Jesse de Leon gets honest about doubt, grace, and the emotional weight of guilt in this powerful episode of The Knowing. He tackles the hard questions: Why does God allow suffering? Why do we struggle to forgive ourselves? And why is faith so challenging even for believers?

Through stories about family, missed goals, personal slumps, and everyday setbacks, Jesse reminds us that belief doesn't require perfection—it requires hope. He explains how shame keeps us stuck, but grace allows us to rise again tomorrow. If you've fallen short in your fitness, relationships, faith, or purpose, this conversation will help you release the heaviness and move forward with courage.

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00:00 Why Is Faith So Hard?

01:15 What Is Faith & Grace?

02:30 The Gift You Can't See

03:25 Why Do Bad Things Happen?

04:30 Understanding God's Permitting Will

05:40 Parenting, Love & Letting Go

07:00 Faith During Life Transitions

08:45 Even the Disciples Doubted

10:20 Give Yourself Grace

11:30 Does Faith Mean Giving Up Fun?

12:45 The Power of Self-Forgiveness

14:15 Breaking Free From Shame

15:30 Falling Short of Goals

16:45 Slumps, Support & Accountability

17:45 Run Toward the Struggle

18:45 Receiving Unseen Grace

19:40 Start Again Tomorrow

How much are you willing to invest in your future health and happiness today? Jesse de Leon opens up about the reality of turning 62 and why he believes you are your own best investment. This episode dives into the crucial intersection of financial planning and physical well-being, urging listeners in their 20s, 30s, and 40s to start planning now. Jesse discusses the "rainy day" realities of home maintenance, the transition from expensive vintages to $15 wine gems, and the importance of whole foods over statins. He offers a vulnerable look at the ups and downs of entrepreneurship, admitting to times of overspending and the discipline required to course-correct. By looking at retirement through the lens of spirituality and common sense, Jesse provides a refreshing perspective on aging with grace and intention.

Subscribe to the podcast and follow @the_jesse_de_leon on social media for more life stories and inspiration.

00:00 Introduction to The Knowing Podcast

00:48 Facing the Reality of Retirement

01:13 Feeling Young While Turning 62

01:34 Health and Diet as Investments

02:14 Defining "Enough" for Your Future

02:48 Calculating Real Retirement Expenses

04:13 Lessons from My Younger Years

04:47 Creating an Expenditure List

05:15 Financial Discipline for Self-Employed

06:05 Investing in the Stock Market

06:55 Advice for the Next Generation

07:44 Being Vulnerable About Financial Mistakes

08:24 Cutting Costs Without Losing Quality

09:46 Navigating Social Security and Medicare

10:30 Seeking Advice from Financial Experts

11:23 Power of Community and Feedback

12:05 Health Habits for Longevity

13:00 Identifying What Makes You Happy

13:58 Take Action and Final Blessings

Feeling unsafe during a conflict usually leads to one of two things: explosive anger or total withdrawal. Jesse de Leon explores the middle path in this moving episode, documenting his journey from "shutting down" to standing his ground with grace. Jesse discusses the importance of eye contact, active listening, and the bravery required to call out inappropriate behavior in real-time. Whether it's a sibling, a partner, or a lifelong friend, the people who matter most deserve your honesty, not your absence. Tune in to hear how Jesse navigated a heated debate to reach a place of mutual respect and renewed trust.

Subscribe to The Knowing and follow @the_jesse_de_leon on social media for more life-changing stories.

00:00 Welcome to The Knowing Podcast

00:48 Power of Empowering Conversations

02:00 Crucial Conversations Book Review

03:00 Childhood Impact on Communication

04:00 Tools for High-Stakes Talking

05:10 The Christmas Eve Conflict

06:45 Managing Anger and Confusion

07:50 Addressing Conversation Hijacking

09:25 Value of Vulnerability

10:45 Breaking Old Habit Patterns

11:55 Handling Abrupt Communication

13:40 Learning Assertiveness Skills

15:05 Repairing vs Running From Conflict

16:40 Role Models in Communication

18:15 Healing Relationships Through Action

20:25 Staying in Important Relationships

21:40 Final Thoughts and Resources