Hugh Hefner is an ageless source of broad interest — and not just because he stuffed his magazine and his life full of naked women. His success has nothing to do with naked women. Well, it has a lot to do with naked women, but not quite as much as you might think.

There’s a reason Hefner is a cultural icon and a regular subject of features in magazines like Esquire, which just published an article by Chris Jones about Hefner’s “perfect life.” (Apart from the fact that he’s an 86-year-old man who recently married a woman in her twenties.)

From Jones’s article, here are three lessons for lawyers, from newbies to veterans, inspired by the secret of Hefner’s perfect life.

Lesson 1: Appeal to Reason and Logic, Not Emotion

I know it when I see it,” said Justice Potter Stewart in that famous pornography case (Jacobellis v. Ohio) parsing the line between obscenity and constitutionally-protected free speech.

In other words, sex is emotion, and few people understand that better than Hefner.

But before Hugh Hefner was Hugh Hefner, he was just Hugh, who worked as a copywriter at Esquire before starting his own magazine in 1952. That magazine became Playboy, and out of its success came the Playboy brand and empire, which grew during the turbulent period of the 1960s.

When African American members were denied entry to franchised Playboy nightclubs, Hefner bought those clubs back from the owners. Shortly thereafter, as Jones writes, Hefner sent out a memo banning discrimination at Playboy. Dated 1961, it read in part:

We believe that any form of racial discrimination is illogical and we have great respect for logic. We do not practice racial discrimination and we have no sympathy for those who do (although we do respect the rights of others to hold and peacefully advocate any [political position] no matter how idiotic and off-base it might seem to us).

Hefner founded his business on logic, not emotion. That’s what good lawyers do, too, both as entrepreneurs and as legal counsel. Lawyers appeal to logic and reason. Read, for example, Matthew Salzwedel’s post about appealing to reason and logic in your legal writing. (And, because it’s apropos, read this one about ending sexism in legal writing.) Logic is “the most persuasive form of rhetoric in legal writing,” writes Salzwedel, a fact that obviously wasn’t lost on Hefner.

Lesson 2: So You’re Young (or Old). So What?

Jones writes about the men and women Hefner invites into his home to hang out. (By “hang out,” I’m not talking about sex. I’m talking about conversation.)

Jones writes:

For years [Hefner] was ahead of the culture, and today, in his house, under his roof, nobody will be written off because of the number of years they have or have not yet lived. Neither experience nor inexperience will be considered a sin. Nobody here will be judged by such uncontrollable things.

In other words, Hefner’s “house rules” acknowledge the banality of using age and experience as a benchmark for anything that matters. If you’re a young lawyer without experience, that doesn’t necessarily disqualify you from doing a good job. If you’re an older lawyer, age shouldn’t stop you from learning and improving your craft one step at a time.

(Of course Hefner may not practice what he preaches, here, given his parade of twenty-something wives. And while age does not appear to matter, appearance certainly does — but hey, you can change that with a bit of plastic surgery and Viagra.)

This reminds me of Josh Camson’s post about how to deal with senior members of the bar when they make fun of you in front of a client. Some of your colleagues and critics will use age and experience — things you can do absolutely nothing about — as a lever to pull in negotiation or to assert their perceived authority. The only thing you can do is recognize and acknowledge it, and move on.

Lesson 3: OK, Throw a Little Emotion in There, Too

In his Esquire piece, Jones includes an anecdote about an early failure in love. A girl spurned Hefner in favor of a friend. (This was pre-Playboy.) After that, Hefner started dressing better and presenting his best face to the world. If you need help in that department, get Leo Mulhivill’s advice on clownshoes and ties and preparing your wardrobe for spring.

Fashion and looking good is an emotional thing, but if you look deeper, it’s got logical ties to credibility and self-confidence. And self-confidence is one thing you can’t deny Hefner. The other thing you can’t deny, and which I’ve ignored up to now, is that Hefner’s Playboy empire was built on the perpetuation of stereotypes and the objectification of women. Sex sells, after all.

But I remain struck by Hefner’s appeal to logic — nearly lost behind the centerfolds and silk pajamas — as the greater contributor to his success.


  1. Funny take on tips for lawyers in a humorous tone. Thanks for the post.

  2. Avatar Kate says:

    Not to be a total troll, but I think it needs to be said that Hefner’s success certainly had a lot to do with his commodification of sexualized images of women’s bodies, generally at the expense of women’s agency and self-esteem. I also think that Hefner was a guy with the right idea at the right time in history. Just because he got rich off a smutty magazine at a time when there was no competition for smutty magazines, does that mean we all ought to emulate him in our businesses, competing for legal jobs in a market that is over-saturated with lawyers?

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