The nuclear fallout of an accidental reply all.

And a hard won lesson on owning mistakes.

👋🏼 Hey, I’m Anna! I’m a founder and operator in an ongoing relationship with writing. Welcome to my weekly newsletter where I share business, career and life lessons with a dash of humour and vulnerability.

---

Several years ago I was consulting for the CEO of a multimillion dollar business, helping secure a partnership that was key to their growth. The process had taken months, our chess moves laid out well in advance to ensure we got the best terms. But in the final stages of negotiation the CEO made a colossal error that led to the deal falling apart. They pressed ‘reply all’ on an email chain exposing our strategy, which was (to put it nicely) to ‘go hard and take them for every dollar we can’.

Imagine viciously venting about a coworker in Slack then accidentally sending that message directly to them. The CEO, panicked and embarrassed, tried to grovel and explain their way out of the situation but by then, the damage was done.

The other side reacted as you might expect: shocked, horrified, appalled. They dropped the deal.

But our side reacted unexpectedly: the CEO didn’t cover up their screw up, nor did they play it down or keep it quiet. Instead they printed out copies of the entire email thread and shared it with the team so they’d never make a similar mistake.

Instead of wallowing in the shame of their actions they chose to share them instead.

Everyone screws up.

I’ve always known that failures are there to be celebrated, or at the very least, acknowledged as necessary stepping stones on the yellow brick road to success. But intellectually knowing everyone makes mistakes and viscerally believing it are two very different things. In my experience the only way to close the gap is by broadcasting our own far and wide.

So in the spirit of walking the walk here’s a running list of mine (which is by no means exhaustive):

• In my first year of university I received a big fat 0% in everyone’s favourite subject, Quantitative Methods. I chose to frequent the club not the classroom and didn’t even bother to rock up to the exam. The lesson? Failure is certain if you don’t try.

• In my second year of university my high school invited me to give a speech to the graduating students about life on the other side. It was to an audience of one thousand but because I’m a genius, I decided not to prepare. When I got on stage I mumbled and rambled before slinking off red-faced, tail between my legs. The principal was furious at me. So was I. I haven’t rocked up to anything unprepared since.

• My lifelong dream was to become a spy and I slogged my way through a gruelling ten monthlong recruitment process before being kicked out at the final round (read the full story here). This failure stung bitterly as there was nothing else I could have done. Sometimes we have to accept that life just doesn’t go our way.

• For a time in my twenties I worked in cold hard sales. Every day someone on the other end of the line would slam the phone down in my ear. Once, someone told me I was scum of the earth. After a year of torture, I left. I learnt that there’s absolutely no shame in quitting something that’s just not your jam. Walking away is sometimes the best decision you can make.

• A few years ago my business partner and I were negotiating a high five figure brand deal for our podcast. We’d been working on it for months and three days before Christmas the brand pulled it without any warning. It completely screwed up our cash flow and honestly, it was a dire situation. That year I learned how to cry into my Baileys, and also to never put all of my eggs in one basket again.

All of these experiences taught me things I didn’t want to know but clearly needed to learn. They helped me be more prepared and less reliant, more resourceful and less attached.

They were failures of my own making, but in making them, they made me too.

Go on…hit reply all.

In life’s smorgasbord of screw ups we’re likely to taste failure multiple times. And in response to our mistakes, we can lash out or speak out. Thanks to that CEO, I’m learning to do the latter.

So here’s my sign-off to you: you are the writer of your story. If you’ve screwed up, own it. If you’ve failed, celebrate it. You’ve got it in you to be courageous.

Hit reply all and share your screw ups with the world.

---

↩ Last week’s post

A lot of people reached out to me after I shared my Notion note taking system last week.

If you haven’t read it, check it out here. I may be a Type A psycho but there’s nothing I love more than building systems to streamline repetitive areas of my life so I can focus on more important things, so sue me? Hit me up on LinkedIn if you want to learn how I’ve done it, I’d be happy to help you build yours too.

---

👀 Let me know what you think

Have you ever hit reply all? Do you have a healthy relationship with failure? Share your thoughts.

---

🫶🏼 Subscribe for more ideas

To receive a dose of thought provoking ideas in your inbox each Friday morning, you know what to do.