Good morning, Retirement Starts Today Community. Welcome to "Every Day is Saturday," the newsletter reminding us that in retirement, every day is Saturday (including Thursday mornings).​​​

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​Most people focus on saving for retirement, but what happens when you actually get there? Retirement isn’t just about having enough money—it’s about managing risks that can threaten your financial security and lifestyle.

In this episode, we explore Five Key Retirement Challenges (and Solutions), inspired by a Kiplinger’s Personal Finance article by Walt West. From unexpected market downturns to rising healthcare costs, these challenges can catch retirees off guard if they’re not prepared.

We break down each challenge—financial instability, healthcare expenses, taxes, inflation, and estate planning oversights—and discuss practical strategies to navigate them. Learn how to structure a flexible withdrawal plan, prepare for long-term care costs, use tax-efficient strategies like Roth conversions, and ensure your estate plan protects your loved ones.

Plus, we tackle a listener question about using a MIGA ladder strategy to bridge the gap until Social Security—offering insights into the pros and cons of annuities in a retirement portfolio.

If you want to retire with confidence and avoid costly missteps, this episode is a must-listen. Whether you’re years away from retirement or already in it, understanding these key challenges and their solutions can help you make smarter financial decisions for the road ahead. Click here to listen​

Outline of This Episode

• (0:00) 5 Key Retirement Challenges (and Solutions)
• (1:17) Retirement headline: Kiplinger’s article on retirement challenges
• (1:42) Challenge #1: Financial instability
• (4:09) Challenge #2: Healthcare and long-term care costs
• (6:33) Challenge #3: Taxes in retirement
• (7:33) Challenge #4: Inflation’s impact on retirement income
• (8:32) Challenge #5: Estate planning oversights
• (10:25) Listener question: MIGA ladder strategy for retirement income

Challenge #1: Financial instability

Running out of money in retirement is one of the biggest fears retirees face. Market downturns, unexpected expenses, and longevity risk can all throw off even the best-laid financial plans. While we can’t control market conditions, we can control how we react to them. That’s why having a well-structured withdrawal strategy is key. A flexible financial plan—one that adapts to economic shifts—can help retirees avoid making rash decisions when the market takes a hit.

One way to prepare is by role-playing worst-case scenarios. If the market drops significantly, what’s the game plan? Will you temporarily reduce your withdrawals? Will you turn on Social Security earlier than planned to relieve pressure on your portfolio?

Challenge #2: Healthcare and long-term care costs

One of the biggest misconceptions about retirement is that Medicare covers everything. In reality, retirees face significant out-of-pocket healthcare expenses, and those numbers keep climbing.

According to Fidelity, a 65-year-old couple can expect to spend $165,000 or more on healthcare in retirement—excluding long-term care costs, which can easily add hundreds of thousands more. If you don’t plan for these expenses, they can quickly drain your retirement savings.

Health Savings Accounts (HSAs) are a powerful tool for covering medical costs tax-efficiently, and Medigap or Medicare Advantage plans can help fill coverage gaps. But when it comes to long-term care, retirees need a clear strategy.

Some opt for long-term care insurance, while others explore alternative funding methods like home equity. If a reverse mortgage or home sale is part of the backup plan, that decision should be made well before care is needed.

Challenge #3: Taxes in retirement

Many retirees assume their tax burden will shrink once they stop working. But between required minimum distributions (RMDs), Social Security taxation, and the transition from married to single filing status, taxes in retirement can sneak up fast. Without careful planning, retirees could end up paying far more in taxes than expected, especially if they’ve saved most of their wealth in tax-deferred accounts like traditional IRAs or 401(k)s.

Proactive strategies like Roth conversions and tax-efficient withdrawals can help minimize taxes over the long run. Converting traditional IRA funds into a Roth IRA during low-income years—before RMDs kick in—allows retirees to lock in lower tax rates and avoid future tax spikes.

Additionally, using qualified charitable distributions (QCDs) for charitable giving can reduce taxable income while supporting causes that matter. The bottom line? A little tax planning now can mean tens (or even hundreds) of thousands of dollars saved over the course of retirement.

Challenge #4: Inflation’s impact on retirement income

Inflation is the silent retirement killer. Even at modest rates, inflation erodes purchasing power over time, forcing retirees to increase their income just to maintain the same lifestyle. Over a 30-year retirement, expenses could double or even triple. If a retirement plan doesn’t account for inflation, today’s comfortable budget could feel painfully tight in the future.

The best defense against inflation is investing in assets that grow over time. While some retirees are tempted to pull out of the stock market when conditions get rough, doing so exposes them to a different kind of risk—losing purchasing power.

Equities, real estate, and inflation-protected securities (such as TIPS) can help keep retirement savings growing even as costs rise. It’s all about balance: keeping enough safe assets for stability, but maintaining enough growth investments to stay ahead of inflation.

Challenge #5: Estate planning oversights

Estate planning isn’t just about who gets what after you’re gone—it’s about protecting yourself and your family while you’re still here. While most people focus on having a will, one of the biggest estate planning oversights is failing to set up proper powers of attorney. Without these in place, loved ones could face serious legal and financial challenges if they need to step in and manage affairs due to illness or incapacity.

For retirement assets, it’s also critical to check beneficiary designations on IRAs, 401(k)s, and life insurance policies. Many retirees assume their will covers everything, but these accounts pass directly to named beneficiaries—regardless of what the will says.

Keeping beneficiary designations up to date ensures that assets transfer smoothly to the right people. Additionally, for those with complex estates or specific wishes, trusts can offer added protection and control over wealth distribution.

Resources & People Mentioned

• ​The Retirement Podcast Network​
• ​Kiplinger’s Personal Finance “Five Key Retirement Challenges” by Walt West​
• ​Fidelity’s Healthcare in Retirement Report​

Retirement Starts Today (the book) is Available!

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That's it for our three hundred and seventy-second installment of "Every Day is Saturday." As always, reply to this email with your retirement questions and you might hear them featured on the show! I read and respond to (almost) every email.

Have a great "Saturday",
- Benjamin Brandt (your humble host)

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