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The Brave Blog              
by Andrea

The time I sent a really mean email

8/31/2026

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So!
When I was fresh out of college, I took a job working for a woman who was mean and filled with fear.

I wrote about her as Hannah (not her real name) in The Funny Thing About Forgiveness. In the book, I share more about that experience, how serious a threat it became to my mental health, and what I needed in order to truly recover.

But today, I want to share a story that didn’t make it into the final draft. It’s about the time I sent her the kind of email you only get to send when no one in your house is counting on your health insurance, and you’re too young to care about the bomb 401K match you’re about to lose.

I called her out for her bad behavior. I said she was a bully and a “robot” devoid of empathy or realistic expectations for her staff. I outlined several paragraphs of the egregious nonsense she subjected us to daily.

Folks… I let loose on this woman.

Did it feel good? HELL YEAH!

Do I recommend this approach? ABSOLUTELY NOT.

Hannah learned nothing from my email. She used it as leverage against me, and not one thing about the culture within this behemoth organization changed or improved because of it.

I felt strong and empowered for the first time in that situation, but that’s not the only variable worth considering. I had to quit before she could fire me, and she used that email to blacklist me across the entire organization.

The problem with “tell it like it is” thinking is that it’s often rooted in the delusion that it’s somehow helpful or healthy not to care about the fallout or consequences. So often, the folks spouting off and bragging about their mic drop lines in confrontational conversations justify this like “someone’s got to say it!”

The problem is that saying it doesn’t matter if the other person can’t hear it. And in order for them to hear it, it needs to be receivable.

When I think about the situation with Hannah through the lens of my work now, I see so many avenues and opportunities I just simply couldn’t see back then. When going to HR didn’t work, I went to other leaders at the organization. When that didn’t work, I assumed calling her a “robot devoid of empathy” in writing was my best option.

It never occurred to me that unloading on someone is only partial bravery. It counts as “speaking up,” but it’s a cop-out from the vulnerability of choosing to speak up in a setting where someone might actually engage.

Often when I speak, people ask me if there’s ever a time when my framework “allows” you to just speak your mind, or go ahead and burn a bridge. We tend to assume that the work of repair and forgiveness means that parting is never part of the journey.

The reality is that truth telling is integral to the work. Being willing to part is integral to the work. The framework doesn’t discourage those things, it sets us up to do them well.

Mindful Improv Thinking isn’t about ignoring bad behavior or being a doormat - it’s about using our bravery wisely.

The point of the framework isn’t to stifle your true feelings - the point is to support you in taking next steps that build what you actually want, not just what feels good for 5 minutes before the true consequences catch you.

If there’s a Hannah in your life, I hope you confront her. I just hope you do it in a way where she actually gets to learn, and you don’t wind up having to sign up as a paid participant for invasive research studies in order to pay the rent.

You are totally brave enough to do it right. And if you’re like “I don’t know what right means in this situation!” … yes you do. ;)

Let’s not burn bridges and call it brave. I believe in you and your work of confronting with compassion and openness.

In the work with you,
Andrea
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    Andrea Flack-Wetherald is a social worker turned comedian and #1 bestselling author who brings heart, humor & humanity to leaders building brave, courageous, and functional cultures.

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