From Tokyo backstreets to quiet coastal towns and off-grid cabins, top executives reveal where they holiday and why stepping away makes the grind worthwhile.
5 min
Months of running between meetings and breaking down the working week into 30-minute increments to get through a long list of tasks takes its toll on the most astute business leader.
So, Kanebridge News asked corporate high-flyers where they holiday and how they value their time, which revealed a fascinating insight into not just what makes them tick.
Many told stories of time away from the hustle, spent exploring the dark corners of Tokyo, the beaches of Bali and off-grid tiny homes with loved ones.
They agreed that taking a well-earned break from rigid scheduling and being ruled by a calendar in a high-pressure environment makes the hustle worthwhile.
High-profile Sydney leadership trainer Karlie Cremin leaves the city behind for a break by the beach with her husband and three children, all under 10 years of age.
Having school-aged kids means she’s tethered to the school holiday period for her breaks, but the CEO of leadership program firm Crestcom makes the most of it, driving north of Sydney to the Central Coast for a two-week break at the end of each year at Pearl Beach.
“We love the area because no one goes there, and yet it’s magical. It’s this little oasis away from the traffic jams, which gives us something to look forward to.”
The family hires the same house every year, located within walking distance of the local beach, where they hang out during the day.
“The kids arrive at the holiday house and know where everything is and how to get around. They love the familiarity of hiring the same house every year.”
Karlie loves a bite at nearby eatery Bells at Killcare while in town, which is booked in advance.
“There’s nothing much at Pearl Beach, which is how we like it. Mostly, we barbecue out back, serve salads, and keep it really simple. We enjoy not having complicated dinners when we’re on a break,” Cremin says.
While she would love to completely switch off, the reality is that she does need to be available for work.
“There are some tasks that only I can do in the organisation, but I tend to handle those things that pop up once the kids are in bed, so it doesn’t interfere with family time.”
Running the largest global franchise pool service brand as it continues on a strong growth trajectory is a big job for Nic Brill, who stepped into the global CEO role late last year. (SUBS 2025)
He admits that leading a service business of scale requires clear thinking, good judgement and sustained energy.
“I’m at my best when I’ve had time to step back and reset, so I view downtime as a strategic necessity.”
The company works hard to create environments that elevate people’s quality of life at home.
“We also take a few international breaks throughout the year. For me, the ideal holiday is somewhere warm, relaxed and close to the water.”
“Time is one of those things you can’t manufacture, so I’m very deliberate about how I use it. When I’m taking a break, I try to protect it so I can be present with my family and properly recharge. At the same time, I lead a large franchise network, and I’m always mindful of my responsibility to our people.
Small townships dotted along the northern NSW coastline has become a favourite, where he goes to switch off, spend time with family.
“I’m happiest when the days are simple – time by the pool or ocean, good meals and a chance to slow down and reconnect.
“I also like to keep active, whether that’s swimming, getting out for a run or exploring somewhere new,” Brill says.
The founder of Australia’s largest privately owned flexible workspace operations has spent more than a decade building his business.
Founded in response to the growing number of freelancers and entrepreneurs requiring workspace following the global financial crisis, the pioneering business model has been built on sweat equity.
But when he’s away from the daily grind, Brad likes to book flights to somewhere in Asia, which has emerged as a favourite holiday spot for him and his family. Malaysia, Thailand and Bali are popular spots.
He also recalls a great holiday in Tokyo’s Shinjuku Golden Gai, a collection of mismatched, tumbledown bars lining a darkened corner of the city.
While adventure holidays were a favourite in years gone by, that’s not so much the case these days as a family man. He often spends time trying local cuisine, wandering through retail areas and seeing the local sights, which are his favourite.
Holidays across Australia are also a favourite. “When I’m away, the out of office is on, and the team know that if they need me, they need to call or text me. I’m not contactable on email when I’m on a break, which means I’m not buried in my inbox while I’m away. Keeping yourself off the emails or Slack or whatever it is gives you that distance from work that enables you to take a good break.”
He also likes to take a break by himself occasionally to recharge. “I try to take all my leave each year, because it helps me be better when I’m at work.”
Brad has taken a few breaks at an Unyoked Cabin, an off-the-grid cabin in a remote area, both alone and with his daughter.
Quick little nature getaways that mean you’re completely disconnected are the best. And I never finish a holiday without having booked your next one,” he admits.
Spending his working days at the helm of a Perth-based wealth management and financial planning firm is where Justin Gilmour belongs.
But when he’s on a break, he prefers to get in the car rather than a plane, driving to the regional area of Yallingup in the southwest of Western Australia in the Margaret River region.
He loves to slow down and enjoy warm, sunny days and gentle coastal breezes when relaxing. “The beaches in the south-west are world-class, offering pristine sands and crystal clear waters that rival any international destination. For me, there’s simply nowhere better to unwind and recharge than this spectacular corner of the country.”
His break is spent with his wife and kids, but he admits half of Perth heads up to Yallingup as well.
“We’re always bumping into people (and even clients) that we know. But spending time in Yallingup allows me to slow down and enjoy the simple pleasure of life with my family.”
He prefers not to stay in touch with the office too much while he’s down there, using the time to reset and recharge, but does chat to clients when he bumps into them.
“I think it’s important to have that period of clear headspace and take a step back and look at the bigger picture, both in terms of my personal life and for the business. A daily swim is certainly a must when I’m down there.”
Rugged coastal drives and fireside drams define a slow, indulgent journey through Scotland’s far north.
A haven for hedge-fund titans and Hollywood grandees, Greenwich is one of the world’s most expensive residential enclaves, where eye-watering prices meet unapologetic grandeur.
Their careers spanned the personal computing, internet and smartphone waves. But some older workers see AI’s arrival as the cue to exit.
4 min
Luke Michel has already lived through two technology overhauls in his career, first desktop publishing in the 1980s and online publishing later on. But AI? He’s had enough.
So when his employer, the Dana-Farber Cancer Institute, made an early-retirement offer to some staff last year, the 68-year-old content strategist decided to speed up his exit. Before, he had expected to work a couple more years.
“The time and energy you have to devote to learning a whole new vocabulary and a whole new skill set, it wasn’t worth it,” he said.
It isn’t that he’s shunning artificial intelligence—he is learning Spanish with the help of Anthropic’s Claude. But, at this point, he’s less than eager to endure all the ways the technology promises to upend work.
“I just want to use it for my own purposes and not someone else’s,” he said.
After rising for decades and then hovering around 40% in the 2010s, the share of Americans over 55 years old in the workforce has slipped to 37.2%, the lowest level in more than 20 years.
The financial cushion of rising home equity and stock-market returns is driving some of the decline, economists and retirement advisers say.
But for some older professionals, money is only part of the equation.
They say they don’t want to spend the last years of their career going through the tumult of AI adoption, which has brought new tools, new expectations and a lot of uncertainty.
Many people retire when key elements of their work lives are disrupted at once, said Robert Laura , co-founder of the Retirement Coaches Association and an expert on the psychology of retirement.
“Maybe their autonomy is being challenged or changed, their friends are leaving the workplace, or they disagree with the company’s direction,” he said.
“When two or three of these things show up, that’s when people start to opt out.”
“AI is a big one,” he adds. “It disrupts their autonomy, their professionalism.”
Michel, whose work required overseeing and strategizing on website content, has been here before.
When desktop publishing arrived in the 1980s, he was a graphic designer using triangles and rubber cement.
The internet’s arrival changed everything again. Both developments required new skills, and he was energized by the challenge of learning alongside colleagues and peers.
It felt different this time around. “Your battery doesn’t hold a charge as long as it used to,” he said.
He would rather spend his energy volunteering, making art, going to operas and chairing the Council on Aging in North Andover, Mass., where he lives.
In an AARP survey last summer of 5,000 people 50 and over, 25% of those who planned to retire sooner than expected counted work stress and burnout as factors.
About half of those retired said they had left work at least partly because they had the financial security to do so.
In general, older Americans are less likely than younger counterparts to use AI, research shows.
About 30% of people from ages 30 to 49 said they used ChatGPT on the job, nearly double the share of those 50 and older, according to a 2025 Pew Research Center survey of more than 5,000 adults.
Baby boomers and members of Generation X also experienced the sharpest declines in confidence using AI technology, according to a ManpowerGroup survey of more than 13,900 workers in 19 countries.
“We as employers aren’t doing a good enough job saying (to older workers), we value the skills that you already have, so much so that we want to invest in you to help you do your job better,” says Becky Frankiewicz , ManpowerGroup’s chief strategy officer.
Jennifer Kerns’s misgivings about AI contributed to her departure last month from GitHub, where the 60-year-old worked as a program manager.
Coming from a family of artists, she said, it offends her that AI models train on the creative work of people who aren’t compensated for their intellectual property. And she worries about AI’s effect on people’s critical-thinking skills.
So she was dismayed when GitHub, a Microsoft-owned hosting service for software projects, began investing heavily in AI products and expecting employees to incorporate AI into much of their work. In employee-engagement surveys, the company had begun asking them to rate their AI usage on a scale of 1 to 5.
When it came time to write reports and reviews, colleagues would suggest that she use ChatGPT.
“I’d be like, ‘I have no idea how to use that and I have no interest in using AI to write anything for me,’” she said.
It would have been more prudent to work until she was closer to Medicare eligibility, she said. But by waiting until her children were out of college and some of her stock grants had vested, the math worked.
Her first act as a nonworking person: a solo trip to Scotland, where she took a darning workshop and learned how to repair sweaters.
“The opposite of AI,” she said.
Employers already under pressure to cut workers—such as in the tech industry—may welcome some of these retirements, said Gad Levanon , chief economist at Burning Glass Institute, which studies labor-market data.
“The more people retire, the fewer they have to let go,” he said.
Some of the savviest tech users are also balking at sticking around for the AI upheaval. Terry Grimm, who worked in IT for 40 years, retired from his senior software consultant role at 65 last May.
His firm had just been acquired by a bigger firm, which meant learning and integrating the parent company’s AI and other tech tools into his work.
Until then, Grimm expected he might work a couple more years, though he felt that he probably had enough saved to retire.
“I just got to the point where I was spending 40 hours at work and then 20 hours training and studying,” said Grimm, who has since moved with his wife from the Dallas area to a housing development on a golf course in El Dorado, Ark.
“I’m like, ‘I’ll let the younger guys do this.’”
