Perfect Game Retirement

A new proposal out of Washington is adding a fresh angle to the Social Security conversation, and Ryan is breaking down what it could mean. He walks through what’s being discussed, who it might impact, and how it fits into the bigger picture of Social Security’s future. The details may change, but the reality is this: something will eventually have to give. Understanding the possibilities now can help you make better decisions late...

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Most retirement conversations are about saving enough, but Ryan flips the script and talks about what happens after you get there. Why is it so hard to actually spend the money you worked decades to build? This episode dives into the mindset shift, the emotional hurdles, and the r...

Long-term care is one of the biggest financial risks in retirement, and one of the most uncomfortable topics to talk about. Most people know it’s important, but few have a clear plan for how they’ll actually handle the cost if care is needed. Today, Ryan provides practical tips on how to think through long-term care planning from multiple angles, and how to decide what makes sense based on your health, assets, and goals.

Here’s wha...

When should you take Social Security? It’s one of the biggest financial decisions you’ll make in retirement, and one of the easiest to get wrong. It’s not about finding “the best” age, it’s about making an educated decision based on your health, income needs, taxes, and long-term goals. Today, Ryan breaks down the key tradeoffs between claiming early, waiting until full retirement age, or delaying all the way to 70.

Here’s what we ...

Nobody likes tax season, but for new retirees, the rules can feel completely different. Income changes, required withdrawals begin, and decisions that once lowered taxes can create bigger bills later. Ryan unpacks some of the most common retirement tax mistakes and how they show up in real life. A little forward planning can make a dramatic difference over the long run.

Here’s what we discuss in this episode:

💸 RMD Deadlines: Miss...

The Oscars have passed, but we’re handing out a few awards of our own. Not for films, but for financial planning. Because when you think about it, a great retirement plan has a lot in common with a great movie: strong characters, a clear storyline, the right support, and a structure that holds up no matter what twists come your way. Ryan shares the key elements of an “award-winning” retirement strategy, one that’s not just impressi...

Target-date funds are one of the most common investments inside retirement plans, largely because they’re simple and automatic. But are they really the best option for your long-term portfolio? In this episode, Ryan explains how these funds work, why they’ve become so popular, and where they may fall short for investors who want a strategy tailored to their situation.

Here’s what we discuss in this episode:

🎯 Target-Date Basics: F...

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It’s one of the most common investing questions: should you keep funneling money into retirement accounts or build accessible capital you can use anytime? Both paths can work and both have tradeoffs. Today, Ryan explores the strategic thinking behind each approach and why the righ...

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Roth conversions have gained serious attention over the past several years. With fewer income limitations and more flexibility in today’s tax code, many investors are asking the same question: Should I be converting my IRA to Roth?

Ryan explains how Roth conversions actually work ...

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Everyone’s got an opinion about money (especially the people with a book deal or a TV show). Some of that advice is useful. Some of it sounds better on a stage than it works in real life. Today, Ryan breaks it all down. Financial hot takes can be entertaining, motivating, and occa...

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Many people assume Roth strategies are only for younger savers, but that belief might narrow your options later in life. In this episode, Ryan responds to a question that highlights how career changes and timing can reshape retirement decisions. The real issue isn’t age, it’s unde...

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One of the biggest retirement decisions most people make has nothing to do with the stock market. It’s a choice buried deep in pension paperwork, and once it’s made, it’s usually permanent. In this episode, Ryan walks through a common pension tradeoff that many retirees underestim...

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There’s no shortage of retirement advice, but not all of it holds up in real life. Many widely accepted beliefs sound reasonable on the surface yet quietly undermine long-term security when tested by market volatility, taxes, health changes, or longevity. Today, Ryan exposes ten r...

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A new government-backed savings account for kids is coming, and on the surface, it sounds like a no-brainer. Ryan shares his take on what these new accounts really offer, and what you need to consider if you choose to utilize it. The money is real, but so are the limitations, and ...

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Having a large cash balance can feel reassuring, but it can also raise questions about missed opportunities. Ryan tackles a common concern: whether holding a significant amount of money in the bank is smart planning or unnecessary caution. Turns out, the answer depends on more tha...

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Are you ready to make a move that could impact your finances for decades to come? Join Ryan as he reveals what really goes into deciding the best time to claim Social Security, especially as age 62 approaches. Discover why picking the right strategy, not just a date, can make all ...

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These days, retiring with $1 million might feel like falling short, especially when everyone around you seems to have more. In this episode, Ryan tackles a listener question that gets to the heart of retirement anxiety: is $1 million actually enough to retire? Are you worried you’...

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A lot happened in 2025: political swings, stubborn inflation, new tax rules, and even a historic government shutdown. But headlines alone don’t determine your retirement outcome; how you respond to them does. In this episode, Ryan reflects on the five biggest financial events of t...

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You’ve heard the phrase, “There’s no such thing as a bad question.” But in retirement planning, the quality of your questions often determines the quality of your outcome. Today Ryan reframes common retirement questions, and shares how clearer question lead to better strategies, a...