Shortly after Sarah Coomber moved her parents into a retirement community and started sorting through her childhood home, she discovered the mold.

Seeing those telltale spots was only the beginning of an enormous undertaking that involved hiring contractors to remove sections of walls and flooring and clean the entire house. When Ms. Coomber, who is 56, described the ordeal to a colleague, he reassured her that she was not alone.

“Now I see so many people are going through this, and they always have been,” she said.

Last year, about 11,400 Americans, on average, turned 65 on any given day. That wave of aging is continuing this year, too. Families, particularly those headed by members of Generation X, are confronting what older relatives may need and from whom — whether loved ones or professionals. It is the part of retirement no one wants to consider, yet for many it will touch every facet of life, like finances and health care, and the most fundamental questions of where and how to live.

Retirement in very advanced age is a possibility that longevity experts say could become a reality for more Americans than most people realize. Surya Kolluri, who leads the TIAA Institute, the research arm of the retirement plan provider, warns that many Americans underestimate how long they could live.

In a 2025 survey by the institute, only 33 percent of respondents answered correctly when asked how long a 65-year-old typically lived. The answer: For a woman, the average is 87 years and for a man, 84.

Despite recent reports of a decline in average life expectancy, the chance that someone who is 65 reaches 90 can’t be overlooked: It’s 40 percent for women and 30 percent for men, Mr. Kolluri said.

“We are racing toward 100-year lives,” he said.

When The New York Times asked readers about their own experiences, dozens of stories came flowing in: a relocation that revealed a painful illness, a son’s need to sell his house, spouses arriving at a tough realization. Here is what some of them shared.

You may have to help pay their bills.

When Paul Stanley’s mother was diagnosed with cancer, he and his sister initially took turns checking in. But with a demanding career as a software engineer and his mother’s increasing health care needs, Mr. Stanley knew she needed more care than they could give. At first, he and his sister relied on in-home aides, but it became expensive — about $10,000 a month — and insufficient after their mother had a hip replacement and needed round-the-clock care. So with their mother, now 83, they found an assisted-living community near her home in Florida.

“Putting a parent in an assisted-living facility is one of those things that you usually see in a movie and the person hates it and it’s terrible,” said Mr. Stanley, 41, of Berkeley, Calif. “But my mom knew that she needed the help, and she had struggled for long enough that she appreciated it.”

Understanding their mother’s limited resources, Mr. Stanley and his sister, who lives in Atlanta, each contribute $1,900 a month to help her cover her bills. Mr. Stanley and his partner even sold their home and became renters to free up money and time.

“We’re fortunate that we can generally afford my mom’s care,” he said. “But it competes with kids’ college funds, retirement and homeownership.”

Your mother’s dream could be your burden.

When Jenn Adrien’s parents uprooted themselves in their 60s from their Tacoma, Wash., community and moved to what they called their dream home 2,000 miles away in rural Illinois, “it was a big shock,” she said. Most of their family lived in the Tacoma area.

Her mother “didn’t consult any of us,” Ms. Adrien, 51, added. “She just did it.”

Although Ms. Adrien, who still lives in Tacoma, and her brother visited, they missed what she now suspects were some early signs that their parents were struggling. It wasn’t until their new neighbors called that she learned her parents needed help or were in a hospital. Her mother had several operations, and her father, who had kidney failure from diabetes, was in and out of the hospital.

“It had been my mom’s dream to live in a nice house and have lots of land,” Ms. Adrien said. But there were downsides — long drives to doctors, for one. “It was really neat to see my parents flourish in their retirement, but then the reality seeped in of what it’s like to care for a 4,000-square-foot home for two people and what it is like to live in a rural area.”

Your career may suffer.

At the start of the Covid-19 pandemic, Ms. Coomber and her husband hatched a plan to move from Washington State to Moorhead, Minn., to be closer to her family and, she hoped, get help with their son, who has special needs. She recalled asking herself, “Why are we so far apart?”

Ms. Coomber’s parents were getting older, and she had noticed her mother was forgetful sometimes when they talked on the phone. Soon after moving, however, Ms. Coomber became concerned when she saw her mother losing interest in what had been lifelong pleasures in gardening, cooking and seeing friends.

“For me, it was a little bit of a selfish move, that I was coming back to get help,” she said. “But once we got here, we really started to see my mom’s dementia was worse than I realized.”

In 2022, her parents agreed to some in-home care, but it was inconsistent, and Ms. Coomber urged them to consider moving to a retirement community. Not long after the move in March 2023, Ms. Coomber’s mother’s health declined. She advanced to hospice care and eventually died. A month later, her father had a stroke.

For Ms. Coomber, helping her parents so much cut into her work as a writer and took over entirely. On top of health concerns, she had to sort through what she calls their “very full home” of more than 30 years.

“I have felt many times my life is on hold, my career is on hold,” she said. She writes as a freelancer now, including a Substack column called Sandwich Season, which focuses on her experience assisting two generations. “And yet here I am writing about it,” she added. “Maybe I end up helping other people.”

You need a support network.

In 2020, Ram Rajagopal and his wife, Nidhi Gupta, faced a challenge: Mr. Rajagopal’s mother moved in with them and their two young children in Upper Saddle River, N.J. Mr. Rajagopal, a management consultant in the technology industry, and Mrs. Gupta, a physical therapist, felt the stress mounting. They all seemed to be waking one another up in the middle of the night.

“It’s difficult for your partner to love your parent the way you do,” Mr. Rajagopal said of those days together. “And they’re seeing your parent at their most weakened state — difficult, cantankerous and needy.”

But that experience caring for his mother, who died in 2022, is now helping Mrs. Gupta and her parents, who increasingly need assistance. They are still active, but Mrs. Gupta’s father had extensive surgery last summer and a tough recovery.

“I say to Ram now, some of the stuff that I didn’t quite understand when his mom was going through it, now I see,” she said. “He’s able to help me probably better than I was able to help him now that I’m having that experience.”

Mr. Rajagopal and his former classmates at the University of Pennsylvania’s Wharton School have a WhatsApp group, Elder Care Connect, where he offers support and advice. “I don’t know if it’s an uptick or that people need to connect, but people are going through the same stuff,” he said.

You should take a hard look at yourself.

It is impossible to predict how each person will age, but watching how your parents and grandparents did may lend valuable insight for your own future. Hal Hershfield, a professor of marketing and behavioral decision making at the Anderson School of Management at the University of California, Los Angeles, studies how envisioning your future self can help you plan. He describes older relatives’ experiences as either associative or dissociative, or behaviors and habits that you choose to emulate or avoid entirely.

“To some extent, your parents are the closest proxy for your future selves,” Dr. Hershfield said.

He said optimism bias leads us to be overly positive about our projections. For some people, he added, watching a parent falter could offer a realistic counterpoint to a rosy view of the future.

Dr. Atul Gawande, a surgeon at Brigham and Women’s Hospital in Boston and the author of “Being Mortal,” said discussing preferences with family members was a vital part of helping them sustain a fulfilling life, especially those with serious health problems. He recommends a series of questions, called the Conversation Project, to help guide family decisions. The questions include: What does a good day look like for you? What activities bring joy and meaning to your life? If your health gets worse, what are your most important goals?

“It’s almost embarrassing that it took me writing a whole book, interviewing 200 families and patients and scores of experts, to come to a pretty simple conclusion,” Dr. Gawande said. “People have priorities in their lives besides just living longer, and in order to understand what those priorities are, you need to ask them.”

For Ms. Coomber, seeing her parents struggle prompted conversations with her husband about what the two of them want. An overstuffed house isn’t on the list.

“We’re setting deadlines,” she said. “By the time we’re 65 or 70, we’re going to downsize the heck out of the situation.”

By some measures, the legal cannabis industry is flowering. It has grown to around $30 billion today from less than $20 billion just six years ago. But investors have remained wary of its high taxes, marijuana’s illicit status at the federal level and the operational costs of complying with a patchwork of state regulations.

Now the Trump administration is pushing major policy changes that could hand marijuana companies a huge windfall and unlock new investment in the industry.

Last week, the government relaxed federal controls on medical marijuana. While that does not make medical marijuana legal under federal law, it moves the product from a class of highly addictive drugs, such as heroin, to a category of lower-risk medicines, like prescription Tylenol, that are overseen by the D.E.A. The Trump administration has also started a process to reclassify cannabis more broadly.

For some cannabis businesses, reclassification could cut tax bills in half. Companies that sell marijuana are currently taxed largely on their income, rather than their profits, resulting in effective tax rates of around 70 percent, more than double those of other businesses. Under the new category, those licensed to sell medical marijuana can claim common tax deductions for expenses like rent and payroll, according to accountants and tax lawyers. A broader reclassification would do the same for recreational marijuana.

The Treasury is considering making the tax relief retroactive, which would be a boon for the industry. Legal cannabis companies owed the Internal Revenue Service $2.24 billion in 2025, according to Whitney Economics, a cannabis research firm. A handful of publicly traded companies, including Trulieve, Florida’s largest medical cannabis company, and Curaleaf, a global juggernaut based in New York, owed more than $1.6 billion in federal taxes, according to their financial disclosures.

It is unclear how the change would be put in place and how extensively businesses would benefit. The Treasury and Internal Revenue Service have yet to issue guidance, though the Drug Enforcement Administration has begun allowing businesses to register with the agency. And there are questions about how the many businesses that sell both medical and recreational cannabis will be treated.

“I’m ecstatic that this happened,” Joe Andreae, the chief executive of CULTA, a cannabis company in Maryland that sells both recreational and medical marijuana. “But it creates a challenge. Will they force us to actually delineate?”

Despite the confusion, and the exclusion of recreational marijuana, many in the industry have welcomed the administration’s acknowledgment of the medical benefits of cannabis as a meaningful first step toward broader reform and public acceptance.

Patrick Rea, the managing director of Poseidon, a cannabis-focused venture capital firm, said the tax relief will make the industry more attractive to investors. “The upshot here for investors is that you can invest and get a return,” he said.

A windfall in sight

Nationally, cannabis businesses are facing rising supply-chain costs, and a glut of legal crops is driving down prices. Beau Whitney, an economist specializing in cannabis, said that 24 of the 40 states that have legalized medical or recreational marijuana, or both, saw revenues decline in 2025.

A big tax break could offer significant help. Austin Ownbey, a Washington, D.C.-based partner at Akerman LLP, said the tax break will make some businesses profitable or more profitable.

Many cannabis companies have delayed filing taxes in anticipation of rescheduling. Jeffrey Schultz, a cannabis lawyer at Foley Hoag LLP in New York, said that he was advising clients who have been granted extensions from the I.R.S. to consider holding off longer, while telling those that have filed already to think about amending their returns. “They may not owe that money,” he said.

Paying less in taxes could help cannabis companies fund research required for marijuana to gain approval from the Food and Drug Administration, which would make it legal to prescribe at the federal level.

The chief executives of Trulieve, Curaleaf and Tilray, a New York-based alcohol and pharmaceutical company with cannabis operations in Canada, said in interviews that they wanted to invest in research to gain approval for cannabis-based treatments for cancer, nerve pain and seizures.

Kim Rivers, the chief executive of Trulieve, said rescheduling cannabis was a long overdue step that recognizes how much the industry has evolved. Rivers was instrumental in persuading President Trump to issue an executive order last December directing the Department of Justice to quickly reclassify marijuana.

“This is not some plants in a closet or on a dirt floor,” she said in an interview. “This is real, regulated, highly nuanced business. Millions of Americans are finding relief and want to have assurance that these products are backed by real research in the United States.”

Left out

It came as a surprise to many in the industry that recreational marijuana was left out of the initial rescheduling. Shawn Hauser, the co-chair of the cannabis practice at Vicente LLP, based in Colorado, said the treaty powers that the Trump administration used to bypass the bureaucratic rule-making process allowed the reclassification only of medical cannabis.

The Trump administration is seeking the same change for recreational marijuana at a hearing scheduled to begin on June 29. But it is certain to be opposed by anti-legalization groups like Smart Approaches to Marijuana, which led opposition that ultimately derailed an earlier attempt to reschedule marijuana under President Biden.

Businesses that sell cannabis solely for adult recreational use are worried that the new rules for medical marijuana could put them at a competitive disadvantage.

That includes Beak & Skiff, a 115-year old apple orchard in New York that makes a line of cannabis and hemp products called Ayrloom. In addition to the possibility of being excluded from rescheduling, the company is preparing for a looming national ban on hemp products containing more than .4 milligrams of THC per container. For Beak & Skiff, the ban would reduce the number of states in which it sells hemp from 13 states to just one, New York.

“It feels like we’re just getting crushed in the middle of two things,” Eddie Brennan, the company president, said.

Hurdles remain

Moving medical marijuana to a lower-risk category does not make it legal, which would require either an act of Congress, F.D.A. approval or removal from the federal controlled substances list. Companies will still contend with the legal risks associated with cannabis that have kept banks, institutional investors and insurance companies on the sidelines, leaving them with limited access to financial services and higher borrowing costs.

The effect can be seen at the dispensary register, where consumers are required to pay with cash or PIN debit because major payment processing companies like Visa and Mastercard do not allow cannabis transactions. Even the Drug Enforcement Administration is requiring the medical cannabis businesses now seeking federal registration to submit their application fees using PayPal or bank transfer.

Efforts in Congress to pass legislation providing protections for federally regulated financial institutions that serve state-licensed businesses have been unsuccessful so far.

It is also unclear how rescheduling will interact with state laws.

“There’s just a lot of questions, a lot of murkiness,” Whitney, the economist, said, adding: “The devil’s in the details.”

IN CASE YOU MISSED IT

Spirit Airlines is preparing to shut down. The distressed airline, which has filed for bankruptcy twice in the last two years, had been hoping to secure a $500 million loan from the government before running out of funds. But the deal fell apart as some of Spirit’s investors and some Republican lawmakers opposed it.

Fed drama continued. Kevin Wash, Trump’s nominee for Fed chair, cleared an important Senate Banking Committee vote and is expected to be confirmed in time for the next Fed meeting in June. The Fed voted on Wednesday to keep rates unchanged at a range of 3.5 to 3.75 percent, and the current chair, Jerome Powell, announced that he will break with tradition to remain a governor at the central bank after his term as chair ends on May 15.

A.I. spending set a record. Google, Amazon, Microsoft and Meta reported more than $130 billion in quarterly capital expenditures on Wednesday, about 70 percent more than they spent in the same quarter last year.

The F.C.C. ordered a review of ABC’s broadcast licenses. The extraordinary order came amid a fight between President Trump and Jimmy Kimmel over a joke by the late-night host and represented an escalation by the Trump administration to punish media outlets for their coverage. It faces long odds in court.

More big deals: Bill Ackman’s new fund had a lukewarm I.P.O. PayPal is said to be spinning out Venmo. G.D.P. grew 2 percent in the first three months of the year. And the Senate banned its members from trading on prediction markets.

Taylor Swift’s deepfake defense

A.I. threatens the business of being a celebrity, and Taylor Swift’s legal team just set up a new layer of defense. Last week, the artist filed applications to trademark snippets of her voice and a photo of herself, which lawyers who specialize in intellectual property say could help build a legal argument against unauthorized deepfakes. The actor Matthew McConaughey has made similar moves.

DealBook’s Sarah Kessler talked with Josh Gerben, the head of a trademark-focused law firm that was one of the first to point out the applications, about Swift’s legal strategy. The conversation has been condensed and edited.

How do these trademarks potentially help in a case over deepfakes?

One potential defense is right to publicity law, which basically says, I can’t put Taylor Swift’s image on a T-shirt and go sell it, because that would violate her right to exploit her name, image and likeness. If I were to take her voice and make a new song, I’m arguably violating her right to publicity.

But courts haven’t really looked at this yet. So we’re not sure how they would view it.

Now you’re also trying to trademark the voice to have another cause of action, where you could say, by using my voice, you’re also violating my trademark rights.

Is there something about trademark law that makes it particularly useful in this context?

Trademark law gives you the ability to police against anything that’s confusingly similar. So it doesn’t even have to be an identical copy, or it doesn’t have to actually be Taylor or her voice. It could just be something that’s similar to that. So it’s arguably a little bit of broader protection.

Why haven’t we seen a big lawsuit over celebrity deepfakes yet?

It looks like everybody’s kind of setting up. You’re going to be testing novel legal theories and you want to make sure that if you’re actually going to spend the time and money to litigate it, that you have a really good chance of setting a good precedent.

Because the last thing you want to do is lose and set a bad precedent, where then it just becomes kind of open season on your intellectual property.

Are your clients worried about this?

Even brand owners are starting to pay attention, because you could use A.I. to create fake advertisements that say something that’s untrue or derogatory about a brand.

Quiz: Palantir’s new merch

This question comes from a recent Times article. Click an answer to see if you’re right. (The link will be free.)

On Thursday, the technology company Palantir added a new product to its online store that Eliano Younes, the company’s head of strategic engagement, told The Times was intended to demonstrate a commitment to “re-industrializing America.” What was it?