We’ve got good news and bad news.

The recently published Social Security Trustees report paints a worrying picture of the program’s long-term financial outlook, with Congressional action required before 2034 to prevent sizable benefit cuts. It’s an important message, but it somewhat obscured another story, namely the current state of customer service quality after a period of significant change within the Social Security Administration.

The agency’s commissioner Frank Bisignano testified in Congress last week, just one day after the Trustees report landed, telling lawmakers that the under 5-minute average wait time on the SSA’s 800-number achieved in May 2026 was the best level in a decade, down 89% from the all-time monthly high of 42 minutes measured a year earlier. Bisignano attributed the achievement to a combination of technology innovation and the adoption of a customer service mindset taken from the private sector.

Democratic lawmakers, policy experts and consumer advocacy groups have questioned the veracity of Bisignano’s testimony, suggesting the metrics are probably obscuring deeper problems caused by significant staff cuts and decades of chronic underinvestment. Some independent observers, however, seem to think that service conditions have at least marginally improved, and that’s a good thing for the more than 330 million current and future beneficiaries of the program.

Room for Improvement

Bisignano’s statement included a number of positive metrics:

• Average field office wait times have shrunk 30%, from 30 minutes at the end of fiscal year 2024 to 21 minutes so far this year, with 6 minutes of waiting for those who schedule an appointment.
• The initial disability claims backlog has decreased 32%, with disability hearing wait times down by nearly 80 days compared with FY2024.

Kathleen Romig, senior fellow at the Center for Budget and Policy Priorities, said that while the numbers are impressive, she worries the commissioner is being selective, and even potentially misleading. “I hope I’m wrong and conditions really have improved so dramatically, but it strains credulity after they slashed staff and made so many other significant changes,” Romig told Advisor Upside. “SSA faced serious challenges when the second Trump administration started. Leland Dudek, who was acting commissioner at the time, was impressively honest about that.”

Technology changes and a redeployment of staff toward manning the phone banks may have improved certain parts of Social Security’s operations, Romig said, but it’s hard for her to believe things are suddenly as rosy as Bisignano’s testimony would suggest.

The Skeptical Take. Social Security Works, a group that advocates for the expansion of Social Security and Medicare, said in a statement that its experts don’t believe Bisignano’s message about vastly improved customer service. The group points out that Social Security has lost over 8,000 workers during the second Trump administration, including “many of the most experienced and skilled.”

Clients thought saving money was the hard part. They should try spending it.

Retirement is supposed to be the reward for decades of work. But with so much time, energy and, of course, money going into preparing for retirement, a lot of people come out on the other side asking, “Now, what?” Fewer than a third of pre-retirees aged 55 and older actually have a decumulation plan for how they’ll withdraw money in retirement, according to a survey from Corebridge Financial.

Advisors can play a pivotal role, helping clients overcome the anxieties that often linger long after their working years are over. “Even when a client has saved well, spending from the portfolio can feel very different than adding to it,” said Dwight Dettloff, founder of Winding Trail Financial Planning. “It’s less about telling clients, ‘You can spend more,’ and more about giving them a framework, or map, that helps them feel comfortable.”

Where’s the Treasure Map?

For many retirees, income becomes far more complicated than the bi-weekly paychecks they relied on during their careers. It may come from Social Security, defined contribution plans, pensions, annuities, investment accounts and even rental properties. That complexity can be overwhelming, Dettloff told Retirement Upside. “From there, we can start thinking about how to best use those resources together to create a new retirement paycheck,” he said, adding that he revisits withdrawal strategies with clients at least annually.

The Corebridge survey found:

• Just 14% of retirees have a detailed strategy for managing required minimum distributions.
• Only 31% of people ages 45 to 79 even know what the term “decumulation” means.
• A quarter of retirees align income sources to specific expenses.

X Marks the Spot. That’s an issue Jim Crider, founder of Intentional Living Financial Planning, likes to address early. “Before we talk withdrawal rates, we build a statement of financial purpose, one sentence that captures what the money is actually for,” he told Retirement Upside. “The questions matter more than the math here.” He asks clients what their ideal year would look like, where would they go, who would join them, and what’s something that they used to love but haven’t done in years. “You learn more from those answers than from any risk questionnaire.”

The housing market these days is giving off A Tale of Two Cities vibes.

The national median home price is projected to hit $1 million by 2050, just as millennials reach the traditional retirement age, according to a new report from the National Association of Realtors. That’s tremendous news for the tens of millions of millennials who are already homeowners, as upward pressure on housing prices will make their homes valuable assets in the retirement planning equation. Renters face a different outlook, however, with many feeling priced out of residential real estate. While home ownership is still a part of the American Dream for them, they may be better off relying on long-term stock market participation to gear up for retirement.

It’s an interesting new dynamic that could help advisors better forecast their clients’ retirement readiness.

A Generation Divided

The millennial generation is not monolithic, however, and older members are benefiting from the housing price inflation trend, while younger ones are suffering, said Jessica Lautz, deputy chief economist at the National Association of Realtors. “This generation is 27 to 45 years old,” she said. “That’s a big span, and older millennials and younger millennials are not behaving the same in the housing market.”

Association data shows older millennials (ages 36 to 45) are leveraging existing equity to become move-up buyers:

• They had a high median household income of $132,700.
• They bought the largest homes with a median of 2,100 square feet, and were far less likely to be first-time buyers.

Younger millennials who don’t own homes face a far different reality. Starter homes, defined as those worth a third of the median local property value, now cost at least $1 million in a record 242 cities, per Zillow. The number of cities with million-dollar starter homes has nearly tripled since February 2020, highlighting how pandemic-era housing pressures continue to reshape affordability across the country. While the typical starter home nationwide is still worth $198,649, million-dollar entry-level homes are spreading well beyond traditional high-cost coastal markets.

Stick With Stocks? For financial advisors helping millennial renters think ahead to retirement, it’s worth asking tough questions about buying into a red-hot real estate market. From a pure mathematical standpoint, research from the Association for Financial Counseling and Planning Education shows, renting is the financially optimal decision. The logic is driven by two factors. First, the costs of homeownership are significant, including transaction costs, property taxes and maintenance.

Second and even more significant, the opportunity costs of homeownership are enormous. Money used for a down payment and mortgage (above what would have been spent on rent) could have been invested elsewhere. Consequently, any analysis of the financial implications of homeownership must compare the expected return of a house to the expected return of other investments, most notably stocks. In practically all backtested scenarios, money invested in broad stock indices has a far greater return.