Description

Why does achieving the goal still feel like nothing changed?

In this episode of Outreach With Reggie, Reggie Holloway unpacks the quiet disappointment many people feel after reaching milestones they were told would bring happiness — graduating, landing the job, checking the box, or “doing everything right.”

We explore why success without purpose feels hollow, how fear keeps people stuck after failure, and why so many New Year’s resolutions collapse within weeks. Reggie also speaks honestly about the pressure to perform, social comparison, and what happens when you no longer believe you can become more than what the system — or your past — told you.

This episode includes a powerful discussion on foster youth and post-secondary success, challenging deficit-based narratives and highlighting the resilience, leadership, and overlooked potential of young people navigating broken systems.

You’ll hear:

• Why achievement doesn’t always equal fulfillment
• How fear of failure and fear of hope shape our decisions
• Why “success” is often defined by systems, not purpose
• What the data says about foster youth outcomes — and what it misses
• Practical ways to redefine success on your own terms

This conversation is for anyone who has hit a goal and still felt empty, anyone questioning their path, and anyone ready to pursue meaning instead of metrics.

🎧 New episodes of Outreach With Reggie explore faith, justice, mental health, foster care advocacy, and what it means to heal while challenging broken systems.