If you’ve spent any time on social media or read personal finance blogs, you’ve likely encountered a buzz around Roth IRAs and, specifically, Roth conversions. This week I’m discussing the details of Roth conversions, what they are, how they work, and why they’re crucial for those looking to optimize their retirement finances.

Roth IRAs hold a special appeal: the promise of tax-free income in retirement. And most people would agree that having tax free income in retirement is preferable over having taxable income. Yet, for many people, especially those in their 50s and older, most of their retirement savings sit in pre-tax accounts such as traditional IRAs or 401(k)s. Roth conversions offer a pathway for transforming those tax-deferred assets into tax-free retirement income.

This episode is packed with practical insights to help you make informed decisions about your financial future. Tune in to learn more and get ready to take your retirement planning to the next level!

Retirement planning is an ever-evolving process, and staying informed about changes to Social Security, Medicare, and tax limits is crucial to making the most of your golden years. On this episode of Retire with Ryan, I’m sharing important updates on the 2026 Social Security cost of living adjustment (COLA), projected changes to Medicare Part B premiums, and strategies for managing income in retirement. 

The newly announced cost-of-living adjustment (COLA) for 2026 will see benefit checks rise by 2.8%. I break down how the yearly adjustments are calculated, why they matter for seniors, and the impact of inflation on Social Security. I also discuss the expected jump in Medicare Part B premiums, what IRMAA means for higher-income retirees, and important changes to the Social Security wage base and retirement earnings limits. 

Whether you're thinking about when to start your benefits or you want to strategize your retirement income, this episode will give you practical tips and resources to help you make the most of your retirement planning.

With the term “financial advisor” being used so broadly these days, it’s harder than ever for retirees and investors to make sense of who’s actually guaranteed to act in their best interest. So let’s talk about the key responsibilities of fiduciaries, explore the differences between fee-only advisors and those who earn commissions, and go through why full disclosure and ongoing advice matter so much in your financial planning relationship.

I share practical tips on how to vet potential advisors, whether you’re unhappy with your current one or searching for the right fit for the first time, and discuss online resources designed to help you find an aligned, trustworthy professional. If you want to make sure your advisor is truly putting your interests first, this episode is for you.

Every year, Medicare Open Enrollment presents an important opportunity for retirees and individuals enrolled in Medicare to review, update, and make changes to their health and prescription drug coverage. If you’re on Medicare or approaching retirement, understanding the enrollment period and your options is crucial to ensuring comprehensive and cost-effective health care.

I’m sharing the seven essential things you need to know to make the most of this important window. Whether you’re already enrolled in Medicare or want to stay ahead of your retirement planning, I explain key dates, your options for switching plans, how to review or update your prescription drug coverage, and what to do if your health or coverage needs have changed. 

Tune in to learn about navigating Medicare Advantage, Medigap, and everything you should consider before December 7th to keep your health and finances on track as you plan your ideal retirement.

This episode is essential listening for anyone who’s inherited an IRA, especially in light of the game-changing SECURE Act. If you’ve inherited a retirement account from a non-spouse since 2020, this episode is packed with details you need to know to avoid unexpected tax bills and penalties.

I explain the new rules for inherited IRAs, explaining the requirements and options for non-designated, non-eligible, and eligible designated beneficiaries. Whether you’re figuring out minimum distributions or seeking smart tax-planning strategies, you’ll get clear guidance on how these updates affect you, plus tips to steer clear of common mistakes in 2025 and beyond.

You might have seen those viral articles promising a mysterious multi-thousand-dollar Social Security “bonus,” but are they actually legit? On the show this week, I separate fact from fiction, debunking the myths and sharing seven actionable strategies to help you get the most out of your Social Security over your lifetime. 

Whether you’re curious about how working longer, delaying your benefits, checking your earnings record, or understanding tax implications can impact your retirement paycheck, this episode is packed with valuable tips to help you make sure you’re not leaving money on the table.

The Social Security Fairness Act, which was signed into law at the start of 2025, has been in effect for about nine months since this game-changing legislation repealed both the Windfall Elimination Provision and the Government Pension Offset, restoring and increasing Social Security benefits for millions of retirees, especially teachers and public employees who worked in jobs exempt from Social Security.

In this episode, I discuss exactly who qualifies for these newly restored benefits, explain how the Social Security Administration is handling the rollout, and give you a step-by-step guide on what to do if you haven’t received your payment yet. I’ll also walk you through critical tax changes you’ll need to consider if you’re now receiving this extra income, and practical strategies to avoid any nasty tax surprises at the end of the year.

It’s one of the most frequently asked questions by my clients as they prepare for retirement. And while a million dollars may sound like a lot, the reality is a bit more complex.

There are several key factors to consider when planning your retirement, including factoring in taxes, evaluating withdrawal strategies, and understanding the cost of living where you plan to retire.

Let’s break down how you can determine whether your nest egg will support your ideal retirement.

Are you turning 65 soon or starting to think seriously about healthcare in retirement? This week, I discuss the complicated world of Medicare—with a focus on the seven most costly mistakes people make when enrolling. 

From missing crucial deadlines and underestimating penalties, to overlooking the true costs Medicare doesn’t cover and getting tripped up by income-related surcharges, I give practical advice to help you avoid expensive pitfalls and make confident choices for your health and your wallet.

Whether you’re working past 65, exploring Medicare Advantage and Medigap, or just want to sidestep penalties, this episode unpacks the essentials so you can enter retirement feeling prepared and protected. Let’s get into the key rules, deadlines, and decisions every retiring listener needs to know!

Paying for education is a major expense for many families, so I’m breaking down why 529 plans remain the preferred way to save for college, thanks to their tax advantages and flexible growth. I unpack updates, such as increased limits for K-12 tuition withdrawals, expanded uses for trade and vocational schools, and the new ability to roll funds into ABLE accounts for individuals with disabilities.

Plus, learn about the new Trump accounts, the option to roll over leftover 529 funds into your child’s Roth IRA, and strategies to make the most of your education savings. Whether you’re a parent, grandparent, or simply curious about planning for future expenses, this episode is packed with actionable insights to help you build a successful financial future for your family.

For married couples planning their retirement, understanding spousal Social Security benefits can seem like a labyrinth. This week, I’m answering a listener's question about how spouses can maximize their Social Security benefits. Join me as I break down the key rules, eligibility requirements, and strategies that can help you and your spouse make the most of your benefits over your lifetimes.

Whether you're nearing retirement or still a few years away, I can help you understand primary insurance amounts, full retirement age, and what happens if one spouse claims benefits early. If you want to ensure you and your loved one have a smart plan for Social Security, this episode offers essential insights and actionable advice.

The power of Health Savings Accounts (HSAs) as a tool for both managing health expenses and building your retirement savings is often overlooked. On this episode, I’m sharing the basics of HSAs, highlighting their triple tax-free advantage, and explaining why they might be one of the best ways to maximize your retirement savings, even compared to more familiar accounts like IRAs and 401(k)s.

I also unpack some important upcoming changes to HSAs thanks to the One Big Beautiful Bill Act, set to take effect in 2026. These changes expand HSA eligibility, especially for those on healthcare exchange plans and direct primary care memberships. Whether you’re new to HSAs or looking to fine-tune your retirement strategy, my practical tips—like how to track reimbursements, invest your HSA funds wisely, and ensure you’re making the most of every retirement planning opportunity.

The future of Affordable Care Act (Obamacare) subsidies is a pressing issue for retirees and anyone shopping for health insurance on the ACA marketplace. With the generous subsidies brought by the American Rescue Plan Act set to expire at the end of 2025, I break down exactly how these subsidies work, what changes are coming in 2026, and what that means for your wallet.

We’re talking eligibility thresholds, how income is calculated, why premiums might rise, and—most importantly—shares practical strategies for lowering your adjusted gross income to continue qualifying for subsidies as the rules tighten. Whether you're planning to retire before age 65 or just want to make sure you're making the most of affordable health options, this episode is packed with actionable advice to help you navigate the shifting health insurance landscape. Stay tuned to hear how you can prepare before the subsidy cliff arrives.

The One Big Beautiful Bill Act affects charitable contributions for retirees and individuals considering their tax strategies.

I’m walking you through three major changes: the restoration of the charitable cash deduction for non-itemizers, new limitations on how much can be deducted for larger contributions, and a cap on itemized deductions for high earners.

Whether you give to charity every year, are planning a large gift, or just want to maximize your tax benefits, I’m sharing practical tips about when and how to make your contributions in light of these updates.

The brand-new “Trump account” is a tax-deferred savings option for American children created by the One Big Beautiful Bill Act. I break down who’s eligible for up to $1,000 in free government contributions, how these accounts work, and how they stack up against other popular savings vehicles like 529 plans, IRAs, custodial accounts, and regular brokerage accounts.

If you’re a parent or grandparent thinking about the best way to jumpstart your child’s financial future, you’ll want to tune in for my honest comparison of the Trump account's pros, cons, and quirks, plus tips on making the most of these new opportunities.

The One Big Beautiful Bill Act, signed into law on July 4th, brings about several important tax changes. I’m discussing what these updates mean, especially for retirees, and sharing practical advice on how to take advantage of new deductions and avoid unexpected tax hits.

From permanent adjustments to tax brackets and an increased standard deduction, to special benefits for those aged 65 and older, I cover everything you need to know to optimize your retirement strategy. Whether you're curious about Social Security taxation, itemized deductions in high-tax states, or planning smart Roth conversions, this episode is packed with insights to help you make informed financial decisions for your golden years.

This week on the show, we’re discussing the specifics of Required Minimum Distributions (RMDs) as we head into the second half of 2025. Whether you’re approaching your first year of RMDs or have been taking them for a while, I break down everything you need to know, from when you need to start taking distributions based on your birth year, to how RMDs are calculated, which accounts are affected, and the potential tax consequences for missing a withdrawal.

I’m also sharing eight practical strategies you can use to lower your future RMDs, including asset diversification, Roth conversions, tax-efficient income planning, optimizing Social Security timing, and even using charitable contributions to your advantage. With real-world examples and actionable tips, this episode is packed with valuable insights for anyone looking to navigate their retirement withdrawals as tax-efficiently as possible.

With the recent passage of the Inflation Reduction Act, also known as the Big Beautiful Bill, significant changes are coming to both solar panel and electric vehicle tax credits.

I break down what these changes mean, how they can affect your savings, and what steps you might want to take before these credits disappear.

From figuring out if solar panels make sense for your home to understanding how electric vehicle credits work (and when they’re expiring), this episode is packed with actionable insights and tips, especially for those planning for retirement or looking to cut down on monthly expenses.

This week, I’m addressing a listener's question: Should you collect Social Security at age 62 and invest the money, or wait until your full retirement age, or even age 70, for a bigger benefit?

I break down the math and the risks, weighing the advantages of guaranteed annual increases and cost-of-living adjustments against the potential (and pitfalls) of stock market returns. 

I also explain key rules, such as the earnings limit for early filers, tax implications, and who might benefit from collecting early.

Whether you’re eager to take Social Security as soon as you can or are considering holding out for a larger payment, listen in for the practical insights you need to make a smart decision for your financial future.

I’m exploring a common dilemma faced by anyone receiving a lump sum of money, whether from an inheritance, the sale of a business, or another windfall: Should you invest in a traditional brokerage account or opt for an annuity?

On this week's episode, I discuss the key differences between annuities and brokerage accounts, highlighting the five major pitfalls of annuities that are often overlooked.

You'll learn why transparency, flexibility, and tax efficiency make brokerage accounts a better fit for many investors, especially those seeking to beat inflation and maintain control of their funds.