5 Tax Mistakes To Avoid In Your Initial Retirement Years, #323
Retire With Ryan
As you transition into retirement, tax planning might not be at the top of your to-do list—but overlooking it can lead to costly mistakes. This week, I break down the five biggest tax pitfalls new retirees face, from unexpected taxes on Social Security benefits to costly Medicare premium surcharges and missed Roth conversion opportunities. I’m also sharing a few of my favorite strategies to avoid unnecessary state taxes and manage your retirement distributions with confidence. You will want to hear this episode if you are interested in... [01:45] Without planning, your risk...
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5 Year Roth IRA Rule People Get Wrong, #322
Retire With Ryan
Roth IRAs are a powerful retirement tool, much loved for their promise of tax-free growth and withdrawals. But embedded in the rules for Roth IRAs are two little-understood 5-year rules. Misunderstanding these can trip up even savvy savers, potentially exposing your hard-earned gains to taxes and early withdrawal penalties. This week I’m giving you an expert breakdown to clarify how the rule works and bust some common misconceptions. You will want to hear this episode if you are interested in... [01:13] Tax-deferred growth and conditions for tax-free distributions [05:39] Taxes...
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4 Best Options To Pay For Long-Term Care, #321
Retire With Ryan
Long-term care coverage is an essential, yet often misunderstood, aspect of retirement planning in the United States. Although many people will require some form of long-term care as they age, most are unprepared for the high costs and limited coverage options available. On the show this week, I’m debunking common myths like the notion that Medicare will fully cover all long-term care costs and taking a deep dive into the four main ways retirees can pay for these expenses. You will want to hear this episode if you are interested in... 00:00 Understanding the options for...
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Are Bonds Still A Good Investment For Your Retirement Portfolio, #320
Retire With Ryan
On the show this week, I’m helping you understand why bond prices have been dropping, what actions investors should take, and whether bonds still have a place in a retirement portfolio. I discuss the different types of bonds and how interest rates impact bond prices. I also dig into the importance of maintaining a diversified portfolio and the role bonds can play in reducing overall volatility during retirement. You will want to hear this episode if you are interested in... [02:03] Types of Bonds and issuers [03:21] Risks of investing in junk bonds [04:39] Why have bond prices...
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Top 5 Reasons Retirees Run Out Of Money, #319
Retire With Ryan
Retirement is often imagined as the reward after decades of hard work—a time for travel, relaxation, and quality time with loved ones. But for many Americans, the anxiety of running out of money casts a long shadow over these golden years. Studies reveal that concerns about outliving savings are more prevalent than fears of dying prematurely. This week we’re discussing the five key reasons retirees run out of money and sharing practical steps you can take to secure your financial future. You will want to hear this episode if you are interested in... [02:16] Even high-income...
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What Order Should I Start Withdrawing From My Investment Accounts In Retirement, #318
Retire With Ryan
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. You will want to hear this episode if you are interested in... [00:00] Retirement withdrawal strategy options [06:37] Roth IRA and...
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3 Ways To Make The Most of Your Restricted Stock Units, #317
Retire With Ryan
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. You will want to hear this episode if you are interested in... 00:00 Explanation of...
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Accessing Your 401k Early With The Rule of 55, #316
Retire With Ryan
For many Americans, the idea of retiring before age 59 and a half 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. You will want to hear this episode if you are interested in... [00:00] Overview of the Rule of 55 and...
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How To Avoid Taxes On The Sale Of Your Primary Residence, #315
Retire With Ryan
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 break down what this exclusion means, who qualifies, how to maximize its benefits, and the critical planning steps to avoid...
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Give Your Child or Grandchild A Head Start On Retirement With a Trump Account, #314
Retire With Ryan
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. You will want to hear this episode if you are interested in... [00:00]...
info_outlineOn 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.
You will want to hear this episode if you are interested in...
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[00:00] Getting started with Social Security
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[05:22] monthly Social Security benefit calculations
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[06:11] Reasons to take the lump sum
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[07:48] Health concerns and social security benefits
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[08:27] When passing on the lump sum is a better choice
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[10:24] Your lump sum may increase your taxable income
Should You Take the Social Security Lump Sum?
When you apply for Social Security after your full retirement age (FRA), the Social Security Administration may offer a lump sum payment. This option is generally given to individuals who delay collecting benefits past their FRA. The lump sum typically covers up to six months of retroactive benefits.
For example, if your FRA is 66 and you apply a year later, you might be eligible for a lump sum equal to six months of prior payments. However, there’s a catch: your monthly benefit will be calculated as if you started receiving Social Security six months earlier, resulting in a lower monthly payment going forward.
The Math Behind the Decision
Let’s look at the numbers. Suppose your current monthly Social Security benefit is $2,500. If you elect the lump sum, your payment will be based on your benefit from six months ago—roughly 4% lower, or about $2,350 per month. You would receive a lump sum ($2,350 x 6 = $14,100), but your ongoing monthly benefit would start at the lower amount. Dividing the lump sum ($14,100) by the monthly difference ($150) gives about 94 months, or almost eight years. In other words, it will take eight years of receiving the higher benefit to make up for not taking the lump sum.
Reasons to Take the Lump Sum
There are situations where the lump sum makes sense:
1. Immediate Financial Need:
If you have bills, a major expense, or want to fund something important like a vacation, accessing the lump sum offers flexibility.
2. Health Concerns:
If your health is poor, the lump sum may be preferable. Social Security benefits cease at death, except for a $255 survivor payment. Taking the lump sum ensures you receive more of your entitled benefits within your lifetime.
Reasons to Decline the Lump Sum
For many, passing on the lump sum will be the wiser move, if you’re healthy and likely to live at least eight years, your higher monthly benefit will surpass the lump sum. Something else to consider is if you’re the higher-earning spouse, your survivor’s benefits will be based on your monthly payment. Opting for a lower benefit reduces what your spouse would receive after your passing.
Future cost-of-living increases are based on your initial benefit. Starting at a lower monthly payment means smaller dollar increases over time. Historically, Cost of Living Adjustments (COLA) average 2.8% per year; these can add up and compound. You also need to remember that receiving a lump sum may increase your taxable income for that year, possibly pushing you into a higher bracket or increasing taxes on your Social Security benefits. Ultimately, the decision is highly personal. Assess your health, financial needs, family longevity, and whether your spouse would depend on your benefit. Crunching the numbers will clarify your breakeven point.
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