5 Things You Should Evaluate During Medicare Open Enrollment, #328
Retire With Ryan
Medicare open enrollment is here, running from October 15th to December 7th, and it's especially important for those who rely on Medicare. Plans change each year—and so may your needs. Not reviewing your Medicare coverage could leave you exposed to unexpected costs or disrupt your access to preferred doctors and medications. On this week's show, I explore five key steps to help ensure you get the right coverage for 2027. You will want to hear this episode if you are interested in... [01:40] Reviewing Medicare coverage for 2027 [02:49] How to check provider status: annual notice of...
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Year-End Tax Moves For Pre-Retirees To Consider in 2026, #327
Retire With Ryan
For those actively planning for a secure retirement, smart tax planning is essential—especially as 2026 comes to a close. Tax laws and contribution limits keep evolving, and timely adjustments can help you keep more of your hard-earned money. On the show this week, I share seven critical tax strategies that can boost your retirement savings while minimizing your tax liability. Here’s a deeper look at each move and how to integrate it into your financial plan. You will want to hear this episode if you are interested in... [01:41] Maxing out pre-tax retirement plans [04:32] Making...
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Social Security 2027 COLA Update, #326
Retire With Ryan
I break down the upcoming Social Security cost-of-living adjustment (COLA) for 2027, share my predictions on the new numbers, and explain what you should do to prepare. With inflation still affecting retirees, I explain how the COLA is calculated, what it means for your benefits, and the factors that could affect your retirement income next year. This episode has essential tips to help you make the most of the upcoming increases and manage your retirement finances confidently. You will want to hear this episode if you are interested in... [01:10] projected 2027 COLA estimates ...
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What If I Retire Right Before A Market Crash? #325
Retire With Ryan
What should you do if the stock market crashes right after you retire? In this episode, I discuss what happens if you experience a major market decline in your early retirement years, explain the concept of sequence of return risk, and share a few strategies to safeguard your hard-earned nest egg and maintain peace of mind. You will want to hear this episode if you are interested in... [01:20] What to do if the stock market crashes right after retiring [04:09] Sequence of return risk explained [07:14] Preparing for market declines in retirement [13:43] Tax strategies during market...
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What Happens To My HSA When I Enroll In Medicare? #324
Retire With Ryan
How much have you thought about Health Savings Accounts (HSAs) and what happens to them once you enroll in Medicare? Whether you’re nearing age 65, wondering if you can keep contributing to your HSA, or curious about how you can use your HSA funds in retirement, this episode covers it all. I explain the rules around HSA contributions after enrolling in Medicare, the types of medical expenses you can pay for tax-free, and what happens to your HSA if there’s still money in it after you pass away. You will want to hear this episode if you are interested in... [01:51]...
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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...
info_outlineWhat should you do if the stock market crashes right after you retire? In this episode, I discuss what happens if you experience a major market decline in your early retirement years, explain the concept of sequence of return risk, and share a few strategies to safeguard your hard-earned nest egg and maintain peace of mind.
You will want to hear this episode if you are interested in...
- [01:20] What to do if the stock market crashes right after retiring
- [04:09] Sequence of return risk explained
- [07:14] Preparing for market declines in retirement
- [13:43] Tax strategies during market decline
- [15:24] Roth conversions and retirement planning
- [16:54] Market declines are recurring and necessary for capturing market returns
Risks Retirees Face
Retiring at a market peak brings risks. When still working, a market downturn lets you buy investments at lower prices. You have time on your side—and a regular paycheck. In retirement, however, your portfolio often becomes your primary income source. After years of building a $1.5 million nest egg, imagine seeing it drop by 25%, to $1.125 million, just months after retiring—without paychecks to replenish it. Your portfolio potentially shrinks, and you're withdrawing money from a diminished resource, hampering its ability to recover as markets eventually rebound.
Understanding Sequence of Return Risk
A key concept is sequence of return risk, which refers to the danger that poor investment returns strike early in retirement. Two retirees may earn the same average annual return, but if one encounters downturns at the start of retirement while the other faces them later, their financial outcomes can be drastically different. Early losses, combined with withdrawals, can irreparably harm a portfolio, making recovery much harder—even if average returns are the same.
Five Steps to Safeguard Your Retirement Portfolio
How can you prepare for, and withstand, a major market correction right after retiring? Here are my five key steps:
1. Hold Short-Term Reserves
Every retiree should allocate a portion of their portfolio to short-term bonds, cash, or money market funds. This “bucket” provides a buffer, covering your withdrawals during market downturns so you don’t have to sell stocks at a loss. Depending on your risk profile, aim to set aside 5 to 10 years' worth of expected withdrawals in these safer assets.
2. Regularly Review Your Asset Allocation
As you approach retirement, your investment mix should grow more conservative. Adjusting your asset allocation—perhaps settling on a portfolio of 60% stocks and 40% bonds or cash—can help limit losses. Ask yourself: How much of a decline can you stomach? Even diversified portfolios can lose 25% in significant downturns, which, on a $2 million portfolio, means a $500,000 drop.
3. Stay Flexible with Retirement Spending
Categorize your expenses into essentials (housing, food, insurance) and wants (travel, memberships). If markets fall and portfolio withdrawals become a high percentage of your assets, consider temporarily reducing want-based spending. This flexibility buys time for markets to recover and helps your assets last longer.
4. Tax-Smart Withdrawal Strategies
If you hold both taxable and tax-advantaged accounts, be strategic. In a downturn, withdrawing from taxable accounts—especially if they contain holdings at a loss or long-term capital gains taxed at lower rates—may minimize your tax burden compared to pulling from traditional IRAs or 401(k)s.
5. Consider Roth Conversions in Down Markets
A market drop can be an opportunity: converting pre-tax IRA assets to Roth IRAs at lower prices means a lower tax bill and the chance for future tax-free growth as values recover.
Should You Delay Retirement During a Market Crash?
Ensure your financial plan, reviewed with a professional, can weather market shocks before taking the leap 16:25. Stock market declines are inevitable but have historically been followed by recovery and growth—especially for those who avoid panic and keep a steady course.
A stock market crash immediately after retirement is daunting, but it doesn’t have to ruin your plans. By building robust short-term reserves, adjusting your asset allocation, retaining spending flexibility, employing smart withdrawal strategies, and seizing opportunities like Roth conversions, you can navigate downturns with confidence. Remember: market declines are normal, and with a well-constructed plan, your retirement can weather any storm.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
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