Welcome to the Don’t Pick the Scab Podcast, where we get real about what it takes for men over 40 to recover, rebuild, and thrive after divorce. I’m your host, David, and in this episode, I’m joined by Frank Sinclair—the Chief Encouragement Officer at Dream Again Business Consulting, acclaimed author, and host of the “Be Encouraged” podcast show.

Frank brings years of hands-on experience empowering men and entrepreneurs to find hope and overcome life's toughest setbacks—including divorce. In this candid conversation, we dive deep into the unique challenges men face after 40, from isolation and discouragement to rebuilding self-esteem, developing healthy habits, and setting new boundaries.

What You’ll Learn in This Episode:

• The Power of Encouragement: Why hope is the foundation of any successful recovery, and how to nurture it in your daily life.

• Frank’s Personal Story: From growing up in poverty to almost losing his wife—Frank shares how he turned life’s toughest moments into fuel for growth.

• Facing Your Own Role: Discover why true healing starts with honest self-reflection, not blaming your ex.

• Building Resilience: The role of “failing forward,” embracing mistakes, and why small, steady goals beat lofty, vague dreams.

• Self-Care for Men (Finally!): Why men often neglect their own needs, and practical ways to develop self-discipline, self-respect, and compassion—even if you’ve never done it before.

• Boundaries & Expectations: How to set and KEEP boundaries, communicate them clearly, and adjust your expectations for future relationships.

• The Role of Therapy: Breaking the stigma for men (especially men of color) and why seeking support is a sign of strength, not weakness.

• Recognizing Discouragement: Spotting the red flags (like isolation, fatigue, and loss of hope), and practical steps to reconnect and re-engage with life.

Frank also shares some of his favorite books and resources, including “Mindset” by Dr. Carol Dweck—tools that have helped countless men move from simply surviving to truly thriving after divorce.

If you’re a man over 40 feeling stuck, discouraged, or unsure how to move forward after divorce, this episode is for you!

👉 Listen now and start your journey toward hope, healing, and a better future.

💬 What’s been your biggest challenge or breakthrough in divorce recovery? Drop a comment below! Your story could help another man on his journey.

Don’t forget to like, subscribe, and share this episode with someone who needs a little encouragement today! And check the show notes for Frank’s book recommendations and links to his podcast.

Frank Sinclair on LinkedIn

Be Encouraged Podcast

#DivorceRecovery #MenOver40 #Encouragement #SelfCare #Boundaries #DontPickTheScab #Podcast

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Welcome to the Don’t Pick the Scab Podcast—the place where men over 40 find their path to real healing and personal growth after divorce. I’m David, your host, and today’s episode is a true game-changer for anyone feeling stuck in the same old relationship patterns, confused by the emotional rollercoaster of dating after divorce, or simply wanting to break free and build something better.

In this powerful conversation, I’m joined by CT Kaupp, a relationship and attachment style coach who has personally transformed heartbreak into wisdom. CT’s journey—from years of anxiousness and overthinking to genuine self-awareness—holds the key for men like us who are ready to stop “fixing” partners and start understanding ourselves.

What You’ll Learn:

• Attachment Styles 101: Discover the four main attachment styles—secure, anxious, dismissive avoidant, and fearful avoidant—and how they secretly shape your relationships from childhood through every date post-divorce.

• Why We Repeat Unhealthy Cycles: Learn why so many men over 40 find themselves stuck with the same types of partners and how self-awareness can finally break the cycle.

• The Anxious-Avoidant Trap: Get the real talk about why opposites attract but often crash, and how to spot this dynamic before it derails your next relationship.

• Boundaries, Expectations & Self-Care: Practical strategies for setting healthy boundaries, communicating your needs confidently, and practicing self-care that actually works (especially for anxious types!).

• Love Languages & Miscommunication: How understanding love languages can save your next relationship—and why so many divorces are rooted in simple misunderstandings.

• Dating After Divorce: Red flags and green flags to spot different attachment styles in online dating, plus tips for men who want to move from “insecure” to “secure” in their relationships.

• Co-Parenting & Attachment: How your attachment style might impact your co-parenting approach and what to watch for as a dad post-divorce.

CT brings compassion, actionable advice, and hard-earned wisdom to help men stop overthinking, boost their self-esteem, and create the connections they truly want. If you’re tired of buzzwords and want real, practical tools to rewire your relationship habits—this episode is for you. 🛠️

If you found this episode helpful, please hit LIKE, SUBSCRIBE, and SHARE with another guy who needs this message. 💬 Drop a comment below: What’s your biggest challenge when it comes to dating or healing after divorce? Let’s start the conversation and support each other!

CT's Website

CT on Spotify

CT on Instagram

#DivorceRecovery #MenOver40 #AttachmentStyles #RelationshipAdvice #DontPickTheScab #HealingAfterDivorce

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Welcome to the Don’t Pick the Scab Podcast! I’m David, and today’s episode dives deep into the overlooked struggles—and surprising strengths—of men over 40 navigating divorce, fatherhood, and even incarceration. 🎙️

We’re joined by Khaled Ashraf, a trailblazing school principal who leads a unique school inside a state correctional facility. Khaled’s journey began as a Philly police officer, but what he discovered in classrooms—and later, behind prison walls—shattered stereotypes about fathers, especially those facing the “double whammy” of divorce and incarceration.

Are you a dad over 40 feeling shut out of your child’s life after divorce? Do shame, outdated stereotypes, or legal barriers make it seem impossible to reconnect? This episode is for you.

Khaled reveals how schools and society often silence and sideline fathers—especially those who are incarcerated—by defaulting to mothers as the main point of contact. He exposes the “hidden curriculum” that keeps dads out, even when they desperately want to be involved. 🏫

But here’s the truth: Disconnection isn’t about dads not caring—it’s about lack of access, voice, and invitation. Khaled shares eye-opening stories of fathers who, despite unimaginable odds, stay engaged with their kids’ homework, milestones, and growth—even from behind bars. 📚✉️

We tackle common misconceptions:

• "Incarcerated dads don’t care." (False! Many fight daily to connect.)

• "Fathers are only called when discipline is needed."

• "You’re too late to rebuild your relationship."

You’ll learn:

• The first steps to re-enter your child’s educational life (hint: start with a simple email or text!)

• How shame and trauma hold men back—and how to break free

• Why schools need to update their approach to father engagement

• The importance of never giving up, even if you can only connect from a distance

• Resources and practical strategies for men over 40 to rebuild connections—no matter your circumstances

Khaled’s message is powerful: Every day is a new chance to reach out. Even a simple “thinking of you” can change everything. Your involvement matters—don’t let anyone tell you otherwise.

If you’ve ever felt alienated from your kids, stuck in shame, or unsure how to reconnect after divorce, this episode will inspire you to take action. You are not alone—and it’s never too late.

👇 Drop a comment below:

Have you faced barriers as a father after divorce or incarceration? What’s helped you reconnect with your kids? Let’s support each other—your story matters!

Don’t forget to LIKE, SUBSCRIBE, and SHARE if this episode resonates with you or someone you know. 💬👊

#DivorcedDads #FatherhoodOver40 #Don’tPickTheScab #DivorceRecovery #MenOver40 #RebuildFatherhood #ParentalAlienation #KhaledAshraf #Resilience #MenSupportingMen

Khaled's LinkedIn

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