Welcome to Digital Nomadland | WIRED

Seen from afar, the parish of Ponta do Sol looks as compact and picturesque as a postcard. There is a small roundabout in the center, a petrol station, a small shopping complex and a group of modest buildings topped with terracotta tiles. Undulating green slopes of bananas, palms and pines stretch behind, houses dotted among the hills. All of this is surrounded by a dramatic escarpment and made subtropical by the many small waterfalls that gush from the rock face, filling centuries-old irrigation channels. When Gonçalo Hall first drove through the area in September 2020, the words that came to mind were, “What the fuck.”

Ponta do Sol is on the south coast of Madeira, the main island of the Portuguese archipelago of the same name. Hall had visited Madeira once when he was a child, but he couldn’t remember it being so beautiful, so wild. Now, as he said in an interview, he saw the place “through the eyes of a digital nomad”. He had returned to help organize a remote working conference in Madeira’s regional capital, Funchal. The day after his long drive through the countryside, he approached the regional economic secretary and asked him bluntly: Why are you sleeping on digital nomads?

Hall, 35, is tall and burly, with blonde hair, blue eyes, a jovial demeanor and a propensity for talking in hashtag mantras like “life is good” or “be happy, make millions.” He grew up in Lapa, the most chic neighborhood in Lisbon, but he now has an apartment in Ponta do Sol with his wife, Catarina: Lisbon, he complained when we first met, had become too empty. Hall had long dreamed of finding a lifestyle where he could show up to work in flip-flops and shorts rather than the suit and tie of his family’s bankers. In early 2019, the couple moved to Bali for two months, where Hall landed her first remote contracts, including a marketing gig for a company called Remote-how, and amassed a long list of contacts in the process. Then they went to Thailand, Malaysia, Vietnam and Bali, spending a month or two in each before returning to Europe.

Back in Lisbon, after less than a year as a digital nomad, Hall was organizing conferences on remote work and digital nomadism, identifying as an expert in both. When he landed in Madeira, he took advantage of its low cost of living, fast internet speeds, surfable beaches, and Instagrammable beauty, the pillars of digital nomad marketing. He also recognized something else in the pastoral rhythm. A small nomadic project he had visited in rural Spain, just before his arrival in the archipelago, had impressed him; it was charming, more intimate than the bustling city centers he had known until now.

Hotspots for established digital nomads, like Chiang Mai, Thailand, or Canggu, Bali, tend to be bubbles where wealthy, mostly white foreigners congregate in cafes, coworking spaces and other businesses that meet their needs and comfort in English. If he built a destination for digital nomads in small-town Madeira, Hall thought, things would be different. Itinerant teleworkers could live like locals, alongside locals: they could live in the same neighborhoods, eat in the same restaurants and mingle in gatherings coordinated by a “community manager”. Hall decided to present his idea to the government of Madeira.

It was an easy sell. Tourism in the archipelago had dropped due to the Covid-19 the travel bans that had barred travelers from leaving the Schengen area in Europe, and so Hall pitched digital nomads as the cure. Portugal’s urban centers were already saturated with remote workers, but Madeira, less than a two-hour flight from Lisbon, was still under the radar. Higher-earning professionals could inject money into local businesses, Hall told regional officials. All they needed to accommodate them was a welcoming infrastructure and a ready-made network to land on. If he built it, Hall promised, they would come.

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