510: Managing Investment Risk When You've Already Won The Game with William Bernstein
Retire With Purpose - The Retirement Podcast
Release Date: 07/14/2025
Retire With Purpose - The Retirement Podcast
Gold has been surging lately, but is it truly a golden opportunity for retirees, or just another glittering distraction? Join us as we break down what’s really driving gold’s rise, explore its role as a diversification tool, and reveal what the data says about whether it deserves a spot in your portfolio. In this episode, we discuss: Gold’s big run Historical data of gold vs. equity returns Inflation confusion Central banks’ role How to diversify and own gold wisely Today's article is from the Of Dollars and Data titled, . Listen in as Founder and CEO of ,...
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Could striving for the “perfect” portfolio be holding you back from the fulfilling, financially confident life you’ve worked so hard for? Join us as we explore why embracing a “good enough” mindset can lead to greater happiness, balance, and confidence in retirement. In this episode, we discuss: The myth of the “perfect” portfolio Satisficers vs. Maximizers The Boglehead Paradox Your life’s “cups” of energy Today's article is from the Morningstar titled, . Listen in as Founder and CEO of , Casey Weade, breaks down...
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Today, I’m speaking with David McKnight. David is a best-selling author, world-renowned tax strategist, and financial educator who challenges some of the most popular (and misleading) retirement gurus and influencers in the financial advice space. He’s also a great friend, and beloved guest on the show and I’m excited to welcome him back for a 3rd time on the podcast. David is well known as the author of The Power of Zero which was made into a full-length documentary film. In his latest book, The Guru Gap, he exposes why one-size-fits-all financial guidance from so-called experts often...
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Discover what new research reveals about how retirees actually spend their money — and why front-loading your retirement income plan could be the key to enjoying your healthiest, most fulfilling years first. In this episode, we discuss: Pitfalls of traditional retirement income plans What to know about the “retirement spending smile” Spending regret factors for retirees Health and longevity perceptions Today's article is from the ThinkAdvisor titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful...
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What if the key to a fulfilling retirement isn’t about relaxation — but about doing the hard things you’d rather avoid? From rewiring your brain to deepening your sense of purpose, discover how challenges — big or small — can restore meaning, resilience, and joy in your next chapter of life. In this episode, we discuss: Why comfort can erode resilience How to leverage “controlled challenges” Ways ancient wisdom encourages (positive) discomfort Freedom vs. discipline in retirement Today's article is from The Net Worthwhile® Weekly titled, . Listen in as Founder...
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What’s really holding you back from taking that next financial step? Join us as we explore how avoidance slowly erodes confidence, why shame and fear create roadblocks, and how to replace procrastination with purposeful progress. In this episode, we discuss: Why avoidance = erosion, not explosion The Hurricane vs. Tornado analogy How to conduct a “Shame Audit” Why small steps can create big financial changes Today's article is from the Money Changes Everything titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides...
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The belief that more data equals more control is an illusion. Our obsession with finding the “perfect” financial plan and receiving constant information often leads to anxiety, not peace. Join us as we explore why embracing uncertainty, focusing on what you can control, and leading with purpose can help create true financial (and emotional) freedom. In this episode, we discuss: How to balance control with surrender The pitfalls of too much information Dangers of financial fundamentalism How to go from analysis to action Today's article is from The Net...
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Today, I’m speaking with Edward McQuarrie. Ed is the Professor Emeritus at Santa Clara University, where he taught in the marketing department for more than three decades before retiring in 2016. After stepping away from teaching, Ed pursued a new passion in researching financial market history and retirement income planning. His work has been featured in the Wall Street Journal, MarketWatch, and Barron’s, and he frequently contributes to our Weekend Reading for Retirees series. He was introduced to us by past guest William Bernstein, who insisted Ed would be a must-hear voice on the...
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What if the common advice to wait until age 70 for Social Security isn’t always the best move? Could claiming earlier actually give you more freedom and peace of mind in retirement? In this episode, we discuss: Risks of “blanketed” Social Security advice Determining your expected value vs. expected utility Mortality, sequence of returns, and policy risks Pinpointing your “personalized discount rate” Today's article is from the Kitces.com blog titled, . Listen in as Founder and CEO of , Casey Weade, breaks down the article and provides thoughtful...
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Retirement is about more than finances — it’s about meaning and growth. Join us as we explore common “belief traps” that can hold you back, how to reframe your story, and expand what’s possible in the years ahead. In this episode, we discuss: How the echo chamber and certainty traps limit perspective and growth Why the comfort trap keeps you stuck — and how to break free The danger of the perfection and irrelevance traps in later life A powerful exercise to reframe your time horizon and live with greater purpose Today's article is from our own blog titled . Listen in...
info_outlineToday, I'm speaking with William Bernstein. Bill is a renowned investment advisor, author, and retired neurologist. He's the co-founder of Efficient Frontier Advisors, a leading voice in the world of personal finance, and the author of several acclaimed books, including The Four Pillars of Investing, The Investor's Manifesto, and The Intelligent Asset Allocator.
With a unique background in neurology and finance, Bill brings a practical and evidence-based perspective to long-term investing, risk management, and financial behavior—especially for retirees and those nearing retirement. You'll hear why Bill believes the purpose of money isn't to buy things—it's to purchase autonomy, time, and peace of mind.
In our conversation, we explore what it really means to "win the game" of investing—and why continuing to play after you've won could jeopardize your retirement security. Bill breaks down the risks investors often overlook, including deep risk versus shallow risk, the need versus capacity and tolerance framework, and why having a basic understanding of financial history is an underrated skill set.
They also discuss how aging affects investment decisions, how burn rate should influence equity allocation, and why a purposeful retirement plan extends far beyond growing net worth.
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In this podcast interview, you’ll learn:
- Why investors should reduce risk once they've “won the game”—and what that means in real terms.
- The critical differences between deep risk and shallow risk, and how to guard against both.
- How age and withdrawal rate should shape your stock-to-bond ratio in retirement.
- Why Treasury Inflation-Protected Securities (TIPS) can play a key role in risk management.
- The emotional traps investors fall into—and why historical financial knowledge is a great asset.
- What purpose in retirement really looks like—and why forging connections may be more valuable than money.
Show Notes: HowardBailey.com/510
📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu
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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