In case you missed it, Hugh Hefner, the famed, bathrobed founder of Playboy magazine, died yesterday at the age of 91. Hefner lived a very full life (to put it mildly), and depending on your point of view, was a groundbreaking social activist or an egotistical hedonist that proudly objectified women.

Either way, it’s hard to discount his achievements; he built one of the world’s most successful media empires. And whether or not you were a fan of Playboy (I, um, bought them for the articles), there are a few things we can learn from the man behind the bunny ears.

Here are six career lessons from Hugh Hefner.

Do what you love

“Life is too short to be living somebody else’s dream,” Hefner once said, and if there’s anyone that really embodied that sentiment, it’s this guy:

Hefner with Bunnies

You might assume that Hef’s dream involved sexcapades with a variety of scantily clad women. I’d argue, though, that it was creating a great magazine. As a child, he spent his time writing and drawing, and by the age of nine, had already started a neighborhood newspaper. He would eventually land a job at Esquire, a magazine he loved.

Along the way, he worked a number of odd jobs, including stints at a cardboard manufacturer and a department store. The key thing, though, was that he never lost sight of what he wanted to do.

When it comes to your career, ask yourself what you really want to achieve, then like Hef, be single-minded and focused.

Know the rules (so you can break them)

At Esquire, Hefner learned how to publish and distribute a magazine, but he also realized that times were changing. A men’s magazine, he thought, could be as intelligent and stylish as Esquire – but much more daring. It could show nude photos and actually have a mainstream audience.

“For the first time in my life, I felt free,” Hefner said in a Saturday Evening Post interview. “It was like a mission – to publish a magazine that would thumb its nose at all the restrictions that had bound me.”

Before he could get there, though, he needed to know what those restrictions were – both from a societal point of view, and within the publishing world.

This is a valuable lesson for just about anyone. If you really want to stand out at the office or when applying to a job, take some time to understand conventions and expectations (including the way resumes are written and read), then look for creative ways to push those boundaries.

Don’t be afraid to take chances

If there’s one lesson to take from Hefner’s life, it’s this one.

After all, Hefner quit his job at Esquire to work on Playboy (itself a risk), and then made a nude photo of Marilyn Monroe the focus of the first issue. The existence of this photo was well-known, but magazines had never published it, for fear of being sued.

If Hefner took the risk, it was because he needed to make a splashy debut. The gamble paid off: he was not sued and all 54,175 copies of the first edition sold out.

Publishing photos of naked celebrities might not help your career, but taking a few chances can. Quitting your job or changing careers can feel risky, but if you’re unhappy, it’s a gamble worth taking.

Don’t be afraid to ask for help

A nude photo of Marilyn Monroe may have launched Playboy, but the magazine would not have seen the light of day without another woman: Hef’s mom. Hefner borrowed $1,000 from his mother to get the first edition published. I repeat: Hef asked his mom to pay for Playboy.

Remember that the next time you’re worried about asking for a reference or recommendation…

Don’t lose sight of what you believe in

When the U.S. Post Office refused to deliver Playboy to subscribers, Hefner took them to court and won a landmark ruling for free speech.

He also challenged America’s “sodomy laws,” writing: “If the pursuit of happiness has any meaning at all as it is written in the Constitution, the government’s intruding into one’s bedroom, into personal sexual behaviors, is as unconstitutional as anything can be.” This wasn’t a one-off; he would later be an outspoken supporter of same-sex marriage and transgender rights.

The 2010 documentary Hugh Hefner: Playboy, Activist and Rebel also argues that Hefner played a role in the civil rights movement. Apart from running interviews with icons like Muhammad Ali and Martin Luther King Jr., Hefner featured artists and comedians like Dizzy Gillespie and Dick Gregory on his TV shows.

This isn’t to say that you should be bringing politics to work. In fact, we think it’s one of the things you shouldn’t share at the office. That said, it is important to find work that aligns with your personal beliefs. Not only will it help you stay motivated, you’ll end up feeling much more fulfilled.

Stay current

“I always think, quite frankly, that pop culture is a lot more important than a lot of people realize,” Hefner once said, and this idea was central to the magazine’s success. After all, if Playboy wanted to push the boundaries, it needed to stay on top of the cultural zeitgeist.

Over the years, Hefner “published an extraordinary range of writers, serious literary writers who you were not otherwise getting when you went into the grocery store,” PEN USA’s Jamie Wolf acknowledged. The list includes names like Joseph Heller, Haruki Murakami, Roald Dahl, Margaret Atwood, and Jack Kerouac, among many others. 

Publishing writers like this may have been a way to legitimize a magazine many derided as smut, but it also ensured that Playboy stayed a step ahead of the competition.

Similarly, staying current is a key component of career development, especially with the speed at which technology evolves. From signing up to a coding bootcamp to brushing up on your on-the-job skills, there’s always something you can do to improve your performance and marketability.