Your Social Security Playbook: How the System Works

From Retirement Answer Man by Roger Whitney, CFP®, CIMA®, RMA, CPWA®

September 2, 2026 · 55 min · Episode 659

About this episode

Roger Whitney begins a five-week series on building a Social Security playbook, discussing its history, funding, and future outlook.

Social Security is one of the most important pieces of a retirement plan, but how does the system work, and will it remain financially viable for future retirees? Roger begins a five-week series on building your Social Security playbook by exploring the program’s history, funding structure, and current financial outlook. He also discusses potential paths to solvency, how he accounts for Social Security in retirement planning, and why building a resilient plan remains essential. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN [00:00] Roger introduces a new five-week series designed to help you build your Social Security playbook. [01:37] The Retirement Answer Man YouTube channel is relaunching with weekly videos that complement the podcast. PRACTICAL PLANNING SEGMENT [02:35] Roger outlines the five-week Social Security series and explains what you need to understand to build your own playbook. [05:02] A brief history of Social Security provides context for how the program and its purpose have evolved. [08:18] Roger explains how today’s workers fund benefits for today’s retirees through payroll taxes. [11:58] Demographic changes and longer lifespans have caused benefit…

People in this episode

Host: Roger Whitney

Topics covered

Social Security
retirement planning
financial viability
funding structure
solvency paths

Keywords

Social Security
retirement
financial planning
payroll taxes
solvency

Mentioned in this episode

Organizations: Social Security, Retirement Answer Man