Chris Orestis, founder & president of Retirement Genius, explains how to make more informed Social Security decisions.

Social Security is one of the most important decisions in retirement.

And yet, many people approach it the same way they approach a casual conversation—based on opinions, assumptions, and what someone else did.

As Chris Orestis put it, people are often making decisions based on “the myths of Social Security, not the math.”

That’s where things start to go wrong.

Because Social Security isn’t just another income source. For many retirees, it becomes a foundational piece of their financial security. In fact, Chris pointed out that for a large percentage of retirees, Social Security can represent more than half of their income.

When a decision carries that much weight, guessing isn’t a strategy.

Why Social Security Feels So Confusing

Part of the challenge is complexity.

Many people aren’t clear on the differences between Social Security, Medicare, and Medicaid. Others assume that because they’ve “paid into the system,” everything will work itself out when they need it.

That assumption can be costly.

Chris highlighted a broader issue: people often spend more time researching a car purchase than they do understanding the benefits that may fund decades of their retirement.

That gap in understanding creates a ripple effect of poor decisions.

The Decision That Locks Everything In

Unlike many financial decisions, Social Security isn’t easily reversible.

Once you claim, you are largely locked into that decision. There is a limited “do-over” window early on, but beyond that, your choice determines your monthly benefit for life.

That makes timing critical.

You can claim as early as 62, but that locks in a lower lifetime benefit. Waiting until full retirement age—or even age 70—can significantly increase your monthly income.

So how do you decide?

It Starts with Life Expectancy

Both Chris and Jeremy emphasized that the most important factor in deciding when to claim Social Security is life expectancy.

You’re essentially making a bet:

Claim early → you’re betting you won’t live as long
Delay benefits → you’re betting you will

But here’s where many people go wrong.

They guess.

Chris pointed out that people tend to underestimate how long they’ll live and overestimate how long their money will last.

That combination can lead to decisions that reduce long-term income at exactly the time it’s needed most.

Instead of guessing, there are tools available—like longevity calculators—that can give you a more realistic estimate based on your situation.

Know Your Numbers Before You Decide

The second major mistake is not knowing your actual Social Security benefit.

Your benefit is based on your earnings history. And the estimates provided assume you continue working until full retirement age.

If you plan to retire earlier, those estimates may be overstated.

That’s why it’s essential to go directly to SSA.gov, review your earnings history, and run projections based on your actual plan.

Without that step, you’re making decisions without accurate data.

Coordination Changes Everything

The third—and often overlooked—piece is coordination.

Social Security doesn’t exist in isolation.

It interacts with:

Other income (which can affect taxation)
Earned income (which can reduce benefits before full retirement age)
Medicare premiums (which are deducted directly from your benefit)

For example, many people hear that “85% of Social Security is taxed” and assume that means an 85% tax rate.

In reality, it means up to 85% of the benefit may be taxable, depending on your overall income.

That distinction matters.

Because the real outcome depends on how Social Security fits into your broader income plan.

The Real Goal: Stop Guessing

If there’s one takeaway from this conversation, it’s this:

You don’t have to guess.

There are tools, data, and professionals available to help you make an informed decision. As Chris said, if you go into this blindly when those resources exist, “that’s your bad.”

In the Retire Today framework, Social Security falls under the MAKE step—creating reliable income.

But how you claim it affects everything else:

What you SPEND
How much you KEEP after taxes
How you INVEST your remaining assets
What you ultimately LEAVE behind

Social Security isn’t just a checkbox.

It’s a decision that shapes your entire retirement.

And it’s one worth getting right.

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About the Author:

Jeremy Keil, CFP^®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.

Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.

Additional Links:

Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
Chris Orestis on LinkedIn
RetirementGenius.com
Chris Orestis Website
“The Retirement Genius” podcast with Chris Orestis
www.longevityillustrator.org

Connect With Jeremy Keil:

Media Disclosures:

Disclosures

This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.

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Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.

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