If You’re in Your 20s and Feel Behind, Watch This - Jake Caffee opens up.
Sat Feb 07 2026
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Are you happy—or just doing what you’re supposed to do?
Jake Caffee joins David for a raw, reflective conversation about faith, anxiety, identity, and becoming the kind of person you’re proud of.
If this conversation helped you think deeper about who you are and who you’re becoming, follow on Sptofiy so you don’t miss future episodes.
🎟️ Get tickets to our LIVE show – February 28th at the Downtown Austin Public Library 👉 DSNSB.com
In this episode of David’s Saturday Night Sit Back, Jake Caffee opens up about the tension so many young men feel but rarely articulate.
At just 23 years old, Jake is thoughtful, disciplined, and deeply introspective—yet still wrestling with self-doubt, faith, anxiety, and the pressure to “get life right.”
This conversation covers:
Identity beyond job titlesThe chaos of your 20sFaith, religion, and asking hard questionsPerfectionism, fear of failure, and self-beliefRelationships, integrity, and regretWhat really matters when you look back on your lifeThere’s no preaching here. No pretending. Just an honest dialogue about life as it is—and life as it could be.
If this episode resonated with you, David would love to hear your story:
📩 SitBackWithDavid@gmail.com
Support the show
https://www.dsnsb.com/
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Send us a text Are you happy—or just doing what you’re supposed to do? Jake Caffee joins David for a raw, reflective conversation about faith, anxiety, identity, and becoming the kind of person you’re proud of. If this conversation helped you think deeper about who you are and who you’re becoming, follow on Sptofiy so you don’t miss future episodes. 🎟️ Get tickets to our LIVE show – February 28th at the Downtown Austin Public Library 👉 DSNSB.com In this episode of David’s Saturday Night Sit Back, Jake Caffee opens up about the tension so many young men feel but rarely articulate. At just 23 years old, Jake is thoughtful, disciplined, and deeply introspective—yet still wrestling with self-doubt, faith, anxiety, and the pressure to “get life right.” This conversation covers: Identity beyond job titlesThe chaos of your 20sFaith, religion, and asking hard questionsPerfectionism, fear of failure, and self-beliefRelationships, integrity, and regretWhat really matters when you look back on your lifeThere’s no preaching here. No pretending. Just an honest dialogue about life as it is—and life as it could be. If this episode resonated with you, David would love to hear your story: 📩 SitBackWithDavid@gmail.com Support the show https://www.dsnsb.com/