Career transitions require clarity and confidence. Alessandro, a chemistry and tech professional, shares how the Designing Your Life (DYL) program helped him realign his career and personal goals through reflection, community, and intentional choices.
From chemistry to tech: a journey of reinvention
Alessandro’s career has been anything but linear. Originally from southern Italy, he moved to Amsterdam to pursue a PhD in chemistry. However, his passion for computing and technology led him to a successful 15-year career in the tech industry. Over the years, he built a strong presence in professional communities, gaining a following of over 10,000 on LinkedIn.
“I’m all over the place,” Alessandro says with a laugh. “I love coding, I love technology, and I love bringing people together through community events.”
But even a strong career trajectory can be disrupted. In April last year, Alessandro was laid off. While he had no trouble finding freelance work, he quickly realized that the independence of freelancing didn’t fully satisfy him.
“For some people, freelancing is the dream,” he explains. “For me, it was good money, but it didn’t check all my boxes. I thrive in a team environment.”
So, he began his search for something more meaningful, a theme that aligns strongly with the Designing Your Life framework, which encourages individuals to rethink what energizes and motivates them.
The Crossroads: Between a Startup and a Return to Microsoft
During his time between jobs, Alessandro explored launching his own startup. However, as the process unfolded, he faced unexpected challenges.
“I totally failed,” he admits. “But I learned a lot. The startup isn’t dead; it’s just on hold for now. It was a valuable experience, but I knew I wanted to return to a structured role.”
He set his sights back on Microsoft, his former employer, and after months of interviews, he secured a role there once again. But before that transition was finalized, an opportunity arose: Designing Your Life.
Why Join Designing Your Life?
Alessandro joined DYL alongside his wife, Meg, who was also navigating career transitions. When asked what motivated him to sign up, he credits a personal referral.
“My friend Marie recommended it,” he says. “That’s what made me take a closer look. When someone I trust suggests something, I pay attention.”
At the time, Alessandro wasn’t actively seeking guidance. He wasn’t researching career coaching or looking for structured programs. Yet, the timing felt right.
“We love growing together as a couple,” he explains. “DYL sounded like a great way to reflect on our next steps, together.”
Key Takeaways from Designing Your Life
Reflecting on his experience, Alessandro highlights two major insights:
● The Work-Life View Exercise
- “Writing down your lifeview and workview forces you to stop and think,” he says. “Where am I going? What do I actually want? That exercise alone made a huge impact.”
- This exercise is a fundamental part of the Designing Your Life methodology, helping participants clarify what matters most.
● The Power of Community
- “I met great people like Hugo and Jorge. We still check in with each other and discuss our Odyssey Plans. Having a group of like-minded people keeps you accountable.”
- The community aspect—central to both the workshop and the book—helped Alessandro stay engaged long after the sessions ended.
- Inspired by the DYL framework, Alessandro even reread the book and began applying its principles more consistently.
Life After Designing Your Life: Applying the Lessons
Since completing DYL, Alessandro has embraced a more structured approach to his goals.
“I started a new job at Microsoft in January, and I’ve been busy,” he says. “But I’ve kept up with the small habits, going to the gym, learning Greek, staying connected with my DYL peers.”
Even in a demanding corporate role, he ensures that personal growth remains a priority.
“When I do something like Duolingo or working out, it’s just for me,” he says. “It’s not for anyone else’s agenda, and that’s important.”
His relationship with Meg has also strengthened.
“Because we both work full-time now, we make the most of our time together. We don’t just watch TV; we talk, we share ideas, we make sure our time is meaningful.”
Community Beyond the Workshop
The sense of connection cultivated during the Designing Your Life workshop didn’t end with the last session. Alessandro sees immense value in ongoing meetups, informal gatherings, and community-driven discussions.
“In my tech meetups, people come for the talks, but they stay for the in-between moments, the conversations over pizza, the spontaneous ideas that emerge,” he says. “That’s where the real magic happens.”
With this in mind, he strongly supports the idea of a free DYL community to keep past participants engaged, along with a paid mastermind-style group for those seeking deeper guidance.
“Learning should have a cost,” he acknowledges. “But never underestimate the power of informal connection, it’s invaluable.”
Final Thoughts: Is Designing Your Life for You?
For Alessandro, Designing Your Life wasn’t about finding a job, it was about finding clarity. Whether you’re in a career transition, an entrepreneur, or just seeking direction, he believes the process is invaluable.
“If you’re thinking about it, just do it,” he says. “It’s a rare opportunity to stop, reflect, and design the life you truly want.”
