Top 10 Classic Resignation Letters

The resignation is probably the most rehearsed thing anyone ever writes  – disgruntled employees will often write fantasy resignation letters to get them through particularly bad days. I know I wrote four different resignation letters to one crappy and low-level job – most never got handed in and one got shredded. The irony was that I never got to quit that job for real. When I left, it was through a transfer to another site as management. Oh, the shame!

So, for a document so practiced, how come it never comes out as killer as you want it to? It’s always a bit too generic, never really putting the boot in for fear of burning your bridges. But that’s not true for everyone – some people really have nailed the art of writing the perfect resignation letter.  From the poignant to the ridiculous, via the admirably sassy here are the Top 10 Classic Resignation Letters:


10. James Whittaker – Google

One of the many tech-based resignation letters on the list. James Whittaker pulled no punches in his resignation letter to Google, and it quickly spread across the net. His chief gripe was that the Google he knew had changed entirely since he’d been working there and was so obsessed with selling advertising space that they could no longer see the bigger picture. He admitted that Google had always been keen on selling ad space, but that “Google was an ad company only in the sense that a good TV show is an ad company: having great content attracts advertisers.” According to Whittaker, this drive to be the top advertising space on the web manifested itself in a fierce rivalry with Facebook, even though Facebook wasn’t necessarily playing.

He goes on to attack Google founder Larry Page, whose obsession with beating Facebook led to another obsession with their own social network, Google+. Whittaker says that “ideas that failed to put Google+ at the center of the universe were a distraction” and that Google was no longer empowering people, just making them tow the party line.

As it happened, no-one else really cared about Google+, least of all Facebook, and there was never a mass exodus from one to the other. James Whittaker found himself caring less about Google+ too and quit to work for Microsoft. But he leaves behind a resignation letter which is an intriguing look into the heart of one of our biggest tech companies.


9. Richard Peppiatt – Daily Star

A story from a British newspaper now. If anyone should know how to put together a resignation letter, you’d think it would be a journalist, right? And Richard Peppiatt certainly showed what he was being paid for with this nicely vicious letter to the paper’s proprietor Richard Desmond, where he discusses the shame he feels at working for a paper that’s so guilty of spreading hatred.

The paper in question – the trashy Daily Star – had run several stories attacking or mocking Muslims, notably when they “discovered” plans for Muslim-only bathrooms in a mall. It was this story and other bits of “light-hearted Islamaphobia” that pushed Richard Peppiatt to finally quit, but he made sure the world knew about it. That’s a real journalist for you!


8. Steve Jobs – Apple

From one devastating letter to another, but in such a different way. Steve Jobs resigned from Apple in August 2011, just months before his death and his resignation letter was a shining example of how to resign with grace and dignity. In it, he mentioned that he believed “Apple’s brightest and most innovative days are ahead of it” and cited his reasons for going by saying:

I have always said if there ever came a day when I could no longer meet my duties and expectations as Apple’s CEO, I would be the first to let you know. Unfortunately, that day has come.”

Read back as the words of someone who knew the end was coming, it’s beautiful and poignant and a fitting tribute to a man who quietly changed the world.


7. Andrew Mason – Groupon

The most recent entry on our list, this story broke on Feb 28 and the jokey letter spread quickly to the news sites. In it, the CEO of Groupon says that he wants to spend more time with his family before quickly adding “Just kidding I was fired today”. He spends most of the letter reassuring his former employees that he’ll be fine and they shouldn’t worry about him. He compares Groupon to Battletoads, saying it’s like he  got “all the way to the Terra Tubes without dying on my first ever play through”. It’s a great, unselfish letter from a guy who sounds like he would have been really fun to work for, even if he didn’t quite deliver all those boring financial targets.


6. Greg Smith – Goldman Sachs

Here’s a way to resign in style – do it in the New York Times. The headline read “Why I left Goldman Sachs” and what followed was a scathing indictment of practices at the firm, which he described as “toxic and destructive”. He also made reference to how senior managers referred to their clients as “muppets” (a derogatory term in the UK). Of course, a full scale public attack against a powerful company is going to backfire, and when he later tried to cash in by turning hisd letter into a book, he was savaged by industry experts and reviewers alike. Inevitably, there was only one word that most people chose to describe him, and that was…”muppet”.

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