Episode
The Courage Tax: What you pay every time you delay the conversation that needs to happen
- Podcast
- You Might Try This
- Published
- May 11, 2026
- Duration seconds
- 1714
- Processing state
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Summary
Why do difficult conversations feel so much harder the longer we avoid them? In this episode, Stacey and Cade unpack the hidden “taxes” leaders pay when they delay hard conversations at work; from damaged relationships and declining performance to mental overload and unnecessary anxiety. They explore why silence often costs more than honesty. The conversation offers practical tools for leaders, including how to start difficult conversations, avoid climbing the ladder of inference, and use curiosity instead of judgment. Takeaways Avoidance has real costs Silence is often misinterpreted The story in your head is usually worse than reality Start with observable facts, not assumptions Choose the right opening Chapters 00:00 The Cost of Avoiding Difficult Conversations 01:11 The Conversation You’ve Been Putting Off 03:05 The Hidden “Taxes” of Avoidance 06:50 Why Leaders Avoid Giving Feedback 08:22 The Cognitive Load of Unspoken Issues 10:26 Why Difficult Conversations Feel Worse Than They Are 17:52 How to Start a Difficult Conversation If you’re a leader struggling to bring up hard topics, this is the episode for you. To learn more about us and the podcast, visit youmighttrythis.com and check us out on social media @youmighttrythis