So Many Questions...

Craig Calcaterra is the author of Cup of Coffee, a daily newsletter about baseball and pretty much everything else. In this episode, Craig traces the unlikely path from litigation attorney to sports blogger to NBC Sports writer to newsletter creator—and talks honestly about the luck, timing, and self-sabotage that shaped all of it.They talk about writing authentically when the world feels overwhelming, how sabermetrics changed baseball and then started to ruin it, his book Rethinking Fandom, and the strange feeling of being genuinely content with your work.

This week on So Many Questions..., Kendall talks with author and designer Joshua Graves about why tough conversations are so hard, how kindness differs from “niceness,” and the tools we all need to navigate conflict with more clarity, compassion, and confidence.Joshua shares stories from his upbringing in the South, how workplace dynamics and power structures shaped his communication style, and what he learned while researching and writing his book. They explore generational shifts in communication, boundaries vs. requests, and how to listen without losing yourself.They also talk about mindfulness, trauma-informed approaches, why younger generations communicate so directly with leaders, and why giving yourself grace might be the most revolutionary practice you can adopt.In this episode:• Joshua’s path from jukebox-obsessed kid to designer and author• How culture and power dynamics shape how we handle conflict• “Nice” vs. “kind” — and why the difference matters• Why difficult conversations feel so scary• How to listen with presence (without disappearing)• Setting boundaries that protect you• Generational shifts in workplace communication• Why many people fear talking to people in power• How to prepare for a tough conversation• What gives Joshua hope right now• Joshua’s powerful question of the weekAbout the book:We Need to Talk: A Survival Guide for Tough Conversations offers practical, human-centered tools to help anyone approach high-stakes conversations without scripts, gimmicks, or forcing yourself into “fake” authenticity. A quick, accessible read packed with real stories and flexible frameworks.

Director of Photography Ken Seng (Deadpool, Terminator: Dark Fate) joins Kendall to talk about his journey from business school to shooting massive IMAX action films, including the upcoming Street Fighter movie now filming in Australia.Ken shares how he fell in love with cinematography through the French New Wave, how his time with the National Outdoor Leadership School (NOLS) shaped his leadership on set, and what it takes to create stunning visuals on blockbuster productions.From Deadpool's gritty tone to Terminator: Dark Fate's high-speed intensity to building the visual world of Street Fighter, Ken breaks down the art and craft of lighting, camera movement, and collaboration between the director of photography, director, and production team.Topics include:- How DPs develop visual language and style- What makes great IMAX cinematography- Collaboration with directors, VFX, and stunt teams- Balancing art, craft, and pressure on big-budget films- Why Ken believes "long live cinema"Listen to the full conversation and subscribe for more interviews with filmmakers, artists, and storytellers.#StreetFighter #Deadpool #TerminatorDarkFate #Cinematography #DirectorOfPhotography #IMAX #Filmmaking #KenSeng #SoManyQuestionsPodcast

Baseball writers Jake Mintz and Jordan Shusterman (a.k.a. Cespedes Family BBQ) join me to talk about life inside the clubhouse, their journey from teenage bloggers to covering MLB for Yahoo! Sports, and what it’s really like to build a career in baseball media.We talk about:A friendship that led into a careerThe evolution from baseball tomfoolery to being members of the Baseball Writers Association of AmericaHumblebrags, locker room dynamics, and Bryce Harper storiesWhy empathy matters in baseball writingWatch the full conversation now and don’t forget to subscribe for more episodes of So Many Questions...

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