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 week

About 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.

Marketing executive and Contentful CMO Elizabeth “EMax” Maxson joins Kendall to talk about the pivotal career moves, personal risks, and honest moments that shaped her leadership journey. From a life-changing cross-country internship, to navigating male-dominated industries, to building a mothers’ community that now supports nearly 1,000 women, EMax shares what it means to lead with vulnerability, courage, and clarity.

She opens up about advocating for women and caregivers, the mental load of parenting, redefining boundaries, and why she rejects “work-life balance” in favor of harmony. EMax also talks self-care routines, slowing down, improv’s “yes and” mindset, and how to build a career grounded in humanity.

Whether you're a parent, leader, woman in tech, or someone trying to find stability in a chaotic world, this conversation is full of wisdom, humor, and heart.

#Leadership #WomenInTech #WorkingMoms #Caregivers #MarketingLeadership #CMO #CareerGrowth #WorkLifeHarmony #BoundarySetting #Vulnerability #CommunityBuilding #Contentful #SoManyQuestionsPodcast

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

In this episode of So Many Questions, I sit down with Rob Bell—author, speaker, and former pastor—for a wide-ranging conversation that begins with memories of church-basement punk shows in suburban Chicago and stretches into creativity, vulnerability, and how suffering shapes the art we make. Rob talks about discovering the sermon as an art form, moving through criticism, and learning to surrender outcomes while still giving everything to the work.We also dig into his shift from the stage to more intimate workshops, his podcast, and why presence, curiosity, and risk are central to living a creative life.#RobBell #SoManyQuestions #Creativity #Spirituality #Podcast #Inspiration

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 career

• The evolution from baseball tomfoolery to being members of the Baseball Writers Association of America

• Humblebrags, locker room dynamics, and Bryce Harper stories

• Why empathy matters in baseball writing

Watch the full conversation now and don’t forget to subscribe for more episodes of So Many Questions...

Ethan Marcotte, the pioneer who coined the term "Responsive Web Design", joins So Many Questions... for a deep and thoughtful conversation.

We explore the early web, inclusive design, tech worker power, and the values that shape Ethan’s work. From designing websites in the '90s to writing You Deserve a Tech Union, Ethan shares how community, justice, and craft guide his approach to the internet.

We discuss:

• The origins and impact of responsive web design
• Crafting accessible, inclusive experiences
• The evolution of the web and independent publishing
• Labor issues in tech and why tech workers deserve unions
• Creativity, critique, and unlearning old habits

If you’re a designer, developer, or anyone curious about the intersection of technology and ethics, this episode is for you.

QUESTION OF THE WEEK (answer in the comments):

What is your favorite thing that you've read recently?

Ethan’s website: https://ethanmarcotte.com

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