Perfect Game Retirement

The 146th US Open tennis tournament gets underway at the end of August, so Ryan figured it was a good excuse to see what tennis can teach us about financial planning. Turns out, more than you'd think. Every great tennis player has a game plan, but also the discipline to adjust it mid-match without losing their nerve. That's not a bad description of good financial planning either.

Here’s what we discuss in this episode:

🎾 Sin...

Somewhere in a drawer, a filing cabinet, or a shoebox in the closet, most of us are holding onto financial paperwork we don't actually need. And we’re probably missing a few things we do need. Ryan sorts out what stays, what goes, and where it all belongs. Nobody loves paperwork, but a little bit of organization now saves a lot of scrambling later for you and for whoever has to help sort it out someday. When in doubt, ask us ...

More people in their 60s and 70s are staying on the job than ever before, and it's not always about the money. Today, Ryan digs into the real reasons retirees keep showing up to work. Working longer isn't automatically the wrong call. Sometimes it's exactly right. The real question is whether it's a choice or a fallback. That's worth figuring out before you assume the answer.

Here’s what we discuss in this episode:

👥 Extende...

When it comes to financial planning, everybody has something that bothers them. Today, Ryan’s walking through some of the most common pain points we see and the real conversations that happen around them. Nobody walks into retirement without at least one of these on their mind. The good news is that most of them have real answers. And all of them are worth talking about. If any of these hits close to home, that's exactly wher...

There's an entire television network dedicated to doing things yourself — home renovation, landscaping, interior design, all of it. And the DIY mentality is genuinely admirable. But when it comes to retirement planning, Ryan says that the stakes of a bad install are a little higher than a crooked backsplash. DIY has its place. But some projects are worth calling a professional, especially when the cost of getting it wrong fol...

According to a recent Kiplinger article, there are five keys to a retirement plan that hold up over time. They all happen to start with the same letter, which either means it's a great framework or someone really wanted it to work out that way. In this episode, Ryan walks through the “5 D’s” of retirement planning and how each one plays a role in helping retirees build a plan that can hold up over time.

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Dave Ramsey has built one of the most recognized brands in personal finance. Millions of people have followed his advice out of debt and into savings. But when it comes to how much you should pull from your retirement accounts each year, Ramsey takes a position that some financial professionals find hard to get behind. Today, we break it down: what Dave says, what the research says, and what Ryan thinks.

Here’s what we discus...

Financial information has never been more available — TV, podcasts, YouTube, Reddit, and now AI that will answer any question in about three seconds. And yet some of the worst financial decisions we see come from people who did a ton of research first. Today, Ryan’s talking about why this happens and what good research actually looks like. Being informed is a good thing. Being confidently misinformed is a different thin...

Over the past year, one retirement video on YouTube pulled in 3.7 million views. The title: "Sell These 5 Things Before You Retire." We thought it was worth a conversation, not to tear it apart, but to react honestly. Does Ryan agree? Let's get into it: 3.7 million people watched this video for a reason. It touches something real. Retirement isn't just about what you've accumulated. Sometimes it's about what you're willing to let g...

Risk is unavoidable. The only question is whether the risk you're taking actually makes sense for where you are in life. Today, Ryan looks at three stages of the financial journey, and at each one, we've got three types of people with three very different approaches. Whether you're decades away from retirement or already living it, this conversation will help you think differently about risk and opportunity.

Here’s what we di...

Summer's here. And somewhere between the excitement of planning a big trip and the anxiety of what it costs, a lot of retirees end up doing something that surprises us… they feel guilty about it. They worked hard, saved, planned for decades, and then second-guessed a beach vacation. Today, Ryan talks about how travel fits into a real retirement plan and how to enjoy it without guilt. You didn't save for decades so you could ...

When retirement is around the corner, some of the biggest decisions aren’t about when to retire, they’re about how income continues if one spouse is gone. Ryan walks through a listener question about pension survivor options and why these decisions often become more emotional and permanent than people expect. A thoughtful retirement income strategy can make these choices much easier to navigate down to road, so start ea...

Ryan’s doing something a little different today. Three listeners wrote in with variations of the same question, “Am I ready to retire in 2026?” Same question, three very different situations, three very different answers. If retiring in 2026 is on your mind, your version of this question is the one that matters most. And it probably has its own wrinkles, its own gaps, its own version of “almost ready”....

Spend five minutes on Reddit or YouTube and you’ll find people being brutally honest about what they wish they had done differently with money. Today, Ryan’s pulling from some of those real conversations and breaking down the lessons behind them. The best time to learn any of these lessons was at 25. The second-best time is right now. If you're ready to stop leaving opportunity on the table, let's talk about what that l...

Financial planning isn’t really about spreadsheets, rates of return, or chasing the perfect investment strategy. At its core, it’s about making sure the people you love are protected if life takes an unexpected turn. Ryan discusses the often-overlooked side of financial planning and shares how to navigate difficult family moments with clarity. Tune in to make sure you’re protecting what matters most.

Here’s ...

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You’ve done a great job managing your money over the years, but retirement changes the game. Ryan looks at the decision many investors face: should you keep doing it yourself, or bring in a financial advisor? He walks through what actually changes in retirement, where costl...

It’s a question a lot of people ask at some point: if your investments aren’t keeping up with “the market,” is it time to move on? Ryan breaks down what you’re actually comparing against, why that comparison can be misleading, and what really matters when evaluating performance. The right benchmark isn’t the market, it’s your plan.

Here’s what we discuss in this episode:

📊 Wrong Benc...

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 de...

📅 Book a 1-on-1 with Ryan: https://speakwithryan.com/

📦 Grab your FREE Tax-Free Retirement Toolkit: https://toolkit.blackoakam.com/podcast-toolkit.html

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...