How to Know If You’re Ready to Retire: The 6 Key Checkpoints (Income, Taxes, Risk, and Stress-Testing) | Episode 146 episode artwork

EPISODE · Feb 7, 2026 · 55 MIN

How to Know If You’re Ready to Retire: The 6 Key Checkpoints (Income, Taxes, Risk, and Stress-Testing) | Episode 146

from Safer Retirement Radio · host Brian Decker - Owner and Founder - Decker Retirement Planning

How do you really know if you’re ready to retire—before you turn in your notice? In this episode of Safer Retirement Radio, Brian Decker and Arrin Wray break down the six key checkpoints they use to help families move from guesswork to clarity, including the two questions that matter most: How much can you safely draw each month? How do you protect that income when markets change? You’ll learn how Decker Retirement Planning approaches retirement with a math-based distribution plan that coordinates income sources (Social Security, pensions, rental income, and portfolio withdrawals), prioritizes tax efficiency, and helps reduce the risks that can derail retirement—especially in volatile markets. In this episode, we cover: The 6 key points of a retirement plan: plan, tax minimization, risk reduction, portfolio optimization, income optimization, and fee minimization Why a pie-chart portfolio isn’t a retirement plan (and what a real distribution plan should show) Income needs assessment: how to calculate your retirement “gap” and plan withdrawals over time Planning for healthcare before and after Medicare, plus long-term care considerations What a retirement stress test is, and why it helps “future-proof” your plan A fast rundown of advanced tax strategies discussed on the show (e.g., donor-advised funds, CRTs, NUA, ILITs, dynasty trusts, cost segregation, GRATs), and when they may apply If you’re within 5–10 years of retirement (or already retired), this episode will help you pressure-test your assumptions and understand what it takes to retire with more confidence and fewer surprises. Learn more: DeckerRetirementPlanning.com Schedule a visit / ask a question: 833-707-3030

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