Dare to Disappoint

This morning, I did an amazing podcast interview on the topic of daring to disappoint

I shared that for much of my life, I was nice. I was accommodating. I was good.

I was so afraid that if I wasn’t those things someone would be disappointed with me. And I couldn’t think of anything worse than people being disappointed with me.

It feels awful.

But there came a point when I realized that being nice and trying so hard to be good was so constraining. It really didn’t work for actually getting what I wanted in my life.

Sometimes what I want, or what is true for me, is going to upset somebody and potentially disappoint them. Going through my life trying not to disappoint is like going through life with my hands tied behind my back.

It was a point of no return.

I decided this whole being nice thing was an absolute energy drain. Something had to give.

We all do this, to some extent, right? 

It’s the thing you just won’t ask for. 

It’s the conversation you’re unwilling to have with your partner. 

It’s the boundary you won’t draw with your employer. 


You have a place you’re holding back in order to keep the peace and avoid rejection, disappointment or ___ insert what you’re avoiding here ___.

And you have a good reason why you do it. You’ve bought into your own bullshit.

The thing you rarely look at is -- what is it costing you to live that way? What is the cost of holding back, keeping it in, and biting your tongue? 

What’s the cost of avoiding disappointment?

When I started looking at myself, I could see it was costing me connection in my relationships. It was costing me energy and self-expression -- it takes energy to hold back what’s really true for you. 

Avoiding disappointment was getting in the way of wholeheartedly going after what I wanted in my life. 

It was much too high a price to pay!

My questions to you are...

  • Where are you avoiding disappointment?

  • What’s the price you’re paying for it?

If you’re at a place in your life where you're ready to be more courageous and live more of what’s true for you-- you’re at a perfect spot to come on retreat with me.

On retreat, we do the deep inner work that makes it possible to show up and be the person you most want to be in your life.

You can see details here. And, if you’re leaning in but have questions or would like to talk to me personally about whether the retreat is a right fit for you...

Alright, you guys -- DARE TO DISAPPOINT -- I promise there are beautiful, bold things on the other side!

Ashlie Woods