And as he gazes out from his glass-walled office to the snow-flecked hills of central Italy, the luxury fashion magnate always spots something more he can do.
"It is like another emperor, Marcus Aurelius, said - live each day as if it was your last - but plan as if it was for eternity," he tells AFP in an interview at Cucinelli headquarters in his native Umbria.
Now 63, Cucinelli has long been celebrated for combining enlightened employment practices with commercial success. He is the tycoon who bans his staff from working after 5:30 pm and checking emails outside office hours.
"Why wouldn't I?" he says. "We already work too much, we're too connected. For all of history, man has been afflicted by a sickness of the soul, and in our permanently connected world this sickness has gotten worse."
Lunch at Cucinelli's airy factory is a 90-minute affair: long enough to pop home for a nap after a few courses in a company canteen serving up outstanding fare sourced from local farmers and on-site kitchen gardens.
Ask him why he went to the expense of fitting his factory with floor-to-ceiling windows and he cites the French philosopher Jean-Jacques Rousseau's observation that proximity to creation drives creativity.
Cucinelli has poured millions into Solomeo, the lovingly renovated 13th-century hilltop village that is home to his empire. Work started with the medieval castle and, over three decades, he has added a theatre, a library and a school offering practical courses in art, gardening and tailoring.
But now, as he contemplates his remaining time, Cucinelli's focus has switched to the town's surroundings.
"Particularly in Italy, but it is also true for much of Europe, the historic centres of our towns have generally been well looked after and restored," he tells AFP. "But things have not gone so well in our peripheral areas and yet that is where 70 percent of human beings live. We have to make them liveable spaces linked to the historic centres."
The project has involved renovating or demolishing abandoned industrial buildings to create new production facilities for Cucinelli's own workforce alongside two other parks -- one providing six hectares of playing and sporting space for children, the other a 70-hectare park producing everything from apricots and broccoli to wheat.
"When we started the renovation of Solomeo in 1985 I was inspired by something that Rousseau said about needing to withdraw from the cities, go back to our villages and rethink the future of humanity," he said.
"In this little 'borgo' there is silence, there is culture, spirituality. Loneliness cannot take over and I think that is something very important at this moment in history."
Similar themes run through Cucinelli's musings on work and how to run a company that is on track to shift 450 million euros ($470 million) worth of eye-wateringly expensive clothes and accessories this year.
Cucinelli imports his key raw material, cashmere, from China and Mongolia. But unlike many of his rivals he has kept all his manufacturing operation in Italy.
Shareholders may grumble about the 20 percent premium over industry norms that the Solomeo workers receive. But they knew what they were buying into when the company was floated in 2012.
The company's ethics and clearly identifiable roots in the Italian countryside are important elements of a brand that has quadrupled in size in a decade and has yet to disappoint investors.
Its leader says he is not challenging the bottom-line tenets of capitalism: simply trying to give them a more human face, something he says has becoming more pressing in light of the widespread disaffection among Western workforces that has been linked to the rise of Donald Trump and Brexit.
"It is exactly right to say that many people feel forgotten," Cucinelli says. "The internet has redrawn the map of the world of work. Italy, and Europe as a whole, can no longer compete at the lower level and this has created some unemployment.
But the essential problem is one of dignity.
"We cannot have companies that earn incredible amounts and our workers earning tiny sums to work 12 hours a day staring at a wall under an electric lamp. We have to put dignity back at the heart of our economic activity."
It is a vision, he says, that was born of witnessing his father's struggle to survive, as a tenant farmer and later as a factory worker.
"It is something that has always stayed with me, a bit painfully," he admits, insisting that he will take the time to enjoy the fruits of a business he built from scratch.
"Already there are some areas of the company where my role is that of a senior advisor, and I like that idea. I got it from an abbot friend who told me he was going to retire and leave the abbey to the young monks.
"The average age of our employees is 37, 40 for the managers. The fourth age is a time of wisdom but also of looking for spirituality and taking stock of what happens next."
By Angus MacKinnon