David Conti has spent decades writing about retirement, Social Security, Medicare, and personal finance. After helping others prepare for retirement throughout his career—including his time at Fidelity Investments—he reached an important milestone himself: turning 65. That experience gave him a new perspective on what retirement looks and feels like when the advice you've shared for years becomes your own reality.

Jeremy and David explore the lessons that surprised him most, including why retirement is about more than financial independence, the importance of keeping your investment strategy simple, navigating Medicare after enrolling for the first time, preparing emotionally for retirement, creating multiple streams of income, and finding greater purpose through charitable giving. David also shares why he believes everyone should "practice retirement" before leaving work and why taking time to reset may be one of the smartest retirement decisions you can make.

Whether you're five years from retirement or already making the transition, this conversation offers practical lessons from someone who has spent a career studying retirement—and is now living it himself.

For disclosures and conflicts visit keilfp.com/disclosures.