how to kill that "nice guy" anxiety

Hey brother,

Like most men with “nice guy syndrome,” I used to struggle with anxiety.

I never felt comfortable, grounded, or at ease in my own skin. Ever.

In my relationships, this led me to:

• Smile excessively, even when I didn’t feel like it.

• Let people walk all over me.

• Laugh at things that weren’t funny.

• Agree with everyone and lose sight of who I was.

• Drop my values and goals whenever someone asked me for something.

Social interactions were exhausting. Relationships felt like a chore.

So, I started avoiding them altogether.

I felt like a low-status loser — especially around “masculine” men.

I tried everything to heal the anxiety beneath it:

• Breathwork helped a little.

• Better sleep reduced my stress.

• Challenging my thoughts gave me perspective.

But nothing truly changed… until I discovered the power of assertiveness.

The Real Reason I Was Anxious?

I had no backbone.

I didn’t trust myself to meet my needs or stand up for myself. And deep down, the little boy in my mind knew it.

Without that trust in myself, I was constantly on edge, worrying about what might happen.

So I started working on my assertiveness skills:

• I created a list of things I was tolerating from others.

• I audited my draining relationships to understand why they existed.

• I wrote out conversational frameworks to handle conflict with confidence.

• I reframed confrontation as necessary and healthy.

• I repeated to myself: “I am here to be respected, not liked.”

• And I started sticking up for myself.

This wasn’t easy, but it was life-changing.

What Happened Next

The anxiety in my chest began to lift.

I started feeling calmer and more grounded.

I made confident eye contact. My voice deepened.
I noticed people listening to me when I spoke.
And the women in my life? They treated me with more respect.

It was a transformation.

The Hard Truth

Until a man knows he’s capable of asserting himself, meeting his needs, and drawing boundaries, he will NEVER feel safe in his own skin.

He won’t respect himself — and neither will anyone else.

But when you develop assertiveness, everything changes.

• Respect from men.

• Admiration and desire from women.

• Deep, unshakable self-worth.

This is why I created the 12-week Pleaser to Leader program — to guide men through this transformation.

Here’s What We’ll Do Together

• Role-play real-life situations so you’re prepared for anything.

• Use practical tools to clarify your boundaries and assert them confidently.

• Overcome the limiting beliefs that keep you stuck (like “putting myself first is selfish”).

By the end, you’ll become a more confident, assertive, and unapologetic leader in your life and relationships.

This program isn’t for everyone. If you’re not ready to put in the work, this isn’t for you.

But if you’re ready to take control of your life, this could be the start of something incredible.

Click here to learn more and apply now.

I can guide you, but I can’t do the work for you.

Take care, brother.

Stay courageous,
Oliver