Cover Your Assets KC Podcast

Most people ask good retirement questions, but not always the right ones. In Part 2 of this series, David Dickens shares five more “better questions” pulled straight from real client meetings, revealing how small shifts could lead to better retirement decisions.

From Social Security timing to mortgage payoff strategies and more, we’ll explain how reframing the way you ask the question might change the quality of the answer.

This ep...

Sometimes the smartest move in retirement planning isn’t knowing all the answers. It’s about learning to ask better questions.

In this episode of Cover Your Assets KC, David walks through five common financial questions people ask, and then explains how to reframe them to get better results. From “How much money do I need to retire?” to “Where can I pay the lowest fees?”, we’ll explain how slight shifts in perspective can help lead...

Most people think financial planning is about calculators, spreadsheets, and strategies. But that’s only half the story. The fact is, your feelings about money can have just as much impact on your retirement as the numbers do. Today, David explores the emotional side of planning and how your legacy goals can be shaped by what you feel, not just what you know.

Here’s some of what we discuss in this episode:

🧩 Whole-Person Planning:...

Before we get started, please note that when we use the terms ‘safe,’ ‘safety,’ or ‘safe money’ in today’s discussion, we’re referring generally to strategies designed to help manage risk, not to any product or investment that is guaranteed or free from loss or any other risks. All investments involve risk, including possible loss of principal. While some products may offer a level of protection against market losses, they may invo...

Most people don’t feel wealthy. But what if your day-to-day habits are quietly building serious financial strength? A recent article from Kiplinger outlined five surprising signs that you might be richer than you think, and none of them involve yachts or private jets. In this episode, David walks through each sign and explains why they might matter for both today and your long-term future.

Here’s some of what we discuss in this epi...

We’re back with another mailbag edition of the show! This week, we tackle two thoughtful financial planning questions from listeners.

First up: a retiree who received a federal tax refund wonders if it’s a smart strategy or a sign to adjust withholdings. David explains the pros and cons of overpaying taxes in retirement, why minimizing refunds often makes more sense, and how to create a smoother retirement income stream. Then, a pa...

Today is a listener question edition of the show and we’re diving into two relatable retirement planning scenarios that may mirror your own concerns.

First up: a listener wants to quit his corporate job to start a business. David shares how age, funding source, and risk tolerance play important roles in that decision, and why raiding your IRA might not be your best move. Then, they respond to a retiree who recently realized their p...

Big tax law changes always bring big rumors. But before you assume Social Security is now tax-free or that you’re getting a $40K deduction just for breathing, let’s set the record straight on what this new bill didn’t actually do. This episode, David breaks down 6 of the most common myths floating around about the new “One Big Beautiful Bill Act.”

Here are the myths we discuss in today’s show:

Myth #1: “Social Security is no longer...

A new tax bill has officially passed (you’ve probably heard it mentioned as the “Big Beautiful Bill”). And while most headlines are focused on politics, we’re focused on what it means for your retirement. The choices you make in the next year or two could have a significant impact on how much you keep and how much goes to Uncle Sam. Today, David breaks down key parts that are most likely to affect retirees.

Here’s some of what we d...

Markets crash. Taxes shift. Congress waffles on Social Security. You can’t control any of that. And stressing over it won’t help. What will? Focusing on the four things that can actually help move the needle in retirement.

Today, David walks through four key factors you can control and how they could make a lasting difference in your financial future. From managing market risk and creating lifetime income to building tax-smart weal...

This Father’s Day, give your family something that lasts: financial confidence. In this special episode, David outlines three essential financial steps every dad should prioritize, whether you’re chasing toddlers or preparing for retirement. From building a strong financial base to adjusting your budget as life changes, these timeless moves can help set your family up for long-term independence.

Here’s some of what we discuss in th...

Health Savings Accounts (HSAs) might just be the most powerful and overlooked tool in your financial toolbox. Today, David is breaking down six key things everyone should know about HSAs, from eligibility and contributions to how they can grow over time and work across job changes.

Here’s some of what we discuss in this episode:

🩺 Who qualifies and who doesn’t

💰 Maximize annual contributions the smart way

📈 Using an HAS as an in...

Retirement planning can feel like a whirlwind, flooded with choices, tight timelines, and the pressure to “get it right.” In this special mailbag episode, David answers real questions from listeners who are navigating this very moment. One is preparing to retire and feeling overwhelmed; the other is already retired and sorting through the complexities of Roth conversions.

Here’s some of what we discuss in this episode:

📬 Structu...

Taxes don’t stop when your paycheck does, and they certainly don’t skip your heirs. In this episode, David tackles two common listener questions that reveal just how much tax strategy plays into smart retirement and estate planning. If you’ve been worried about how much your kids will owe in inheritance taxes or if you’re sitting on a pile of tax-deferred savings, David offers practical tips on ways to help you avoid getting a surp...

The headlines are loud, the markets are messy, and your gut might be telling you to do something — anything — right now. But what should you actually do when your portfolio takes a hit?

Instead of guessing what’s next or obsessing over breaking news, David walks you through four critical questions every investor should ask during turbulent times. From re-evaluating your plan and risk tolerance to exploring rebalancing and tax-loss ...

We’re back with another mailbag episode! In this week’s edition, we’re tackling 3 great questions from listeners like you. These episodes are some of David's favorites, as they provide a chance to dive deep into key topics and explore the finer details.

Ted is curious about how to manage the wealth he'll leave behind for his children. Roger is wondering if setting up a trust is the best way to help minimize the tax burden on his ki...

Each year, David gets a lot of questions from his clients about required minimum distributions. Some are just beginning to take them, while others have been withdrawing for years but still have specific concerns. In this episode, he breaks down the 7 key things you need to know about RMDs.

We’ll start with the basics, like what they are, when you need to start taking them, and which retirement accounts are affected. Then, we’ll div...

Ever wonder what other people talk about with their financial advisors? A new survey of nearly 400 experienced advisors reveals the biggest concerns and challenges, their clients are facing today. Today we’re breaking down the four biggest concerns clients have about retirement and how to overcome them.

Here’s some of what we discuss in this episode:

📉 Outliving Your Assets – Why a written plan is crucial for financial security.

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Today ​we ​are ​covering ​two ​different ​listener ​questions. ​James ​is ​asking ​about ​starting ​Social ​Security ​at ​62. ​You ​might ​be ​amazed ​how ​many ​times ​I ​get ​that ​question ​in ​my ​office. ​And ​then ​Barry ​wants ​to ​talk ​through ​life ​insurance, ​seems ​to ​think ​he ​has ​a ​lot ​of ​it ​and ​wants ​to ​know ​whether ​he ​should ​cancel ​some ​of ​it. These are two core areas of planning so let’s talk thro...