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The Dream & The Fear

It was 2007 but I remember it like it was yesterday. 

You see, I was terrified because it was the end of my Stand-Up Comedy class and we were about to go on stage. 

9 weeks of training had led to this moment.

We had learned how to write a joke. We had learned what makes a punchline. We’d trained in set up, punch, tags, toppers and callbacks.

But at that moment it meant nothing.

My face was red, my heart was pounding and sweat was dripping down my back. 

Every member of my class had gone on stage but…

I. Just. Couldn’t. Do. It.

I felt ashamed when we went home that night because I was the only member of my class who didn’t go on stage. 

A few were good, a few were ok and a few were bad. 

But every single one of them had more courage than me.

So, a week later, I dragged myself back to the comedy club and I summoned up every tiny ounce of courage in my system and I found myself walking on stage to do my bit.

It was around 3 minutes. It felt like 3 hours.

But I did it.

And people even applauded. 

Ok, I didn’t give up the day job but that didn’t matter. 

I did it.

There are only two things that really count when you are coaching a client. 

The Dream. And the Fear.

Here is a selection of powerful coaching questions to help your clients dive deep into both. They are not prescriptive. Choose the ones that feel right to you.

The Dream… 

1. If you were to look back 3 years from now, and say, They have been the best 3 years of my life—what has to have happened, for you to feel thrilled with your progress?

2. What else? What else? What else?

3. What fills you with energy?

4. What did you love to do when you were 6 years old?

5. What are your top 3 professional successes? (Put humility to one side and really own your successes). 

6. What are your 3 top strengths? (Put humility to one side and really own your gifts). 

7. What is the dark side of each of these strengths? (Eg. the dark side of being highly independent is that it’s hard to accept help).

8. Think of 3 people—alive or dead—who you really love and admire. For each one:
– What 3 qualities or mindsets do you love the most?
– What quality or mindset is holding them back the most?

9. What one small habit—if you did it almost every day for the rest of your life—would have the biggest positive impact on your life?

The Fear… 

  1. If you go after what you really, really want – what could that cost you? (Eg. time away from your family, your health, your reputation if you don’t succeed, your reputation if you don’t succeed because you’ll feel like an imposter).
  2. What are you tolerating?
  3. What are you hiding?
  4. What are you afraid of?
  5. What drains you of energy?
  6. How do you slow yourself down, get in your own way and stop yourself from getting what you want?
  7. What is the dark side of each of your gifts?
  8. What one habit—if you continue to do it almost every day for the rest of your life—would have the biggest negative impact on your life?
  9. If you went back 25 years and spoke to your younger self, could they have imagined the impact, the income, the achievements you’ve had, or the struggles you’ve endured? What would they say, if you heard your story?

What’s your biggest dream? And what’s the biggest fear standing in your way?

Love. Rich


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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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