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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


PS. Sign up for my Coaching Excellence Masterclass on August 10. You will learn the frameworks and mindset shifts that the top 4% of coaches use to thrive in life and business. I will share powerful distinctions and key frameworks so you can assess what you need to get to your next level. There’s no charge for this Masterclass – you just need to commit to show up and to apply your insights.


PLUS… Whenever you’re ready, here are 4 ways you can increase your income and impact as a world-class coach:

1. Join me on How to Coach a Superhero, to learn how to coach highly successful clients and do high-level group coaching. Or join me on Money. Money. Money, to handle your limiting beliefs around money, and become financially fearless. There’s a special price to join both…

2. If you want your success and your thinking dramatically re-framed, join me on the 4PC Accelerator. It’s a once-a-year opportunity to join the members of 4PC (my private club for top performers) at an 8 day training – to drastically increase your influence. 

3. Join Project Kairos and spend a year being mentored by me – to learn the skills, mindsets and strategies needed to create a powerful and profitable coaching practice. 

4. Daniel Coyle, author of the Talent Code, says: “Seek out coaches who are authoritative, who know their stuff and take charge. A little scary is good.” 

If you are ready to be pushed and stretched, intellectually and emotionally – to drastically expand your business and your life – there are 3 very unique ways to work with me one-on-one: (1) Thinking Partnership, (2) Protegé, (3) Concierge Trusted Advisor. Apply for an interview. [Note: Investment from $47K to $158K].

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.

Learn more about ways to work together