What I Wish I Knew in My 20s: A Conversation Across Generations - Messages For Men

If you could go back and speak to your 20-year-old self—what would you say?

In this episode of Messages for Men, Brad sits down with Riley to bridge the generational gap and dig into the hard-earned lessons that don’t show up in textbooks or highlight reels. From career decisions to relationships, faith, and identity, this conversation peels back the layers of performance, pressure, and pride that young men carry today.

Brad shares the experiences, regrets, and breakthroughs that shaped him—offering not just advice, but perspective. Riley brings honest questions, reflections, and a hunger to grow. What unfolds is a raw and practical dialogue about masculinity, humility, and how to stop drifting and start living with purpose.

This episode is for every man who’s tired of guessing. For the ones navigating uncertainty, craving mentorship, and ready to hear what’s rarely said out loud. It’s not about having all the answers—it’s about finding the courage to ask better questions.

What’s something you wish you had learned earlier?
Where do you feel like you're still trying to figure it out?

Drop your thoughts in the comments—we want to hear your story.
If this spoke to you, hit like 👍
And if you’re here for real conversations that sharpen men and stir something deeper, subscribe 🔔

#MessagesForMen #MensWisdom #MentorshipMatters #MasculinityDefined #ManhoodJourney #BradDombaugh #LifeAdviceForMen #MensPodcast #FaithAndManhood #PurposeDriven #ManhoodUnfiltered #MensGrowth #YoungMenMatter #MasculineStrength #ConversationsThatMatter #WhatIWishIKnew #LifeInYour20s #ManhoodAcrossGenerations #IronSharpensIron #RaisingMenRight