In this deeply introspective and emotionally charged episode of That’s My Time Podcast, Tolu Afilaka sits with Olushola Olaleye for a profound conversation about masculinity, vulnerability, spiritual responsibility, success, pain, leadership, and the silent emotional battles men fight daily.
From the first moment, it becomes clear that this episode is not entertainment it's therapy, mentorship, and revelation wrapped into one. Whether you’re a man trying to understand yourself or a woman trying to understand men, this conversation will shift your mindset forever.
Olushola Olaleye takes us through the story of his calling, the spiritual nudges that shaped him, and the mentorship of Pastor Emmanuel Iren that grounded and refined his purpose. He speaks openly about his mother’s sacrifice after losing his father, the humility she instilled, and how her resilience became the foundation of his emotional and spiritual maturity.
This episode explores childhood wounds, the pressure of parental expectations, how success is actually maintained, and why self-leadership not talent—is the true mark of greatness. We dive into masculinity, male emotional repression, why men struggle to open up, and the staggering reality of suicide among men worldwide.
The conversation goes deeper into relationships, marriage preparation, adulthood, societal pressure, and the burden many African men carry. Pastor Olaleye confronts cultural misconceptions, unlearning toxic masculinity, empathy for men, and how emotional maturity is essential for building healthy homes.
We also touch on AI’s disruption of jobs, what young Nigerians need to survive the future, and the kind of leadership he would implement if he were president.
This episode is raw, insightful, confronting, and healing. Share it with every man and every woman who loves a man.
TIMESTAMPS
00:00 – 15:00 The Calling, The Presence & Early Spiritual Nudges
• Introduction to Pastor Olushola Olaleye
• Tolu reflects on his grace, presence, and spiritual weight
• How Olaleye knew he was called from childhood
15:00 – 30:00 | Childhood Pain, His Mother’s Strength & Foundations of Masculinity
• Losing his father and watching his mother carry the family
• Lessons of humility, tenderness, compassion
• How pain shaped his emotional intelligence
• Accepting spiritual responsibility early
• How upbringing prepared him for deeper leadership
• The moment he realized he was born different
30:00 – 45:00 | Convincing Parents, Building Track Record & Understanding Real Success
• How to make your parents trust your choices
• Why many young adults fail at communicating with parents
• Track record: the language parents understand
45:00 – 60:00 | Male Vulnerability, Emotional Repression & Suicide Awareness
• Where men’s emotional pain comes from
• Why the pain of men is invisible in society
• Emotional maturity: can women handle the truth?
• Why we MUST be kinder to men
• Men vs women: emotional processing differences
• SLK being underrated & men who feel unseen
• Why men should cry more—even if not as much as women
1:00:00 – 1:39:00 | Brotherhood, Marriage Pressure, AI Disruption & Hope for Nigeria
• Why every man needs a brotherhood circle
• What it means to “chest" things as a man
• Teasing SLK about never dating
• Financial pressure of marriage preparation for men
• How to prepare for marriage the smart way
• Major on the minor: principles for adulthood
• AI disruption and job loss—how to survive it
• Why AI is about knowledge application
• Is there hope for Nigeria?
• What Pastor Olaleye would do if he were president
• Final thoughts & blessings
QUESTION FOR YOU:
What’s the most misunderstood thing about men today?
Comment below we read everything.
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