How a Visionary Leader Changed the Way I See the Future
The Mentors Who Made Me
Most people look to the future with caution. Umberto looked at it and said, “What if?”
He isn’t just a brilliant leader—he is the first person who showed me how to face the unknown not with fear, but with curiosity and confidence.
That mindset changed everything for me—as a developer, a mentor, and a human being.
I met Umberto at the end of the last century, and we worked together through the internet frenzy that led the world into the new millennium. Since the first project we worked on together—me as the web developer and him as the project manager—we clicked. He’s one of the most brilliant, curious, and eclectic people I know, but that’s not what made our collaboration special.
What set Umberto apart was his ability to look ahead—way ahead—and face whatever impossible challenge was coming with complete confidence. While others focused on what was proven and safe, Umberto was always asking,
“What if...?”
I remember endless late-night phone conversations, dreaming up solutions that shouldn’t have been possible. Most of those crazy ideas never saw the light of day. But some did. And with fireworks.
Building the Impossible: EVA, the First Human Digital Assistant
Like in 2005, when he decided we should create the world’s first real-time, photorealistic virtual assistant that could work on any device without installing software.
This was 2005. 3D graphics were still considered exotic, demanding serious computing power and mostly confined to video games and expensive movies.
He asked me to lead the technical team despite my lack of experience in that field. I still remember vividly the night he took me out to dinner and drew his vision on a scrap of yellow paper from the placemat. He already had some brilliant 3D people on board, and he wanted me to figure out how to make it all work together.
Honestly, I had no idea how to do what he was describing. But Umberto had this way of making the impossible feel inevitable.
“We’ll figure it out,” he said.
Obviously, I believed him.
And boy, we did figure it out.
We built EVA (Caren, for her friends, aka us), the first Human Digital Assistant. A revolutionary product that was years ahead of anything else on the market. We even came up with the perfect tagline for our talking virtual assistant: “Face the Future.”
The Mentoring Lesson
Years later, when I became a mentor, I realized what Umberto had been showing me all along: The best mentors don’t just share what they know from the past—they help you develop the courage and vision to face whatever’s coming next.
Umberto didn’t just give me tasks. He gave me a mindset.
Every conversation with him expanded my vision—not just of the project, but of myself. He modeled something that stuck with me: curiosity over fear. Possibility over safety.
This is the mindset I strive to bring into every mentoring relationship today. From the very first conversation, I help my mentees develop their own forward-looking perspective.
Because the future belongs to those who can face it.
From Inspiration to Practice
While Umberto’s natural ability to face the future is remarkable, I’ve learned that developing this mindset systematically requires more than intuition.
Professional mentoring provides us with the structure, skills, and tools to consistently help others build their forward-looking vision.
It’s the difference between occasional inspiration and reliable transformation.
But let’s be real—my courage to face the unknown still wavers sometimes.
When doubt creeps in, I remember Rossella’s mantra:
Whenever I catch myself feeling hesitant, I remind myself of a simple mantra: trust yourself, trust the process, and trust the other person.
Something magical happens when someone helps you see the future as an opportunity rather than a threat.
You stop asking, “What if it doesn’t work?”
And start asking, “What if it does?”
What Facing the Future Really Means
Here’s what I’ve learned and integrated as a mentor:
Curiosity is more powerful than certainty. The best ideas begin with “What if…?”
Mentors model courage. It’s not about having all the answers—it’s about walking toward the unknown together.
The future rewards those who face it. Not just with skills, but with presence, boldness, and belief.
And when you have doubt, remember what my mentor, Rossella, says (and yes, the fictional Scarlett does too):
“Trust yourself. Trust the process. Trust the other person.”
Umberto taught me that the true gift of a mentor goes far beyond advice. It’s about modeling what it looks like to stand on the edge of the unknown—and step forward anyway.
Who has helped you face the future with more confidence? How did they change your perspective on what’s ahead?
In Becoming the Mentor, you’ll meet Scarlett, an experienced mentor helping Nemo discover new possibilities for his future with curiosity and courage.
Read how she does it in the book →
P.S.: I didn’t tell Umberto I was writing this, so I hope he won’t mind. 🙂