In the summer of 1995, a freelance writer set out on a family holiday to Portugal, a trip intended for relaxation but soon interrupted by work commitments. Shortly after arriving, he received an unexpected invitation from a UK magazine to interview actress Meg Ryan in Los Angeles within a few days. Despite the holiday setting—with his wife and mother-in-law watching their infant son by the pool—the writer accepted the assignment, quickly packing up and flying first to London, then onward to LA.

Throughout the trip, the writer reflected on the challenges of maintaining work obligations while trying to embrace the spirit of vacation. He described the freelancer’s tendency to never fully detach from professional responsibilities, constantly carrying work along and agreeing to assignments even when away from home.

Back at a remote countryside cottage in Portugal, he struggled with limited phone reception and unreliable internet access. Although emails arrived inviting him to participate in a live radio interview the following week, the lack of connectivity initially made him hesitant. However, he ultimately agreed to take part in the broadcast despite the technological constraints.

During a weekend marked by fine weather and social visits from friends, the writer found himself negotiating bandwidth usage within the household. He noted the irony that even when guests weren’t actively using their phones, those devices nonetheless drained the limited internet capacity.

On the day of the radio interview, he stayed behind while family and friends went to the beach. Connecting via a link provided by the radio programme, he faced technical glitches but managed to complete the segment. He later recounted that the interview went smoothly and was largely directed by the show’s host, Janet Street-Porter. Meanwhile, visitors enjoyed the local surroundings without much awareness of his behind-the-scenes efforts.

Later in the week, additional social engagements overlapped with his continued attempts to work remotely, compounded by the demands of managing shared resources like a single shower and scarce internet connectivity. A further complication arose when a fallen tree knocked down the phone line leading to the cottage, severing the primary means of communication.

With no internet or phone service inside the house, the writer resorted to walking half a mile uphill, laptop in hand, to find a signal—a reminder of the pre-digital realities he once routinely experienced. His wife pointed out that this was a familiar routine from earlier times, underscoring the ongoing balance between work and leisure that defined his “working holiday.”

The experience highlighted the difficulties that remote locations and limited infrastructure can pose to professionals accustomed to constant connectivity, even as the lure of a holiday setting pulls in the opposite direction.