Best In Wealth Podcast

Retirement planning is often seen as a numbers game—ensuring that you have saved enough, invested wisely, and built a strategy that will comfortably carry you through what should be your golden years. But those numbers only tell part of the story, the test of any retirement plan is not just whether it works on paper for two people, but if it can be carried by the one who is left after loss.

This episode is inspired by real-world challenges clients face, so I am sharing my survivor stress test to help you refine your financial strategies before life throws the unthinkable your way.

Almost all plans in America focus on a couple, but the reality is that over half of married people will face widowhood or widowerhood, many while still managing mortgages, careers, and family responsibilities.

Even if a plan “works” on paper—if the accounts are titled correctly, the math checks out, and the legal documents are in place—it could still fail the test of usability. The plan needs to be more than mathematically correct; it has to be understandable and executable by the survivor, who, in their time of greatest stress and vulnerability, may face complexities and choices they have never encountered before.

The survivor stress test is a framework for couples and individuals to ask a critical question: If one of us were to die first, would the other understand the plan and feel able to carry it forward? Passing this test requires looking beyond adequacy to usability. In many households, one person manages the finances, knows the passwords, talks to the accountant, and understands the cash flow. The other often does not, and this can leave the survivor in a precarious position, especially when they are grieving.

One of the most immediate and impactful changes after the death of a spouse is the income cliff. Social Security survivor rules are not always intuitive, and when one spouse dies, the surviving spouse receives the larger of the two checks, but the smaller check disappears permanently. This can mean an instant loss of 30-40% of household Social Security income, even as most expenses, like mortgages and property taxes, remain largely intact.

Pension decisions loom even larger. Choosing a single-life payout maximizes current benefits but leaves the survivor with nothing, whereas a joint and survivor annuity, though slightly smaller each month, ensures continuing income. These decisions, made far in advance, cannot be revisited and must be carefully weighed in light of the survivor’s probable needs.

Most people are unprepared for the surprising tax “penalties” that come with widowhood. Filing status shifts from married filing jointly to single, which often means higher effective tax rates on lower household income because of compressed tax brackets and a much smaller standard deduction. This can translate to hundreds of thousands of dollars in additional taxes over years of retirement—a burden that few anticipate.

Additionally, surviving spouses may be affected by Medicare’s IRMAA surcharges, which, due to a two-year income lookback, can kick in just as income falls. Fortunately, forms like SSA-44 allow survivors to appeal IRMAA surcharges based on current-year income, but many do not know about this relief.

Grief can impair memory, concentration, and decision-making, right when the most consequential financial choices arrive. Survivors must re-title accounts, file claims, and sometimes manage pressure from family—all in an emotional fog. Prioritizing urgent actions (maintaining cash flow), deferring important but non-critical choices, and holding off on irreversible decisions (like selling a house) can prevent double grief where hasty choices compound heartache.

The best way to pass the survivor stress test is communication, both partners should understand the plan, know where assets are, and feel confident in their ability to carry it forward. Conversations and second-opinion reviews with a qualified advisor can uncover hidden vulnerabilities and help ensure that whoever is left behind is secure. 

• [00:52] The survivor stress test and financial planning for surviving spouse
• [04:23] Discussing family financial roles
• [08:59] Claiming Social Security benefits
• [10:18] Pension options: single life vs. joint and survivor payout 
• [13:29] The widow’s penalty tax surprise 
• [17:54] Importance of tax strategy while both spouses are alive
• [21:03] A decision-making framework for survivors

• Form SSA-44

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The Best In Wealth Podcast is hosted by Scott Wellens. Scott Wellens is the principal at Fortress Planning Group. Fortress Planning Group is a registered investment advisory firm regulated by the US Securities and Exchange Commission in accordance and compliance with securities laws and regulations. Fortress Planning Group does not render or offer to render personalized investment or tax advice through the Best In Wealth Podcast. The information provided is for informational purposes only and does not constitute financial, tax, investment or legal advice.

Most of us equate a satisfying retirement with achieving a specific savings goal. We dream of the day when the work alarm clock is silenced, the 401(k) is plump, and we can finally enjoy life on our terms. But recent research challenges this traditional thinking, revealing that while money matters, it’s far from the only factor—sometimes not even the most important one. 

Only about half of retirees say their retirement is “very satisfying,” with most others falling into the “moderately satisfied” category and about 10% not satisfied at all. This leaves a pressing question—what separates those beaming with contentment from those just “okay” or unhappy after leaving the workforce?

There is a tendency to assume money is the main culprit. Yet new research suggests a much smaller role for finances than is commonly believed, especially compared with other often-overlooked factors.

• Savings:Your total nest egg, everything you’ve saved apart from your home.
• Lifetime Income:The predictable, recurring payments you’ll receive for life—think Social Security and pensions.
• Health:How you rate your physical condition.
• Social Connections:The strength and depth of your relationships, measured by how connected and supported you feel.

I talk about how these four pillars interact, and—most importantly—how none alone can compensate for a shortfall in another. For instance, having vast savings won’t make up for a lack of social connections or poor health.

While retirees with over $1 million in savings and high lifetime income are the most satisfied (77%), those with far less in savings but significant guaranteed income (like Social Security) closely trail in happiness (73%). The reliability of a regular paycheck in retirement can be more psychologically satisfying than simply having a large pile of assets.

But the single strongest predictor of retirement satisfaction, after controlling for all factors, was not money at all—it was social connection. Having a strong circle of friends was associated with higher satisfaction than having a seven-figure bank account.

Positive social connections can even offset the effects of deteriorating health. Retirees with fair health but strong friendships are nearly as satisfied as those with excellent health but few friends.

These factors stack rather than substitute. You can’t out-save your way out of loneliness, nor can vibrant health buy your way out of financial insecurity. Satisfaction is governed by your weakest link—so maximizing all four areas is key.

So, how can you prepare for a truly satisfying retirement? 

• Strengthen Social Ties: Identify work-based friendships at risk of fading after retirement, and make efforts to integrate them into your new routine. Join clubs or volunteer—even before you retire—to lay strong social foundations.
• Prioritize Health: Invest in your well-being through activities that blend exercise and social engagement (think pickleball or group classes).
• Maximize Lifetime Income: Consider strategies like delaying Social Security to increase your guaranteed monthly income.
• Develop a Holistic Plan:Don’t just focus on your “magic number.” Plan for your daily life—how you’ll spend your time and with whom—after the paychecks stop.

In the end, financial security is essential, but it’s only half the equation. To enjoy the best years of your life, cultivate health and meaningful relationships, and find purpose beyond work. Start addressing your weakest pillar today, and you’ll build not just a wealthy retirement, but a happy one.

• [04:10] Understanding retirement satisfaction
• [07:41] Different types of retirement money
• [10:26] Explaining the Income Lab tool
• [14:45] Importance of health and connections
• [17:05] Balancing life priorities
• [20:31] Work as social infrastructure
• [23:41] Importance of holistic retirement planning

• Health and Retirement Study
• Income Lab
• WHO Commission on Social Connection
• Our Epidemic of Loneliness and Isolation: The U.S. Surgeon General’s Advisory on the Healing Effects of Social Connection and Community
• David Blanchett    

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The Best In Wealth Podcast is hosted by Scott Wellens. Scott Wellens is the principal at Fortress Planning Group. Fortress Planning Group is a registered investment advisory firm regulated by the US Securities and Exchange Commission in accordance and compliance with securities laws and regulations. Fortress Planning Group does not render or offer to render personalized investment or tax advice through the Best In Wealth Podcast. The information provided is for informational purposes only and does not constitute financial, tax, investment or legal advice.

Retirement is the beginning of a new chapter, full of opportunity, challenges, and critical decisions about your financial future. Protecting your retirement means understanding and proactively managing the most significant risks you will face. On the show this week, I explore the five biggest risks to a secure retirement and outline strategies to help you and your family prepare for the road ahead.

Most people underestimate how long their retirement might last. According to Social Security actuarial data, a 65-year-old man has a 50% chance of reaching age 84; for women, it’s 87. For couples, there is an even chance at least one partner will live past 90, and a one-in-five chance one will reach 95. Planning for “average life expectancy” is not enough—by definition, half of retirees will outlive that average. Structure your retirement plan and savings to last up to 30 years.

Future investment returns are unknowable, especially as you near retirement. The sequence of those returns—the order in which market ups and downs occur—can determine whether you run out of money. A retiree who encounters a bear market early in retirement is far more vulnerable than someone hit with poor returns later on. I recommend you:

• De-Risk Your Portfolio Before Retirement: Gradually shift to safer assets in your final working years.

• Build a Cash Buffer: Maintaining three years of living expenses in cash or similarly stable assets lets you weather bear markets without selling investments at a loss.

• Stress Test Your Retirement Date: Can you still retire if the market drops 30% the year before retirement?

• Adopt a Flexible Withdrawal Plan: Use guardrails—predefined spending increases or cuts—to respond to market conditions.

Healthcare costs are one of the largest and least predictable components of retirement expenses. About 70% of people turning 65 will need some form of long-term care, which can cost upwards of $75,000–$130,000 per year, depending on the type of care. Critically, Medicare does not cover most long-term care needs. Evaluate whether you can self-insure or if you need to purchase long-term care insurance. Your decision window closes in your 50s and early 60s.

The risk of making poor decisions—especially under stress—or falling victim to fraud is rising. Cognitive decline can begin well before it is noticeable, and with the rise of AI, scams are more convincing than ever. Put defensive measures in place, maybe add trusted contacts to your accounts, update power of attorney and beneficiaries, and set a family code word to combat scams involving cloned voices.

Over a 30-year retirement, even a modest inflation rate can erode your purchasing power by half. At 3% inflation, today's $60,000 lifestyle will require $120,000 in just 24 years. We all need to plan for rising costs, so periodically review and adjust your projections and spending patterns as prices change.

• [05:41] Optimizing Social Security Strategy
• [09:52] Managing Retirement Portfolio Risks
• [13:08] Planning for long-term care costs
• [14:47] Assessing long-term care options
• [19:20] Preparing family financial safeguards
• [21:50] Preparing for future challenges

• Cost of Care Report | Carescout 

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The Best In Wealth Podcast is hosted by Scott Wellens. Scott Wellens is the principal at Fortress Planning Group. Fortress Planning Group is a registered investment advisory firm regulated by the US Securities and Exchange Commission in accordance and compliance with securities laws and regulations. Fortress Planning Group does not render or offer to render personalized investment or tax advice through the Best In Wealth Podcast. The information provided is for informational purposes only and does not constitute financial, tax, investment or legal advice.

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Are you ready for the next grizzly bear?—not the animal, but a major market downturn. He discusses the history of market corrections, bear markets, and the rare but devastating grizzly bear markets, illustrating why it is crucial to evaluate your portfolio’s risk level during strong market conditions—not during times of crisis. Whether you are approaching retirement or still in your wealth-building years, this episode will prompt you to reconsider your risk tolerance, portfolio diversification, and readiness for inevitable market storms.

• [03:34] Importance of communicating about conflict before it arises 
• [06:27] Discussing market downturns and returns
• [10:16] Understanding Market Corrections
• [11:31] S&P 500 correction frequency
• [16:51] Assessing portfolio risk levels
• [18:01] Understanding risk and portfolio deviations
• [24:03] Preparing for market downturns
• [25:11] Preparing for market downturns

Much like in relationships, it is best to address potential conflicts before they arise; investors address risk before markets turn volatile. Re-evaluating your comfort with risk and your portfolio's construction when things are calm puts you in the driver’s seat. Waiting until a downturn hits can leave you reactionary and vulnerable to poor decisions—like panic selling when it hurts the most.

I break market volatility into three categories:

A correction is a market drop of at least 10% from its recent high. While the news can make a big fuss about corrections, they are common and, historically, have historically recovered relatively quickly. The S&P 500 has seen 28 corrections since 1969—that is about one every two years. The best move during a correction is strategic rebalancing, not panic.

Bear markets are drops of 20% or more. Since 1969, they have happened eight times—about once every seven years. Bear markets are more serious than corrections and can be emotionally challenging, but they are still a normal part of the investing cycle. If you are lying awake at night during a bear market, it probably means your portfolio risk was not suited to your comfort level before the downturn.

A grizzly bear market is a severe drop of 30% or more, and these are rare but devastating. Since 1969, only three have occurred: during the oil and stagflation crisis of the ‘70s, the dot-com bubble in the early 2000s, and the 2008 financial crisis. These markets can take years to recover—some up to 91 months for a portfolio invested solely in the S&P 500.

What separates those who weather grizzly bear markets from those who do not? Preparation and portfolio construction. A diversified 60% stocks/40% bonds portfolio has historically fared much better during grizzly bear markets—experiencing smaller drawdowns and much faster recovery times than a pure stock portfolio. By owning more than one asset class and maintaining an “airbag” of bonds and cash, retirees can draw on their safer reserves during downturns, giving stocks time to recover.

If you are living off your investments, in or near retirement, now is the time to ask:

• Is my plan set up for the next grizzly bear?
• Can I withstand a major downturn?
• Do I have the right mix of stocks, bonds, and cash?
• Has my advisor “back-tested” my plan against worst-case scenarios?

Grizzly bear markets, though rare, are inevitable over a long investing life. The pain is real—but so are the solutions. Assess your risk now, diversify, prepare your cash and bond airbags, and ensure your plan has been rigorously tested for rough times. Addressing risk in your portfolio now leaves you sleeping soundly—no matter what the market throws your way.

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The Best In Wealth Podcast is hosted by Scott Wellens. Scott Wellens is the principal at Fortress Planning Group. Fortress Planning Group is a registered investment advisory firm regulated by the US Securities and Exchange Commission in accordance and compliance with securities laws and regulations. Fortress Planning Group does not render or offer to render personalized investment or tax advice through the Best In Wealth Podcast. The information provided is for informational purposes only and does not constitute financial, tax, investment or legal advice.

While most of us spend our working lives worrying about running out of money in retirement, Many retirees actually die with far more money than they anticipated—often missing out on the experiences, generosity, and freedom that their hard-earned savings could have provided. In this episode, I discuss why so many family stewards struggle to enjoy their wealth, and offer practical steps to find balance, conquer financial fears, and ensure you fully live the retirement you planned for. 

• [04:03] Why retirees struggle to spend
• [08:02] Encouraging retirees to spend
• [09:53] Inheriting money later in life
• [16:48] Enjoying life during retirement
• [17:54] Avoiding a life half-lived

There are several reasons behind this:

1. Habitual Saver Syndrome

Decades of saving, budgeting, and controlled spending form a deeply ingrained mindset. The wealth behaviors that enabled financial abundance are difficult to turn off suddenly at retirement. The decision to start drawing down your assets can even feel like an identity crisis: Spending then can feel like a failure, after years of associating self-worth with accumulation.

2. Fear of the Unknown

Even with a robust nest egg, fear is powerful: fear of running out, fear of the next market crash, fear of inflation or healthcare expenses. This anxiety may cause retirees to under-spend, even when the math says they are safe.

3. Identity and Psychological Attachment

For many, growing their savings has become part of their identity. Watching account balances grow is emotionally satisfying; drawing them down is not. Even after retirement, some people feel pressure to preserve and accumulate, rather than to enjoy their wealth—leading to decades with little change in their net worth.

Research shows that many retirees retain nearly 80% of their nest egg even 20 years into retirement. At the same time, spending naturally declines as we age due to reduced energy, declining health, and fewer active experiences. The risk is missing out on the vital “go-go years”—the healthiest, most mobile phase of retirement—only to find that it’s too late to use those savings for the adventures and family moments we dreamed about.

After years of working with retirees, I consistently hear the most common regrets of wishing they’d retired sooner, traveled more, spent more time with family, or helped children and grandchildren earlier. Rarely does anyone say, “I wish I died with more money in my account.”

Make sure you enjoy what you’ve built by defining the purpose of your money and clarifying what your savings are for—security, freedom, experiences, a legacy, or charitable impact. You also need to separate fear from reality, using financial planning tools, like Income Lab, can give you clarity and permission to spend by showing what’s truly sustainable. Consider starting a memory budget, instead of only budgeting for bills, earmark resources for family trips, special experiences, and gifts while you are alive.

The real goal isn’t reckless spending—it’s alignment. Let your money serve your life, not the other way around. The greatest retirement tragedy isn’t running out of money, but failing to live the life your savings could have enabled. Plan wisely—then give yourself permission to spend, to give, and to make memories. That’s how you avoid the retirement trap nobody is talking about.

• Income Lab

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Watching the news recently has been an uneasy experience for investors and retirees. War headlines dominate the airwaves, oil prices have surged to new highs, and portfolio balances may not look as reassuring as they did months ago. For family stewards looking to safeguard their financial futures, the temptation to react to these global shocks is powerful. But it’s crucial not to make emotional financial decisions. 

In March 2026, military strikes in the Middle East led to severe disruptions in the Strait of Hormuz—a global oil supply chokepoint through which 20% of the world’s daily oil supply flows. Although the U.S. itself is less directly dependent on Middle Eastern oil, oil’s status as a globally priced commodity means any disruption impacts global prices and, by extension, markets everywhere. Brent crude prices quickly soared, spiking 10–15% in a day and peaking at $120 per barrel, amid fears it could rise further.

Unsurprisingly, the financial markets responded with a bout of volatility. The VIX index—a gauge of investor fear—jumped from 19 to 25. Though jarring, Speaker A reminds us that these numbers pale compared to the shock during the COVID crisis when the VIX broke 80 (07:02). Recognizing this scale is the first step toward a measured response.

Many assume a direct, simple link: oil prices soar, stocks tumble. While sometimes true in the short term, history tells a more nuanced story. The real variable is the duration of the oil shock, not the shock itself. In the 1973 Arab oil embargo, prices quadrupled, sustained for months, and the S&P 500 lost 37% in real terms, and recovery took six years.

In the 1990 Gulf War, oil prices rose 75% in two months, but once the conflict was resolved, markets rebounded in just 28 days. In 2003, fears about Iraq pushed prices up, yet the S&P 500 delivered a 25% return the following year as disruptions were short-lived. In general, short, contained shocks resolve quickly with strong recoveries. Prolonged crises cause lasting damage.

Withstanding economic storms starts with thoughtful preparation, and ideally, we want to create a “fortress portfolio”—not a flimsy wall, but a robust structure capable of weathering attacks. This involves deep diversification:

• U.S. small-cap and value stocks
• International and emerging markets
• Real estate investment trusts
• Short-term and inflation-protected bonds

Diversification means that even when panic causes correlations to rise temporarily, the portfolio is designed for resilience, not prediction. Selling during a crisis, by contrast, locks in losses and exposes investors to the impossible challenge of timing the market's rebound—a decision research shows most people get wrong.

War and oil shocks always ignite fear, but history and evidence are clear that those who stay disciplined, trust a well-built portfolio, and avoid emotional, short-term decisions are the ones who preserve and grow wealth. It isn’t easy to hold the line, but it is the surest path to security and freedom for your family’s future.

• [00:00] Retirement planning during uncertain times
• [01:09] Don’t make emotional financial decisions
• [07:02] Understanding the VIX Index
• [08:57] The nuanced story of oil prices and your portfolio
• [14:08] Impact of oil on investments
• [18:13] Why timing the market is hard
• [23:26] Staying disciplined during volatility

• VIX Volatility Products | Cboe 

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The Best In Wealth Podcast is hosted by Scott Wellens. Scott Wellens is the principal at Fortress Planning Group. Fortress Planning Group is a registered investment advisory firm regulated by the US Securities and Exchange Commission in accordance and compliance with securities laws and regulations. Fortress Planning Group does not render or offer to render personalized investment or tax advice through the Best In Wealth Podcast. The information provided is for informational purposes only and does not constitute financial, tax, investment, or legal advice.

• [00:00] 100 years of market insights
• [03:14] Football transformed by data analytics
• [07:32] Moneyball, markets, and data
• [11:06] Insiders vs. outsiders on stocks
• [16:17] Human ingenuity in investing
• [17:26] Investing discipline drives long-term success

• Moneyball Synopsis 
• 3 lessons from investing’s moneyball moment in Fortune 
• University of Chicago’s Center for Research on Security Prices (CRSP) 

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• [03:59] How bubbles in investing have formed in the past
• [05:09] The largest 7 companies in the United States believe that AI is the future
• [06:59] What price-to-earnings ratios reveal about AI-focused companies
• [10:18] Toyota vs. Tesla: An example valuation comparison
• [13:10] Should you invest in companies that use AI?
• [15:07] An S&P 500-only portfolio is not diversified
• [20:54] Diversify globally for the best chance of financial success

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• 02:24 Best in Wealth Podcast future plans.
• 03:57 AI in daily life and finance.
• 04:51 Advantages of AI for do-it-yourself (DIY) investors.
• 08:08 Using AI for financial information.
• 12:29 Limitations and dangers of AI in financial planning.
• 16:57 Limits of AI financial planning.
• 19:30 No behavioral guardrails when it comes to your taxes.
• 25:43 If a decision affects your lifestyle for the rest of your life, don't outsource it to AI.

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• [04:27] Tax act extension highlights.
• [07:22] Inflation adjustment for tax brackets.
• [10:38] Tax deduction and SALT cap changes.
• [13:23] Maximize your deductions and minimize taxable income.
• [18:53] Estate tax and deductions update.
• [22:08] Permanent deductions and brackets.
• [23:45] Tax benefits for families.

• One Big Beautiful Bill Act 

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