Steve Jobs
When: 1985
Position: Apple Chairman
Why he left: Mac sales were declining in 1984-85, and it caused Jobs to often clash with John Sculley, the former Pepsi CEO that Jobs himself brought in to head Apple.
Eventually, Sculley and Apple’s board stripped Jobs of all managerial duties and “demoted” him to the Chairman position. Jobs resigned on Sept. 15, 1985, and went on to launch another company called NeXT. (He later returned as Apple’s CEO on Sept. 16, 1997.)
Best lines: “I find myself both saddened and perplexed by the management’s conduct in this matter which seems to me contrary to Apple’s best interest...I am but 30 and want still to contribute and achieve.”
Read the full letter here.
Max Schireson
When: 2014
Position: MongoDB CEO
Why he left: Schireson left his job as CEO of MongoDB, a popular database firm valued at over $1 billion, so he could spend more time with his family.
Schireson said it was his ‘dream job’ that he was leaving behind. He also raised the question of why male professionals are not asked about work-life balance as much as female professionals are.
Best lines: “As a male CEO, I have been asked what kind of car I drive and what type of music I like, but never how I balance the demands of being both a dad and a CEO...Right now, I choose to spend more time with my family and am confident that I can continue to have an meaningful and rewarding work life while doing so."
Read the full letter here.
Stewart Butterfield
When: 2008
Position: General Manager of Flickr
Why he left: Butterfield was the founder of Flickr, and sold it to Yahoo for $35 million in 2005. But his tenure at Yahoo didn’t go too well. He calls Yahoo a “terrible joke,” and believes Flickr missed out on many opportunities under Yahoo because of Yahoo’s own “screwed up-ness.”
In his metaphor-filled resignation letter, Butterfield calls himself an “old tin-smithing friend.” Although it’s still unclear what the tin was supposed to represent, many suggest it’s a metaphor for innovation. Butterfield is now CEO of Slack.
Best line: “I will be spending more time with my family, tending to my small but growing alpaca herd and of course getting back to working with tin, my first love.”
Read the full letter here.
Andrew Mason
When: 2013
Position: Groupon CEO
Why he left: Mason founded Groupon in 2008 and turned it into a massive social commerce site. He even took it public in 2011. But after declining sales and failing to meet revenue expectations, Mason was fired in 2013.
Best lines: “After four and a half intense and wonderful years as CEO of Groupon, I've decided that I'd like to spend more time with my family. Just kidding - I was fired today. If you're wondering why...you haven't been paying attention."
Read the full letter here. (If you want the hidden meanings behind his letter, read this, instead.)
Steve Ballmer
When: 2014
Position: Microsoft Board member
Why he left: Just a year after resigning from Microsoft’s CEO role, Ballmer stepped down from the company’s board last week.
In his resignation letter, Ballmer said he’s leaving Microsoft to concentrate on his new basketball team, the LA Clippers, and teach classes at USC. This was Ballmer’s last step in leaving Microsoft.
Best line: “I bleed Microsoft —have for 34 years and I always will.”
Read the full letter here.
Steve Jobs #2
When: 2011
Position: Apple CEO
Why he left: Jobs was suffering from various health issues, including pancreatic cancer, and was on indefinite medical leave when he wrote this letter in August 2011.
In the letter, Jobs recommends Tim Cook as his successor, who became CEO shortly after. Jobs died about three months later, on Oct. 5, 2011.
Best lines: “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 the full letter here.
Jonathan Schwartz
When: 2010
Position: Sun Microsystems CEO
Why he left: Just a week after Sun was acquired by Oracle, Schwartz stepped down as Sun’s CEO.
Under his tenure, Sun’s sales continued to decline, and Oracle’s CEO Larry Ellison publicly said he expected Schwartz to resign after the acquisition was complete.
Best line: “Financial crisis/Stalled too many customers/CEO no more.” (He tweeted this haiku as his resignation letter.)
Read the full letter here.
“Samsung Man”
When: 2007
Position: Unknown
Why he left: Back in 2007, an unknown man who only identified himself as “Samsung Man” posted his resignation letter on the company’s website.
The letter went viral, sparking public debate over Korea’s bureaucratic work culture.
Best lines: “Since I started working here, so many things happened that I cannot understand. Why do they drink so much? And then why do they use company credit cards all the time? Why are there so many dinner engagements after work which nobody likes?”
Read the full letter here.
Karen Cheng
When: 2012
Position: “Was working on Excel” at Microsoft
Why she left: In her resignation song, Cheng says she’s leaving Microsoft to join a startup in San Francisco. It’s unclear what exactly prompted her to leave, but she says she's proud of her three years of work there.
But more than anything, it’s just the way she turned Don McLean’s “American Pie” into this charming resignation song that makes it so great.
Best lines: “Long, long lines of code/ It can take a while for Excel code to compile/ I am glad I’ve had the chance/ To make the cells and numbers dance, and maybe make some customers smile”
Listen to the full song here.
