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November 11, 2026

The Social Security Regret I See Most in Seven-Figure Retirement Portfolios

Written by: Nathan Lee, CFP®
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Key Takeaways

  • Your Social Security Statement shows how your check changes depending on when you claim, but it doesn't account for your tax situation or other retirement savings.
  • Claiming early adds taxable income in years when your income might otherwise be low, which may shrink the window you have for Roth conversions before Required Minimum Distributions begin.
  • Your claiming age both drives and is driven by the other retirement decisions you’re making, which is why settling it on its own tends to produce an answer you later regret.

If you’ve logged into ssa.gov lately, you’ve seen the page with three big estimated monthly benefits on it. One number shows your benefit if you claim at 62, one at full retirement age, and one at 70, all laid out like a menu you’re supposed to pick from.

What the page can’t show you is how your choice affects other retirement decisions you’re making.

If you’ve saved $1.5 million or more in a traditional IRA or 401(k), those three numbers represent just a small portion of your monthly retirement income. So for you, when you claim Social Security is less about the income than about what it does to your tax situation.

Clients who claimed Social Security before we began working together often realize they hadn’t fully considered how that choice would affect their taxes, investment withdrawals, and overall retirement plan.

What Your Social Security Statement Shows

The Social Security Statement estimates the amount of your monthly benefits if you claim at different ages.

If your full retirement age is 67, claiming at 62 permanently cuts your monthly benefit by about 30%. Every cost-of-living adjustment (COLA) after that applies to the smaller figure, so the gap widens over time. Wait past full retirement age, and you earn roughly 8% more each year you hold off, which means claiming at 70 pays about 77% more per month than claiming at 62.

It’s tempting to look at the largest number and assume waiting is the right call if you can afford it, and often that’s true. But when your portfolio — not Social Security — will cover most of your retirement income, the numbers themselves shouldn’t be the only drivers of your claiming decision.

What Else Affects Your Social Security Claiming Decision

For households with a large pre-tax balance, it’s important to weigh what claiming early does to your taxes as well as to your spouse should you pass away first.

If you’re in your late fifties or early sixties with a seven-figure retirement account, you’re probably making decisions around at least the following five questions:

  1. When can you actually stop working?
  2. How will you cover health insurance between your last day and Medicare at 65?
  3. Which account will you draw from first?
  4. Should you do Roth conversions, and how much should you convert?
  5. How can you prevent Required Minimum Distributions and Medicare surcharges from piling up on you later?

Each of those decisions affects the others. Your claiming age changes how much room you have for Roth conversions each year, what your Medicare premiums look like two years later, and how quickly you spend down your retirement accounts.

It works in reverse as well. When you stop working and how much you hold outside your IRA determine whether waiting to claim Social Security is even practical.

Your Statement describes just one benefit on its own, which leaves you making a six-part decision with a one-part tool.

Free Resource

Not sure when you should claim Social Security?

Download the Social Security Decision Worksheet, a free guide that walks through the trade-offs and shows how your claiming age interacts with the rest of your retirement plan.

[Download the Social Security Decision Worksheet]

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The “Golden Window” Before RMDs Kick In

When you stop working, taxable income usually drops. You’re no longer bringing in a paycheck, bonuses, or vesting equity compensation. If you don’t immediately file for Social Security and you’re not old enough for Required Minimum Distributions, you may have several years where your reportable income is the lowest it’s been since early in your career.

I call that stretch the Golden Window, and for someone with a large pre-tax balance, it’s one of the best planning periods you have.

Claiming at 62 fills part of that valley. If your benefit runs $2,100 a month, that’s about $25,000 a year arriving in the years you wanted to keep income low. Depending on your other income, as much as 85% of your benefit may be taxable. Whatever bracket room the benefit takes up is room you can’t use for conversions.

The effect compounds, because the IRA you don’t draw down keeps growing. I’ve seen a $1.8 million IRA grow to $3.6 million in 10 years because the client didn’t need to touch it. While the growth was exciting, it resulted in a first RMD around $136,000+. Stacked on top of a pension and Social Security income, that client found himself in a higher tax bracket than he’d ever been in.

The real question is whether you want to spend a limited tax-planning window on benefit income you may not need yet.

“But What If Social Security Runs Out?”

This concern comes up often in my conversations, and many of my clients lean toward claiming early for this reason alone.

The 2026 Trustees Report projects that the retirement and survivors trust fund will run out of reserves in the fourth quarter of 2032, with payroll taxes still covering about 78% of scheduled benefits at that point. Considered together with the disability fund, which would take an act of Congress, the date moves to 2034 with roughly 83% payable.

So what’s projected is a smaller benefit rather than no benefit, because payroll taxes keep coming in and the program keeps paying what they cover.

If Social Security will be 15% of your retirement income, a 22% reduction to that slice is something your plan may absorb. Claiming eight years early to get out ahead of it means accepting a permanent 30% reduction to avoid a possible 22% one, and putting pressure on the conversion window while you’re at it.

For a household that depends more on Social Security to cover expenses, that math works out differently. I’d never tell someone in that position to shrug it off.

How Your Social Security Claiming Age Affects Your Spouse

If you’re married and you earned considerably more than your spouse did, your claiming age sets their income too, for as long as they outlive you.

So ask yourself whether your spouse has a good chance of living into their eighties or nineties. If the answer is yes, delaying may do two jobs at once, giving you a larger benefit if you live a long time and giving them a larger one if you don’t.

However, you must also consider taxes. A surviving spouse files as a single taxpayer, with narrower brackets and lower IRMAA thresholds, often on income that hasn’t changed much. Conversions during the Golden Window and a larger survivor benefit both help with that.

When Should You Claim Social Security Early?

My position isn’t always to wait as long as possible. When a client who has saved plenty tells me they’re thinking about claiming early, I don’t immediately jump to calculations. I ask whether that monthly income would actually change what they do in their healthiest retirement years.

Their answer tells me which problem we’re solving. The plan often already shows success at a high confidence level, so it’s more about feeling the ‘permission’ to spend than the actual numbers.

Watching a portfolio balance go down, even when the plan says it’s supposed to, is hard for some people. They won’t spend it no matter what the projection shows. A deposit arriving from outside every month solves a psychological problem in that case.

If claiming at 64 is what gets somebody on the Alaska cruise, or over to Europe while the knees still cooperate, or taking the grandkids to Disney when the grandkids still want to go, then the conversion math doesn’t matter. Those years don’t come back, and a plan that saves taxes while the client stays home hasn’t really done its job.

So this is a trade-off rather than a rule, and I’d want to know whether you’re short on tax flexibility or short on permission before I had any opinion about your claiming age.

There are also situations where claiming early is simply the better answer, like a health diagnosis that changes your expectations, a lower-earning spouse whose household survivor benefit runs off someone else’s record, or needing the income so you aren’t selling investments into a down market in your first years of retirement.

How To Determine When You Should Claim

I can’t tell you the best age to claim Social Security from here, and I’d be careful with anyone who offers one without knowing your full situation. What I can tell you is which questions change the answer.

  1. How large is your pre-tax balance, and what might your first Required Minimum Distribution look like if you leave it alone until 73?
  2. How many years sit between your last paycheck and that first distribution?
  3. Can you cover your spending from taxable and cash assets through those years without selling at a bad time?
  4. Would the monthly income actually change what you do, or would it sit in an account?

If you come up with conflicting answers, that’s normal. This isn’t an easy decision. But since your optimal claiming age is tied to your tax situation for the next 20+ years, it's worth deciding alongside the other five questions you’re juggling rather than in a silo.

Free Resource

Not sure when you should claim Social Security?

Download the Social Security Decision Worksheet, a free guide that walks through the trade-offs and shows how your claiming age interacts with the rest of your retirement plan.

[Download the Social Security Decision Worksheet]

Frequently Asked Questions (FAQs)

Q: Does claiming Social Security stop me from doing Roth conversions?

A: No, you may convert at any age with or without Social Security. What changes is the cost, because your benefit adds to your taxable income, which uses up room in the lower brackets you’d otherwise convert into. It may also increase the share of the benefit itself that’s taxable.

Q: How much of my Social Security benefit is taxable?

A: It depends on your provisional income, which combines your adjusted gross income, tax-exempt interest, and half of your Social Security benefit. For higher-income households, up to 85% of the benefit may be subject to federal income tax, which is one reason claiming early while also taking IRA withdrawals can be inefficient.

Q: Can I undo my Social Security claim?

A: Within 12 months of your first month of entitlement, you may file Form SSA-521 to withdraw your application. It’s available once in your lifetime and requires you to repay all benefits received, including Medicare premiums withheld and any benefits paid to family members on your record. After that window closes, your remaining option is voluntary suspension, available once you reach full retirement age, which pauses payments and earns delayed retirement credits without repayment.

Q: What happens to my spouse’s benefit if I claim Social Security at 62?

A: Spousal benefits are capped at your full retirement age amount and don’t grow with delayed credits, so claiming early has a limited effect there. Survivor benefits, on the other hand, are generally based on what you were receiving or entitled to receive, which means claiming early may permanently reduce what your spouse collects if you pass first. For couples with a significant earnings gap, this is often the largest dollar consequence of the claiming decision.

Q: Is Social Security going to run out before I retire?

A: The 2026 Trustees Report projects that the retirement and survivors trust fund will deplete its reserves in the fourth quarter of 2032, with continuing payroll tax revenue covering an estimated 78% of scheduled benefits at that point. Depletion means a reduction in what’s payable rather than an end to payments, and Congress could act before then. For households where Social Security will be a minority of retirement income, this is something to plan around rather than a reason to claim early.

Q: When do Required Minimum Distributions start?

A: Distributions begin at age 73 for most people retiring now, moving up to 75 for those born in 1960 or later. The years between when you stop working and when they begin are the ones worth protecting, because that’s when conversions tend to be most efficient.

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Content in this material is for general information only and is not intended to provide specific advice or recommendations for any individual.

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About the author: Nathan Lee is a CERTIFIED FINANCIAL PLANNER® and Behavioral Financial Advisor at Servet Wealth Management in New York City. He works with individuals and families navigating important financial decisions, including retirement planning, tax strategy, investing, income planning, and wealth management. Through his blog and YouTube channel, Nathan explains complex financial topics in a practical, easy-to-understand way.

I read every email and would love to hear if this blog helped you.