The Uncertainty E.D.G.E. Podcast explores what judgment looks like in practice when certainty is impossible.
I am a judgment guide. I help people act when the stakes are real, tradeoffs are unavoidable, and certainty isn’t coming. My value is not tactical insights, prediction, or optimization. It is guiding people to build their capacity for judgment under uncertainty.
Each episode examines a real decision moment—where real outcomes, real people, and real tradeoffs were at stake. Rather than focusing on outcomes or hindsight explanations, the conversations stay close to the decision itself: what could not be known at the time, what pressures were present, and how judgment was exercised without guarantees.
This is not a podcast about best practices, leadership slogans, or forecasting the future. It is about how people responsible for consequential decisions actually decide when responsibility can’t be delegated and waiting for clarity is itself a risk.
The podcast is for people accountable for decisions that matter—often without full control or authority—who must act with clarity and judgment when certainty is impossible.
Listeners might be interested in The Uncertainty E.D.G.E. newsletter as well. Check out at www.theuncertaintyedge.com. Hosted by Sam Sivarajan.
The Uncertainty E.D.G.E. Podcast explores what judgment looks like in practice when certainty is impossible.
I am a judgment guide. I help people act when the stakes are real, tradeoffs are unavoidable, and certainty isn’t coming. My value is not tactical insights, prediction, or optimization. It is guiding people to build their capacity for judgment under uncertainty.
Each episode examines a real decision moment—where real outcomes, real people, and real tradeoffs were at stake. Rather than focusing on outcomes or hindsight explanations, the conversations stay close to the decision itself: what could not be known at the time, what pressures were present, and how judgment was exercised without guarantees.
This is not a podcast about best practices, leadership slogans, or forecasting the future. It is about how people responsible for consequential decisions actually decide when responsibility can’t be delegated and waiting for clarity is itself a risk.
The podcast is for people accountable for decisions that matter—often without full control or authority—who must act with clarity and judgment when certainty is impossible.
Listeners might be interested in The Uncertainty E.D.G.E. newsletter as well. Check out at www.theuncertaintyedge.com. Hosted by Sam Sivarajan.
Episode Overview
In this episode of The Future-Ready Advisor, host Sam Sivarajan sits down with John Kailunas, a wealth advisor, author, and retirement mentor who brings a fresh perspective to one of life's most important transitions. John has spent decades helping clients build, preserve, and transition wealth, but noticed a troubling pattern: clients who had all the financial pieces in place were still floundering in retirement.
They discuss the emotional and psychological aspects of retirement planning often overlooked by advisors, the importance of having purpose beyond financial security, and how advisors can evolve their practice to meet clients' deeper needs. John shares powerful client stories and practical insights from his book Mission Retirement, offering a roadmap for creating fulfilling post-career chapters.
Key Quote
"All money does is give you liberty. The art is how you make people feel and how you leave them." --- John Kailunas
Key Takeaways
Sound Bites
Topics Discussed
01:09 -- The Importance of Purpose in Retirement 05:59 -- Planning for a Fulfilling Retirement
10:05 -- The Consequences of Lack of Purpose 16:01 -- The Evolving Role of Financial Advisors 20:26 -- The Importance of Small Steps in Retirement Planning
Resources Mentioned
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