Corey Strickland spends his days shuttling passengers, spinning music sets and working a third job on Oahu to keep up with Hawaii’s high cost of living.
Across the island, Chevelle Davis balances Ph.D. studies and a professional job yet still feels the strain on her pocketbook.
Their stories capture the growing pressure on Hawaii’s Millennial generation — those roughly between 29 and 44 — who are finding that even steady work, advanced degrees, and relentless effort no longer guarantee financial stability in the islands or the opportunity to become homeowners.
The top financial pressures that financial literacy and wealth management firms say are facing Millennials — housing costs, student debt, consumer debt, and a lack of retirement savings — are even more pronounced in Hawaii, where each strain is magnified by the state’s extreme cost of living. A December 2024 University of Hawaii Economic Research Organization (UHERO) report found that Millennials, or Gen Yers, in the state tend to pay more for housing than other generations while earning less on average than Gen X.
Their predicament reflects a widening generational gap: Strickland and Davis say Millennials are falling behind and fear Gen Z will fare even worse. With three-quarters of local workers now considering leaving the state due to cost-of-living pressures, Hawaii risks losing the very generation it depends on to sustain its economy, care for its elders, and raise the next.
Strickland, 38, lives in half a duplex with two roommates to economize his housing expense. He is also debt-free, but has no savings for retirement and primarily earns a living as an Uber Premium rideshare driver with a Tesla Model Y midsize SUV.
“It’s a struggle every month,” Strickland said on a recent day waiting near Honolulu’s Daniel K. Inouye International Airport for a fare opportunity from arriving passengers. “Most months I’m fairly good. And then some months, when tourism is down, it’s like, ‘All right, I got to figure it out — work harder, work longer hours.’ ”
Getting by
Strickland said he spends around 50 hours a week on average engaged with Uber, and has two supplemental jobs as a touring music DJ, whose artist name is Sketch Muzic, and a relations manager for artists visiting Hawaii through music events firm Audiophile Entertainment.
Gen Yers make up a large share of the nation’s gig workforce, and in Hawaii many of those jobs are tied to tourism-driven service work that rises and falls in ways that don’t keep pace with the state’s high cost of living.
Strickland, who moved to Hawaii six years ago from Alabama, initially lived in Waikiki where his monthly rent over about five years rose from $1,700 to $2,200 not including $400 a month he spent for parking during much of that time.
Now, Strickland pays $1,200 a month for his share of half a duplex in Aliamanu that he rents with two roommates, a setup he views as a deal especially because they have little to no monthly utility bill due to rooftop solar.
“We definitely got lucky on that,” he said.
Homeownership, however, is something Strickland doesn’t ever anticipate attaining in Hawaii, where the median sale price for previously owned single-family homes and condominiums has been around $1.1 million and $510,000 in recent months, respectively.
One expense Strickland said uncomfortably eats into his budget is food, which has gotten considerably more expensive in recent years of high inflation followed by ongoing modest inflation.
“It’s sad when you can’t eat healthy because healthy is expensive,” said Strickland, who for several years worked for a Hawaii food distribution firm. “I understand that there are costs, but it seems like everything is inflated more than it should be for profits over sustainability.”
Income imbalance
According to the UHERO report, Millennials spend more on housing compared with other generations in Hawaii. Yet on average, they earned less from labor — $64,360 in 2022 — compared with the preceding generation, Gen X, which had the highest average income at $72,344 among generations.
“None of my friends that are my age are even remotely in the realm of buying property in Hawaii,” Strickland said.
The preceding generation, in Strickland’s view, had a benefit of establishing better financial foundations before the last wave of high inflation and spike in interest rates that made homeownership much more difficult. And he believes the generation after his, Gen Z, is going to have the toughest time yet with Hawaii’s cost of living.
Davis, a part-Native Hawaiian Millennial who grew up in Leeward Oahu, also has a dim view of her future homeownership prospects, and believes the generation of her parents is more fortunate.
“It’s extremely difficult for us as Millennials,” said Davis, 39. “Things are just so much harder for us than it was for our parents.”
Davis said her parents were homeowners at a younger age than she is now. Davis earns more than her parents did at her age, but she still feels at a disadvantage in trying to become a homeowner, even after living with them until four years ago to save money while pursuing a doctorate in public health at the University of Hawaii.
Davis, who directs early childhood and health policy at the nonprofit Hawaii Children’s Action Network, knows child care is another major expense burdening many Millennials. On another hand, as a single person, she has no one with whom to share expenses.
“I’m just one income,” she said. “Everything is on me — the rent, the utilities, my car, my food — everything.”
Davis also has about $30,000 in student loans, which she said is not a relatively high amount but still adds to her cost of living.
In four years living on her own, Davis has had varied success finding affordable housing by some, but not all, standards.
Initially, she split a $3,200 monthly cost of a two-bedroom, two-bathroom home in Ewa with a roommate. Then Davis moved into a one-bedroom unit reserved for households earning under 80% of the median income that came with below-market monthly rent of $1,800. Yet after landing a new job, her new annual income eclipsed the limit by $4,000 and forced her to move out. Now, she lives in a two-bedroom accessory dwelling unit on a single-family property in Makakilo and pays $2,100 a month, which she said is 55% of her take-home pay.
Severe burden
The federal Department of Housing and Urban Development considers households to have an economic housing problem if they pay more than 30% of their monthly income on housing costs including utilities, and if the expense is over 50% then it represents a “severe cost burden.”
Davis is frustrated that housing costs in Hawaii far outpace wages. Not long ago, she looked at a new two‑bedroom condo in Kapolei listed at $600,000 but knew it was out of her range given that a 20% down payment alone would be $120,000.
“Who has that laying around,” she asked rhetorically.
A recent survey by the local nonprofit Holomua Collective found that a rising number of working families have considered leaving the state due to what the organization described as a deepening cost-of-living crisis in Hawaii.
The survey of 3,200 workers statewide found that 75% of respondents said they will, or are unsure if they will, move to a less-expensive state in the coming years due to financial pressures, up from 70% who had the same answer in 2024 in the first year Holomua conducted such a survey.
Holomua’s new survey also found that the reported financial pressure to leave only begins to decrease for households with annual income of $150,000 or more, up from $100,000 in 2024.
“The data confirms the financial strain we identified a year ago is intensifying, reaching deeper into a variety of income levels,” Josh Wisch, Holomua executive director, said in a statement. “When three out of four local workers who are the fabric of our community worry they may have to leave, we face an accelerating threat to the Hawaii we know and love.”
Davis said she not only loves Hawaii too much to leave, but expects that she may one day be called upon to care for her parents as the oldest of six siblings.
There’s also a responsibility, or kuleana, that Davis feels to the place where even older generations of her family lived.
“I refuse to be forced off my ancestral lands, even if that means that my life is going to be harder,” she said. “I have a kuleana to this place, to its communities, to its people. Because this place has raised me, and it has fed and sustained generations of my family.”
Generation Y (Millennials)
Born 1981 to 1996
Ages 29 to 44
Three top economic challenges:
>> Housing costs
About 69% spend more than 30% of their income on housing in Hawaii, according to a recent statewide survey by Holomua Collective.
>> Saving for retirement
Average respective 401(k) and IRA balances of $67,300 and $25,109, nationally, according to Fidelity.
>> Student and consumer debt
$132,280 average consumer debt nationally, second behind Generation X, according to Experian.
Share your insights
This series is ongoing, and we want to hear from you. If you have story ideas, experiences or sources related to Hawaii’s generational economy — from the challenge of making it on your own to the cost of raising a family to the realities of retirement — please reach out to Weekend and Special Projects Editor Allison Schaefers at allison.schaefers@staradvertiser.com or at 808-529-4700.
About this series
Hawaii is hitting a generational breaking point as inflation and soaring housing and health care costs squeeze residents of every age. This series looks at how each generation is navigating mounting economic strain — and what’s at stake for the state’s future.
Sunday: Gen Z fights to launch amid high costs, unstable wages and student debt.
Today: Millennials delay milestones as they juggle unaffordable housing and childcare.
Tuesday: Gen X strains under debt, caregiving and rising expenses.
Wednesday: Boomers face a harsh retirement reality shaped by inflation and limited savings.
Sunday: Lawmakers weigh how to support seniors while investing in Hawaii’s young.
