The 10 Questions You Must Ask Before You Retire episode artwork

EPISODE · Jan 17, 2026 · 43 MIN

The 10 Questions You Must Ask Before You Retire

from Safe Money Radio with Brad Pistole · host Brad Pistole

Most people picture retirement as endless Saturdays, but the real question is what those Saturdays look like and how you’ll pay for them. We take you through the ten questions that shape a confident future: how to define your daily purpose, where to live without inflating costs, how much income you truly need, and how to build an income floor that stands up to market swings. Along the way, we dig into Social Security timing strategies, the sequence of returns risk, and why annuities with lifetime income riders can secure essentials while freeing your investments to grow.We also tackle the hidden budget breakers: health care and taxes. Medicare leaves gaps, so we walk through Medigap vs. Medicare Advantage, drug coverage, and long-term care options that keep your choices open. Then we shine a light on the “stealth debt” in tax-deferred accounts. Required minimum distributions, IRMAA surcharges, and Social Security taxation can erode cash flow unless you plan ahead. Thoughtful Roth conversions can cut lifetime taxes and protect surviving spouses and heirs.Rounding it out, we cover the must-do estate checklist—wills, powers of attorney, health directives, and those often-missed beneficiary forms on bank and retirement accounts—and the emotional side of retiring. If work has been your identity and rhythm, a phased transition or purpose-driven plan helps you avoid the post-retirement slump. Ready to turn uncertainty into a plan you trust? Subscribe, share this with someone who’s five to ten years from retirement, and leave a review with the question you’re wrestling with most. Need help now? Visit Ozarksretirement.com and click Contact Us for a free financial consultation.Send us Fan MailTo learn more about Brad Pistole and the Ozark Retirement Group, please visit www.ozarksretirement.com 

Most people picture retirement as endless Saturdays, but the real question is what those Saturdays look like and how you’ll pay for them. We take you through the ten questions that shape a confident future: how to define your daily purpose, where to live without inflating costs, how much income you truly need, and how to build an income floor that stands up to market swings. Along the way, we dig into Social Security timing strategies, the sequence of returns risk, and why annuities with life...

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The 10 Questions You Must Ask Before You Retire

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Frequently Asked Questions

How long is this episode of Safe Money Radio with Brad Pistole?

This episode is 43 minutes long.

When was this Safe Money Radio with Brad Pistole episode published?

This episode was published on January 17, 2026.

What is this episode about?

Most people picture retirement as endless Saturdays, but the real question is what those Saturdays look like and how you’ll pay for them. We take you through the ten questions that shape a confident future: how to define your daily purpose, where to...

Is there a transcript available for this episode?

Yes, a full transcript is available for this episode. You can read the complete transcript on the episode page.

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