How Millionaire Retirees Should File for Social Security

 When I first started creating content and discussing Social Security, many of my colleagues were skeptical. Some even asked, “Why are you focusing so much on this? Wealthy people don’t worry about Social Security.”

But I quickly learned that wasn’t true at all.

Some of the most financially successful retirees I’ve worked with were more concerned about making the right Social Security decision. And it makes sense. They weren’t dependent on the check from Day One. They had flexibility. They had choices. And that made the decision even more important.

For them, the question wasn’t “When can I file?” It was “When should I file to get the most strategic value from this benefit?”

Because when you’re not forced to rely on Social Security immediately, you gain the ability to be strategic. You can time your filing to reduce taxes, coordinate investment withdrawals, and strengthen your overall retirement plan.

What this Means for Millionaire Retirees

In this post, we’ll walk through how millionaire retirees should think about Social Security. We’ll cover why the decision is more important than most people realize and how to use this benefit as part of a smart, coordinated retirement income strategy.

There’s a lot to consider here. I host a webinar where I typically speak for about an hour, and even then, it doesn’t cover everything. My goal is to offer you a clear framework that helps you start shaping your own decisions.

It All Begins with One Key Question

At a high level, it all starts with one question: 

“What’s your primary goal with Social Security?”

Because depending on what matters most to you, your ideal filing strategy could look very different.

For some of you, the top priority is providing for your spouse. You want to ensure that if something happens to you, your spouse is left with the highest possible benefit. That’s an emotional decision, but also a very strategic one. And it should factor into when you file.

For others, the focus is on building a solid foundation of guaranteed income. You want to know that no matter what happens in the market or the economy, a big portion of your income is locked in for life. For you, Social Security isn’t just a benefit. It’s a tool for stability.

And then some want a full, comprehensive plan that connects Social Security with withdrawals, taxes, and even Roth conversions. You don’t just want to make a good decision. You want to make the best decision based on all the moving pieces of your retirement plan working together.

These priorities often overlap, but breaking them down one by one can help you find your clearest path forward.

Let’s start with the first and most emotional decision: protecting a surviving spouse. Then we’ll move into guaranteed income and full optimization.

Priority 1: Protecting a Surviving Spouse

While we could explore all the technical details such as survivor benefits, the widow’s limit, and other complexities, the core of this decision is quite straightforward.

If one spouse was the higher earner, delaying their Social Security filing can significantly increase the benefit left behind for the surviving spouse. That’s because when one spouse passes away, the smaller benefit ends, and the larger one remains.

But this isn’t just a math problem, it’s a bigger-picture question. Before you can evaluate which filing age makes sense, you have to answer a couple of key questions:

• How much income will your surviving spouse need?
• How much of that income should come from guaranteed sources?

It’s true that expenses often decrease after a spouse passes. There’s one less person to support, fewer travel or dining costs, and possibly lower healthcare or insurance bills. But how much they drop depends heavily on your specific lifestyle, spending patterns, and which spouse passes first.

My recommendation: Set up two versions of your retirement budget: one for when you’re both alive and one for after death. You can use my free Retirement Budget Calculator to map this out, or simply jot it down on a notepad. What matters is that you take the time to get clear on the numbers.

For example, many of my clients dedicate a significant portion of their budget to travel, but in some cases, only one spouse is truly passionate about it. If the travel-loving spouse passes first, that expense might disappear entirely. That kind of adjustment can have a real impact on what your surviving spouse needs to live comfortably.

Once you know what your surviving spouse will likely need, ask yourself:

“How much of that income should come from guaranteed sources”

In other words, what’s more important to you: leaving behind a larger portfolio they can draw from, or securing the highest possible guaranteed income through Social Security?

Because filing early or filing later will change the balance between those two. If you delay, you’re creating a larger monthly benefit for your spouse, but you’re also likely spending down more of your investment accounts in the meantime. If you file early, you may preserve more assets, but the guaranteed income you leave behind could be smaller.

This is why survivor-benefit testing has to be part of the conversation. It’s not necessarily the deciding factor unless there’s a known health issue. It’s essential to include this in your planning as a stress test: If the higher earner passes away early in retirement, how will your plan hold up? Will the plan still work? Will your surviving spouse be okay? That’s the kind of clarity you want before you file because a good strategy isn’t just about ideal outcomes. It’s about resilience.

Now let’s look at another powerful reason retirees choose to delay their filing: maximizing guaranteed income.

Priority 2: Maximizing Guaranteed Income

Many people aim to establish a guaranteed income floor in retirement—covering essentials such as housing, groceries, utilities, and healthcare regardless of market fluctuations. Discretionary expenses such as travel, gifts, or hobbies can then be comfortably funded from savings.

Others don’t necessarily draw that hard line between essential and discretionary spending. Instead, they prioritize maximizing income from guaranteed sources. For them, that predictable, reliable income helps reduce worry. It gives them peace of mind and makes life feel a little less stressful.

Social Security plays a critical role here. Unlike your portfolio, Social Security pays a monthly check for life. The longer you wait to file (up to age 70), the larger your monthly benefit becomes.

So if guaranteed income is your priority, the answer is simple: Wait to file.

That doesn’t mean the decision is automatic or that you shouldn’t look deeper. But when you’re thinking purely about guaranteed income, Social Security is one of the best tools you have. It doesn’t fluctuate with interest rates or market returns. It’s not subject to a sequence of returns risk. It’s stable. And that kind of stability is exactly what many retirees are searching for.

To help with this, we built a free break-even calculator on our website. It shows you which filing age likely results in the highest total lifetime Social Security payments. It also allows you to input your filing age and estimated cost-of-living adjustments to see a more personalized estimate.

Priority 3: Coordinating Social Security With Your Full Retirement Plan

The most comprehensive strategy is developing a coordinated plan that integrates Social Security, taxes, withdrawals, and long-term goals into a cohesive framework.

If you haven’t filed for Social Security yet and are drawing income from IRAs or brokerage accounts, the timing of your Social Security claim affects:

• How much you withdraw from investments
• Your taxable income each year
• How much of your Social Security benefit is taxed
• Your Medicare premiums down the line
• Whether Roth conversions make sense

Every decision you make has a ripple effect. And that’s especially true when it comes to when you file for Social Security.

Delaying Social Security creates a “tax planning window” between retirement and required minimum distributions. During this window, you may be able to lower your tax bill through smart Roth conversions and income smoothing. I’ve seen clients reduce their lifetime tax liability by six figures thanks to this approach.

If your goal is full optimization, you can’t look at Social Security in isolation. The right strategy often blends delaying benefits to strengthen survivor income, running Roth conversions to manage tax brackets, and ensuring you have enough guaranteed income to feel secure.

That’s the real advantage of flexibility because it gives you room to design a plan that fits your goals, your lifestyle, and your tax picture.

So how do you put this into action?

Bring It All Together

If you’ve built a substantial portfolio, don’t think Social Security is just a side note. The more flexibility you have, the more important this decision becomes.

Whether your top priority is protecting your spouse, maximizing guaranteed income, or integrating Social Security into a comprehensive, tax-efficient retirement plan, how and when you file can significantly influence your financial future.

The real question is: What’s the smartest way to use your flexibility?

There’s no one-size-fits-all answer. The right filing age isn’t just about maximizing a monthly check, it’s about aligning Social Security with your bigger goals, tax picture, income needs, and long-term plan.

Ready to Get Clarity?

If you’re ready to build a well-rounded retirement strategy, I’d love to guide you through it. Schedule a Retirement Clarity Meeting, a focused, one-on-one conversation designed to give you insight, direction, and confidence about your financial future.

We’ll take a comprehensive look at Social Security, taxes, investments, and income needs so you can see how all the pieces fit together.

No pressure, no sales pitch. Just real clarity to guide your next steps with confidence and purpose.

Here is the link to grab a spot on my calendar. Thanks for reading!