When it comes to planning for retirement, one of the most commonly faced decisions is how to invest for long-term growth and stability. In turbulent times, market volatility often generates renewed debate on whether index funds, or their actively managed counterparts, offer the better path for accumulating wealth. On this episode of the show, I’m unpacking what index funds are, how they stack up against actively managed funds, and what the latest data reveals about performance during both quiet and volatile markets.

This week, I’m tackling a question that’s on the minds of many investors: How safe is your money with major brokerage firms like Fidelity and Charles Schwab? In light of recent high-profile bank collapses and widespread concerns about financial security, I discuss how banks and brokerage firms operate differently, what protections exist for your investments, and what would happen if a major brokerage firm were to collapse. Whether you’re considering how best to safeguard your assets or wondering about the real risks of brokerage failures, this episode will provide the clarity and peace of mind you need for your retirement planning.

When it comes to planning for retirement, Roth IRAs have gained widespread attention for their tax-advantaged status and the promise of tax-free withdrawals in retirement. Financial experts, YouTubers, and podcasters have been touting the benefits of contributing to or converting assets into Roth accounts for years. But an often-overlooked vehicle could empower you to manage your investments just as efficiently: the humble taxable brokerage account. Surprisingly, with the right strategy, you can even pay 0% capital gains tax, mirroring one of the biggest appeals of a Roth. 

Variable annuities are often promoted as a secure way to generate guaranteed income during retirement, drawing the attention of retirees seeking stability for their nest eggs. But beneath the surface, these products frequently come with complications and costs that can erode your savings and limit your financial flexibility. In this episode, I share the details of the often-overlooked downsides of variable annuities and give you some important insights every investor should consider.

This week, we tackle the alarming rise in financial scams targeting retirees and their hard-earned savings. With insights straight from the FBI and real-world examples of scam attempts, I break down the key tactics used by fraudsters and reveal the subtle ways they can gain access to your retirement accounts. From sophisticated account takeovers to fake invoice emails, you'll learn the warning signs to watch for—and, most importantly, practical strategies to protect yourself and your financial future. 

Retirement planning extends well beyond simply saving enough during your working years—it plays out with every decision you make once you stop working. One crucial, sometimes overlooked, aspect is managing Required Minimum Distributions (RMDs) from your retirement accounts. If you have a retirement account approaching your RMD age, this episode breaks down the essential rules based on your birth year, how to calculate your distribution using the IRS tables, and key tax implications to keep in mind.

You’ll also get actionable tips to help minimize your future RMDs, from optimizing your income plan and leveraging Roth conversions to using qualified charitable distributions. 

Are you getting your full entitlement, spousal Social Security, or—like one of my recent clients—missing out on hundreds, even thousands, of dollars each year? This week, I discuss how spousal benefits work, what the eligibility requirements are, and the critical steps you need to take to ensure you aren't leaving money on the table. If you or your spouse are nearing retirement or already collecting benefits, this episode will equip you with the knowledge to maximize your Social Security income and avoid common mistakes.

When many investors approach retirement, one of their most pressing questions is how their portfolio will generate the income needed to fund their lifestyle. It’s a common belief—often repeated by financial pundits and well-meaning friends—that you should simply “live off the dividends” from your investments. It sounds appealing: a steady stream of payments, without having to sell any shares, but relying solely on dividend-paying stocks in retirement can create hidden risks and may not be the best path to financial security. I explore what it actually means to live off dividends in retirement, the benefits and risks of relying on high-dividend-paying stocks or funds, and why diversification might be a smarter approach for long-term financial security.

On this episode, I’m digging into the ins and outs of in-plan Roth conversions. You'll learn what it means to convert pre-tax 401(k) dollars to a Roth 401(k), who is eligible, and why it might make sense for your retirement strategy. I cover the practical steps for making these conversions, and highlight the benefits and drawbacks. I also share a real-life example of how a client navigated her options to maximize her retirement savings.

For many Americans, the idea of aging in place, or remaining in your own home as you grow older, represents comfort, independence, and familiarity. Most people understand the emotional benefits of remaining in a familiar environment, but often overlook the financial challenges, from home modifications and repairs to healthcare and in-home support, that could threaten their retirement savings. On the show this week, I break down the five key areas where your budget could take a hit and offer strategies to help you plan ahead, evaluate your options, and secure your ideal retirement lifestyle. If you’re thinking about your future living situation or helping a loved one prepare, you won’t want to miss this episode.

For many Americans approaching retirement, financial planning means more than just maximizing savings and deciding when to claim Social Security. If you’re not yet eligible for Medicare and rely on health coverage through the Affordable Care Act (ACA), your Social Security claiming decision at age 62 could have a dramatic effect on your insurance costs. On the show this week, I explore the nuances of how your income, and especially the timing of your Social Security benefits, can impact your eligibility for ACA premium tax credits—and what you can do to avoid costly surprises.

As April 15 approaches, marking the end of the 2025 tax filing season, many filers are facing an unpleasant surprise: tax penalties are rising, especially for those who miss timely payments or underestimate their quarterly taxes. In this episode, I’m taking you through the reasons behind the recent surge in tax penalties and highlighting how retirees, the self-employed, and investors are increasingly affected. I'll also break down the key rules, safe harbor provisions, and practical steps you can take to avoid underpayment penalties.

On this milestone 300th episode of the Retire with Ryan podcast, I dig into whether the Social Security lump sum payment option is right for you. After a client reached out with questions about whether accepting a lump sum is a good deal, I want to break down how the option works, who it’s available to, and the key factors to consider when making this important decision. If you’re approaching retirement, this episode offers practical guidance on weighing the lump sum versus higher monthly benefits, health considerations, and the impact on survivor benefits and taxes.

The Iran War, which began on February 28, 2026, is impacting global markets and I’m pretty sure it’s having an effect on your portfolio too. Over the past month, the S&P 500 has dropped about 6%, largely due to surging oil prices. With crude oil climbing as high as $100 a barrel and lingering uncertainty around the conflict's resolution, volatility is weighing heavily on retirement investments. 

We'll explore the implications for investors, discuss historical parallels with previous market shocks, and offer practical tips to navigate the fallout—whether you're looking to rebalance, automate your contributions, or take advantage of tax-loss selling. Stay tuned as I break down actionable strategies to manage your portfolio through these turbulent times and hear why it's important to avoid overreacting despite the dramatic headlines.

On the show this week, I’m talking all about the topic of probate and how adding a Transfer on Death (TOD) or Payable on Death (POD) beneficiary designation to certain assets can help you avoid your estate being tied up in the probate process. You’ll learn which types of accounts allow for TOD or POD beneficiaries, why these designations might be preferable to joint tenancy, and the pros and cons of setting them up. I break down step-ups in cost basis, the impact on estate taxes, and touch on differences across states and how to make sure your estate plan actually fits your wishes.

In the last episode, I discussed seven mistakes to avoid when filing your 2025 taxes. So, in this episode, I'm going to discuss the tax-filing mistakes people can make when filing an extension. Here are the four most common extension errors that could cost you money, including misconceptions about payment deadlines, underestimating taxes, and the importance of understanding state-specific extension rules.

Tax season is here, and if you’re just now gathering your documents to file your return—or preparing them for your CPA—this is the time to slow down and make sure you’re not making costly mistakes. In this episode, I walk through seven tax mistakes I frequently see both tax preparers and self-filers make when filing their returns. Some of these errors seem simple on the surface, but they can lead to penalties, missed deductions, delayed refunds, or paying more taxes than necessary. My goal in this episode is to help you avoid these pitfalls so you can file confidently and keep more of your money where it belongs.

If you watched President Trump’s recent State of the Union address, you probably heard about the new Trump accounts, also known as 530A accounts. In this episode, I break down how these tax-advantaged investment accounts are designed to work, who qualifies, and—just as importantly, what we still don’t know. There’s been a lot of excitement, especially around the $1,000 seed money for eligible children. But before you rush to open one, there are several unanswered questions that deserve your attention.

If you have children and you’ve been thinking, “Why wait until I’m gone to help them financially?”—this episode is for you. In Episode 294, I walk through the biggest things to consider before making gifts to your kids while you’re still alive, and I break down some of the smartest ways to do it without triggering unnecessary taxes.

I’m seeing this trend more and more with my clients, and it makes sense. Financial markets have performed well, real estate has surged, and many retirees are in a stronger position than generations before them. But just because you can gift money doesn’t mean you automatically should. There are several financial and family dynamics you need to think through first.

If you’re approaching age 65, Medicare can feel overwhelming fast. Between Parts A, B, C, and D and the timing rules tied to each—it’s easy to make a costly mistake if you don’t understand how the pieces fit together.

In this episode, I walk through the Medicare “alphabet,” explaining what each part does, when enrollment matters most, and how your decisions interact with the rest of your retirement plan. We also cover common questions that come up when clients transition from employer-sponsored coverage to Medicare for the first time.

Whether retirement is right around the corner or still a few years away, this episode is designed to help you avoid penalties, coverage gaps, and surprises down the road.