When you’re moving into retirement, you’re most likely to be starting to ask yourself which investment accounts you should start drawing from first. There’s really no universal answer—retirement withdrawal strategies are deeply personal and situation-dependent. But understanding the implications of each account type and the factors that influence withdrawal order can have a massive impact on your tax burden and the longevity of your assets. 

On the show this week, I answer a listener question about restricted stock units, or RSUs—what they are, how they're taxed, and the best strategies for managing them as they vest. I'll take an in-depth look at different types of vesting schedules, tax implications, and the practical choices you have when your RSUs become available. This episode is all about giving you clear guidance to help you make informed decisions about RSUs and making sure your retirement strategy is on the right financial track.

For lots of Americans, the idea of retiring before age 59½ often seems out of reach, particularly when the bulk of their savings sits in an employer-sponsored 401(k) or 403(b) plan. Traditionally, the tax code penalizes early withdrawals from these accounts. However, the Rule of 55 could open the door to a more flexible, penalty-free early retirement. On this episode, I’ll share more about this IRS provision, who qualifies, how to use it wisely, and potential hazards to avoid.

For many retirees, their home isn't just a place of comfort, it’s one of the largest assets on their balance sheet. However, beyond the emotional value and the years of accumulated equity, there's an often-overlooked reality: selling your primary residence can bring an unexpected tax bill. If you’re contemplating a sale or want to ensure you’re planning wisely, understanding the IRS’s primary residence capital gains exclusion is essential. On the show this week, I discuss what this exclusion means, who qualifies, how to maximize its benefits, and the critical planning steps to avoid a nasty tax surprise.

On July 4, 2026, a groundbreaking opportunity opened for parents and guardians aiming to give their children a head start on their financial journey: Trump Accounts. Created as part of the OBBA Tax Act (“One Big Beautiful Bill” Tax Act) of 2025, these tax-advantaged investment vehicles provide a unique way to grow wealth for minors. In this episode, I break down what Trump Accounts are, who’s eligible for generous bonuses, how to get started, and how they compare to other common savings options like 529 plans.

Medicare brings peace of mind to millions of retirees, but for those with higher incomes, there’s an added layer of complexity called IRMAA—the Income Related Monthly Adjustment Amount. If your modified adjusted gross income (MAGI) crosses certain thresholds, you may end up paying substantially more for your Medicare Part B and Part D coverage. In this article, we break down how IRMAA works, outline common scenarios that may unexpectedly raise your premiums, and offer actionable strategies to help you avoid unnecessary costs during your retirement years.

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.