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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What if confidence doesn’t come from hype, but from training yourself? We sit down with communication coach Jeff Callahan to carve out a practical path from social anxiety to authentic connection that's built on reps, helpful self-talk, and simple frameworks anyone can use. As a child, Jeff’s story began with a severe stuttering problem but today he has a thriving coaching practice featured by Inc., Time, and Business Insider. The main lesson is to become competent at communicating, because competence breeds confidence.
We dig into why so many adults feel behind on soft skills (years of technical focus, the rise of screens and algorithms, and the slow disappearance of third spaces) and how we can overcome deficiencies. Jeff shares a weekly audit to surface hidden micro-opportunities for practice, a method to stack small wins, and a mental model to replace harsh, inaccurate stories with neutral, helpful interpretations. You’ll also learn the “spokes” method to keep conversations flowing without memorized scripts. More reps = less pressure.
The professional upside is real. Jeff explains how clearer self-advocacy can translate to raises, promotions, and leadership visibility, with an example of a client who landed a 10% salary bump and a path to promotion by refining his message. If you’ve ever felt isolated or stuck waiting to “feel ready,” this conversation provides a way forward: show up, practice small, choose helpful stories, and let confidence flow out of your competence.
Resources From Jeff:
Email: [email protected]
Free 56 Minute Training on Group Conversations: https://www.becomemorecompelling.com/group
Link Tree: https://linktr.ee/becomemorecompelling
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Where to Find Us:
Web: https://clutteredpath.com/
Patreon: https://patreon.com/clutteredpath
Questions/Comments: [email protected]
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Follow us on Social Media:
Chapters
1. Welcome (00:00:00)
2. Introduction (00:00:12)
3. Jeff’s Childhood (00:05:10)
4. Stuttering Problem (00:09:26)
5. Positive Impact of Youth Sports (00:12:14)
6. Communication BEFORE Social Media (00:13:35)
7. Technology Isolates Us (00:18:09)
8. Reverse-Engineering Social Anxiety (00:25:22)
9. Mental Prep for Social Interactions (00:28:35)
10. Learning to Get Out of Your Head (00:36:29)
11. Why Adults Lack Social Confidence (00:40:43)
12. How to Build Social Confidence (00:43:53)
13. Teaching Others What He’s Learned (00:50:51)
14. Where to Connect With Jeff (00:55:45)
15. Closing Thoughts (00:56:48)
26 episodes
