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Extraordinary Requests create Extraordinary Results

Last week, I shared that my clients and I play a game called Outrageous October every year. Based on the simple idea that Extraordinary Requests create Extraordinary Results, our only goal is to make bold requests, collect NOs and fail spectacularly!

Well, this is the age of facebook, so this year I created a page and invited a few friends and within a week, almost 200 people had signed up to play along with us:

I have been impressed by how willing people have been to really play this game. They have been asking for—and getting—everything from free coffee in Starbucks to having meals comped in restaurants.

But free coffee is not the reason for this game.

And I want to share with you an article I just wrote for the players:


This is Outrageous October.
Lean into your edge.
Get uncomfortable.

Life’s too short.
Stop holding back.
It’s time to ask for what you really, really want.

You are playing Outrageous October for a reason. And I’m pretty sure it’s not for more free coffee.


Let me take you back in time for a moment…

What’s your name? I asked the beautiful woman in front of me.

Her hair was jet black and her eyes were deep pools I was ready to drown in. My eyes were drawn to the tiny diamond nestled at the base of her throat, her long black dress was off the pages of Vogue and she had legs I would have fought—and died—over.

My heart was racing and my tongue was sticking to the roof of my mouth. I has no clue how I was somehow standing in front of her. But here I was.

And terrified as I was, I knew enough to ask her name.

She looked back at me and smiled.

My heart exploded.

Could she really be talking to ME?

But what the hell did she say? All I’d heard over the thumping nightclub bass line was, “Mxfwny.”

Pardon? I replied.


Oh my God. The most beautiful woman I’ve ever met is speaking to me and I haven’t got a clue what she just said.

I pretend I’ve heard her and I make my move. Is this your first time here?


Thank you, Lord.

I have no idea of her name but I heard that reply.

And then I freeze.

In that split second, my mind empties of any semblance of normal human social interaction.

I am aware of a cold trickle of sweat dripping down my back. My mouth hangs open as I gather my thoughts. And then a guy in a ripped t-shirt strolls over.

Hey! He says to the goddess in front of me.

One word.

And it is all over.

As if in slow motion, she turns away from me. And suddenly she is laughing and giggling. The guy catches my eyes for a second but he seems to look right through me.

And, I turn away with a sense of sadness and resignation.

You see, this moment was very familiar to me.

For most of my life, I’d hated meeting women in bars and nightclubs. Because, as you may have gathered, I was really, really bad at it.

From the time I was a teenager, I’d go out with friends with the hope of meeting a girl I liked. But I hated loud clubs. I didn’t much enjoy drinking. I wasn’t a great dancer. And I’ve never understood how to make small talk.

So one day I decided to finally learn how to do this. I read books, went to trainings and studied with men who had this down. I learned clever lines to use when talking to a woman I didn’t know. And I learned how to approach a woman in a club or even a coffee shop.

In fact, over time, I got really good at it.

The guy from the story above would have been proud of me.

Except, it turned out that it didn’t matter.

You see I’d become masterful at speaking to random strangers. But that simply wasn’t a useful skill in having what I really, really wanted in life—deep and meaningful connection with a woman who was interested in personal growth, traveling the world and living a life of adventure. A woman who was passionate and fun and intelligent.

So I stopped doing it. I stopped meeting women in bars and clubs.

And I started doing what I really loved: traveling, doing yoga, diving and attending workshops.

And I began to meet women on beaches and in classes and on trainings. My socially awkward friend David taught me something powerful when he met his girlfriend at a party. He said to her, I’m sorry but I’m only interested in two things. Talking about God. And sex.

She replied, Me too.

And then I met Monique in 2006. We were at a workshop about sensuality and intimacy. I proposed to her 10 days after I met her.

She said yes.

You are playing Outrageous October for a reason. And I’m pretty sure it’s not for more free coffee.

Want to make a $100,000 proposal? Don’t wait. Want to ask your boyfriend to marry you? Don’t wait. Want to ask your boss for a raise? Don’t wait. Want a million dollar donation for your charity? Don’t wait.

I can’t promise you’ll get a yes. In fact, you’ll probably get a no. At least the FIRST time you ask.

Don’t let that stop you.

This is Outrageous October.
Lean into your edge.
Get uncomfortable.

Life’s too short.
Stop holding back.

It’s time to ask for what you really, really want.

Overcome Regular


So, what do YOU really, really, want?
And who would you be willing to ask for it?

Come and join us for the next two and a half weeks:

PS. Dramatically increase your confidence as a coach by mastering enrolling clients. Drastically increase your ability to raise your fees and up-level your clients. And learn to have fun making money. Join me on The 90 Day Money Game. There’s still time to join us…   


PLUS, whenever you’re ready – here are 4 more ways you can drastically increase your income and impact as a world-class coach:

  1. Assess your current coaching level and learn how to get to your next level. Read – or remind yourself of – The Litvin Levels, from The Prosperous Coach.
  2. Watch me coach some of the top coaches on the planet, in order to drastically uplevel your coaching skills. Join me on How To Coach A Superhero: The 4PC edition
  3. Imagine joining a Deep Coaching experience alongside the members of 4PC, my community of high-level coaches… We only offer The 4PC Accelerator once a year and it always sells out in advance. Save $1,000 with early-bird pricing.
  4. Learn how to enroll and coach successful, talented and ambitious clients – with power and impact. Join my flagship program, Project Kairos – for 8 months of guidance, challenge and support to master creating clients.


Transforming world-class leaders into world-class coaches.
That’s what we do.

If this sounds like you, let’s talk and explore if working together is a good fit.

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