Last spring, I found myself in Malaga for the European World Commerce Contracting Summit, where I was invited to give a speech about the economics of empathy in contracting. It was an exciting, vibrant event—a whirlwind of ideas, inspiration, and fun with participants from most of the European Countries.
I remember most of the conversations I had with the participants, but one specific quote has stuck with me months later:
“If you haven’t felt embarrassed in the last 12 months, you’re probably doing something wrong.”
When I heard that quote, I had one of those “Oh yeah, I should write a blog post about this” moments. Because it resonates so deeply with my perspective.
I’m serious. In the VUCA world we live in (you know, volatile, uncertain, complex, ambiguous), embarrassment might actually be one of our greatest tools. The world is evolving at breakneck speed. Industries are transforming, paradigms are shifting, and the skills that once guaranteed success are no longer enough. The only way to thrive in this environment is by embracing several uncomfortable—but essential—practices.
Some Examples?
- Unworking. Let go of old habits, routines, and systems that no longer serve you. How about stepping back and questioning even the most deeply ingrained assumptions about how things should be done?
- Reskilling. Acquire new skills, often in areas where we have no prior expertise. Even if it means starting from scratch, making mistakes, and enduring the awkwardness of being a beginner again.
- Unlearning. One of the hardest ones—at least for me. Let go of knowledge that was once useful but has now become obsolete. Clear space in your mind for new ideas, even if it means admitting that what we once knew was wrong.
- Failing. Another tough one. Trying new things inevitably means failing. But failure isn’t just about falling short of your goals; it’s about what you learn in the process. When we fail, we develop resilience. We learn to adapt. We discover new ways of approaching problems. And yes, we embarrass ourselves.
- Prototyping. One of the most valuable lessons I’ve learned after years of legal design is the importance of adopting a prototyping mindset—not just in work, but in life. This means approaching everything you do as an experiment, a work in progress. Prototyping is about iteration, not perfection. It’s about fostering creativity, innovation, and—most importantly— embracing the messy moments that come with trying something new.
So here I am, still striving to be the dumbest person in the room, constantly asking questions—even if they make me feel foolish, and loving the process of doing things that spark the curiosity of my inner child.
All of this might feel awkward in the moment, but it’s where the magic happens. Because every time I do something that feels stupid, I know I’m taking a step toward something new, something better, something that might just change my life.
Does it make me vulnerable? Hell, yeah. But I’ve always invested in the long term, not the short term. I’m the guy that focuses on spreading the seeds in fertile soil, not the one obsessed with quarterly earnings.
So go ahead. Sign up for a course in a field you know nothing about. Pitch an idea that’s only half-formed. Try that new AI tool everyone’s been talking about.
It might just be the best thing you ever do.
