Perfect Game Retirement

Being named the executor of someone's will can feel like an honor. It can also feel like a lot of pressure. It's more than handing out inheritances. It's paperwork, accounts, taxes, property, creditors, and sometimes family dynamics, stretched out over months or even years. A lot of clients end up in this role without ever planning to, and we're often the first call they make. Today, Ryan talks through how he can help. He’s n...

Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Ryan goes over a few today that he thinks are worth asking. None of these questions are really about money. That's kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely.

Here’s what we discuss in this episode:

🧠 Beyond Math: Look past numbers alone

🕙 Tue...

There's a 7-minute animated short that got nominated for an Oscar this year called Retirement Plan. It's free on YouTube, narrated by Irish actor Domhnall Gleeson, and it follows a middle-aged man named Ray who spends his days listing everything he plans to do once he finally retires. Ryan uses the short as a jumping-off point for a bigger conversation about the expectations we build around retirement and the life we’re livin...

Worrying about future tax rates can make retirees feel like they need to act before the rules change. In this episode, Ryan explains why taking extra money out of an IRA simply out of fear may create new problems if it isn’t part of a larger strategy. He looks at the importance of understanding how one tax decision can affect the rest of your financial plan. Don’t guess where tax rates are headed, make intentional decis...

If you’re ready to leave your career but think your retirement accounts are keeping you trapped, you may have more options than you realize. Ryan answers a listener question from a 56-year-old who wants to retire after 25 years with the same company but assumes the money is still off-limits. Before assuming you have to keep working for several more years, it’s worth finding out what options are actually available to you...

Today, Ryan walks through a potential retirement story in chapters. As each new detail comes in, he’ll react to it the way a financial advisor would in a real-time meeting. Ron's 64, figured a lot of this out on his own, and this is his first time sitting down with a professional. Ron always figured he'd know when he was ready to retire. Turns out, sometimes retirement decides for you. The good news is his plan still has opti...

Receiving a financial gift from your parents can create a great opportunity, but also plenty of questions about what to do next. Ryan walks through several ways families might use gifted money and explains why the intentions of the person giving the money and the goals of the person receiving it should both be part of the conversation. A generous gift can go much further when there’s a thoughtful plan behind it.

Here’s ...

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...