The Unexpected Gift of Getting It Wrong

There's a special kind of terror that comes from realizing your mistake will land in over 25,000 inboxes simultaneously.

The other week, I made the kind of mistake that makes your stomach drop and your face flush, all while knowing there's absolutely nothing you can do about it.

If you're a subscriber, you probably know what happened. I sent out my newsletter with a subject line that was horrifically inappropriate given the tragic events unfolding in DC. It's that moment when your blood runs cold because you know it's too late to take it back.

My wife read the email and immediately pointed out my error. But the thing about email newsletters is that once they're out, they're out. You can't put that toothpaste back in the tube.

The responses started rolling in. A dear friend reached out with the gentlest possible opener: "Hey, can I give you some loving feedback?" Others were more direct. "Insensitive." "Clickbait." One person even called me a monster, something I haven't heard since my daughter was eight and I wouldn't let her have cookies for dinner.

I felt awful. (About the email, not the cookies. That was solid parenting.)

The piece I'd written? I was proud of it. But now a dumb oversight was overshadowing the work, overtaking my morning, and worst of all, potentially hurting thousands of readers. Adding salt to the wound, some colorful language in the newsletter wasn't exactly helping my case.

So this week, let's talk about screwing up publicly, facing the music, and what happens next. Because let's face it: we're all going to mess up sometimes. The real test isn't whether we make mistakes, but how we handle them when we do.

What do you do when you screw up publicly?

The first instinct is to hide. To delete the evidence, go off the grid, perhaps start a new life somewhere quiet away from it all. But life doesn't really work like that.

So, I did the only thing I could: I owned it. I sent a follow-up email, acknowledging the mistake, apologizing sincerely, and clarifying my intent. It wasn't defensive. It wasn't over-explained. Just a real, human response to a very human error.

Because here is something I believe in my bones: Making mistakes isn't what breaks trust. Hiding from them is. People don't expect us to be perfect; they expect us to be accountable. And in a world where the knee-jerk reaction is often to double down, deflect, or disappear, a straightforward "Yep, I messed up. I'm sorry" can go a long way.

The Unexpected Gift

So, what happened after I apologized?

People replied.

I don't usually get a ton of responses to my newsletter. I've always assumed people either read it (or don't) and then move on with their day. But this time, message after message came in, not to pile on, but to let me off the hook.

Mistakes happen, they told me. It's OK, they told me.

And what's more? They didn't just extend grace. They took the time to tell me how much they love my work.

Here are a few of the responses that honestly made my day:

And this one, which I think I am gonna have framed and put up over the mantle:

And boy, did I feel a huge sense of relief when I read these. But I remembered something deeper: owning your mistakes isn't just about damage control. It's about connection. It reminds people (and yourself) that you're human, that you care, and that your work is about more than just getting it "right" every time.

Turning Mistakes Into Gold

People think I'm a dork about this, but I'll say it anyway: I've kinda fallen in love with mistakes. Not the comfortable kind that everyone quickly forgets. The messy ones. The beautiful ones. The ones that change us.

Cause I believe that most mistakes represent opportunity. When something goes wrong, it's a chance to look for chinks in the armor, to ask what we can do differently next time. To feel the pain of the error so we can better empathize with others when they stumble. To be a living, breathing, failing, authentic human being.

Looking at my process with fresh eyes, I realized I needed to build in some guardrails:

• Creating a pre-publish checklist that includes checking current events context

• Setting up a quick review system with my team (aka my wife) for subject lines

• Building in a 30-minute buffer between writing and sending for a fresh-eyes review

Small tweaks, but ones that could help me avoid unforced errors in the future.

Mistakes sting, I get that. They feel enormous when they happen and threaten to engulf you in the moment. But they happen to us all and they can also make us better... if we let them.

So, if you've been avoiding a mistake, dreading a hard conversation, or replaying an email you wish you could unsend, consider this your permission to face it head-on. Have grace with yourself. Learn from it. Own it, fix what you can, and then move forward.

Because the world needs your work more than it needs your perfection.

As always, thanks for reading,
— Derek

p.s. Have something interesting you think I should write about? You can reply to this email (or any previous Chief Rabbit email) to suggest it. Even better: tell me about a mistake that taught you something valuable.

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