoughts. I explore how love, connection, and even the quiet presence of others can help us recognize that our lives are deeply intertwined—and that simply staying alive may be the greatest gift we give to the people around us.

• Why emotional pain often feels most overwhelming in the middle of the night
• What Baldwin meant by “the miracle of love”
• Why drugs, alcohol, work, and distraction can soothe us but cannot truly save us
• How Martin Short’s grandchildren gave him a reason to keep going
• The ripple effect of our lives on partners, family, friends, and strangers
• How we influence one another through our habits, consistency, and simple presence
• Practical questions to ask yourself when you’re struggling at 4 a.m.

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 why failure is not something to hide, but something to study, share, and even celebrate. Drawing inspiration from the “Flops” exhibition at the Musée des Arts et Métiers, I look at how psychology, religion, science, and art all reveal the same truth: my mistakes are often the very things that shape my character, deepen my relationships, and point me toward a more meaningful life.

• Why failed products like BIC for Her and New Coke can teach us about resilience
• The psychology of growth mindset, self-compassion, and learning from mistakes
• How traditions like Kintsugi and teshuvah honor repair over perfection
• Stories of famous failures from Thomas Edison to J.K. Rowling
• Books, movies, songs, and poems that remind us to “fail better”
• Reflection questions to help me turn every flop into wisdom and purpose

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 a hard drive crashes, people will spend thousands—or even hundreds of thousands—of dollars to recover what they thought was lost. In this episode, I explore what data recovery can teach us about resilience, meaning, and suicide prevention.

In this episode, I discuss:

• Why we often don’t realize the value of something until it’s gone
• How our bodies, relationships, and memories are more fragile than we think
• The surprising parallels between data recovery specialists and suicide hotline counselors
• How a single grain of dust—or a single thought—can cause outsized damage
• Why emotional crises are often about imbalance rather than total failure
• The idea that the story we create from loss may be more valuable than what we lost

Article referenced: https://www.newyorker.com/magazine/2026/04/27/when-your-digital-life-vanishes

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.

Typically, when we vent, it causes more harm than good. How do we vent our emotions in a healthy 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.

"Eat the apple. Plant the seeds." How does this quote pertain to suicide prevention?

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 do you do when your mind feels like the Drake Passage—violent, unpredictable, and overwhelming? In this episode, we break down what it actually takes to survive extreme conditions, both at sea and in your mental health.

This isn’t about powering through. It’s about learning how to stay on the ship.

What We Cover:

• Why the Drake Passage is so brutal—and why no one is surprised by it
• The myth of “toughing it out” vs. adjusting to real conditions
• How tools like meclizine and scopolamine parallel mental health support
• The “stay low and hold on” strategy for emotional survival
• Breaking overwhelming time into manageable moments
• Why asking for help isn’t weakness—it’s survival
• The core mindset shift: you don’t have to control the waves, just don’t go overboard

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.