Brian Skrobonja breaks down two retirement curveballs that most people don’t see coming until it’s too late. He covers how your Social Security decisions can make or break your retirement, and what really happens to your income when your spouse passes away. From the math behind claiming early versus waiting, to the hidden tax traps that arise when one spouse passes away, this episode walks you through the real-life scenarios that can make or break your retirement plan.

• Brian starts by introducing Joe and Jane, a blend of real-life clients whose story brings clarity on the right way to claim Social Security and what happens to your income when a spouse passes away.
• He highlights how to understand the impact of Social Security and the math behind what you keep and what you lose.
• Brian explains how Social Security isn’t just about retirement timing. It’s about your income, your long-term tax exposure, and your ability to stay financially independent. 
• You’ve worked your whole life to earn these benefits, you shouldn’t allow the tax man to take more than necessary just because of bad timing or misinformation.
• Why is retirement planning so important? For married couples like Joe and Jane, the right decision on when to claim benefits can be a six-figure decision. 
• According to Brian, filing before full retirement age means you accept a permanent reduction in your benefit. 
• For example, if Joe starts drawing Social Security at 65 and Jane at 62, Joe’s full retirement benefit is $3,000 a month, and Jane just $2,000 a month. 
• But since they’re drawing before their full retirement age, there’s a permanent reduction. Joe gets $2,600 a month and Jane gets $1,400 a month. That’s $1,400 a month total. Multiply that across 25 years and you land at about 1.2 million in lifetime benefits.
• Brian walks through a smarter path—Joe waits until 70, Jane until 67. With this strategy, Joe’s benefit increases substantially thanks to delayed credits, while Jane locks in her full amount. The result is $5,720 per month and a total retirement income that’s $172,000 higher than the early-filing option.
• If they both wait until age 70, their monthly income jumps to $6,200—and over the same 25-year period, that choice results in $1.398 million in total benefits. That’s nearly $200,000 more than the “default” approach. 
• Why does this matter so much? Because those additional dollars don’t just boost your lifestyle, they can help protect your surviving spouse, increase your flexibility later in life, and reduce your reliance on investment withdrawals.
• Every strategy has trade-offs. Waiting requires income from other sources, which means you need a plan in place. But if you can do it, the long-term gain is not just higher monthly income, it’s peace of mind that you’ve made a decision that protects both you and your spouse for life.
• Brian highlights how the survivor benefit is a critical retirement planning piece that many people overlook.
• Brian explains how Social Security doesn’t have to be a guessing game and how you can use it to design a retirement plan with confidence.
• Most people think retirement planning ends when you start withdrawing income from your accounts, but Brian believes that’s actually where the real planning begins.
• He explains why it’s not just about having enough money. It’s about how that money behaves in retirement, how it stretches, how it responds to market shifts, and how it continues to support you when something unexpected happens.
• Brian shows how lower income in retirement can sometimes lead to higher effective tax rates—especially when you factor in things like Social Security taxation and Medicare surcharges.
• Filing status changes everything when one spouse passes away. The surviving spouse becomes a single filer, which means half the standard deduction and compressed tax brackets. Even with a smaller income, they could end up paying significantly more in taxes.
• Learn how Joe and Jane’s provisional income pushed them into the 85% tax zone for Social Security. With IRA withdrawals and benefits combined, their adjusted gross income hit nearly $83,000. After the standard deduction, their taxable income was just under $53,000—enough to land them in the 12% bracket and trigger nearly $6,000 in federal tax.
• Brian emphasizes why tax planning isn’t optional. You can run all the retirement projections in the world, but if you’re not planning for survivorship and changing tax dynamics, you’re only seeing half the picture.
• This is where strategies like Roth conversions come in. By converting part of your IRA while both spouses are still alive—and still filing jointly—you can lock in today’s low rates. Later, the surviving spouse benefits from a source of income that’s entirely tax-free.
• The cost of losing a spouse isn’t just emotional—it’s financial. And it often happens at the exact moment when a household is least equipped to absorb the hit. Without a plan, what should have been a smooth transition can become a financial scramble.
• One way to fill the gap is life insurance. A properly designed policy can deliver a tax-free lump sum that replaces lost income and offsets new tax liabilities.
• Brian encourages couples to model survivor income today. Waiting until someone passes away to find out what’s left is a mistake. Knowing what the future looks like allows you to prepare now and avoid painful surprises later.
• He explains why your retirement plan can’t rely on assumptions. It needs to function even when life doesn’t go as planned. The goal is not just to survive retirement—but to do it with confidence, clarity, and control.

Mentioned in this episode:

BrianSkrobonja.com

SkrobonjaFinancial.com

SkrobonjaWealth.com

BUILDbanking.com

Common Sense Financial Podcast on YouTube 

Common Sense Financial Podcast on Spotify

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