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How Much Should You Convert to Roth? Finding Your Personal Sweet Spot May 20, 2025

Choosing to convert to Roth could be one of the most impactful moves you make in your retirement income strategy. But like any powerful tool, a Roth conversion can become costly, or even counterproduc...

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The Widow’s Tax Penalty: What Every Married Retiree Needs to Know May 17, 2025

When one spouse passes away, the surviving spouse often faces a painful financial surprise. Income may drop, but taxes and Medicare premiums can increase. 

This is known as the widow’s tax penalty, a...

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The QCD Explained: A Tax-Smart Way to Give From Your IRA May 05, 2025

The QCD is a big deal. If you’re over 70½ or planning for the day you will be, don’t wait another day to understand how this strategy can work for you.

A Qualified Charitable Distribution (QCD) allow...

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The Hidden Taxes in Retirement (No One Is Talking About) May 01, 2025

What if the very thing you trust most to protect your retirement is secretly setting you up for a crushing tax bill?

We’ve all been taught to use conservative assumptions when planning for retirement...

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Flat Fee Financial Advice: How To Get Expert Help Without Hiring a Full-Time Advisor Apr 28, 2025

More people than ever are looking for one-time flat fee financial advice. But finding this type of service can still be surprisingly difficult. Most of the financial industry is built around long-term...

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Is Social Security Taxable? (Updated for 2025) Apr 26, 2025

Is Social Security taxable? It is a question almost every retiree asks at some point. The answer is not a simple yes or no. It depends on how much other income you have coming in.

In this guide, I wi...

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Boldin: Should You Use the Basic or Detailed Budgeter? Apr 25, 2025

When you're building a retirement income plan in Boldin, or any other financial planning software, getting your budget right is arguably the most important step. Your budget forms the foundation for a...

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Boldin: Planning for Long Term Care Apr 16, 2025

Many of my readers know I’m a big fan of Boldin. For those unfamiliar, Boldin (formerly known as NewRetirement) is a retirement planning software that helps individuals build and test their own retire...

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Bear Markets Happen. Smart People Don’t Panic. Apr 08, 2025

It takes a lot for market volatility to shake me. Over the past two decades, I’ve watched the market react to everything from housing bubbles to pandemics to flash crashes. Through it all, one truth h...

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Retiring in a Bad Market: 3 Steps to Stay on Track Apr 03, 2025

What happens when you’ve spent decades saving, planning, and dreaming about retirement, only to watch the market tumble just as you’re ready to step away from work?

It’s frustrating. It’s nerve-wrack...

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How Sequence of Returns Risk Affects Your Social Security Filing Strategy Mar 23, 2025

When most people think about when to file for Social Security, they usually don’t factor in what’s happening in the stock market. But they should.

Your Social Security filing strategy plays a critica...

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Index Funds vs. Actively Managed Funds: What the Data Really Says Mar 21, 2025

When choosing how to invest in the stock market, the debate on index funds vs. actively managed funds is still very much alive. Many investors are pitched the idea that actively managed funds — guided...

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