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Retire With Ryan

Retire With Ryan

By: Ryan R Morrissey
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 If you’re 55 and older and thinking about retirement, then this is the only retirement podcast you need. From tax planning to managing your investment portfolio, we cover the issues you should be thinking about as you develop your financial plan for retirement. Your host, Ryan Morrissey, is a Fee-Only CERTIFIED FINANCIAL PLANNER TM who lives and breathes retirement planning. He’ll be bringing you stories and real life examples of how to set yourself up for a successful retirement.2020 Retirewithryan.com. All Rights Reserved Economics Personal Finance
Episodes
  • Facts vs. Fiction in Retirement Planning, #259

    Facts vs. Fiction in Retirement Planning, #259
    Jun 24 2025
    From the truths about making large purchases in retirement to whether you really need to pay off your mortgage before you stop working, I’m sharing years of financial expertise to challenge a few retirement myths so you can make balanced, informed decisions. We’re talking strategies for charitable giving, clearing up misconceptions about reverse mortgages, and explaining why inflation may be your biggest risk in retirement. If you’re looking for practical advice on enjoying your savings while still planning for the long run, or if you want to protect yourself from financial scams and fraud, this episode is full of actionable tips to build your financial confidence for the years ahead. You will want to hear this episode if you are interested in... [02:02] Leaving money to charity after death reduces estate value for taxes, but offers no immediate tax deduction.[04:17] Qualified charitable distributions and large donations can reduce taxable income, but are only deductible if you itemize.[08:11] Don't rush to pay low-interest mortgages; invest instead, as returns can potentially exceed mortgage interest rates.[13:03] Balance stocks with bonds and cash to manage risk and volatility.[10:10] Reverse mortgages can be a great idea in certain circumstances. Navigating the Maze of Retirement Myths Retirement often brings a sense of relief; finally, you get to enjoy the fruits of your labor! However, it’s also a period rife with uncertainty, especially when so much advice and information clash or seem outdated. In this episode, I’m tackling six of the most persistent myths retirees face. 1. Myth: Leaving Money to Charity Is Best Done After Death Many retirees assume that bequeathing assets to a charity upon passing is the most virtuous and tax-efficient way to give back. While this is always an option, leaving money to charity at death doesn’t net you a tax deduction; it simply reduces the size of your taxable estate. For the vast majority, it’s more impactful to consider gifting while alive. There are several ways to make charitable giving work for you, including: Qualified Charitable Distributions (QCDs): Donate part or all of your required minimum distribution directly from your IRA, reducing your taxable income.Cash Donations: If you itemize deductions, you can deduct cash gifts, potentially even enough to tip you into itemizing territory if the gift is large.Gifting Appreciated Assets: Donating highly appreciated stocks or real estate can minimize capital gains and offer you an income stream. 2. Myth: Large Purchases Are Off-Limits in Retirement Worried that buying a boat or funding a dream trip will doom your financial future? It’s a myth that large expenditures are always ill-advised. With a solid withdrawal strategy, say, 5% of a $2 million portfolio, making a one-time, reasonable purchase might slightly reduce your yearly income, but if balanced against market growth and overall planning, it’s rarely catastrophic. Thoughtful, planned spending helps you enjoy retirement, so don’t deprive yourself unnecessarily! 3. Myth: The Less You Spend, the Better Many retirees become excessively frugal, reluctant to draw down the savings they worked so hard to accumulate. But can’t take your money with you. While it’s wise to have a budget and withdraw at a sustainable rate, being too conservative may rob you of life’s joys, like travel, hobbies, or supporting family, while you’re healthy enough to enjoy them. The key is balance: know your withdrawal rate and revisit your plan regularly. 4. Myth: You Must Pay Off Your Mortgage Before Retiring It’s comforting to be debt-free, but urgently paying off a low-interest mortgage could backfire. If your mortgage rate is 5% or lower and your investments are earning more, you could be better off keeping the mortgage and leaving your assets to grow. Plus, withdrawing large chunks from retirement accounts to pay down a mortgage could trigger higher taxes or Medicare premiums and leave you with less liquidity. Carrying a modest mortgage into retirement is not a financial failure; it may be a savvy move. 5. Myth: Reverse Mortgages Should Be Avoided Reverse mortgages have a bad rap, often viewed as predatory or risky. While there were issues in the past, today’s products are much more regulated. If you’re 62 or older, a reverse mortgage can provide tax-free cash, letting you access home equity without moving. It’s especially valuable if much of your net worth is tied up in your home, or unexpected expenses crop up. Investigate carefully, but don’t dismiss this option out of hand. 6. Myth: A Market Crash Is the Greatest Retirement Risk Market volatility grabs headlines, but inflation and the risk of outliving your money are bigger threats. The right asset allocation, mixing stocks for growth with bonds and cash for stability, is essential. Yet, don’t forget about inflation: stocks have historically been the best hedge. Also, financial ...
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    17 mins
  • Seven Smart Reasons to Leave Your Old 401(k) with a Previous Employer, #258

    Seven Smart Reasons to Leave Your Old 401(k) with a Previous Employer, #258
    Jun 17 2025
    Building on last week’s discussion about why rolling over your old 401(k) into an IRA could be a smart move, this episode flips the script. It explores seven compelling reasons you might want to leave your 401(k) with your previous employer instead. I break down factors like fees, company stock advantages, penalty-free withdrawals, legal protections, and unique investment options that could all influence your decision. If you're approaching retirement or just planning your next career move, this episode is packed with insights to help you make the best choices for your financial future. You will want to hear this episode if you are interested in... [04:12] Leave company stock in 401k to use net unrealized depreciation, potentially saving on taxes via long-term capital gains.[08:55] Consider keeping company stock in an old 401(k) to avoid taxes and penalties if under 59.5 years.[10:01] IRA withdrawal exemptions and strategies.[16:01] Consider keeping your old 401 (k) for potential loan access, but check if your provider permits non-employee loans.[17:50] Deferring 401(k) distributions explained. When to Leave Your Old 401(k) With Your Previous Employer Changing jobs often means making quick decisions about retirement savings. While rolling over your old 401(k) into an IRA is a common choice, there are significant advantages to leaving it where it is. This week, I’m discussing the situations when maintaining your previous employer’s retirement plan is advantageous. 1. Potential for Lower Fees If you worked for a large organization, their 401(k) plan might offer exceptionally low administrative and investment fees, especially if they’ve chosen robust menus with index fund options. While IRA costs have dropped due to strong competition among major financial institutions like Schwab, Fidelity, and Vanguard, some large employer plans still offer a lower cost. Always compare fees before making a move; sometimes, your old 401(k) will be the most cost-effective option available. 2. Tax Benefits of Company Stock (Net Unrealized Appreciation) Do you have significant company stock in your 401(k)? You could benefit from the unique tax break called Net Unrealized Appreciation (NUA). This allows you to pay lower long-term capital gains rates on your stock’s growth instead of higher ordinary income rates. However, to take advantage of NUA, you must carefully roll out your stock and be mindful of any 10% penalty if you’re under 59½. Know your stock’s cost basis and consult with a tax professional to determine if waiting is best, especially if your cost basis is higher. 3. Penalty-Free Access Between Age 55 and 59½ Left your job between 55 and 59½? Here’s a little-known benefit: you can tap your old 401(k) penalty-free before age 59½. If you roll the balance into an IRA, that door closes, unless you qualify for rare exceptions. This rule can be crucial if you need those funds to bridge the gap to retirement, so consider leaving at least part of your balance in the plan until you turn 59½. 4. Enhanced Creditor Protection Federal law (ERISA) offers 401(k) plans strong protection from creditors and judgments, even in bankruptcy. While rollover IRAs are also protected under federal and many state laws, the details can get complicated. Certain states may limit IRA protections, so it’s wise to investigate your state’s rules. Segmenting rollover IRAs from contributory IRAs can also help simplify tracking and protection. 5. Access to Stable Value Funds Some 401(k) plans offer stable value funds, a low-risk investment choice that often comes with a guaranteed minimum rate of return. While money market funds are currently paying more, that could change if interest rates drop. In lower-rate environments, stable value funds could offer an edge and a safe harbor for your retirement assets. 6. Possible Loan Availability Need to borrow against your retirement savings? Some plans allow you to take a loan from your 401(k), even after leaving the company. However, this isn’t universal, since loan repayments are usually tied to payroll. Check with your plan administrator to see if this benefit applies; if it does, it could be an important safety net. 7. Required Minimum Distribution (RMD) Deferral if Still Working If you work past age 73, keeping your funds in a 401(k) with your current employer lets you defer required minimum distributions (RMDs). That’s not the case with IRAs. Consolidating old 401(k)s into your current plan can simplify RMD timing and let your funds grow tax-deferred a bit longer. Make an Informed Move Rolling over your 401(k) may seem automatic, but there are times when staying put is the better choice. Carefully assess fees, tax implications, creditor protections, and your unique needs. Most importantly, consider working with a fiduciary, fee-only financial advisor who understands your entire financial picture. Resources Mentioned Retirement Readiness ReviewSubscribe to the Retire...
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    20 mins
  • Five Reasons to Roll Over Your Old 401k into an IRA, #257

    Five Reasons to Roll Over Your Old 401k into an IRA, #257
    Jun 10 2025
    In today's episode, I’m diving into a topic that’s top-of-mind for anyone who’s switched jobs: what should you do with your old 401(k) plan? I discuss five key reasons why moving them into an IRA could simplify your financial life, from consolidating accounts for better control to gaining access to a broader range of investment options, reducing fees, optimizing Roth and after-tax funds, and making it easier to work with a financial advisor. Whether you’re planning your next career step or just want to make your retirement savings work harder for you, this episode is packed with practical advice to guide your decision. Stick around until the end, and don’t forget to tune in next week when I cover situations where rolling over your 401(k) might not be the best choice! You will want to hear this episode if you are interested in... [00:00] Vested retirement funds offer four options: keep them in the plan, or withdraw and pay taxes[04:46] Rolling over a 401(k) to an IRA offers more control and access to your retirement funds, preventing forgotten accounts as you change jobs[06:41] Consolidate investments for simplicity and control; update records if keeping old retirement accounts[12:05] Convert Roth contributions to a Roth IRA to start the five-year period and ensure future gains grow tax-free, especially for after-tax funds in a 401(k) without in-plan Roth conversions[13:13] Rollovers to an IRA can facilitate Roth conversions and allow financial advisors to manage retirement accounts. Consolidate Old 401ks for a Smoother Future When you change jobs, it's important not to leave your old retirement accounts behind. For many Americans, the primary vehicle for saving for retirement is their employer-sponsored 401(k) plan. But what should you do with that 401(k) once you’ve moved on? Rolling it into an Individual Retirement Account (IRA) may be the smart move, offering control, flexibility, potential cost savings, and tax advantages. Let’s walk through five compelling reasons why a 401(k) rollover into an IRA might make sense for you. 1. Greater Control and Account Consolidation One of the biggest headaches of changing jobs multiple times is having various retirement accounts scattered across different institutions. Not only is it difficult to keep track of these accounts, but there’s the risk that you might forget about them entirely. By rolling old 401(k)s into a single IRA, you consolidate your investments, making it easier to manage and monitor your retirement savings. With all your funds in one place, you’ll have more control over your asset allocation and will be better positioned to implement a cohesive investment strategy. Additionally, consolidating accounts reduces the administrative burden of managing multiple logins and statements. 2. Expanded Investment Choices and Flexibility Most employer-sponsored 401(k) plans offer a fairly limited menu of investment options, typically ranging from a dozen to twenty funds. These may or may not align with your preferred asset allocation strategy, and some plans are more limited than others. By rolling over your 401(k) into an IRA at a major discount broker like Schwab, Fidelity, or Vanguard, you unlock a much broader universe of investment possibilities, mutual funds, exchange-traded funds (ETFs), stocks, bonds, CDs, and more. This flexibility lets you fine-tune your portfolio, properly diversify, and better tailor your investments to your risk profile and retirement timeline. 3. Potential for Lower Investment Costs 401(k) plans, particularly those from smaller employers, often feature higher administrative and fund expenses, sometimes reaching 1% or more in annual fees. These extra costs chip away at your investment returns over time. With an IRA, especially when investing in low-cost ETFs or mutual funds, you can often significantly reduce the expense ratios you pay. Over decades, even a modest reduction in annual fees can translate into thousands more in retirement savings due to the power of compounding. 4. Managing Roth and After-Tax Contributions Many 401(k) plans now offer a designated Roth component as well as avenues for after-tax contributions. When you roll over your account, this is a valuable opportunity to ensure your Roth and after-tax money are treated with optimal tax efficiency. For example, rolling Roth 401(k) funds into a Roth IRA starts the five-year clock for tax-free withdrawals on earnings, which is critical for planning your retirement withdrawals. Additionally, an IRA rollover can be structured to split after-tax contributions into a Roth IRA, giving those funds tax-free growth potential rather than the more limited advantages offered inside the 401(k). 5. Access to Professional Management If you want professional help managing your retirement investments and financial planning, rolling your assets into an IRA is almost always a prerequisite. Advisors generally cannot manage assets held within a former employer's ...
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    16 mins
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