I’m coming out of the post-launch haze, and I’m doing just fine: working on a few essays for the newsletter, but the combination of extreme heat and school holidays means they need a little longer in the oven. So this week, I’ve remastered a 2022 essay on the myth of unlimited vacation and the importance of time off. Have a great weekend, and stay cool!
Manchester is a town primarily known for two things: 1) great music and 2) terrible weather.
Correlation isn’t causation, as every statistics nerd knows. But there’s a connection here: some believe cities like Seattle and Manchester punch above their musical weight because wet weather leads to more time indoors, searching for a hobby—playing the guitar, for example—to keep you occupied in a city where it rains more than half of the year. Others, including an incredibly biased local news outlet, say there’s nothing to worry about: there are much wetter places than Manchester—look at all those cities in Northern Ireland, for instance. At least Manchester gets a few weeks of sun during the summer holidays.
But for some (read: yours truly), that fleeting period of staring strangely at a glowing circle in the sky would be missed. My parents, who emigrated from Northern Ireland a few years before I was born, would both work during the summer. So they’d take the same steps as many of us still do today: lean on the grandparents. When summer commenced, we’d get on a plane: three small kids armed with a British Airways travel pack, colouring pages and wax crayons secured safely inside, grasping tightly onto the hand of a lovely flight attendant we’d just met, and take the 70-minute flight from Manchester to Belfast. We’d get collected by an uncle on the other side, and spend our summers in Northern Ireland—the only place wetter than the city I called home.
My mum and dad would come eventually, but vacation days were hard to come by back then. My mum recalls 10 days of paid vacation when we were kids, plus 8 public holidays. They’d head to Ireland for the last week of summer, using one precious week of their holidays, saving the second for a return trip at Christmas. Today, UK workers receive 28 days of leave, including public holidays. The increase can be attributed to the EU Working Time Directive, introduced in 1993, which cited working excessive hours as “a major cause of stress, depression, and illness.” The directive aimed to better protect the health and safety of European citizens, giving workers across the region the right to four full weeks of paid annual leave. It wasn’t enacted into law in the UK until 1998 (with no statutory entitlement before then), and some in the UK Government attempted to block its progress. 28 days is great, but it places the UK in a mid-table position—they’re not fighting relegation, but they’re unlikely to qualify for the Champions League. Spain ensures its citizens have 36 vacation days a year, while Estonians enjoy 28 days of paid holiday, supplemented by 12 public holidays, for a total of 40 glorious days off.
Counting holiday days was, for a while, supposed to be on the way out. There was a 178% increase in job positions offering “unlimited vacation” between 2015 and 2019, and The Wall Street Journal reported in 2025 that 7% of US companies now offer unlimited vacation time for employees. This so-called perk sounds great, in theory. “You like holidays? Well, HAVE ALL THE HOLIDAYS YOU WANT!” But while the greatest trick the devil ever pulled was convincing the world he didn’t exist, his second greatest trick was unlimited time off. These policies are fraught with issues, a key one being that employees don’t accrue vacation days, meaning no end-of-year carryover and no payout of unused time at year-end or upon termination of employment. When living in SF, one HR worker informed me that the policy was established after a startup went bankrupt, couldn’t pay owed holidays to employees, and a legal precedent was set: Californian companies must have the cash on hand to pay all accrued holidays by year’s end. That unlimited time off policy that looked so juicy when you signed your contract? It might be nothing more than a creative accounting loophole.
Making matters more complicated is the fact that, in the US, vacation hits different. This is the only industrialised nation where workers are not legally entitled to a single day of paid holiday. Where 1 in 4 workers have zero paid time off. Where, in 2018, 55% of vacation days weren’t used, leading to 768 million days unused and 236 million forfeited. That’s a lot of loungers going empty. And research has shown employees with unlimited time off actually take 2 vacation days LESS each year than those with a “regular” vacation policy.
And then we get into the office politics of it all. It’s no accident that Netflix, the original “No Vacation Policy” company, is also the one with the famous “keeper test,” where a team can immediately decide if someone isn’t pulling their weight, leading to an instant firing. Recent “headcount optimisations” (read: mass layoffs) in tech have seen managers feeding office attendance data into performance reviews and redundancy decisions.
With these headwinds, how do you think unlimited time off policies play out? Taking more holidays than your boss? There’s no way any sane employee would do it. Not when it could affect your salary, bonus, potential promotion, and the likelihood of keeping your job. You’ll be seen as lacking commitment, not a team player. And if you’re thinking this, you can bet your manager is thinking it too. And their manager. And their manager. And so on. And so on. It’s fucked-up game theory, keeping you at your laptop, turtles all the way up.
Those grey summers in Ireland? I look back on them with love. 6 weeks with my Granny Mo, who would’ve turned 98 this week. As a god-fearing Catholic, she wouldn’t have let us get away with murder. But everything up to that line was fair game. (When I was 14, my parents were celebrating their wedding anniversary in Paris, and she came to the UK to look after us. That week, I got suspended from school for hitting a kid with a backpack in the playground. She signed all the forms and agreed to keep it quiet forever: a promise she took to her grave. Always grateful for that one.) In Ireland, she worked as a lunch lady in the local high school. Her summers were her own, so she provided childcare whilst my parents worked their jobs. And what kid wouldn’t want to spend 6 weeks under Grandma’s Law?! I see how much leeway my kids get with theirs, and the joy they all find amidst the chaos.
Imagine picking your kids up after 6 weeks with their grandparents. All that sugar. All that independence. One uncle would bring over his PC for a few weeks in the middle of summer, and I’d sit inside playing Tie Fighter and Sim City 2000. It might have been glorious outside, but I wouldn’t have noticed. Another uncle would pick the three of us up from the airport and drive us home, banging out some new dance compilation from the current club du jour. I still know every mix cue on the Back Room CD from 1995’s Cream Anthems, my ears enthralled by this new genre termed house music, sounds from another galaxy, audible colours my brain had yet to experience, basslines thumping through the best in-car subwoofer my uncle could’ve afforded at the time. Those trips in the front seat of his ride subtly, but irrevocably, nudged my life in a different direction.
By the time my parents arrived, we’d have spent a month and a half without them, running riot around a small village in Co. Tyrone, going “up Main St and down the same street” as the locals tell it. We’d then spend a week together as a family before turning the car around and returning on the Belfast-to-Stranraer ferry, the worst possible mode of transport for a family of five without a pair of sea legs between them. I’ve made it a personal policy to avoid boats today—having learned this the hard way, on too many holidays to count. My family will, one day, vacation in a place where they can watch whales; my feet will remain firmly on solid ground.
The primary downside of existing outside the net of salaried employment is a lack of stability, of not knowing when work might appear or dry up. In 2020, post-pandemic, we spent four months with zero income—the project pipeline dried up completely, we slipped through various hastily assembled government safety nets, and spent a significant chunk of the year wondering where work would come from. But the upside of being independent is there in the name: the freedom. The ability to run your own schedule, be your own boss, and make decisions you believe are best for you and your family. Being able to go on holiday without worrying how many days off you’ve accrued, needing to balance it with the fear of being replaced, or anxious that taking your dream vacation will somehow, like a butterfly flapping its wings in Mexico, lead to you being passed over for that promotion you’ve been chasing for years.
With that freedom comes a chance to think about vacations in a different way. The need for a regular income will be a key driver of how much holiday you take, but your own insecurities, your ego, and attitude to risk will also play a part, as you battle with what psychologist Lee McKay Doe termed “internalised capitalism.” Many friends who are independent have spoken about the discomfort that comes from turning down paid work to take a vacation with their family.
You might choose, like a child-free freelance friend, to work every hour that comes your way, but down tools for four weeks every four years to drag your TV into the back garden, put the beers on ice and watch every World Cup game possible. Others have been even more creative when experimenting with time off—you may recall the famous Stefan Sagmeister TED Talk from 2009, where he talked about closing his studio for a full year after being open for seven, a cadence that led Dan Pink to suggest we replace “going on sabbatical” with “taking a Sagmeister.”
“Right now we spend about 25 years of our lives learning, then there are another 40 years that’s really reserved for working, and then tacked on at the end of it are about 15 years for retirement. And I thought it might be helpful to basically cut off five of those retirement years and intersperse them in between those working years. That’s clearly enjoyable for myself. But probably even more important is that the work that comes out of this year flows back into the company and into society at large rather than benefiting a grandchild or two.”
— Stefan Sagmeister, The Power of Time Off
Sagmeister also touches on Ferran Adrià, owner of El Bulli, who closed his restaurant for 5 months each year to research and develop new innovative cooking techniques. Bill Gates takes two “thinking weeks” every year alone to a cabin, in what I suggest we call “taking a Bon Iver.” These people aren’t undertaking new approaches to holidays for the fun of it—they know that the success of their business depends on recharging the creative batteries that are all too easy to deplete.
A sabbatical isn’t an option for everyone. Neither is unlimited time off. But perks like these offer a chance for deep, intentional time—to actually unplug and unwind, rather than “quickly responding to an urgent email” from a nice hotel, a beautiful sunset wasted in the background. I’ve been there too many times. Even though a vacation with kids can feel like a “parenting away game”, there’s immense value in taking a holiday together, with research showing it improves both parents’ wellbeing and children’s general skills. And for those who run their own company, or sit on senior leadership teams, it provides a chance to lead by example.
The annual cadence of life in the Mediterranean, the place I call home, is different from the rest of the world. August’s extreme heat makes it difficult to do anything. You might have once heard something akin to “Spain and Italy close down for all of August” and wondered how true that was. Didn’t you go there one August when everything was still open? It probably was, if you landed in a popular holiday destination. But even in a tourist magnet like Barcelona, most restaurants and independent retail stores will pull their shutters down for the month. A few years back, a friend shocked our local community by announcing the opposite: his bakery would stay open throughout August. Wild.
Regular readers will see where I’m going with this. I’ll be in your inbox a few more times in July, and then taking a break for a month. One thing I love about writing this newsletter is how it holds me accountable as the dad I want to be. Would my parents have taken those 6 weeks off and spent the summer together in Ireland as a family, if they could? I guess we’ll never know. But as Dan Pink helpfully informed me in the very first TNF podcast episode, we’re twice as likely to regret the actions we didn’t take as the ones we did. Did any man, on his deathbed, ever wonder:
“What would have happened if I didn’t take that time off?”
I’m not planning on being the first.
Good Dadvice
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Your Granny Mo giving you six weeks of "up Main St and down the same street" while your parents worked is doing more cultural transmission than it probably ever got credit for. I think about this a lot with my own daughter, what actually gets passed down usually isn't the planned things, it's the unstructured weeks with the people who aren't us. Hope you get your own version of a Sagmeister this year.
I try to remember that a job will never love me back.