Courageous Conversations: Say the things You’re Scared to Say

The most important conversations we need to have are often the ones that scare us the most.

Whether we want to repair broken commitments, create new boundaries, or surface something that’s been on our hearts for a while…the most important conversations in life take courage.

Which makes sense, because we only feel fear when something we care about is at stake. But the fact that we feel this fear makes it all too easy to neglect these conversations.

They’re simultaneously:

  1. The most important for us to have.
  2. The easiest for us to ignore.

There’s always some excuse why now isn’t the right time to have a courageous conversation. So we kick the can down the road.

But if we make that can-kicking a habit, we’ll check our watches only to realize we’ve gone for months (or years?!) without saying something that needed to be said.


That’s an easy way to find yourself living in Regret City, leading a life you don’t love.

The thing is, there’s never going to be a perfect time to have these courageous conversations. Unless we decide to make THIS the perfect time.

And seeing as we’re all cooped up with each other, sheltering-in-place, these days…Maybe this IS the perfect time for us to have some of the important conversations we may have been neglecting.

This is an area I’m working on a lot more these days.

So I thought I’d share a few things that I’ve found helpful:

1 – A tool to make it easier to start courageous conversations. For some reason, sharing that we’re afraid to say something actually makes it easier to say. So instead of ignoring what we’re feeling, we can mindfully note it as we have the conversation.

For example, try starting a conversation with “The thing I’m kinda scared to say right now is…” or “I feel vulnerable sharing this, but…” or “I feel some fear sharing this with you, but it’s important, so…”

When we reveal our internal experience, it creates opportunities for deeper connection with the person we’re speaking to.

2 – A podcast interview of me, having a courageous conversation. I was recently interviewed on the InKind podcast, by one of our Mindful Ambition community members, Julie Krohner. InKind is all about scaling global empathy.

Julie invites her guests to share a message with someone that’s been unsaid for too long. Basically, coming from the frame that we ALL have things we hold onto for longer than is ideal. And that bringing them into the light by sharing them is a profoundly helpful practice.

Sharing this for two main reasons:

  1. I felt a bunch of fear in having this conversation in the first place. Because I had held a bunch of shame around the events I speak to in the show. (For nearly a decade!) But the idea of this conversation was far worse than the actual experience of it. It was tremendously helpful to speak into the world something that had been held within me for far too long.
  2. I hope listening to me talk about something difficult might help you do the same in your life.

You can listen to the podcast here: Apple Podcasts | Spotify

(And, if you’re interested in being on the show, Julie is currently fielding more guests. You can reach her by email here.)

3 – An invitation. What would it feel like to end the week knowing you finally had that courageous conversation that you’ve been meaning to have? What if this were the week that you started a new habit: using fear as your compass, scanning for the courageous conversation you most need to have, and then doing what’s needed to have it?

How might it feel if you looked back a month, year, or decade from now, knowing that you consistently had the most important courageous conversations that you needed to have?

I don’t know about you, but that would feel AMAZING.

So I’m recommitting to that practice this week.

Scanning for the heightened energy that shows up around the important conversations that I need to have. Then having them. With presence, an open heart, lots of love, and most importantly, a hefty dose of courage.

Wanna join me?

Let’s do this,

More from Mindful Ambition

  1. The Fear Game: Build Your Courage and Accelerate Your Growth, One Bold Action at a Time
  2. A Simple Shift To Overcome Fear’s Consequences
  3. How to Conquer Your Fears and Take Action (Tim Ferriss’ Fear-Setting Exercise)