SS hires Wall Street. Now what?

Hope the week is going well so far. Not every issue has a JPMorgan exec working inside Social Security — today’s does. Read on for what it means for your benefits.

On the money today:

Let's get into it.

The SSA is now managing more than 104 million online accounts with 7,700 fewer employees than it had 18 months ago. That gap has to close somewhere — and for most Americans, it closes with you doing more yourself. Check out our must read for what’s driving the shift.

We want to hear from you. Do you think a Wall Street exec running Social Security’s tech overhaul is a good thing or a red flag? Reply with your take.

Baby Boomers are the wealthiest generation in American history — but the bar for "wealthy" in retirement is higher than most people realize. A million-dollar portfolio puts you squarely at average. Before you assume where you stand, the actual threshold for the top 10% is worth seeing.

Why it matters: The gap between thinking you’re in good shape and actually being in good shape in retirement is wider than most people realize — and it costs years of compounding that can’t be recovered. Retirees who overestimate where they rank tend to underinvest in the moves that would actually close the gap.

At 12, Ray Dalio used his caddying money to buy his first stock and it tripled. He thought he’d cracked the code. What followed was a costly reminder that a lucky win and actual investing skill are two different things — and the lesson he took from nearly losing everything is one most investors never hear.

Why it matters: Dalio borrowed $4,000 from his dad after his 1982 market call wiped him out. What he learned from that collapse — about diversification, knowing what you don’t know and building in protection before optimizing for returns — is the framework behind decades of outperformance. And the principles are simple enough for any investor to apply.

The SSA has shed more than 7,700 employees in just over a year and is pushing hard toward a digital-first model — expanding its online portal, upgrading phone systems across 1,200 field offices and moving more of the disability process online. A former JPMorgan COO is now helping drive that shift, working unpaid. The agency isn’t slowing down, and most retirees haven’t caught up yet.

Why it matters: As the SSA moves more services online and cuts staff, the window to learn the new system is narrowing. Retirees who don’t adapt early will find fewer hands-on options at exactly the moment they may need them most.

Earlier this week, we asked our readers whether they or someone close to them had ever been targeted by a financial scam — inspired by our story on the five things retirees should never disclose. The response was overwhelming. David B. wrote in and wanted to share his family’s story so more readers could protect themselves.

My family has been hit by financial scams twice.

My mother’s situation started with a lottery scam, but what made it devastating was how many times it cycled. I believe her information was sold on the dark web, because every time one scam ended, another began — each one building on the last. By the third iteration, she had been convinced to sell her home to pay the “taxes” on her winnings. We found out too late to stop the sale. After she passed, we learned she had been taking money from other residents at her retirement home to keep feeding the scam.

My brother met a woman through a Facebook group called “Rich Women Looking for Men.” She supposedly lives in San Francisco but he has never met her in person. He has sent her nearly $800,000 to invest in what she calls “gold futures.” His story matched an AARP article on romance scams almost word for word. Our entire family has tried repeatedly to reach him, but he has refused to believe it’s a scam.

The correct answer is C) 30% smaller. Claiming at 62 with a full retirement age of 67 locks in a permanent 30% reduction to your monthly benefit. Wait until 70 and you’d collect 24% more than the standard amount — a gap that adds up to more than $182,000 in lifetime household spending.