The ONE Thing That Creates Change (It’s Not Trauma Healing), with Kassidy Warren

There’s a moment most people reach where they’re no longer confused, uninformed, or unprepared; they’re just hesitant. This episode lives right in that moment.
In this week’s episode, I’m joined by Kassidy Warren, and we go deep into why so many people stay stuck under the idea of “I’m in the process of healing.” We unpack how healing language, self-work, and “doing the inner work” can quietly become a place to stall, especially when real action would require discomfort, risk, or a genuine shift in identity.
Kassidy breaks down why accountability tends to disappear in adulthood, why athletes and high performers understand stakes differently, and how your environment can either stretch you forward or keep you small. We explore the difference between playing it safe and turning pro, why proximity matters more than motivation, and how most people are already standing at the edge of the decision they keep postponing.
If you’ve been telling yourself you’re “working on it,” but nothing in your life has materially changed, this conversation may help you see what’s really going on.
02:30 Why athletes understand accountability differently
04:20 What happens when accountability disappears in adulthood
07:15 Why real change requires stakes
08:45 Investing before results show up
10:40 How your environment shapes your standards
14:45 Why growth often means outgrowing familiar spaces
15:30 The “bucket of crabs” effect and being dragged down
19:38 Spending money to accelerate growth
22:45 Turning pro vs playing it safe
23:40 “What am I pretending not to know?”
About Kassidy
Kassidy Warren is a real estate investor and coach who helps people buy properties that reduce their tax burden, build equity, and create long-term freedom. He previously worked in engineering and IT before leaving corporate life due to burnout. After living in a van with his wife and rebuilding their careers through consulting, they built a portfolio of short-term rentals. Kassidy now leads a mastermind called Escape Velocity, where he supports members through real estate education, community, and mindset work.
Connect with Kassidy
📲 Instagram: @kassidy.warren
💼 LinkedIn: Kassidy Warren
🌐 kassidywarren.com
Stay connected with me
📧 Contact: courtney@smoothmedia.co
👍 Instagram: @slaythegatekeeper
👍 Instagram: @courtlynnjohnson 
💼 LinkedIn: Courtney Johnson
🎶 TikTok: @courtney..johnson