What If Success Is What Scares You Most?

The Fear of Success

(and the Inner Tug-of-War You Didn’t Know You Were Fighting)

Hey friend,

I’ve been writing a lot about fear lately, as you’ve probably noticed.

Last week I wrote about the fear of not being enough. Not enough money. Not enough love. Not good enough, not thin enough, not smart enough. Not enough from others. Not enough from life. Not enough from ourselves.

But this week I want to talk about a different fear—one that might be even trickier than the Not Enough fear. And that’s saying something.

It’s the fear of success.

Or said another way:
The fear of being seen.
The fear of visibility.
The fear of stepping into the spotlight of your own life.
The fear of thriving. Of excelling. Of shining too bright.

This fear is sneaky. If you're lucky, you’ve caught it in yourself. But most of us don’t. I didn’t—for over 40 years. It was completely in my blind spot.

Let me tell you a story.

A friend of mine was at my place the other day and noticed a beautiful guitar hanging on the wall. I told her it was my dad’s—a 1973 Gibson. One of the only things I have left of him. He died a little over a year ago.

She asked if I played. I said no, not really.

Then she said, “Your dad was a musician… and he never taught you?”

I paused. No, he didn’t.

What he did do was perform for me. Pull out the guitar, maybe the harmonica, and put on a show. I was the audience. He was the star.

That was our dynamic. I stayed small so he could be big.

I was always a really good athlete, and even as a kid—whether it was hockey, basketball, or tetherball—when I had the ability to beat him, I let him win. Because being “too good” meant risking something far more important: his approval, his love, his presence.

I remember a therapist in my twenties once said to me, “Stop letting your dad score on you.”

I didn’t understand what he meant at the time.

It took me another ten years to finally get it.

My mom? Same outcome, different path.
She didn’t just need me to stay small—she actively told me I was.

She tore me down, over and over, hoping my failure would validate her story—that it was a mistake my dad got custody of me after the divorce.

If I screwed up in life, she could point to it and say, “See? If I had raised him, he would’ve turned out okay.”

It went so far that she’d even sabotage my achievements as a kid—just to get back at him.

It wasn’t about love.
It was about winning.

So I learned young:
Visibility = danger.
Thriving = abandonment.
Success = punishment.

And yet as I became an adult… I chased success like my life depended on it.

If you’d told me years ago I was afraid of success, I’d have laughed in your face.
“Are you kidding? I’ve started companies, I speak on stages, I was on television—what do you mean I’m afraid of success?”

But here’s the paradox:
You can chase success… and fear it at the exact same time.

Let me say that again—because for some of you reading this, this might be the moment.

You can be doing everything in your power to succeed—
and still be terrified of what will happen if you do.

Let that land.

You can want it with your whole heart…
while unconsciously sabotaging it at every turn.

That’s exactly what I was doing—building and destroying in the same breath.
Pushing forward while simultaneously pulling myself back.
Creating and erasing.
Working against myself.
Fighting myself.

One part of me whispered, “You have to succeed—to finally prove you’re enough.”
The other warned, “If you succeed, you’ll lose love.”

So I stayed locked in resistance.
That’s why life felt like such a grind.
Like Sisyphus—pushing the boulder uphill, only to watch it roll right back down.
Always putting out fires.
Even when nothing was on fire, I was still burning.

I was lifting emotional weights all day, every day—
No wonder I became so strong.

Insane, right?

And just to sprinkle a little more insanity on top:
I prided myself on how much I could take.
How many times I could get knocked down and get right back up.
How many punches I could endure.
How many ass-kickings I could survive without ever quitting.

Hell, do you know what I named my son?
Rocky.
Yup. After the movie.
I was so proud of how much of a beating I could take…
I named my son after my strong chin.

Now, you might be thinking:
“Wow, that’s pretty intense, Tony. Glad my life isn’t like that…”

Well—I’m here to tell you: It is.
You’re just like me.
Your story just looks different.

Because my pride in enduring suffering?
My identity as the one who could “take it”?
That wasn’t strength. That was fear.

Fear wearing a costume.
Or two costumes, really:
Not enough and Don’t be too much.

That one-two punch became the storyline of my entire human drama.
But I promise you—fear is the center of your story, too.

It might be dressed differently…
But it's still fear.

And that’s why the world constantly feels so fractured and insane.
Democrat vs. Republican.
Black vs. White.
Israel vs. Palestine.
Ukraine vs. Russia.

We look around and see division everywhere.
But there is no division.
We are the same.
Brothers and sisters, all of us.

And do you know what makes us the same?
What unites us more than anything else?

Fear.

We’re all scared shitless.
And most of us are choosing to stay that way.

But here’s the thing:
We also have the power to choose something else.

We can choose love.

We’re all enrolled in the same fear/love curriculum.
We’re all here for the same sacred purpose:
To wake up.
And then to help others wake up, too.
We’re all just here to walk each other home.

This curriculum—this walking-each-other-home process—is exactly what we’ll be diving into during my free workshop this Thursday.

Because life is a fork in the road.
Moment by moment.
Every hour. Every choice.

And there are only two paths:
Fear or Love.

That’s it.
That’s free will.

And if we’re being honest?
99.9% of us are choosing fear. All the time.

We don’t even realize it.
Because fear wears a thousand disguises.

I just showed you one of mine.

Now let’s look at some others...


Patterns and Characteristics of a Fear-Led Life

  • Constant striving and pushing
  • Feeling like you’re always behind
  • Control and micromanagement
  • Obsessive thoughts or rumination
  • Self-sabotage at key moments
  • Choosing “wrong” partners, jobs, or timing
  • Overwhelm or burnout cycles
  • Avoidance of rest or pleasure
  • High-functioning anxiety masked as productivity
  • Fear of being seen, fear of being judged
  • Despair, comparison, jealousy
  • External validation seeking
  • Hyper-independence or martyrdom
  • Deep inner loneliness

I'm willing to bet that every single one of you reading this sees yourself in this list.
How am I so sure?

Because this list is what unites us.
This is the manifesto of the human experience.

We are all scared.
We all came into this world with fear in our minds—so we could explore the puzzle:

What would life be like if I forgot I was divine?
What would life feel like with a megaphone in my head called fear?
What would it feel like to believe in limitation? In time? In death?

So if you spot your own particular costumes of fear in this list, congratulations.
That’s a good thing.

The first step in undoing the fear-based operating system that’s running your life—and the world around us—is simply seeing it. Recognizing it. Realizing:

The voice of fear in your mind is not you.
It’s not your voice.
And guess what?
Everyone you know has that exact same voice in their head too.

Think of it like a virus we’ve all been infected with.
We’re all suffering from the same malware.

And the wild part?
We’ve normalized it.
Most people just choose to live with it—because they don’t even realize it’s there.

But here’s the good news:
We infected ourselves—so we could remember how to heal ourselves.

And the antidote?

It’s right there, directly in front of your nose.

The antidote is the voice of love in your mind.

It’s a choice. Just like fear is.
The only reason fear feels easier is because we’ve been choosing it every day, in every moment, for as long as we can remember.
It became the first voice. The loudest voice.
The megaphone.

But love?
Love doesn’t need to shout.
Love doesn’t need to perform.

Love is patient.
Love is soft.
Love is kind.

And that’s what we’ll be learning to choose this Thursday
how to stop buying into the megaphone of fear,
and start listening for the quiet voice of love that’s been waiting for you all along.

Because love doesn’t rush.
It waits for your yes.


Patterns and Characteristics of a Love-Based Life

  • A sense of inner safety and peace
  • Trust in timing, self, and Spirit
  • Willingness to rest and receive
  • Relationships based on mutuality, not performance
  • Creative flow and spontaneous joy
  • Surrender without giving up
  • Saying no with love and yes without guilt
  • Clarity instead of overthinking
  • Action from inspiration, not pressure
  • Abundance without grasping
  • Leadership from service, not ego
  • Playfulness, curiosity, and humor
  • A natural magnetism that draws good things in
  • Deep presence and connection with others

You might look at that list and think:
Wow. That sounds amazing.

And you’d be right.
It is amazing.

But here’s what I need you to know:
You don’t have to earn that life.
You don’t have to hustle your way into peace.
You don’t need a mastermind, a new job, a cold plunge, a breakthrough, or another f***ing retreat.

That love-based life?

It’s already yours.
You already have it.
It’s already available to you—right now.

All you have to do is choose it.

Those patterns on the list?
They’re not things you need to build.
They’re what’s left when you stop choosing fear.

They’re what remains when you stop listening to the voice that says you’re not enough.
When you stop letting fear drive the bus.
When you stop buying into the lie.

The work isn’t to become a better version of yourself.
It’s not about reading another book, trying another practice, perfecting your routine, or hacking your life.

The work is to undo the fear.

That’s it.

Because once you start chipping away at the masks and mechanisms of fear,
what’s left—what’s revealed underneath—is the truth of who you’ve always been.

All the patterns on that love-based list?
That’s not your “best self.”
That’s your real self.

So the only question worth asking is this:

How do I stop choosing fear as my guide?

That’s what we’ll explore together on Thursday.

We’ll name the fears.
We’ll see how they’ve shaped our lives.
We’ll learn how to stop believing them.
And we’ll practice remembering who we were before the fear took over.


Not Enough: The Fear That Runs Your Life
🗓️ This Thursday
🕕 5:00 PM PT
💻 Free & donation-based
📍 Live on Zoom

👉 Click here to register.

This is the most personal and powerful workshop I’ve ever offered.
I truly believe it will help a lot of people.

If fear has been running your life—even secretly—come.
Let’s start making another choice.

With love,
Tony

The Ethical Conman (Who Gave Up the Game)

Real-world insights for moving from fear to love in business, relationships, and self-worth. Wisdom from a recovering persuasion expert learning to live, lead, and negotiate with truth.