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]...
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Avoid These 7 Scenarios to Keep Your Medicare Premiums Lower In Retirement, #313
Retire With Ryan
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. You will want to hear this...
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Do Actively Managed Funds Perform Better Than Index Funds In Volatile Markets? #312
Retire With Ryan
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. You will want to hear this episode if you are interested in... ...
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Is Your Money Safe With Schwab or Fidelity? #311
Retire With Ryan
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...
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How To Make Your Brokerage Account Work Like A Roth IRA, #310
Retire With Ryan
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. You...
info_outlineRetirement 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 retirees are at risk of running out of cash
- [03:43] Three phases of retirement spending: go-go, slow-go, and no-go years
- [04:31] Planning an intentional withdrawal strategy in retirement
- [07:40] Rules of lending or gifting money to family
- [12:46] Managing long-term care costs
- [14:59] Retirement fund inflation risks
- [16:21] Maintaining significant portfolio exposure to stocks (at least 60%)
The Hidden Risk to Longevity
One of the most common pitfalls is overspending, especially in the early years of retirement. The excitement of newfound freedom often encourages retirees to start ticking off bucket-list items such as home renovations, travel, and hobbies without a clear plan. Retirement can last 30 years or longer, and spending too aggressively early on can have dire long-term consequences.
There are three phases of retirement: the "go-go" years marked by active spending, the "slow-go" years when travel and activities slow down, and the "no-go" years when health and mobility may limit expenses. Adopting a dynamic withdrawal strategy, such as the Guyton-Klinger guardrail approach, allows you to adjust spending based on portfolio performance and inflation, reducing the probability of running out of money.
Helping Family at Your Own Expense
Of course you’ll want to help out your kid or the wider family support is natural, but extending excessive financial help can jeopardize your own stability. Gifting or lending money to grown children or other relatives requires careful consideration. Ask yourself if you can really afford to part with the funds, and whether the risk to the relationship is worth the potential fallout if the money isn’t repaid. If you cannot comfortably give the money, it’s wise to set boundaries. Remember, if your retirement funds run dry, returning to the workforce may not be an option.
Underestimating Healthcare and Long-Term Care Costs
Unexpected medical expenses can wipe out retirement funds quickly, especially for those retiring before age 65, when Medicare coverage begins. Private health insurance can cost as much as $1,000 per month for an individual and double for a couple.
Long-term care is another important consideration. Home care may run $40,000 to $80,000 annually, while nursing facility care can reach $190,000 per year, with average stays of 2.5 years. Protect yourself by exploring options like long-term care insurance or irrevocable trusts to shield assets if extended care is required.
Inflation Causes Hidden Erosion
Even low annual inflation compounds over decades, silently shrinking your purchasing power. Social Security, especially with its cost-of-living adjustment, can help offset this, but many pensions and fixed investments cannot. Keeping at least 60% of your portfolio in stocks gives the best chance of growth that outpaces inflation, ensuring your income maintains its real value.
The prospect of running out of money in retirement is daunting, but it’s not inevitable. By balancing spending, setting boundaries around family assistance, preparing for health-related costs, and protecting against inflation, you can stack the odds in your favor.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Allianz Life's 2026 Annual Retirement Study
- Retirement Security Research Center
- Guyton-Klinger Guardrail Withdrawal Strategy
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact