Retire With Purpose - The Retirement Podcast
Casey Weade
Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2026 HOWARD BAILEY FINANCIAL, INC.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and CEO of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2026 HOWARD BAILEY FINANCIAL, INC.
Episodes
Mentioned books
Mar 27, 2026 • 25min
556: By the Numbers: Could the Government Tax Your Roth IRA in the Future? What if Congress Changes the Rules?
They tackle whether Roth IRAs could ever be taxed retroactively or face future rule changes. The conversation compares risks of Roths versus traditional IRAs and explores likely policy shifts like means testing, RMDs, or contribution limits. They highlight recent legislation trends and stress tax diversification as a practical strategy.
13 snips
Mar 20, 2026 • 16min
555: By the Numbers: The Anchors of Retirement Confidence, Part 4 — Building a Retirement That Can't Break
They walk through planning for worst-case retirement scenarios to replace anxiety with clarity. Topics include guaranteed income floors and why they boost spending confidence. They compare income strategies like annuities and bond ladders. Long-term care risk and solutions are explored. Home equity as a last-resort safety net and stacking protection anchors are highlighted.
8 snips
Mar 13, 2026 • 31min
554: Freedom After 50: Why Retirement Fear Might Be a Sign You're Ready
Les McDaniel, a certified retirement coach and financial advisor, explores the psychological side of retiring. He discusses why reaching your retirement number can spark anxiety. Short conversations cover financial independence versus fulfillment. Hear three quick litmus tests to judge retirement readiness and why naming fear can be the first step toward renewed purpose.
11 snips
Mar 9, 2026 • 59min
553: A Step-by-Step Guide to Leverage AI As a Thought Partner & Find Purpose In Retirement with Geoff Woods
Geoff Woods, founder of AI Leadership and author of The AI-Driven Leader, helps organizations use AI to make smarter decisions. He explains AI basics, demos using AI as a thought partner to rediscover purpose, and shares the CRIT prompting framework. Topics include building a personalized AI health coach, privacy controls, balancing AI with professionals, and practical retirement strategies.
5 snips
Mar 6, 2026 • 22min
552: By the Numbers: The Anchors of Retirement Confidence, Part 3 — Why Tax Flexibility Matters More Than Tax Savings
They dig into why surprise taxes can become the biggest retirement risk and how tax concentration limits income flexibility. The three core tax buckets are explained and a one-third/one-third/one-third target is suggested. Learn how Roth accounts create control and why real-life cases sometimes defy textbook advice.
13 snips
Feb 27, 2026 • 18min
551: Freedom After 50: Why Retirement Decisions Feel Heavier — and What to Do About It
Les McDaniel, a certified retirement coach and financial advisor, helps retirees reconnect with intuition and purpose. He explores why decisions feel heavier after 50. Short takes cover how information overload and perfectionism cause paralysis. Practical ideas include filtering noise, trusting practiced instincts, and using simple tools to rebuild confidence.
6 snips
Feb 20, 2026 • 17min
550: By the Numbers: The Anchors of Retirement Confidence, Part 2 — Building a Plan for the Next Market Crash
Marshall Johnson, a CERTIFIED FINANCIAL PLANNER® who shares practical retirement planning perspectives, discusses building plans to withstand market crashes. He talks about why selling in downturns is the real fear. He explains recession buffers, time-based buckets, and separating living money from growth money. Practical strategies aim to replace anxiety with clarity and control.
Feb 13, 2026 • 32min
549: Freedom After 50: The Hidden Link Between Your Money Habits and Your Life
Les McDaniel, a certified retirement coach and financial advisor, explores how investing habits shape life choices beyond money. He discusses using stress as creative fuel, the importance of patience, building a trusted plan, taking the right risks, and margin of safety that protects purpose and relationships in retirement.
Feb 9, 2026 • 1h 2min
548: Conscious Aging: Finding Meaning, Purpose, and Growth in Retirement with Ron Pevny
Ron Pevny, founder of the Center for Conscious Eldering and author focused on intentional aging. He discusses catalysts that led him to eldering, the three-phase transition into elderhood, and why the neutral zone matters. He explores shifting purpose after retirement, identifying signature gifts, and practices and community that sustain meaningful aging.
7 snips
Feb 6, 2026 • 20min
547: By the Numbers: The Anchors of Retirement Confidence, Part 1 — Finding Your Sustainable Spending Range
They break down a flexible spending system that adapts through retirement. They challenge rigid withdrawal rules and promote spending ranges instead of fixed percentages. They explain why small spending adjustments can stabilize outcomes and why many people naturally spend less as they age. They focus on using flexibility and guardrails to turn uncertainty into control.
