The Big Family Fight Is Over How to Work. ‘They Think I’m Insane.’
Generational debates about work may be brewing in the office, but they’re often louder on the home front
Generational debates about work may be brewing in the office, but they’re often louder on the home front
Hybrid work. Hustle culture. Work-life balance.
Tensions over how to work don’t just permeate offices these days. They’re on full display within families.
“They think I’m insane,” Lisa Olson, 53, said of her children when she tells them she skipped lunch during the workday.
Her 25-year-old daughter, Emily Olson, tends to fit her job in advertising around her life, sometimes taking a midday break but also logging on after-hours if there’s work to be done. She thinks her mom struggles to make time for herself.
Like with the Olsons, many of these debates break along generational lines. Many parents in their 50s and 60s built careers in pay-your-dues work environments where 40 hours was the minimum spent in an office each week. They had clear-cut templates for getting ahead.
Their children, in contrast, joined the labor force over the past decade, as the gig economy took off, a pandemic upended 22 million jobs and millions of people embraced working from home. Technologies such as AI are scrambling their careers even more.
These debates about work are often more pointed, and personal, at home than on the job. Parents and their adult children say these conversations are often meaningful in navigating today’s multigenerational workforce.

“These are people who’ve known you all your life—you hope they understand what really matters to you,” said Megan Gerhardt, a management professor at Miami University’s Farmer School of Business and the author of a book about intergenerational workforces.
Emily has worked mostly remotely since graduating from college in 2020. One benefit is that she can integrate errands into her workday. Her mother, who works in financial services, urges her to go into the office.
“When you’re remote, you hop on a Teams call, and you talk about the issue at hand—and you don’t necessarily have extra time in that meeting to chat,” Lisa said.
Emily said that when she does commute to work, she often interacts with co-workers virtually since not all of her team lives in Chicago, where she’s based.
As long as she does good work and is responsive, working set hours in a set place isn’t important to her, she said. When a call was unexpectedly rescheduled to a Friday afternoon, when work is usually winding down, she logged on from the hair salon while getting highlights.
“It doesn’t have to be a rigid workday,” said Emily, who often works more than 40 hours each week.
Lisa, on the other hand, said she spent much of her career leaving for work at 7 a.m., and returning at 7 p.m., five days a week. “In my world, work is a completely separate item from my personal life,” she said.

Kristin Ned, 48, has logged long hours over her career in human resources, ready to respond to emergencies. Her 28-year-old daughter, Maaliyah Papillion, gives priority to rest when she’s not on the clock.
“She and I are not on the same page when it comes to what it takes to get something done,” said Ned, who lives in Lake Charles, La. “I know not everything can happen between 8 a.m. and 5 p.m.”
Papillion started an executive-assistant job this summer in New Orleans. A priority was professional boundaries, especially since she was embarking on a master’s program and had less free time.
“If work is over, work is over,” she said.
One Sunday night, Papillion got a work call. “Can it wait until tomorrow?” she replied. Later, she consulted her mom.
No one wants to make a work call on a Sunday night, Ned said, so it must have been important. Papillion said she now sees that little gestures go a long way, especially when building professional relationships.
Ned said she’s also learned from Papillion’s approach to work, such as when Ned’s company held a back-to-school campaign allowing for more work flexibility as parents adjusted to new school drop-off routines.
“We tried to make it as easy as possible,” she said.

Kendrick Hering, 24, has been patching together temporary gigs in landscaping and fixing up rental properties while he tries to launch his own business as a digital artist. His dad, Doug Hering, wants him to apply for more steady work.
Kendrick lives at home in Colorado Springs, Colo., and pays rent to his parents. He has been applying for more full- and part-time work for months, but with no luck. He also doubts full-time work would come with the job security and benefits that would make all the hustling he’s doing now worth it.
“To actually even find out about a job that I’m probably, just statistically speaking, not going to get, I have to do an exorbitant amount of research,” Kendrick said.
Doug Hering, a 63-year-old financial planner, has recommended his son apply to several jobs each day. He also has suggested he make business cards and perhaps enlist a life or business coach.
“You can’t sit back and do some digital advertising and hope that the floodgates will open,” said Doug, who took Kendrick to a networking event this month.

Lisbeth Darsh, a 57-year-old marketer based in Seattle, said her kids often encourage her to vie for promotions, so that her pay and title reflect her expertise. Her son, Justas Rodarte, 26, said his mum’s skills in writing to engage an audience are hard to match and she is better than he is at social media.
“My son is good at reminding me that there’s great value in what I do, and I owe it to myself to get that value,” Darsh said.
She’s not alone in taking advice from younger generations. About three-quarters of nearly 7,000 workers surveyed worldwide this summer said 20-something co-workers had influenced their attitudes toward issues such as work-life boundaries, fair pay and self-advocacy, according to Edelman, the public-relations firm that conducted the survey.
In the past, employers haven’t fully recognised Darsh’s skills, her son said, but this summer she won a promotion to become a director.
Now, his mum has a position that “fits her skills really well,” said Rodarte, who is pursuing a Ph.D. in immunology. “It’s the sort of thing that I wish I’ll be able to achieve.”
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Artificial intelligence is making it easier than ever to build a business without building a team. As AI takes over coding, customer support, marketing, administration, and other day-to-day tasks, a growing number of solo founders are scaling startups to millions in revenue with few—or even no—employees. While the trend is lowering barriers to entrepreneurship, it is also reshaping hiring, raising questions about the future of work and how businesses will grow in the AI era.
Ben Broca launched a company last December that offers AI tools to entrepreneurs. He’s already added 10,000 paying customers and is on track to bring in $10 million in revenue this year.
One thing he hasn’t added: any other employees.
The 40-year-old is part of a class of entrepreneurs who are launching, and then often running, new companies on their own. Artificial intelligence tools answer Broca’s emails, help write and debug code, field requests from customers, sign up new subscribers and grant refunds when issues arise.
Broca relishes his ability to make whatever decisions he wants on his own, often from his sun-drenched Sausalito, Calif., living room. “I think compromises make lukewarm results,” he said.
Once upon a time, running a business of a certain size required a team. AI is turning that assumption upside down, and more aspiring entrepreneurs are going it alone.
An analysis by the payments company Stripe shows there are thousands of solo operators on the company’s platform that are generating over $1 million in revenue, with their ranks doubling between 2023 and 2025. The number of solo operators crossing the $10 million threshold nearly tripled in that same span.
In the past, people without business contacts or particular savvy might not have known how to get their ideas off the ground, said Ernie Tedeschi, Stripe’s chief economist. “Now, AI can be a built-in business partner,” he said.
AI’s ability to handle various administrative tasks makes it potentially useful for launching solo businesses in many fields. But the technology’s ability to also handle key tasks in tech, like coding, make that field a particular hot spot.
Analyzing Census Bureau data, Bank of America Institute economist Taylor Bowley found that among all industries, new business applications in the information sector have seen the biggest percentage increase—nearly 45%—over the past year. At the same time, the rate of information-sector applicants saying they plan to hire workers has experienced the sharpest decline of any measured industry.
This Census dataset doesn’t track solo-operated businesses. But the numbers broadly show—in tech and beyond—that applications are flat among businesses likely to hire workers, but generally rising elsewhere. Economists say that’s a strong sign that solo operators are on the upswing.
“The bar for getting started has never been lower,” said Julian Weisser, who runs a San Francisco-based accelerator for solo founders working in tech. The accelerator—which offers founders seed money and mentorship in exchange for an equity stake—attracted 4,500 applicants for 10 slots made available in its most recent cycle, nearly five times the number it drew when it launched last May.
Going it alone with AI can still be surprisingly expensive. Broca said he was losing money on many customers’ accounts while paying to access Anthropic’s Claude to run his clients’ requests—that AI company, as well as others, charges based on usage. He has since switched to free open-source AI models from China.
Broca said he has raised $30 million from investors and, at the same time, has saved millions in salary since he hasn’t needed a team of software engineers.
Another risk: If it’s easy for one entrepreneur to launch an AI-assisted business, copying them can be easy, too. This creates anxiety for founders like Troy Johnston, who runs an AI-assisted business alone in Orlando, Fla.
“Everybody has the sword and we all have the ability to unsheathe Excalibur now,” said Johnston, 40, who used AI to code an app that helps people get the most out of credit card benefits. The company makes around $3,000 a month in profit, with no employees, and is continuing to grow.
What one-person businesses will mean for the labor market remains to be seen. Polling has shown Americans are worried that AI will replace jobs, and top economists are wrestling with that possibility, too. But AI is also creating lots of new jobs, and the go-it-alone entrepreneurs show how the technology can both open doors and limit employment opportunities.
“If everyone’s hiring less, but you get four times more firms, what does that do to head count?” said Rembrand Koning, an associate professor at Harvard Business School who studies entrepreneurship. He co-authored a recent study that found that among 50,000 startups the researchers examined, those focused on AI tended to operate with 25% fewer employees.
Koning also believes a soft hiring environment that’s left some people mired in long job searches has encouraged more to try their hand at launching businesses.
Some founders cite different motives. “It’s a perfect storm of post-pandemic burnout and a re-evaluation of one’s priorities, and also booming AI and a sense of what’s possible,” said Samir Ahmad, 39, who lives in Breinigsville, Pa.
Two years ago, Ahmad decided to leave the corporate job he had worked at Verizon for almost two decades to start a solo coaching and consulting business. He had been seeing social-media posts touting the ease and virtues of AI, which he used to chart a business plan and help with marketing. “It was like my chief of staff, a second in command,” he said.
The business ultimately petered out within months, though, and Ahmad is now back to a full-time corporate role with a utility company.
For Claire Vo, 41, AI helped her turn a passing impulse into a business. She was working full-time as a tech executive when she tapped AI in late 2023 to help code an app that would help her manage documentation and design for new products, with customers ranging from financial services to healthcare firms.
“I was copying and pasting from ChatGPT,” said Vo, who lives in San Francisco.
She put the app online for $1 a month, and within weeks people downloaded it thousands of times. Nearly three years later, Vo’s company—which she ran solo for nine months before hiring an engineer—now has 100,000 users and is on track to make seven figures in profit this year. AI handles the company’s marketing, sales and customer support.
While AI is a shortcut, Vo said her network and credibility in the industry were key. “I think people over-index on how easy AI is and under-index on how much I did to get to this point,” she said.
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