The Great Remote Working Delusion - It's Just Annual Leave's Weird Cousin

There is something deeply glamorous about the phrase "working remotely from Cyprus." It sounds like the sort of thing a woman in oversized sunglasses says while casually ordering another iced coffee by an infinity pool. She's chic, making money and doing it all from the comfort of a sun lounger.

Dear reader, working remotely was not remotely chic.

It was me, in a slightly damp apartment, with a laptop balanced on my knees, trying to sort somebody’s HMRC forms while my husband and son marched off to the waterpark looking like the opening scene of a holiday brochure. It was my husband shouting, "don't forget the goggles," while I opened another spreadsheet.

I work for a fully digital business. There is no office or awkward kitchen small talk. I have never stood next to my colleagues at a printer complaining about the weather and exchanging stories of the weekend. I know them only as names on a screen, faces on a Google Meet call, and the little green dots beside their names on Slack. In theory, this means I can work from anywhere in the world. In reality, it usually means I work from the spare room.

But the freedom is there, in the background, tempting me to book... that... trip.

I had already taken one proper holiday earlier in the year and, because I only get paid for the work I actually do, another full week off meant missing another week’s wages. I didn’t fancy that but I wanted sunshine and to leave the country. I wanted my son to have a proper pool holiday instead of yet another cruise where the swimming pool is essentially a confident puddle.

So I had what I believed was a brilliant idea. We would book a cheap late deal to Cyprus, and I would simply… work through it. 

Pause here for laughter.

Because let me tell you now. Never again. I am never working remotely on holiday again.

Not because I am ungrateful. I know how lucky I am. A lot of autistic people struggle to find stable work, and I am genuinely grateful to have a job at all, never mind one that gives me flexibility and trust and the ability to work wherever I need to.

But a line has to be drawn between work and down-time and working remotely meant that this line was a faint squiggle I was constantly navigating.

We know Paphos well. We know the best supermarkets, the best cafes, the best place to get ice-cream and we're confident driving there. We had already been to the Avanti Holiday Village in Paphos for a week in 2024 and we knew the Wi-Fi was exceptionally good and the pool was huge. We stayed in a ground floor apartment that year and the only issue was bugs crawling under the door at night and ants by the pool. If we could get a first floor apartment, we'd be sweet. Luckily, we got one without asking and arrived to find cold bottled water in the fridge and two little bottles of wine on the table along with a note thanking us for choosing to stay there again.

I tested the Wi-Fi. Still easy to connect, still lightning fast. Excellent. I downloaded and signed up for a free trial of a VPN, then logged in to all the work apps and sites. I checked my location - it still said Glasgow. Excellent. Everything was going to be fine.

The first Monday, naturally, my boss wanted an hour-and-a-half meeting. Then there was the usual weekly team meeting. Then the week itself turned absurdly busy, because apparently HMRC waits for no woman, even one trying to achieve a Mediterranean glow. It was relentless. And although I work remotely and it's nobody's business where exactly I am, I felt this guilt all week because I hadn't mentioned to anyone that I was leaving the country. Why? I don't know. I just felt like I'd already had a holiday in February and didn't want to share that I was in Cyprus in case anyone thought I was being paid too much.

I did once have a job where my upline objected to me having two holidays and two weekends away in a calendar year. She developed this bizarre vendetta against me because of it. The next time I was off sick with a heavy cold, she accused me of coming back with a tan. I didn't want to risk any of that nonsense again. So it stayed a secret for me.

The week progressed. Everyone else was on holiday and I was on annual leave’s weird cousin. The worst moment came on waterpark day. To be fair, I did not actually want to go to the waterpark. Last time, I was bitten by some mystery insect that apparently had anger issues. It resulted in a complete autistic meltdown, a trip to first aid, ice packs, antihistamine gel, and me dramatically hating who I am as a person. "Why am I like this?" I wailed to an ex-pat English nurse who just patted my arm and said, "You're just a sensitive soul, my love. The world needs people like you as much as it needs people like me."

So no, I wasn’t desperate to return but watching my husband and son leave without me was still awful. They were covered in suncream, wearing swimming shorts under their normal shorts looking like classic Brits abroad, carrying towels and swim bags, ready for a day of fun. And I was sitting alone with my laptop, doing tax forms.

That was the moment I realised this wasn’t really a holiday for me. It was a working week with better weather.

Not that it was all bad. There were idyllic stretches of poolside sunbathing, stolen little half-hours of holiday vibes. There were warm evenings and harbour walks and the best sleep I've had in years. The hotel entertainment was great. We watched a fire eater one night and joined in a music quiz on another night and took it far too seriously, as all respectable people do. They had a little arcade and one of those 1 Euro for 5 minutes massage chairs in the hotel foyer. The nights were great.

We visited Akrotiri, partly because I liked the idea of technically visiting another country without really going anywhere. Akrotiri is a British Overseas Territory, which means I can now be oddly specific about having been there.

We also went to Petra tou Romiou, the reputed birthplace of Aphrodite, which felt appropriate because if you’re going to have an existential holiday crisis, it may as well happen somewhere associated with the goddess of love and beauty.

And then there was Valentine. Valentine was a Romanian barman and possibly the most entertaining man in Cyprus. Every holiday should include one memorable barman, and he was ours. He swaggered around, calling every man "boss" and being unintentionally funny, making recommendations and embellishing Luke's apple juice with a chunk of apple rather than a slice of lemon. He was brilliant.

The weather, however, was less cooperative. There was rain, a massive thunderstorm and one of the worst dust storms Cyprus had seen in over a decade, which felt particularly rude considering I was there for the sunshine. There was both a literal cloud and a metaphorical one hanging over the whole trip because the thing missing was the real magic switch-off of a holiday. You know that feeling when work ends, your out-of-office goes on and everything unclenches? That never happened.

There was no exhale, reset or joy of being temporarily unreachable. I had this constant low hum of “I should check that.” And looking at my Slack messages and replying to emails from my lounger. That, I think, is the problem with working on holiday. You still earn the wages, you don't waste the annual leave and on paper, it looks clever, but the whole point is being unavailable.