How To Simplify Career Decisions with Winemaker Niccolò Tiberini
- Tosca DiMatteo
- Nov 28, 2025
- 3 min read
"Think easy." It's a simple phrase, but it holds a surprisingly powerful philosophy: stop creating problems that don't exist, clear the cloud around your choices, and return to what feels emotionally true, instead of getting lost in overthinking.
My guest is Niccolò Tiberini, a winemaker from Montepulciano with truly deep roots; seven generations in the vineyard and cellar. I had the privilege of an unforgettable conversation with Niccolò after meeting him at his family’s winery in October 2025, and his clarity around choosing happiness over money, honoring tradition while adapting slowly, and trusting emotions in decision-making left a lasting impression.
From Football Dreams to the Family Vineyard
The road to the cellar began on the pitch. As a teenager living away from home, Niccolò chased a promising football career that looked like success from the outside, yet left him quietly unsatisfied when he considered his option to continue on that path. The turning point came when he chose to step away from status and certainty, to return to the vines, the soil, and the work that truly filled him up.
Grief, Perspective, and What Really Matters
At the tender age of 13, Niccolò lost his mother, which of course had a huge impact and revealed how fragile and precious time really is. That grief became a teacher, nudging him toward presence over performance, gratitude over grasping, and seeking a life that feels good no matter the pay check.
“Think Easy” Decision Making
Clarity for Niccolò lives beneath the noise. He notices when “smoke” gathers around a choice, that may look like justifications, invented problems, expectations and pro and con lists. He pares decisions back to what feels emotionally true. In that quiet, “thinking easy” turns into courage: a reminder that overthinking often disguises fear when the heart already knows. Another way he put it was to think like a child.
Winemaking as a Metaphor for Life
At Tiberini winery, deep tradition and careful evolution move together, season by season. Some changes won’t show themselves for years; patience and humility keep the course steady, while loyalty to an original vision protects identity through each experiment and harvest. This also mirrors life - to remember our true identity as we make our career choices and to honor how we define success - not how someone else wants to define it for you.
Travel and Innovation
Beyond the rows of vines, the wider world keeps his mind open. Travel, conversation, and welcoming strangers to the winery create a table where stories linger. Not only this but getting outside of your small town or experience helps you to see what innovation to adopt, and where you want to hold your ground on your way of doing things.
An Invitation to Choose What Feels Good
If you’re standing at a crossroads, between certainty and the path that quietly lights you up, Niccolò’s story offers a gentle map: simplify your choices, trust your emotions, and plant your life where your roots can deepen.
Hear the full conversation with Niccolò Tiberini and let his story meet you where you are, then take the next step your heart already knows is the best one for you.
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