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_outlineFor 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.
You will want to hear this episode if you are interested in...
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[00:00] The preference for aging in place
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[05:08] Home modifications for accessibility
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[08:28] Considering home maintenance and healthcare costs
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[13:32] Planning housing costs for retirement
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[14:55] Planning for future housing needs
Understanding Aging in Place
The reasons people want to age in place are clear: minimal upheaval, a sense of control, independence, and the emotional security of familiar surroundings. But it's common to underestimate what it actually costs to make this dream a reality. Many retirees fail to plan for the inevitable expenses, which can erode savings and force uncomfortable, last-minute decisions down the road.
Five Major Financial Considerations for Aging in Place
1. Home Modifications
A key prerequisite for staying at home safely is making your living space accessible. While some modifications—like installing grab bars or lever handles—may be relatively inexpensive, needs can escalate quickly. More significant updates, such as walk-in tubs, stairlifts, or ramp additions, can run into the tens of thousands of dollars. Even a basic stairlift installation can cost over $5,000, and major renovations like adding a first-floor bedroom or bathroom can easily be prohibitive, especially if done reactively in a crisis.
2. Maintenance and Repairs
Beyond mortgage payments, insurance, and property taxes, ongoing home maintenance is a substantial, often underestimated expense. Homes age just as their residents do, meaning roofs (with a typical 25-30-year lifespan), HVAC systems (lasting 10-15 years), and even electrical or plumbing systems may require expensive repairs. Consider getting a thorough evaluation of your home’s current state and expected major repairs over the coming decades. Add these projected costs into your retirement budget so they don’t catch you off guard.
3. Upkeep and Outsourcing Chores
When you first retire, you may be able to mow the lawn, shovel snow, or clean gutters. But as you age, these tasks may become physically challenging, if not unsafe, necessitating the hiring of help. The annual cost of landscaping, snow removal, and routine upkeep can add up, sometimes exceeding the maintenance fees of a condominium or senior community. Evaluate the true costs of outsourcing these chores over the long haul. In some cases, a housing alternative with built-in maintenance can be both safer and more cost-effective.
4. Medical and Healthcare Needs
Aging at home often means additional out-of-pocket expenses for home healthcare aides, nurses, and various medical equipment. Many necessities, such as medical alert systems or even prescription medication management solutions, are not fully covered by Medicare or standard insurance. It’s essential to factor in potential costs for in-home care, equipment, and transportation to appointments should you lose the ability to drive.
5. Long-Term Care and Support
A frequent misconception is that Medicare will cover most long-term or in-home care needs. In reality, this type of care—particularly ongoing daily care—typically isn’t covered, aside from certain short-term situations. Long-term care insurance is an option, but only a small percentage of Americans over 50 have it, often due to high premium costs. Given that full-time nursing care can cost as much as $180,000 annually in some regions, having a clear strategy for funding care, whether through insurance, earmarked savings, or asset liquidation, is critical.
Developing a Proactive Aging in Place Plan
To successfully age in place, start planning early. Assess your home’s lifespan and the modifications needed, estimate maintenance and care costs, and integrate these projections into your retirement strategy. If the total costs seem unmanageable, now is the time to explore alternatives like downsizing, moving to a condominium, or relocating to a community with built-in support, especially in today's favorable seller’s market.
Making these plans before a crisis ensures you’ll have more options, less stress, and a better chance at maintaining both your independence and your financial security throughout retirement.
Resources Mentioned
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Subscribe to the Retire with Ryan YouTube Channel
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Planning to age in place? Watch out for these hidden costs. - MarketWatch
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