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312 - Avoiding a Hard Conversation? 3 Plays to Help You Address the Issue Head-On

May 1, 2026
Mentally Stronger Hard Conversations

Pick up a copy of ⁠⁠The Mental Strength Playbook⁠⁠.
 
Have you ever rehearsed an uncomfortable conversation in your head over and over again? Maybe you want to ask for a raise, address something that hurt your feelings, or share bad news—but you keep running the words on a loop, hunting for the perfect way to say it.
 
While we like to practice, rehearsing isn’t actually helping. It’s worrying in disguise. Today, I’m sharing three plays that work a lot better, so you can stop dreading the conversation and find the courage to actually have it.
 
Some of the things I talk about are:
 

  • The webinar I almost got roped into—and how I finally spoke up after weeks of staying quiet.
  • Why rehearsing a conversation in advance often backfires and keeps you stuck.
  • How “Flip the Script” stops your brain from treating the worst-case scenario like a prediction.
  • Why generic affirmations like “you’ll do great” don’t work—and what to use instead.
  • How to create a statement that works for you when the pressure is on.
  • The play that takes the hardest part of a tough conversation and moves it to your prep phase.
  • What to do when you’ve waited too long to raise an issue and it feels too late to speak up.
  • Why you don’t have to feel 100% ready to walk into the room.

 

Key Takeaways:

 

  • Flip the Script: You can develop a more realistic outcome by examining best-case scenarios if you think about the worst case. 
  • Activate Your Power Phrase: A power phrase can give you courage right when you need it most. 
  • Have an If-Then Plan: Prepare yourself with an actionable plan.

 
Avoid Over-rehearsing: Rehearsal can lead to more anxiety.

Notable Quotes:

"Rehearsing a conversation over and over again isn’t actually helping. In fact, it might keep you stuck."

"Rehearsing is often worrying in disguise."

"You don’t have to feel 100% ready to take action."

Timestamp Summary

2:42 Why rehearsing a tough conversation in your head keeps you stuck — and what to do instead

5:08 The webinar I almost said yes to (and the moment I knew I had to speak up)

6:40 The 3 plays I ran to walk into a meeting I was dreading

7:11 How to stop your brain from predicting disaster before it happens

9:38 Why "you've got this" doesn't work — and the kind of phrase that actually calms you down

11:44 The one-line power phrase you can borrow when your brain wants you to back down or apologize

13:09 If-Then planning: how to handle the thing you're most afraid they'll say

14:52 Why you don’t need to be 100% ready

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