10 Years Spent Approaching Strangers to Get Over My Shyness (And Why It Didn't Work)


Hello Reader,

Prague's first warm days have arrived, and as summer approaches, I feel a bittersweet nostalgia wash over me.

For years, I spent these summer days in the streets, approaching strangers. Practicing conversations. Forcing myself into interactions, convinced that repetition would cure my anxiety.

Despite talking to thousands of people over nearly a decade, my social skills barely improved. I felt broken. Like there was something fundamentally wrong with me that I couldn't fix through strategies.

It wasn't until I turned 30 and dove into real inner work that I discovered the truth: I wasn't broken. I was just trying to force my way through an emotional block.

Why I Kept Looking Outside Instead of Within

The response to my recent thread about shyness surprised me. Several people booked calls and a few already joined my program, directly from that single post without even following me before. In our conversations, I kept witnessing the same pattern I once lived: overthinking instead of feeling.

When something uncomfortable happens, most people don't even realize emotions are arising. Instead of feeling what's there, the mind immediately jumps to analysis. "Why is my voice trembling? Why do I have a knot in my stomach? How can I fix it? What's my next move?" We live entirely in our heads, disconnected from what our bodies are trying to tell us.

One reason I went for a PhD was to face my fear of public speaking. I knew I'd have to talk in front of rooms full of students (and full of academics at conferences). I even joined Toastmasters, thinking that with enough practice and structure, I'd build confidence and hide the fear.

It helped a bit, but something felt off. The speeches were memorized, the delivery felt robotic. Everyone in the club sounded the same, like carbon copies of the two best speakers. It felt like I was hiding behind the words instead of showing up as myself.

I wanted to actually feel confident, not just look like it.

If you're new here and want to catch up on my story, here are the previous parts: part 1, part 2, part 3, part 4

The Shame Beneath the Surface

After pandemic restrictions lifted in summer 2020, I returned to the streets. But something had shifted. Then, my first tantric workshop in December 2020 helped me release decades of sexual shame I've been carrying from my family. Yet as layers peeled away, I discovered shame ran much deeper.

Shame around expressing my truth. Shame around my needs and desires. Shame around being fundamentally flawed and seeking approval instead of authentic connection.

This wounded self had been driving everything: my career choices, my relationships, even my approach to personal growth. I was trying to prove my worth rather than expressing my truth.

When pandemic restrictions eased, I approached online dating analytically. Professional photos, optimized profile, strategic messaging. The results were impressive: multiple dates per week, even during lockdown.

But on those dates, I was still operating from my people-pleasing trauma self. Most women didn't want a second meeting. Great strategy, terrible results.

The Investment That Changed Everything

Starting January 2021, I went all in. For two years, I spent practically every weekend in workshops. And during weekdays, I took improv classes, learned salsa dancing, and by synchronicity, discovered how to release tension in water.

I discovered a Total Immersion swimming teacher who was also a Watsu practitioner. For a full year, she taught me not just swimming technique, but somatic practices and breathwork that transformed how I notice and release tension in my body.

Since 2020, I’ve invested over $40k into my personal growth. While some of my friends bought new cars—a Porsche, even—I spent that money on healing, coaching, and growth. No shiny object to show for it, but what I gained changed everything: confidence, clarity, and a life that actually feels like mine. And if I hadn’t done it, I’d probably still be stuck in an unfulfilling career, earning just a little more than I did five years ago.

Instead, a startup CEO who read my last thread approached me, offering to pay more for 8 hours of coaching than I used to earn in 200+ hours of engineering work. And if you're willing to do the inner work, this is possible for you as well.

The Paradox of Surrender

Whether it's inner work or business success, I've witnessed this pattern repeatedly: breakthrough comes when you fully surrender while taking aligned action. When you burn the boats.

At my first "inner work workshop" five years ago, I did something I'd never done before: I shared my truth. Standing in a circle of strangers, I opened up about my decade-long struggle with social anxiety. How I'd been feeling disconnected, wanting approval, and feeling broken, like something was fundamentally wrong with me.

It felt like a breakdown. Shame flooded my system. Sadness. Vulnerability I'd never allowed myself to feel. But afterward? Massive relief. And to my surprise, nobody laughed. They understood. They'd been there (although in different ways) too.

That breakdown became my breakthrough.

Where This Leads You

Without all that inner work, I wouldn't be where I am now. The boy who couldn't speak up in class now holds a safe container for other people's deepest emotions. The engineer hiding behind technical expertise now helps others reveal their authentic self.

Your deepest struggles become your greatest strength. Your healing journey becomes someone else's roadmap.

I used to think my social anxiety was just a burden—something that held me back. Turns out, it's exactly what resonates with so many people who find me.

Whatever you're carrying might be the very thing that prepares you to serve others in a way no one else can. You've probably already walked through something others are still stuck in.

So here's my question: What if the thing you're most ashamed of is actually your gift?

P.S. That startup CEO didn't hire me because I had the best techniques or was the best coach. He joined because I'd been where he is now, and found a way out. The best credibility isn't what you've learned, but what you've lived through. What have you survived that could become someone else's medicine? If you feel like sharing, hit reply and tell me—I read every response.

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