Dear Reader,

One of my clients needs to have an important conversation with her boss about what her future at her company looks like.

We've talked about the conversation. She's thought about the structure and what she wants to say. She knows what she needs clarity on.

There's just one problem. According to her, "It's not the right moment."

So I asked her when the right moment would be.

She looked at me for a few seconds…and started laughing.

Because she knew. There probably wasn't going to be a perfect moment. She wasn't going to wake up one morning feeling 100% ready to have the conversation.

And I think we all do some version of this.

We tell ourselves we'll have the conversation when things settle down.

When the project is over.

When our boss seems less stressed.

When we're more confident about how the other person will respond.

In other words: when it feels easier.

Sometimes waiting is the right call. Timing matters. Emotions sometimes need to settle. And there are conversations that deserve thoughtful preparation.

But there's a difference between preparing for a difficult conversation and postponing one.

And sometimes "it's not the right moment" is just another way of saying "I'm hoping this will feel less uncomfortable later."

That conversation with your employee about their performance? Still uncomfortable next month.

Asking your boss where you stand? Still vulnerable after the next big deadline passes.

Addressing the tension with your colleague? Probably not going to magically resolve itself while you wait.

And in the meantime, look at how much energy we're spending not having the conversation.

We're thinking about it.

Rehearsing it.

Talking to other people about it.

Imagining every possible way it could go.

We've given this hypothetical conversation an enormous amount of our attention, and we haven't even had it yet.

All of this is to say that the conversation doesn't become easier because we waited. It becomes easier because we had it.

Maybe it doesn't go exactly as we'd hoped. Maybe we don't get the answer we wanted. Maybe it's awkward.

But now we have information. We can stop rehearsing and start deciding what to do next.

So, what's the conversation you're waiting for the "right moment" to have? If one came to mind immediately, that's probably the one.

Are you willing to have it this week?

With ease, Tracy

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