Why Mastery Requires Letting Someone See You Fail

I watched a video recently that managed to perfectly captures the journey I’m on these days. Atul Gawande - a surgeon, researcher, and writer known for studying how experts improve - was talking about coaching, and something in what he said hit a place in me I didn’t expect. It felt like a full‑circle moment. One of those times when someone else’s words suddenly give shape to something you’ve been living for years.

As I listened, I realized just how deeply the message resonated with my own experience. Through martial arts, I’ve known for a long time that you can’t grow in isolation. But hearing Gawande say it so plainly made me feel the weight of it in a new way.

Gawande - a top expert in his field - described how, even after thousands of surgeries, he hit a plateau. He stopped improving. His solution wasn’t more knowledge - it was inviting another surgeon to watch him operate. Not to teach him something new, but to observe the tiny things he couldn’t see himself: drifting lights, subtle posture issues, missed cues from the anesthesiologist. The kind of blind spots that only show up when someone is watching you do the real work.

That hit me harder than I expected.

Because in my business life, I had been doing the exact opposite.

Hiding Behind What I Do Well

I’ve spent years building things: coding, designing, creating. It’s my comfort zone. It’s where I feel competent and in control. So I stayed there - head down, producing, refining, optimizing.

Recently though, after months of burning through my savings, I started to feel “the plateau”. That momentum I felt during the first months of building JourneyLoop started to fade. New challenges and setbacks made me feel like I was way in over my head. Self-doubt started to creep in. I knew something had to change…

After a demo Michael and I gave at Simplified Coach, I got the amazing opportunity to work with their founder and top-tier executive coach Teri Dalhbeck.

And let me tell you - It was emotional. Uncomfortably so.

She laid out (very bluntly) everything I didn’t know. Everything I was avoiding. I was hiding behind the parts of the work that felt safe. And I was quietly avoiding the parts that didn’t: the business strategy, the messaging, the uncomfortable conversations, the decisions where I didn’t have mastery. Everything that needed to change if I wanted this project to become an actual business and not just a beautifully crafted idea.

It felt like standing in front of a mirror that reflected not just what I was doing, but who I was being. It showed me that I needed to become “Business Marco”. In those 30 minutes with her, I could not hide. I had not felt this vulnerable in a long time.

The Transformation That Happens When You Stop Doing It Alone

That coaching moment made a dent. It highlighted just how impactful even a single, high-quality coaching session can be, allowing me to take an honest look at myself. It made clear that I wasn’t lacking intelligence or skill - I was lacking visibility. I had no external perspective. No feedback. No one watching me perform the parts I didn’t want to look at.

And once someone did, everything started changing. Not instantly. Not perfectly. But meaningfully. Suddenly, the path forward became crystal clear: I realized how the feeling of “not knowing what I was doing” created a huge amount of anxiety in my life. Shining a light on these blind spots turned the anxiety into achievable goals. Now, all I had to do was learn, execute and persevere - That was something I knew how to do.

This is the power of coaching - A chance to see your blind spots before they become failures. They hold you to a version of yourself you haven’t learned to step into yet.

And that’s when I came full circle with JourneyLoop…

Why This Matters So Much to Me

Experiencing firsthand what it feels like to have someone help you see yourself more clearly is humbling. That’s why hearing Atul Gawande’s story felt so relatable: It challenges the “pull yourself up by your bootstraps” mentality and shows that improving by yourself is not only difficult - it’s impossible.

That’s why I’m so passionate about what JourneyLoop can become.

Not everyone has access to a coach. Not everyone can afford one. Not everyone is ready to sit across from someone and expose their vulnerabilities.

But everyone deserves the chance to grow. Everyone deserves a way to see themselves more clearly. Everyone deserves a system that brings reflection, awareness, and self-coaching into their everyday life.

JourneyLoop is my attempt to build that mirror.

A Question for You

Where are you still trying to grow alone?

What’s one area of your life where you haven’t let anyone truly see you - and what might happen if you did?

Growth doesn’t require perfection.

It requires visibility.

And sometimes, that’s the bravest step of all.