The Wise Money Show™

Small mistakes early in retirement can quietly derail even the best financial plan. In this episode of The Wise Money Show, we share five of the most common early retirement mistakes that can impact your taxes, withdrawal strategy, investment plan, healthcare costs, and long-term income. Learn how to avoid these traps and keep your retirement on track with a sustainable financial plan and proactive tax strategy. 

Season 11, Episode...

Is age 65 still the right retirement age, or has that idea become outdated? In this episode of the Wise Money Show, we break down the key retirement milestones like 55, 59.5, 62, 65, 67, and 70 and explain how Medicare, Social Security, 401(k) access, and healthcare costs all impact your decision. More importantly, we walk through the five factors that truly determine when you can retire with confidence. If you're wondering when yo...

Taxes in retirement could be one of your largest expenses, especially if most of your savings are in pre-tax accounts. In this bonus episode of Wise Money, we are joined by Matt Hoke to break down practical strategies to reduce taxes on Social Security, RMDs, and even avoid costly IRMAA surcharges. 

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Target date funds are one of the most popular investment options inside a 401(k), but are they actually the right choice for your retirement plan? In this episode of The Wise Money Show, we break down how target date funds work, when they make sense, and when building your own diversified portfolio may be the smarter move. We also answer a fan question about choosing a later retirement date to take on more risk, and whether that st...

Before you file your taxes, there are critical financial planning moves you need to understand. In this episode of the Wise Money Show, we break down the most important tax law changes for 2025 and 2026, including SALT cap updates, senior deductions, child tax credits, and new retirement rules. This isn't about getting a bigger refund; it's about using proactive tax planning to pay less tax over your lifetime and avoid costly mista...

After a powerful run in the markets, many investors are asking whether the stock market is too hot and what that means for their portfolio. In this episode of the Wise Money Show, we break down recent market performance, valuations, volatility, and the key forces driving stocks today, including AI, interest rates, and global diversification. You'll learn how to think about risk, rebalancing, and staying disciplined when markets are...

Financial planning with 529 plans has changed in a big way. What was once just a college savings tool can now become a powerful strategy for long-term, tax-free retirement wealth when used correctly. In this episode of the Wise Money Show, we break down the new 529-to-Roth IRA rules, who this strategy works for, and the key pitfalls to avoid. Learn how this little-known opportunity could potentially create six or even seven figures...

If you're 50 years old, how do you decide whether to max out your 401(k), Roth IRA, or HSA? The right answer depends on more than just tax benefits; it requires looking at all six areas of your financial life. In this bonus episode, we break down the risks, trade-offs, and planning considerations to help you make the wisest move for your retirement and tax strategy.

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As the year gets underway, we're answering the seven financial questions people ask us most, covering investing, retirement, taxes, Roth strategies, and Social Security. These are the same questions that come up in almost every planning meeting, regardless of where you are in your financial journey. In this episode of Wise Money, we'll walk through how to think about each one and why the answers are rarely one-size-fits-all. 

Seaso...

As a new year begins, many financial resolutions start strong but fade quickly without a clear plan. In this episode of Wise Money, we break down five financial resolutions that actually create lasting progress, not just good intentions. From building a sustainable cash flow system to improving savings, tax strategy, protection, and long-term planning, we show how small, intentional steps can lead to meaningful change.

Season 11, E...

Most people think financial stress is about income, but it's usually a broken cash flow system. In this episode of Wise Money, we walk through the three-bank account cash flow operating system that helps create stability, reduce stress, and build real financial confidence. You'll learn how to properly manage monthly expenses, plan ahead for non-monthly costs, and stop getting blindsided by predictable surprises. 

Season 11, Episode...

Are you planning to retire in 2026? In this episode of Wise Money, we cover the most important decisions to make in the final stretch before retirement. Learn how to stress-test your plan, align your income and investments, and coordinate taxes, Social Security, and healthcare so you can transition into retirement with clarity and confidence. 

Season 11, Episode 18

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Are Roth conversions only worth it in the 10% or 12% tax bracket? Not always. In this episode of Wise Money, we explain when Roth conversions in the 22% or 24% tax bracket can make sense and when they don't. We cover estate planning considerations, market downturn opportunities, retirement tax "windows", and whether a seven-figure portfolio can still stay in a lower tax bracket.

Season 11, Episode 17

Long-term care is one of the biggest risks to your retirement. In this bonus episode of Wise Money, we are joined by Zach Broadwick, CFP®, to break down how to know whether you need long-term care insurance or if your investment portfolio is enough to self-insure. 

Download our FREE 5-Factor Retirement guide: https://wisemoneyguides.com/ 

As the year comes to a close, it's easy to get swept up in the holidays and forget key financial to-dos that could make a huge impact on your taxes, retirement, and financial confidence. In this episode of Wise Money, we're giving you a comprehensive year-end financial checklist covering all six areas of your financial life to make sure you finish strong and start the new year on a solid financial footing.

Season 11, Episode 16

It's the season of giving, but are you giving in the most impactful and tax-efficient way? In this episode of the Wise Money Show, we break down smart charitable giving strategies that help you support the causes you care about while reducing your taxes before year-end. From donor-advised funds and qualified charitable distributions (QCDs) to gifting appreciated investments and maximizing state tax credits, we walk through the tool...

Roth IRAs are powerful, but also misunderstood. In this episode of Wise Money, we break down the most common Roth IRA questions we hear. From age limits and income rules to the two different 5-year rules, Roth conversions, and when to use your Roth in retirement. We'll cover how contributions and conversions really work, how to avoid penalties, why many people invest their Roth IRA incorrectly, and how to decide whether Roth or tra...

Retiring before Medicare? You might face a tricky balancing act between doing Roth conversions and keeping your health insurance subsidies through the Affordable Care Act (ACA). Tanner Watson, CFP®, helps us unpack a real-life retirement planning case to show how Roth conversions can impact your premium tax credits and what strategies can help you make the most of both.

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Retiring with debt in your 50s can feel like a dead end, but it doesn't have to be. In this episode of Wise Money, we unpack how to balance paying off debt while still making that final push toward a confident retirement. We explain different versions of the debt snowball, how to build a five-factor retirement plan, and how to bring clarity to your financial plan so you can retire with confidence. 

Season 11, Episode 13