1. They’re drop-outs.
Interestingly, Anna’s badass quotient here exceeds Steve by far, having dropped out of secondary school at 16. She briefly returned to school to take some classes in fashion, but soon dropped out with the declaration that “You either know fashion or you don’t.” Meanwhile, Steve waited until he’d completed a semester at Reed College to leave it behind, as he wanted to honor his adoptive parents’ request that he give higher education a fair shot. Anna went back to working at the renowned boutique Biba, and Steve worked at Atari to make money for his spiritual retreat to India.

2. They’re both big fans of “spiritual retreats.”
Maybe we’re exaggerating in Anna’s case, but most would say that disappearing with Bob Marley for a week definitely counts. It may not be the same as Steve’s trip to India where he experimented with psychedelics, shaved his head and became a Buddhist, but the unknown parts of Anna’s adventure were likely just as fascinating.

3. 21 was a good age for them.
At 21, Anna got her first job in fashion journalism and first let it be known that she wanted to be editor of Vogue. Having been hitting up the social scene since her teens, by the time she entered her 20s anything seemed more interesting than a vodka tonic. Meanwhile, Steve founded Apple Computer with his friend Steve Wozniak. It bears comparison that when Steve Wozniak was 21, he was just meeting Steve Jobs – and Jobs was 16, already convincing Wozniak to invent the personal computer that would become the foundation of their company.

4. They don’t date quietly.
Whether it’s denying paternity or dating Joan Baez to get closer to the spirit of Bob Dylan, Steve’s known for pushing the limits of dating. Although Anna doesn’t go for denying parenthood or dating folk singers, she started dating older men at age 15 (in that case, a man 9 years her senior) and kept up the habit for years. It’s safe to say that both avoided dating experiences (and accidental children) that could hold them back, and kept striving to move upwards in the social stratosphere. Despite their obvious adventurousness and love of fleeting power, both have been married and Jobs still is (and has taken back that paternity denial of yore).

5. They’ve clashed with authorities…a lot.
It takes a lot to get fired from a position you created in a company that you created. For anyone who’s watched Pirates of Silicon Valley, it’s evident that Jobs earned his disgrace at the hands of John Sculley. Also, Jobs didn’t limit himself to antagonizing other authorities within Apple – his opinion that IBM (a more powerful competitor, at the time) was the enemy was a driving force behind his work on the Macintosh. Of course, Anna’s no innocent here, either. Fired from her junior fashion editor position at Harper’s Bazaar in nine months for putting the desires of her editor behind her own innovations, Wintour is known for stepping on the toes of many gatekeepers of the industry. Even when she first interviewed to work at Vogue with editor-at-the-time Grace Mirabella, Anna declared that the job she was after was Mirabella’s, and the interview ended shortly thereafter.

6. They clash with subordinates…a lot.
Known as “Nuclear Wintour” as soon as she began working at British Vogue, Anna is legendary for tearing apart the workforces and creative approaches of the publications she’s worked with. Acting as a strict curator, Wintour’s alienated many of the creatives beneath her by demanding new directions despite intense time pressures. Similarly, Jobs is renowned for his tantrums and rages when facing work he doesn’t like. Not limiting his tantrums to verbal bashings, when he first returned to Apple in 1996 he terrorized the campus with impulsive and brutal firings.

7. They define their industries.
I know this was said in the introduction, but it bears repeating – Steve Jobs spearheads innovation and trends in technology as Anna Wintour spearheads innovation and trends in design. The impact they’ve had on their respective industries has shaped the work of their contemporaries and their competitors for years, and will continue to for as long as they are active members. Surely, there’s something to be learned from their common examples of playing with fire, taking the consequences like a baller, and leveraging power with confidence. Just as surely, hanging out with a Marley…it can’t hurt.