545: By the Numbers: Our 2026 Market Predictions
Retire With Purpose - The Retirement Podcast
Release Date: 01/23/2026
546: Freedom After 50: How to Stay Grounded When the Future Feels Unknown
Retire With Purpose - The Retirement Podcast
What if the key to a calmer, more meaningful retirement isn’t having all the answers, but learning how to trust yourself when you don’t? In this episode, we discuss: Why retirement feels more uncertain than working life How identity shifts after 50 can create anxiety What’s true vs. what’s just loud How to focus on what you can control — in life and money A 4-step practice to calm fear and regain clarity Today's article is from our very own blog titled, . Listen in as Founder and CEO of , Casey Weade is joined by...
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545: By the Numbers: Our 2026 Market Predictions
Retire With Purpose - The Retirement Podcast
Will 2026 deliver another strong bull-market year — or a long-overdue reality check as AI, market valuations, and global shifts collide? In this episode, we discuss: 2026 S&P 500 predictions (15.2% vs. 6.7%) AI’s explosive growth The Magnificent Seven’s shrinking dominance Why equal-weighted investing reduces volatility Why bonds, gold, and diversification matter again How pre-retirees can protect gains while staying invested Today's article is from Kitces.com titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and...
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544: Freedom After 50: Are You Living for Your Resume—or Your Eulogy?
Retire With Purpose - The Retirement Podcast
What if the real measure of a successful retirement isn’t what you’ve built, but who you’ve been, and how your money supports the life you want to be remembered for? In this episode, we discuss: Resume virtues vs. eulogy virtues Why many retirees feel “lost” after achieving everything they worked for How purpose changes the way you think about money, work, and time Using financial planning to create freedom, not pressure Redefining identity, success, and legacy after 50 Today's article is from The Root of All titled, . Listen in...
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543: The Stress Paradox: Why the Right Kind of Stress Helps You Thrive in Retirement with Dr. Sharon Bergquist, MD
Retire With Purpose - The Retirement Podcast
Today, I’m excited to welcome Dr. Sharon Bergquist to the podcast. Sharon is a board-certified physician, research scientist, founder of Emory Lifestyle Medicine & Wellness, and an internationally recognized leader in lifestyle medicine. She has led or co-led over a dozen clinical trials that have received $61 million in funding to evaluate lifestyle interventions and identify early biomarkers for chronic disease, including ongoing studies for early detection of Alzheimer’s disease and cancer. Her work is at the forefront of how we understand the role of stress and resilience on...
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542: By the Numbers: From Fear to Freedom — Learning How to Spend in Retirement
Retire With Purpose - The Retirement Podcast
You saved diligently for decades — so why does giving yourself permission to spend still feel so hard? In this episode, we discuss: Why many retirees underspend despite having a secure financial plan Emotional and psychological barriers to spending How lifelong, “saver” habits impact retirement decisions Low-risk strategies to help build spending confidence Today's article is from the Kitces blog titled, Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique...
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541: Your 2026 Reset: The Best of the Retire With Purpose Podcast
Retire With Purpose - The Retirement Podcast
What can our top five Retire With Purpose Podcast episodes of 2025 teach you about avoiding regrets, spending confidently, and living with purpose as you head into 2026? In this episode, we discuss: The most common retirement regrets How to generate flexible, reliable income in retirement The Surplus Bucket Strategy and why it can help spending confidence How to understand your level of retirement readiness Why delaying joy can come at a higher cost than you think Listen in as Founder and CEO of , Casey Weade kicks off the new year with a "Best Of" episode to reflect on the...
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540: Freedom After 50: The Quiet Fear Beneath Retirement (and How to Outsmart It)
Retire With Purpose - The Retirement Podcast
If retirement is supposed to bring freedom, why do so many people still feel unsettled, and what’s behind that tension? In this episode, we discuss: Why fear persists even with a strong financial plan Dangers of letting the news cycle shape your outlook Why retirees often search for a “true sage” — and why that search fails The “Yada” reflective framework and techniques for cultivating presence, peace, and self-awareness Today's article is from our very own blog titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore...
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539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
Retire With Purpose - The Retirement Podcast
Could a counterintuitive tax move today potentially lead to thousands in savings — or an unexpected tax trap tomorrow? In this episode, we discuss: Why some retirees intentionally harvest capital gains How the 0% bracket really works When it may make sense to pay capital gains taxes now How to evaluate tax gain harvesting vs. Roth conversions using long-term projections Key tax-planning windows before Social Security, RMDs, and spousal filing changes Today's article is from the Best Interest blog titled, Listen in as Founder and CEO of , Casey Weade, breaks down...
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538: Freedom After 50: Why Enough Is a Mindset, Not a Number
Retire With Purpose - The Retirement Podcast
What if the biggest obstacle to a joyful retirement isn’t your money — but the belief that you never have enough of it? In this episode, we discuss: Why “having enough” is both a financial and emotional question When saving “too well” creates new problems The FIRE movement cautionary tale The role of curiosity, creativity, and craft in a purposeful retirement Today's article is from The Root of All titled, . Listen in as Founder and CEO of , Casey Weade is joined by Les McDaniel to explore the emotional side of financial security, the pitfalls of oversaving, and...
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537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert
Retire With Purpose - The Retirement Podcast
Today, I’m thrilled to welcome Fritz Gilbert back for his second appearance on the podcast. Fritz is an award-winning blogger and author of The Retirement Manifesto, one of the most influential retirement blogs in the country. He has now been retired for six years, and while many people think the big transition ends the day you leave the workforce, Fritz’s journey proves that retirement continues to evolve in meaningful, surprising, and deeply personal ways. Recently, he announced he is stepping away from full-time blogging to spend more of his life “outside the walls,” shifting his...
info_outlineWill 2026 deliver another strong bull-market year — or a long-overdue reality check as AI, market valuations, and global shifts collide?
In this episode, we discuss:
- 2026 S&P 500 predictions (15.2% vs. 6.7%)
- AI’s explosive growth
- The Magnificent Seven’s shrinking dominance
- Why equal-weighted investing reduces volatility
- Why bonds, gold, and diversification matter again
- How pre-retirees can protect gains while staying invested
Today's article is from Kitces.com titled, 10 Charts To Help Explain The 2026 Market To Clients. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation.
Show Notes: HowardBailey.com/545
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ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process