New Lens
houseChris Maggio Oct 5, 2025

Timing the Market: A New Lens for an Evolving Era

The S&P 500 is up 15.19% YTD through October 3rd. If you've been sitting on the sidelines waiting for better conditions or lower valuations, it's time for honest reflection. This post explores why traditional market-timing frameworks may no longer apply in an era where technology is fundamentally reshaping business economics. Drawing on insights from Jim Paulsen's "Fear Asset" thesis and Joseph Shaposhnik's framework for identifying decade-long compounders, I make the case that today's dominant tech companies aren't just momentum trades. They're businesses with structural advantages that justify their continued outperformance. The greatest risk may not be overvaluation, but sitting out a generational shift because you're measuring it with yesterday's yardsticks.

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Revisiting Buffered ETF - Capital Preservation
houseChris Maggio Sep 15, 2025

When Buffered ETFs Make Perfect Sense - The Capital Preservation Strategy

After publishing my original analysis highlighting the drawbacks of buffered ETFs, I realized I missed a crucial perspective: these products can be invaluable for investors approaching or in retirement who need to manage sequence of returns risk and preserve capital. Whether you're a near-retiree who can't afford a market crash to derail your retirement timeline, a new retiree navigating the dangerous first decade when portfolio withdrawals amplify market volatility, or an overfunded retiree who has "won the game" and prioritizes capital preservation over growth, buffered ETFs offer a compelling solution. By providing downside protection while maintaining equity upside participation, these products address the specific needs of investors transitioning from wealth accumulation to wealth preservation—even if that means accepting capped gains in exchange for peace of mind during life's most financially vulnerable periods.

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Sign - One Life Live It
houseChris Maggio Sep 1, 2025

Don't Wait for Retirement to Start Living: The Power of Income-Funded Happiness

Stop deferring all your happiness until retirement. Your current income is a powerful tool that allows you to enjoy life strategically while still building financial security. Because working longer dramatically improves retirement outcomes through increased savings, delayed withdrawals, and higher Social Security benefits, you can afford to spend thoughtfully on experiences and joy today. Instead of viewing work as pure sacrifice, use your steady paycheck to fund meaningful experiences that make the daily grind more bearable and working longer feel like a choice rather than a burden. The most successful retirement strategy isn't about how much you save, but how well you live along the way.

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It's all about location
houseChris Maggio Aug 5, 2025

The Hidden Tax Strategy That Could Save You Thousands Every Year

Most investors focus on WHAT to buy, but the smartest ones also focus on WHERE to buy it. Asset location—strategically placing investments in taxable, tax-deferred, or tax-free accounts—can save you thousands in taxes every year. It's the difference between paying your ordinary income tax rate on bond interest versus 0% in a Roth IRA. The strategy is simple: Put tax-inefficient investments (bonds, actively managed funds) in sheltered accounts, and keep tax-efficient investments (index funds, individual stocks) in taxable accounts. Small moves, big impact. Your portfolio's location matters just as much as its allocation.

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Employees
houseChris Maggio Jul 24, 2025

ESPP Strategy: The Smart Way to Lock in Guaranteed Returns

If your company offers an Employee Stock Purchase Plan (ESPP), you might be missing out on one of the few guaranteed returns available in today's market. Most employees either skip their ESPP entirely or follow the traditional buy-and-hold approach, but there's a smarter strategy that can deliver consistent 18% pre-tax gains while actually reducing your financial risk. The secret? Sell immediately after purchase to lock in the discount, then use those guaranteed returns to build diversified wealth that's independent of your employer's success. Ready to turn your employee benefits into a strategic wealth-building tool?

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Roth Conversions
houseChris Maggio May 27, 2025

Roth Conversions: Are They the Right Move for You?

Thinking about a Roth conversion? This guide breaks down exactly how they work, when they make sense (and when they don't), and crucial tips for navigating the process and taxes.

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Two men playing chess
houseChris Maggio May 9, 2025

Retirement Income Strategies: Finding Your "Perfect" Approach

Planning your retirement income is a significant step, and understanding your options is key to a confident future. This post explores four popular retirement income strategies: the widely discussed 4% Rule and its adaptations, the organized Bucketing approach, the foundational Safety-First method, and the market-sensitive Bond Tent. By clearly outlining how each strategy functions, alongside their respective advantages and disadvantages, this guide aims to empower you to make informed decisions for a secure and fulfilling retirement.

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Capital Gains Tax on post-it
houseChris Maggio May 1, 2025

Beware of Capital Gains: Why ETFs Could Save You Thousands More Than Mutual Funds

Discover how choosing ETFs over mutual funds could save you thousands in taxes! In this practical guide, I break down the real tax differences between these popular investment vehicles and show you exactly how much money you could keep in your pocket. Plus, learn four actionable strategies to make your investment portfolio more tax-efficient starting today. Your future (and your wallet) will thank you!

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HSA - Health Savings Account
houseChris Maggio Apr 24, 2025

Unlocking the Secret Power of Your HSA: The Ultimate Triple-Tax-Advantaged Retirement Tool

Discover how your Health Savings Account can be more than just a medical expense fund. This article reveals the "stealth retirement account" strategy that leverages the HSA's unique triple tax advantage—tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified expenses. Learn the five-step process to transform your HSA into a powerful retirement tool, including maximizing contributions, paying current medical expenses out-of-pocket, and saving receipts for future tax-free reimbursements. The post also covers additional retirement benefits like Medicare premium payments and addresses inheritance considerations. Whether you're just starting your HSA journey or looking to optimize an existing account, this guide provides actionable steps to unlock your HSA's full potential as a cornerstone of retirement planning.

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Market Downturns
houseChris Maggio Apr 5, 2025

Buffered ETFs: Downside Protection at What Cost? Do They Fit in Your Strategy?

Thinking about buffered ETFs for portfolio protection? This overview examines what these investment vehicles really offer. We explore their benefits and significant limitations, and why traditional bonds might provide better downside protection without the drawbacks. Learn whether the promise of limited losses justifies capped gains, higher fees, and complex timing requirements before adding these instruments to your investment strategy.

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Woman trying to decide to rollover or not to rollover 401(k)
houseChris Maggio Apr 1, 2025

401(k) Rollover Guide: Should You Stay or Should You Roll?

Facing the critical decision of what to do with your 401(k) after leaving an employer? This guide walks you through the two main options—keeping your retirement savings with your former employer or rolling them over to an IRA—with a detailed breakdown of the pros and cons of each approach. From creditor protection and loan options to investment flexibility and tax considerations, you'll learn about key factors that should influence your decision, including important concepts like Net Unrealized Appreciation (NUA) strategies and the pro-rata rule. Whether you're concerned about fees, investment options, account consolidation, or tax implications, this practical guide provides the essential information you need to make the right choice for your unique financial situation, along with step-by-step instructions for completing a rollover if that's the path you choose.

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Is time running out on social security?
houseChris Maggio Mar 26, 2025

Will Social Security ‘Run Out’? Social Security's Future: Understanding the Projected 2035 Trust Fund Depletion

Understand the truth about Social Security's future. We break down the 2035 trust fund depletion, recent legislative changes, and offer practical tips for your retirement planning.

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Senior Scams
houseChris Maggio Mar 17, 2025

Protecting Our Seniors: Recognizing and Preventing Modern Scams

In today's digital age, protecting our seniors from scams is more critical than ever. This post delves into the alarming rise of modern scams targeting seniors, exploring why they're particularly vulnerable and the devastating impact these crimes have. From urgent financial demands via text to sophisticated AI-generated deceptions, we'll uncover the most common tactics used by fraudsters. But it's not all doom and gloom. You'll also find a comprehensive guidance with practical steps to safeguard yourself and your loved ones, including communication safety tips, digital vigilance strategies, and personal protection practices. Empower yourself with knowledge and learn how to recognize and prevent these scams, helping our seniors enjoy their golden years with security and peace of mind. Plus, find essential resources for scam victims. Don't let your loved ones become a target – read on to stay informed and protected.

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Claiming Decisions
houseChris Maggio Mar 10, 2025

The Truth About Social Security Claiming Strategies: A Personalized Approach

Navigating Social Security claiming can feel like deciphering a complex puzzle. Should you claim at 62, wait until 70, or opt for the middle ground at your Full Retirement Age? Forget the one-size-fits-all advice! This post cuts through the noise and delves into the truth: your optimal claiming strategy depends entirely on your unique circumstances. We'll break down the basics, from understanding your Primary Insurance Amount to the impact of early and delayed claiming, and explore the pros and cons of each approach. More importantly, we'll guide you through the crucial factors to consider – your financial needs, health outlook, family situation, and retirement goals. Discover real-life scenarios that illustrate how to personalize your decision, and learn where to find expert help. Don't let generic advice dictate your retirement; empower yourself with the knowledge to make an informed, personalized Social Security claiming decision that maximizes your security and peace of mind.

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Financial Advisor Fee Models
houseChris Maggio Mar 5, 2025

Flat-Fee, Hourly, or AUM: Which Financial Advisor Model Is Right for You?

Beyond AUM: Explore the rising popularity of flat-fee and hourly financial advisors. Discover which model offers the best value and transparency for your unique financial situation.

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Young Professionals
houseChris Maggio Feb 12, 2025

Understanding Your Workplace Retirement Plans: A Quick Guide for Young Professionals

Demystify workplace retirement plans like 401(k)s and 403(b)s with this quick guide designed for young professionals. Learn why understanding your options matters, how to maximize employer matches, and why starting early with low-cost index funds can significantly impact your financial future. Take control of your retirement today and build a solid foundation for long-term financial security.

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Target Date Funds
houseChris Maggio Jan 14, 2025

Target Date Funds: When Do They Make Sense for Your Investment Strategy?

Discover when target date funds make sense for your investment strategy, and when younger investors might benefit from alternatives. Learn about fees, automation, and finding the right fit for your goals.

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Multigenerational Family Vacation
houseChris Maggio Jan 6, 2025

Living Legacy: Integrating Legacy Planning into Your Retirement Strategy | Die with Zero Philosophy

Explore how a family's philosophy of intentional wealth sharing aligns with the principles of "Die with Zero," emphasizing impactful giving and shared experiences over traditional wealth accumulation.

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