The Keep — Retire REGAL®
The Keep/Government Strategies

Stop Guessing on Social Security.

Most people make their Social Security claiming decision based on incomplete information, a rule of thumb, or what they heard from a neighbor. Here’s what the decision actually involves.

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Most people make their Social Security claiming decision based on some combination of the following: a rule of thumb they read somewhere, what their neighbor or sibling did, a rough calculation about how long they think they might live, and the gut feeling that taking the money earlier is better than waiting and “losing” it if something happens. This is not a strategy. It is a guess dressed up as a decision — and it is one of the most expensive guesses most retirees make, because Social Security is not a minor supplemental benefit. For most Americans, it is the largest guaranteed income source they will ever own.

The decision of when to claim — and how, for couples — involves tax consequences, Medicare interactions, survivor benefit implications, and coordination with every other income source in the retirement plan. Getting it right doesn’t require a financial degree. It requires understanding what you’re actually deciding — and most people don’t.

What You’re Actually Deciding

Social Security is not primarily a math problem about break-even ages. It is a structural decision about how much of your retirement income will be guaranteed, government-backed, and inflation-adjusted — versus how much will depend on portfolio performance, withdrawal timing, and market cooperation. Claiming earlier means smaller guaranteed income and more reliance on portfolio withdrawals. Claiming later means larger guaranteed income and less reliance on portfolio performance. The right answer depends not on longevity estimates but on how the claiming decision affects the entire structure of the retirement income plan.

8% Annual increase in benefit for each year of delay past full retirement age, up to age 70
30% Permanent reduction in benefit for claiming at 62 vs. full retirement age (for those born after 1960)
85% Maximum percentage of Social Security benefit that can be subject to federal income tax

The Tax Dimension Most People Miss

Social Security benefits are taxed based on provisional income — a calculation that includes adjusted gross income, tax-exempt interest, and half of your Social Security benefit. Depending on your provisional income, between 0% and 85% of your benefit may be subject to federal income tax. The threshold at which taxation begins is not indexed for inflation — meaning it captures more and more retirees over time as incomes and benefit levels rise.

“The claiming decision is not about when you collect the most dollars. It is about how Social Security fits into the structure of the entire plan — and what that timing does to taxes, Medicare, and portfolio withdrawals.”

This means that the year you claim, and the income environment you claim into, directly affects how much of your benefit you actually keep. A retiree who claims Social Security in a year when they also take a large Roth conversion, receive deferred compensation, or sell an appreciated asset may have 85% of their benefit taxed at a higher marginal rate — an entirely avoidable outcome with proper sequencing. The claiming decision and the income sequencing decision are the same decision. They cannot be made independently of each other.

The Spousal Dimension

For married couples, Social Security claiming is a household decision with survivor implications that often go unconsidered. The higher earner’s benefit becomes the survivor benefit when one spouse dies — meaning the surviving spouse receives the larger of the two benefits, and the smaller one stops. Optimizing claiming for a married couple means evaluating not just the break-even for each individual, but the survivor income scenario — particularly if one spouse has significantly higher lifetime earnings, or if there is a meaningful age difference between spouses.

Before You File for Social Security

  • Request your Social Security statement at ssa.gov and confirm your estimated benefit at 62, full retirement age, and 70
  • Model the claiming decision alongside your projected income sources — not in isolation
  • Evaluate the tax impact of claiming in different years relative to other income events
  • For couples: run the survivor scenario and identify which claiming combination protects the surviving spouse most effectively
  • Consider whether the 2033 trust fund projection changes the calculus for your household — and how much weight to place on it

Social Security is the most valuable guaranteed income source in most retirement plans. It deserves more than a guess. A deliberate analysis — accounting for taxes, Medicare, survivor benefits, and income coordination — takes a few hours and can affect outcomes for decades. The decision is irreversible once made. The preparation is not.

Chris Owens
About the Author

Chris Owens

Founder & President of Owens Financial Group and architect of the Retire REGAL® Process — a structured retirement planning framework built around the belief that retirement freedom is designed, not accidental. #1 Amazon Best Selling author of Retire REGAL®: The Holy Grail of Retirement (Financial Services Industry · April 2026). Chris serves as an Investment Adviser Representative with Foundations Investment Advisors, LLC, an SEC-registered investment adviser.

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This commentary reflects the personal opinions, viewpoints and analyses of the author, Chris Owens. It does not necessarily reflect the views of Foundations Investment Advisors, LLC (“Foundations”) and is provided for educational purposes only. The contents are solely maintained by and the responsibility of Chris Owens. This content is subject to change at any time without notice and does not represent an express or implied opinion or endorsement of any specific investment opportunity, investment strategy or planning strategy. Foundations in no way deems reliable any statistical data or information obtained from or prepared by Chris Owens in this commentary, nor does Foundations guarantee its accuracy or completeness. No legal or tax advice is provided or intended. Investment advisory services are offered through Foundations Investment Advisors, LLC, an SEC registered investment adviser. Investments in securities involve the risk of loss. Past performance is no guarantee of future results. The Retire REGAL® Process and REGAL Stronghold™ are proprietary planning frameworks developed by Owens Financial Group, LLC and do not represent specific investment products or guarantee outcomes.