Jeannine Sheppard sometimes works more than 100 hours a week and averages four hours of sleep a night. Still, the 60-year-old Westbury resident can barely make ends meet.

On a recent day in April, she woke at 5 a.m. and drove 15 minutes to a construction site for an eight-hour shift as a medic. After that, she had a half-hour to get home, shower and head back out to her second job, waitressing at a diner in Wantagh until 2 a.m.

She rarely takes a day off. She is more likely to call out sick than schedule a vacation, even when the sleep deprivation starts to catch up with her. And when she is not at one of her two jobs, she tries to pick up extra work as a housecleaner and private waitress.

She takes home about $80,000 a year, but with roughly $6,000 in monthly expenses and nearly $20,000 in credit card debt that piled up after a health issue left her unable to work for six weeks a few years ago, she is operating on thin margins.

“It’s like you’re constantly in this vortex,” Sheppard said. “What else can you do?”

Sheppard’s struggle reflects a growing reality for Long Islanders across income levels: Working full time or more is no longer enough to cover the bills. For many, extra jobs aren’t about getting ahead, but about avoiding falling behind — and the pressure is taking a toll on workers’ health, time and family life.

Business leaders say the problem is especially severe on Long Island. The Long Island Association, a regional business nonprofit, called the region’s affordability challenge an “existential” crisis in its 2026 policy agenda.

“I think that Long Island businesses and residents are being squeezed in every aspect of the word,” said Stacey Sikes, acting president and CEO at the LIA.

Some experts said wage gains have not been enough to offset elevated housing, insurance and everyday costs after years of inflation, including the steep price increases that followed the pandemic and tariffs.

“The expectation is that wages will stay ahead of inflation," said Lonnie Golden, a professor of economics and labor-human resources at Penn State University. "And maybe they’re keeping up with inflation, but with a lag, so ... your next year’s raise might compensate you for this year’s price increases.”

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While the state Department of Labor does not track how many Long Islanders hold multiple jobs, surveys suggest side hustles have become more mainstream. Nearly three in four Americans rely on at least one additional income stream, according to a January report from MyPerfectResume, and 21% of Long Islanders identified as gig workers in 2025, according to the Community Service Society of New York.

The pressure behind that extra work is clear. Nearly one-third of Long Islanders report being financially strained — meaning they cannot cover an unplanned expense without missing bills or falling into debt — according to a CSS survey of 4,000 adults statewide, including 400 on Long Island.

Rachel Swaner, CSS' vice president of policy, research and advocacy, said the survey showed strain spreading beyond the lowest-income households.

“We’re seeing more of the moderate- and higher-income folks reporting this financial precarity but we’re also seeing a large gap between the low income and the higher income,” she said.

But the message Long Islanders sent in the survey was simpler, she said. Even when “we’re working full-time and we’re doing everything right, we’re struggling.”

For Sheppard, who suffers from migraines, that strain is also physical.

“I think my body has finally fallen into, ‘It kind of is what it is,’ ” she said. “I work harder than anybody you know, and I just keep going.”

‘She is the second income, and not by choice’

Jeannine Sheppard, 60, and her daughter Meghan Sheppard, 21, squeeze in time together between work shifts and school as the family juggles multiple jobs to stay afloat on Long Island.

Many workers are taking on extra hours not to get ahead, but because they’re afraid of slipping backward.

“Some people are doing this less for offensive reasons and more for defensive reasons,” Golden said.

On Long Island, that can be true even in households with more than one working adult.

Helen Barba, 39, of Brentwood, is a full-time healthcare credentialing specialist who also runs social media for a local business. During the holidays, she sells themed products like mason jar cookie kits and treat boxes filled with sweets.

Her husband, Patrick, 44, works five to six days a week, and her father-in-law helps look after their sons — 8 months and 3½ years old — to save on childcare. Barba is also active in Facebook groups where parents trade supplies they no longer need, which she said “has been a huge, huge help.”

“Things that we used to be able to afford five years ago, we can’t now,” said Barba, who has downgraded her car from a BMW to a Kia and cut down on family trips. “I just feel like the price of everything went up tremendously.”

Helen Giordano Barba and her husband, Patrick, juggle multiple jobs, childcare and rising household costs as they raise their two young sons on Long Island.

For Sheppard, there is no partner contributing to the household income. Instead, some of that pressure has fallen to her daughter Meghan.

The 21-year-old is a photography student at Nassau Community College and works from 7 a.m. to 3 p.m. most days as a manager at a store in Roosevelt Field Mall.

“In a way, she is the second income, and not by choice,” Sheppard said. “My daughter and I, it’s really been her and I against the world since she’s been a baby.”

Meghan normally works around 40 hours a week, but when her mom couldn’t work a few years ago due to a health issue, she was pulling more than 70. She had to take off from school for nearly a year and a half because “work was the priority.”

That time “really killed us,” Meghan reflected. “Trying to step up and keep a roof over our head and groceries in the fridge at 19, 20 years old is tough.”

“I feel like at times I’m not really having the same experience as my peers,” she said.

And sometimes, she wonders, “Do I just stay at the shop forever and not even go to school? And then, again, having a mom who’s never home and works — do I just do that for the rest of my life? Do I work two jobs?”

Federal data shows that women, especially single women, are more likely to hold multiple jobs than men. Black women are the most likely to work more than one job, followed by white women, according to the U.S. Bureau of Labor Statistics.

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That burden can be especially complicated for women balancing paid work and caregiving, said David Fish, litigation and employment partner at Romano Law.

“There’s so much institutional bias and historical bias," Fish said. "And something that’s obviously part of this is the fact that women are primary caregivers.”

The problem is compounded by the fact that even a full salary can fall short of childcare costs, he said.

But working too much isn’t healthy, he added.

And for the children of people working multiple jobs — like Meghan — what does that say to them?

Does it say, “this is how much society cares about my mom, or us? Is this where I’m destined to be? Do I have a chance to work a 9 to 5 job, or become an entrepreneur?” Fish said. “It’s hard to think that way when you see your family in that cycle.”

Finding a way to stay

On Long Island, even a median income can leave a family with little room to breathe. In 2023, a family of four with two children in childcare needed a survival budget of $133,380 in Nassau County and $141,456 in Suffolk, according to United Way — leaving little room for savings or unexpected costs.

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The nonprofit uses that threshold to estimate what it takes to cover basics like housing, childcare, food, transportation, healthcare and a basic smartphone plan. Households below that threshold cannot afford those essentials, according to United Way. Median household income that year was $143,408 in Nassau and $128,329 in Suffolk, according to census data.

Still, many people want to remain here. In a Newsday/Siena survey conducted last spring, three-quarters of respondents said they enjoy living on Long Island — but just as many said it’s becoming increasingly difficult to afford their lives in the region.

A recent report from the state comptroller’s office found that the population of young people on Long Island grew 3.6% over the past decade, bucking a statewide trend of young adults leaving because of high costs, debt and a challenging job market.

“The fact that people are working multiple jobs to get by actually demonstrates they want to stay on Long Island,” Sikes said. “They don’t want to leave. They want to be close to their families. They want to enjoy the quality of life.”

But, she added, “how much will they tolerate before it’s just too much to handle?”

Jess Cater, 23, works four part-time jobs while pursuing a career in dance. She is among a growing number of young Long Islanders piecing together multiple sources of income to afford staying in the region.

Jess Cater, 23, moved to Long Island in 2021 to study dance at Hofstra University. After graduating in May, she’s picked up four part-time jobs as she pursues her dream of becoming a professional dancer.

Although she eventually wants to move closer to family and open her own dance studio, there’s more opportunities for her right now on Long Island and in New York City.

“It’s really hard, but I’m so grateful that I get to do this,” she said.

Sheppard and her daughter Meghan are also motivated to stay on Long Island.

Sheppard said she doesn’t have the means to move elsewhere — and Long Island is where her work is, where her 81-year-old mother lives, and where her daughters are.

Her oldest daughter, a 36-year-old a paralegal, is planning her wedding and working on her third master’s degree. And for Meghan, her mom is her best friend.

That means the two have to seize whatever time they can get. Sometimes it is 15 minutes in the middle of the day when they are both on break. Sometimes it is waking up at 2 a.m. to talk for an hour after Sheppard’s night shift.

“I feel like I don’t have a mom sometimes,” Meghan said. “And the stress gets to her too.”

Jeannine Sheppard (l) of Westbury answers questions from her daughters Meghan 22 (c), and Jessica 36 about her jobs and demonstrates some of the equipment she uses at work.

Sheppard does her best to make time for her daughters. She hosted a brunch before work on Thanksgiving, managed a two-hour Christmas dinner between shifts, and later celebrated the holiday again with Meghan by going to a Broadway show.

“Having a meal with my kids is like the world for me, sometimes,” Sheppard said.

She said she has already cut back where she can. She meal-preps to avoid takeout and skips streaming services and other extras, saving splurges for rare occasions. But there is always another expense: like a $600 car repair, or a vet checkup she has been putting off for her 13-year-old cat.

For now, she is relieved that after her landlord sold the house she rents this winter, the new owner let her sign a one-year lease. That means she will not have to search — at least for now — for another apartment in a market where even a studio can cost a few thousand dollars a month.

But there is always another bill, another shift.

“I believe in God. I have faith. But there has to be a break,” Sheppard said. “You want to breathe sometimes, and I feel like the breaths don’t come.”

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