Smart Money Questions

Roth vs. Pre‑Tax 401(k) in Your 50s & 60s: How to Maximize Retirement Income

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In this episode, Matt tackles one of the biggest tax decisions that retirees face: Roth or pre-tax? It’s not just about today’s tax bill. It’s about future flexibility, income planning, and how your choices ripple through the rest of your financial life. Using real-world scenarios and practical strategies, Matt walks through when each approach might make sense, and when it might not.
Here’s some of what we discuss in this episode:
📅 Scheduling Matters – Timing your moves
💰 Roth vs. Pre-Tax – Taxes now or later
📊 Case Studies – Real-world tax strategies
📉 Market Fear – Planning beyond volatility
📞 Next Steps – Getting personalized guidance
 
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Smart Investment Moves Heading Into 2026

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A new year brings no shortage of market opinions and plenty of noise. Matt shares a grounded perspective on how to think about investing as 2026 takes shape, with an emphasis on preparation over prediction. This episode covers several long-term planning decisions that often get overlooked by pre-retirees and retirees. Tired of reacting to headlines? Tune in for a more thoughtful approach in 2026.
Here’s some of what we discuss in this episode:
📊 2026 Investment Strategy: What to prioritize heading into the year
📈 Market Trends & Expectations: Why diversification still matters
🧾 Tax Planning Lens: Deductions and timing that affect outcomes
💼 Retirement Contributions: Making the most of workplace plans
🏛️ Estate & Legacy Planning: Preparing assets for efficient transfer
 
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Personal Estate Planning Stories: What Your Heirs Will Actually Face

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What if everything you thought you'd set up to protect your family turned out to be a maze of red tape and frustration? In this episode, discover the hidden roadblocks that can derail even the most carefully planned estates, as Matt reveals the eye-opening reality facing heirs in 2025, where paperwork alone isn't enough, and the real challenges begin after you're gone.
Here’s some of what we discuss in this episode:
📆 2025 Review: estate planning lessons from a volatile year
🧾 Tax Strategy: how taxes shape investment decisions
⚠️ Disclaimers: know the difference between education and personal “advice”
📑 Estate Challenges: delays and confusion in distributions
🏦 Bank Experiences: inconsistent and frustrating processes you may face
🔍 Institution Rules: protocols to know before it’s too late
 
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The Smart 2025 Year-End Money Review

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As the year wraps up, it’s the perfect chance to step back and make sure your financial plan is aligned, optimized, and ready for the year ahead. Matt highlights key areas worth reviewing before the calendar turns, and what can happen if we don’t. Year-end planning doesn’t have to be overwhelming. A few intentional steps now can create more clarity and confidence moving forward.
Here’s some of what we discuss in this episode:
🗓️ Year-end planning & tax strategies: reviewing contributions, deductions, and opportunities
💼 Retirement contributions & Roth components: maximizing what goes into qualified accounts
🎁 Charitable contributions: using tax-advantaged moves before 12/31
📊 Investment rebalancing: aligning your portfolio with your retirement timeline
📜 Legacy & estate planning: ensuring documents, beneficiaries, and structures match your goals
 
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The Hidden Power of Tax Diversification

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Most people diversify their investments but forget to diversify their taxes. Today, Matt explains why tax diversification is one of the most powerful tools for retirees and how it can dramatically improve the longevity of your money. He shares a real client story that proves smart tax strategy means bigger savings and fewer headaches. Discover why tax diversification could be your most powerful tool for building a resilient retirement plan.
Here’s some of what we discuss in this episode:
🏛️ Government Shutdown & Market Impact: how politics affect investor confidence
👥 New Client Case Study: real-world example of tax-smart planning
💡 Tax Efficiency & Investment Strategies: balancing growth and taxes for flexibility
🕰️ Social Security Timing: understanding benefits and income strategy
🧾 Action Step: review your mix of accounts and adjust for future flexibility
 
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How Much Should I Be Saving?

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“How much should I be saving?” It’s one of the most common financial questions, and the answer isn’t always simple.
The right saving strategy depends on your income, debt, lifestyle, and long-term goals. In this episode, Matt shares the framework he uses with clients of all ages to answer this timeless question. No matter your age or stage of life, the real first step is knowing where your money’s going.
Here’s some of what we discuss in this episode:
💵 How to segment cash flow into essentials, lifestyle, and bucket list goals
🏦 The role of 401(k)s, Roth accounts, HSAs, and brokerage accounts in saving
📝 Estate planning non-negotiables
👨‍👩‍👧 Saving for your kids (including a 529 plan and brokerage accounts)   
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What Are You Saving For?

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Do you know the real purpose behind your savings? Money isn’t the end goal, it’s the tool that helps you build the life you want. In this episode, Matt asks a deceptively simple but powerful question: What are you really saving for? Instead of focusing only on numbers, taxes, and investments, Matt explores the deeper purpose behind our financial decisions. Are you facing a major life transition? Defining your purpose is just as critical as planning your finances.
Here’s some of what we discuss in this episode:
✨ Why your ‘why’ matters more than your balance
🏡 Deciding if a continuing care community is right for you
📊 The Roth mistake most savers don’t realize they’re making
🧭 Finding purpose in retirement beyond the numbers
🎯 Aligning your money with real life goals
 
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Tax Changes, Roth Moves & Renting in Retirement

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What does the newly signed One Big Beautiful Bill (BBB) really mean for your taxes and your future? In this episode of Smart Money Questions, we will explain the most important tax changes in simple terms. From extended tax brackets to new deductions for seniors and enhancements to charitable giving, we’ll tell you what’s permanent (for now), what phases out, and what it all means for retirement planning.
Here’s some of what we discuss in this episode:
📉 Current tax brackets extended—no 2026 “sunset” (for now)🧓 New $6K deduction per person over 65📦 SALT deduction cap raised from $10K to $40K💸 Charitable deduction now allowed even if you don’t itemize🏡 Selling the house and renting? Matt breaks down the pros, cons, and planning points
 
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The Big Beautiful Bill: What It Really Means for Your Taxes

What’s all the buzz about the “Big Beautiful Bill?” With many current tax provisions set to expire at the end of the year, there’s a lot of noise, but very little that’s finalized. Matt walks through the latest version of the Senate proposal, what it could mean for taxpayers, and why the only smart move right now is to stay informed and stay patient.
He also highlights a thought-provoking article from The Wall Street Journal that shows how politics are increasingly influencing investment behavior- and not in a good way.
 
Here’s some of what we discuss in this episode:
🔍 What’s the latest on the “Big Beautiful Bill”?
🧠 How political bias can affect your portfolio
⏳ The massive difference just missing a few market days can make
🛡️ Why discipline is the investor’s secret weapon
 
Fidelity: Staying Invested
https://drive.google.com/file/d/158uFN5GlF5ieaQRhQF-sSWo2EwSJHRoJ/view?usp=sharing
 
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What Should You Actually Do When the Market Drops?

The headlines are loud, the markets are messy, and your gut might be telling you to do something., anything, right now. But what should you actually do when your portfolio takes a hit? In this episode, Matt talks about recent market volatility and reminds listeners why reacting emotionally can cost more than staying the course. He shares stories from client conversations during the dip, explains the dangers of market timing, and reveals just how much the media benefits from our panic.
Here’s some of what we discuss in this episode:
📉 Why bad news spreads faster and hits harder
🧠 The real cost of reacting emotionally to market drops
🏠 Common estate transfer mistakes that hurt your heirs
📊 Why diversification (not timing) still wins
💰 How the media profits from your fear
 
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Want to work with us? Find out how we can help: https://smartmoneyquestions.com/work-with-matt/