

Questions & Quitting with Kirkland
What happens when chronic pain meets comedy, trivia, and unfiltered conversation? Buckle up for a raw, hilarious journey through life's unexpected challenges.
Summary
In this electrifying episode, host Siobhan and guest Kirkland dive deep into the messy, beautiful world of living with chronic pain, sobriety, and finding joy. From Kirkland's sickle cell journey to navigating romantic relationships while managing health challenges, this conversation is a masterclass in resilience. They explore everything from trivia hosting adventures to the complexities of modern healthcare, all while maintaining a razor-sharp sense of humor that turns vulnerability into strength.
Kirkland
Kirkland is a trivia host extraordinaire, navigating life with sickle cell while maintaining an infectious enthusiasm for community, performance, and storytelling. He hosts trivia at multiple venues, bringing people together through knowledge and laughter.
💡 Key Takeaways
Chronic pain doesn't define you - it's just part of your story
Sobriety is a journey of self-discovery
Community and humor are powerful healing tools
Adaptability is key to managing unexpected life challenges
Personal boundaries are essential in relationships
"Sometimes all I can say is we had a good time."
~ Kirkland
1619 Project
Project 2025
Designated Survivor (TV show)