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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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When Vision Meets Uncertainty, Choose Presence
Short Story Long: Life Lessons from Leaders, Coaches, and Entrepreneurs
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Plans rarely survive contact with real life, and that’s where leadership truly begins. Drawing on Kaila’s leap from solopreneur to agency owner while becoming a parent, we explore how to trade grind for grace and control for connection without sacrificing results. I walk through the practical tools that help leaders stay human and effective when the ground shifts: shifting language from I to we to build ownership, setting boundaries that protect strategic focus, and designing systems that let teams share weight while keeping accountability clear.
We dig into the difference between courage and confidence, and why momentum—not certainty—creates the proof you need to keep going. You’ll learn how to use informed intuition when plans are still forming, define scope so perfectionism stops draining innovation, and create check-ins that tell you when work is truly “done enough.” We also talk about the hard, human side: asking for help when no one seems to hear you, spotting subtle cues when your team needs support, and leading with compassion that actually strengthens performance.
If your world is changing—markets shifting, teams evolving, personal priorities reordering—this conversation offers a grounded way forward. Hold vision loosely and purpose tightly. Build containers that protect attention. Step back from the noise so you can hear the orchestra and conduct with clarity. Try the one-week challenge: replace one I or me with we or us where it fits, then watch how engagement changes. If the ideas resonate, subscribe, leave a review, and share this episode with someone who’s ready to lead with more presence and less pressure.
Connect with Beki on LinkedIn: Linkedin.com/in/BekiFraser
Learn more about her coaching: TheIntrovertedSkeptic.com
Follow Short Story Long's LinkedIn Page: Linkedin.com/showcase/shortstorylongpod
Get her book, C.O.A.C.H. Y.O.U.: The Introverted Skeptic’s Guide to Leadership - Amazon
Short Story Long is produced by Crowned Culture Media LLC
Chapters
1. From Conversation To Core Themes (00:00:00)
2. Redefining Success As Life Shifts (00:00:46)
3. Courage, Momentum And Informed Intuition (00:03:35)
4. Language Shifts From I To We (00:06:02)
5. Sharing Weight Without Losing Ownership (00:08:19)
6. Ditching Perfection For Progress (00:10:56)
7. Plans, Pivots And Agility (00:13:28)
8. Boundaries As Sustainable Structure (00:15:01)
9. Compassion That Strengthens Accountability (00:17:14)
10. Advocating For Help And Being Heard (00:19:00)
11. Vision As Direction Not Certainty (00:21:08)
12. Skill Builder: Me To We Challenge (00:22:50)
13. Key Takeaways And Closing (00:24:06)
52 episodes
