Are you afraid to have someone say “no” to you?

Are you going for what you want or what you think you can get?

And what if you are far more powerful and creative and resilient than you tell yourself?

Today you’re going to get a glimpse into a live coaching session and hear how one man’s bold actions are tearing down the story that keeps him playing small.

In this interview:

  • How to stop playing it safe
  • How to build confidence
  • How to do the things that scare you
  • Destroying limiting beliefs
  • Going for what you want vs going for what is safe
  • Changing the story you have about yourself

If you’re interested in the upcoming group coaching program, click here to fill out an application.

From Tripp:

In my experience, many of us are walking around telling ourselves a lie. A big lie.

Regardless of the success we’ve created, deep down we’re telling ourselves that we’re not powerful. We’re telling ourselves that we’re not capable. We’re telling ourselves that we’re fragile.

We’re focused on the things that are scaring us, and we’re forgetting about the times we’ve faced adversity in the past.

We’re forgetting how we’ve overcome things.

We’re forgetting that we’ve been falling down and picking ourselves back up since we were in diapers.

This limiting story is toxic. And believing this story means we play small. We play it safe. We don’t go for what we really want. Instead, we only go for things we think we can get — and there’s usually a huge gap between what we want and what we think we can get.

As a result our lives become more flat and more boring and less fulfilling. Believing these limiting stories kills our quality of life.

Today you’re going to hear a recording from a group coaching call. The real value of coaching and a coaching group like this is not so much about what happens on the call — it’s what we do in between the calls. In between the calls is where we take action, confront our limitations, and transform our lives as a result.

So in this group I gave my guys a challenge. The challenge was to go out and make some bold or crazy request every day. Go ask people for things that you’re scared to ask for. Go ask for things you think people will reject.

I played along, too.

You’ll hear it on the recording — one of the things I did was instead of going to a grocery store I went into a restaurant and asked if they would give me the food on my grocery list. Surprisingly they gave me what I asked for from their stock. They also looked at me like I was insane. Guess what? I survived.

The bottom line is that through this kind of exercise, we begin to realize that we’re living in a little bubble. What we think is possible is far short from what is actually possible. When we’re willing to make bold requests and hear a “no”, it begins to sink in that our lives can be much, much more expansive. We’re only limiting ourselves because we’re afraid to get a “no”. But don’t take my word for it. Go try it for yourself and see what happens.

What you’re about to hear is an exchange I had with one of the group members. He’s a former professional golfer who is switching careers and transitioning into a position at a startup.

In the past he was a guy who felt more comfortable making a big golf shot under pressure, but when it came to taking risks in his daily life he was slowed down by his fears.

That said, he ate this challenge up.

Just in the first week alone, he asked women out, at work he had a difficult conversation and confronted his boss about his equity position and commission, and…

My favorite bold request ever is how he went into a mexican restaurant and asked if he could go in the back and make his own burrito.

Guess what? They said yes!

He learned what we all learn from this exercise which is that the world is far more likely to say yes than it is to say no. Our fears about being rejected are way out of proportion to reality.

So this guy was showing up powerfully and making waves and being bold, but as you’ll hear, he wasn’t quite getting the message — the truth about who he is. He was still living in a story that said he was small.

As a group we all saw him as a powerful and creative man. We saw him as a guy who, even though he was scared, was capable of doing amazing things.

What you’re about to hear is our compassionate yet firm refusal to see him as anything other than the powerful person he is. We refuse to buy into his limiting stories. We know that even if he’s scared, he’s a guy who can show up powerfully and creatively.

Think about that for a second.

What would be possible for you if you had this kind of awareness in your life — to be able to see where you’ve been hijacked by a story that says you’re far less powerful than you truly are?

What would it be like for you to know that deep down, you had it in you to address your challenges head on instead of running away from them?

And what would be possible for you if you had the support and challenge from others to step into your most power self every day?

I’m creating a small, powerful group for guys who are excited to play at this level.

If this kind of coaching experience interests you, go to my coaching website at and fill out the questionnaire.

In the meantime, I have a little challenge for you. For the next seven days, make one bold proposal or request every day. It’s gotta be something that scares you a little bit. It’s gotta be something that will get a “no”. Be playful. Be willing to get that “no”. Go make those requests — in person — and see what happens.

I look forward to hearing about what you learn. Good luck and thanks for listening.


If you’re interested in the upcoming group coaching program, click here to fill out an application.