The Ryan Leak Podcast – “The Dangers of Success”

Host: Ryan Leak
Date: August 25, 2025

Overview

In this episode, Ryan Leak delves into the dangers that accompany success, a topic often overshadowed by the glorification of achievement. Drawing from his personal experiences and insights gained from working with leaders, professional athletes, and high achievers, Ryan candidly explores five specific pitfalls that success can quietly introduce into our lives. His intention is to help listeners pursue success thoughtfully, managing its shadow sides while staying grounded and connected to what truly matters.

Key Discussion Points & Insights

1. Success Can Put You on Cruise Control

• Timestamp: [06:00]
• Insight: Success often leads to complacency. The hunger and discipline that fueled your initial rise can fade, leading to automatic behaviors and loss of intentional growth.
  • “The scariest part is it’s not an intentional decision. You don’t wake up one day and go, you know, I think I’m too lazy today. No, what happens is, you subtly just start coasting because the urgency that got you where you are is now a distant memory.” – Ryan Leak [07:30]
• Takeaway: Growth must remain a core value, even after achieving your goals.

2. Success Can Make You Stop Listening to Others

• Timestamp: [09:30]
• Insight: People are open to feedback when they’re struggling but become resistant when they’re winning. Past wins create false confidence and lead to echo chambers.
  • “When you’re losing, you’ll take advice from anybody... When you’re winning, well, now, you assume that you’re the expert in the room.” – Ryan Leak [10:10]
  • “Feedback isn’t always about fixing what’s broken. It’s often about making a decision to be one of those people that says, hey, today I’m going to get better.” – Ryan Leak [11:40]
• Takeaway: Never outgrow feedback—successful leaders seek growth even in victory.

3. Success Can Lead to Isolation

• Timestamp: [13:00]
• Insight: As success increases, so can a sense of isolation. You may begin outsourcing relationships, only keeping those who benefit from your success close, and ultimately finding yourself alone.
  • “Slowly, your inner circle becomes smaller, and then it becomes silent. Until one day, you look up and realize you’re the only voice in your world.” – Ryan Leak [14:00]
• Takeaway: True success is not a solo sport—nurture authentic relationships.

4. Success Can Make You Afraid to Take Risks

• Timestamp: [15:15]
• Insight: Once you’ve built something worthwhile, the fear of losing it replaces the willingness to take risks. This stifles innovation and long-term growth.
  • “When you had nothing, you tried everything. Now you’ve got something to lose... But the same risk it took to get you there is the same risk it will take for you to go further.” – Ryan Leak [16:05]
• Takeaway: Stay bold—allow wisdom, not fear, to guide your risk tolerance.

5. Success Can Create Relational Tension

• Timestamp: [17:40]
• Insight: At some point, every highly successful person faces a choice between further success and key relationships. Neglecting these conversations early can lead to painful consequences.
  • “If you talk to almost any highly successful person, somewhere in their story, there’s a moment, a crossroads, where they had to choose between their success and a relationship that mattered most.” – Ryan Leak [17:50]
  • “I want to encourage you to normalize being known at home, not just admired online... normalize choosing presence over productivity. And that one’s hard for me.” – Ryan Leak [20:00]
• Personal Example: Ryan reflects on stewing these tensions with his wife and children, advocating for ongoing, honest discussions.

Notable Quotes & Memorable Moments

• On Complacency:
  “Comfort is a subtle killer. And cruise control is a dangerous setting for your purpose.” – Ryan Leak [08:25]

• On Feedback’s Value in Success:
  “Success doesn’t mean you’ve outgrown growth. And just because the numbers are good doesn’t mean the habits underneath them are.” – Ryan Leak [10:50]

• On Relationships:
  “Success was never meant to be a solo sport. But isolation, it can convince you that it is.” – Ryan Leak [14:00]

• On Family and Presence:
  “I want to encourage you to normalize being known at home, not just admired online.” – Ryan Leak [19:50]

• On Slowing Down:
  “We should normalize slowing down not because we’re failing, but because we’re finally paying attention.” – Ryan Leak [21:10]

Actionable Takeaways

• Define success in ways that include both achievement and well-being.
• Continue seeking feedback, even at your peak.
• Maintain vulnerability and close relationships.
• Take risks rooted in wisdom, not fear.
• Protect your presence with loved ones over the lure of more accomplishment.
• Cultivate gratitude and groundedness as you pursue new heights.

Episode Flow & Key Timestamps

• [00:00] Introduction and recap of last week's topic.
• [03:40] Questioning what real success should look like.
• [06:00] The five dangers of success—introductions.
• [07:20] Success and complacency/cruise control.
• [09:30] Success and listening to others.
• [13:00] Isolation brought on by success.
• [15:15] Fear of risk after success.
• [17:40] Relational tension and family challenges.
• [19:50] Normalizing healthy relationship and life patterns.
• [21:10] Reflections and final encouragements.

Conclusion

Ryan bluntly states that “success is a beautiful thing, but what you need to know about it is it’s not harmless.” He encourages listeners to pursue success mindfully, staying grounded, grateful, and growing—without losing sight of who they were before success arrived. The episode ends with a sincere prompt to normalize meaningful connections and conversations, ensuring that success in public doesn’t come at the cost of losing at home.