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My Trip to the Playboy Mansion: The Importance of Challenging Convention

Harrison Barnes
By Mar 06,2024
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Most people assume that those around them are more interested in what they are doing than is the case, and focus on themselves rather than on what the people around them are doing. Rather than worrying about what others think of you, focus on your own forward momentum in whatever you are doing. Do not try to keep things a certain way and protect a norm, but instead challenge conventions to find career and life success.

A couple of years ago, I received a telephone call from a friend of mine who is a pretty well known business motivational speaker, that he had gotten some tickets to a party at the Playboy Mansion. I figured that there was no way in hell my wife would allow me to go, and figured at the time, that this was the sort of thing only single guys did. My immediate reaction to hearing this was that I would like to go, of course, but that it was just something that was not going to happen.

For days my friend sent me one email or another with various details about how fun this party was going to be and various pictures of Playboy models and so forth. He was really quite excited about it. The man was also in his 50s, a lot older than I am, and his enthusiasm was really quite something and not like anything I had witnessed before. In fact, some of the pictures he started to send me began to get just downright dirty and I was afraid to open them in the office because they were bordering on porno.

I told my wife about the invitation after having received a barrage of emails from my friend over a period of a few days. My immediate reaction was that she was going to tell me not to go under any circumstance and that would be the end of it. Instead, she became incredibly enthusiastic.

“Wow!! That’s so cool!! You need to go!”

She also wanted to go to but I told her I had only one invitation. She called up all her friends and was really excited that I was going to be going to the Playboy Mansion for a party. My wife is the greatest and really has a lot of trust and given her incredible endorsement, I made plans to go.

“I told my dad you were going and he said he had gone to a party there several years ago too!” my wife said. The more I thought about the situation the more I realized I had to go. Even my wife’s father was enthusiastic about me going to this party. The next week her parents were over here and her dad came up to me and asked me if I was excited about going to a party at the Playboy Mansion and I told him I was. I am from the Midwest and this is not how parents (or wives) would be likely to behave there. My wife grew up in Los Angeles, however, and she and her parents certainly had some different thoughts about the propriety of this sort of stuff.

The party invitation I received stated that you had to wear pajamas and slippers to it. Since I did not have any pajamas and slippers, I sheepishly gave a copy of the invitation to my assistant and asked her to go pick out some pajamas and so forth for me. My assistant then was also from California, so I should have foreseen her reaction. I was expecting her to perhaps quit over this, or think I was some sort of scumbag for going to this party. However, the exact opposite occurred as well.

My assistant was a professional stalker and had actually started a website dedicated to her stalking activities, www.IamNotaStalker.com. Her stalking activities for the past several years have involved going around to the homes of celebrities, locations of movie shoots and scenes, and taking her picture in front of them. She is the best in the world at celebrity stalking and since quitting her job as my assistant a year or so ago, has been stalking full time.

My assistant was incredibly enthusiastic about me going to a party at the Playboy Mansion as well.

“I wish my boyfriend could go with you, he’d love it!!” she said. I heard her talking to my wife on the phone at one point about how cool she thought it was that I was going to the party.

She purchased me some black silk pajamas and black slippers for the party. Since Hugh Hefner does not have enough parking at his mansion for giant parties, the invitation to the party stated that I was to be picked up in a bus in the parking lot of the Beverly Hills Hilton Hotel. No regular clothes were allowed so I had to meet the bus wearing my pajamas.

The party was on a Saturday night and I took a shower and then put on my bathrobe and slippers. I decided to give myself around two hours to drive from my house to the Beverly Hills Hilton to get picked up for the party because there is a lot of traffic around Los Angeles early Saturday evening. When I stepped into my pickup truck in a pair of pajamas, I became very concerned that I might get pulled over. Nothing about the situation would have looked right. Moreover, I had recently purchased some hay from the feed bin for my goats and sheep I am raising in my suburban back yard, so there were all sorts of loose hay stuck in the truck bed that was blowing around while I drove through the streets of Los Angeles.

I had the distinct misfortune that day, to make it to the Beverly Hills Hilton Hotel in around 30 minutes and not two hours. There was absolutely no traffic whatsoever. When I arrived at the hotel and got out of my truck in the parking lot, I saw absolutely no sign of the Playboy party crowd at all. In fact, walking through the Hotel in my pajamas I was quite worried I might get arrested. I took a seat in the lobby and decided that I would sit there for the next hour or so while I waited for my friend.

I am pretty self conscious; however, sitting around there in the lobby made me feel something worse than self conscious. There was a large wedding going on in the hotel and people were sitting around in tuxedos and very nice suits and I was sitting there in pajamas. The strangest thing happened, however. No one seemed to be acting like there was anything whatsoever out of the ordinary. No one seemed to be looking at me at all. While no one was talking to me, no one was really staring at me either. I felt like disappearing. It was a really bizarre experience.

I decided that I was too self conscious sitting in the lobby of the Hotel in pajamas and that I would go downstairs in the Hotel and try and find somewhere else to hide out. I ended up finding a restaurant in the basement. I walked up the maitre de and asked to be seated. Without batting an eye, he sat me down in a nice table overlooking a bunch of men wearing suits. The biggest problem with the table I was in, however, was that I was seated directly in the middle of the restaurant so everyone there could see me.

The same thing that had happened upstairs happened there: No one seemed at all concerned that there was a guy sitting in pajamas in the middle of a formal restaurant.

At the time, it occurred to me that there was a lesson to this, but I was not really sure what it was. There are lessons here relevant to your career and I will discuss them shortly; however, at the time I was not sure what to make of it.

When I had been a young law student working in New York City during the summers between my second and third year of law school (this is called “a summer associate”), I remember I was out to eat one day, when one of the older associate attorneys, who had been practicing for 8 years or so, started talking to me and other young attorneys about the importance of appearances. While the “elite of the elite” of the highest billing attorneys in New York routinely charge $1,000 an hour nowadays, back then the highest billing attorneys charged $500 an hour.

“If you are charging $500 an hour and you walk into a room, you better look the part!” he said. “You need to have the best suit, the best shirt, the best ties and the best shoes. The client needs to take a look at you and think ‘wholly shit!’ yeah that’s right! This is the guy that is going to save our billion dollar company. We’re in good hands with this superhero!”

The idea that the New York attorneys gave me was that you need to look really good and be really polished if you are going to succeed. Appearances mean everything when you are on the job. This idea was put into me over and over again. I used to see young attorneys polishing their shoes at their desks. When they would get paid, a lot of young attorneys would go out to Hermes and purchase some expensive ties so they could look good at work. Appearances really meant a lot and they were really emphasized.

Here I was sitting in the middle of a restaurant in pajamas, however, and no one seemed to care. The waiter who came up and waited on me acted like it was the most normal thing in the world and I literally did not see a single person in the restaurant look at me in an unusual way.

And this brings me to you. One of the biggest obstacles to our success, I think, is that we think a lot of people are paying attention to us, watching us, and are concerned about us, when in reality they are not. Most people are completely focused on themselves and are not that interested at all in what others around them are doing. In fact, even if you are sitting in the middle of a hotel in pajamas, many people will not care. I think there is a lot of meaning to the fact that most people are so concerned about themselves, they do not notice you. What this means is that rather than worrying about what others think of you, you should be more concerned with your own thoughts and moving forward with whatever you are doing.

I sat in the restaurant ridiculously self conscious, with nothing to read, looking around me every few moments to see if people were laughing at me, for at least an hour. When I finally asked for the bill and it arrived, I tried to explain to the waiter that the reason I was sitting there in pajamas was because I was going to a party at the Playboy Mansion. The waiter smiled and said something like “Yes Sir, I will be right back with your credit card,” and refused to be engaged in the conversation.

Then I finally went upstairs to look for my friend, whom I was supposed to be meeting in the bar. When I got up there, he was sitting there in a giant bathrobe over his pajamas which looked like a Japanese sort of Kimono. He was surrounded by a bunch of girls he knew and seemed to be having a great time. He was a black belt in Karate and probably had a lot of experience wearing robes. The point to me, however, was that he did not look at all out of the ordinary and actually looked pretty cool. I still felt completely out of place. The girls, however, were dressed in a way I could not believe. They were wearing nightgowns that were pretty revealing. As we all sat there in the bar, I could not help but think that it looked like we were getting ready to film a porno.

My friend was also trying to get into show business at the time and had invited a couple of movie producers he knew. We sat there for about a half hour longer than we needed to.

“I cannot believe these guys did not show!” he said. He was pissed and left them two or three messages that escalated in their level of hostility.

I have known so many people in the movie business in Los Angeles and these sorts of things are always the same. A big producer or someone is invited to a party and is supposedly going to show up and they only do around 25% of the time in my experience. This whole thing gets really old, really fast in Los Angeles. It must be fun to be in the movie business and make multiple commitments each night and then only show up for some of them. The thing about Los Angeles is that this sort of behavior has actually spread over the lawyers and others. Everyone I know tries to act like they have multiple commitments each night. It is a front of sorts that people put on and I have found that it is much rarer here than elsewhere. It is something I think requires further investigation…

When we finally got out to the parking lot where we were being picked up by the buses, it was quite a scene. Many of the women were not dressed in nightgowns but what appeared to be fancy bras and underwear. I am not sure how to say this but I will: Almost all of the women going to the party were not that attractive and to an extent, they looked like they had pretty hard lives. There was just something off about them. The guy I was with called them “porn star good looking.” By this I think what he meant to say was that if you put a lot of makeup on them and filmed them under the right conditions, they looked much different than they looked in person. Most of the women were in their early 20s but they looked a lot older. I spoke to several of them and very few of them were from Los Angeles. They were originally from small communities all over the United States. I got the sense that for most of them going to this party was the culmination of all of their hopes and aspirations for their lives. Everyone was incredibly excited. The men that were there also did not appear that professional. Several of them were already drunk. They did things like work as bouncers in bars, worked as waiters, and so forth. There were not a lot of professional types there. I stood there with a couple of hundred people who were going to the party, waiting for the bus to arrive.

When I finally got on the bus headed up to Hugh’s mansion, my friend was surrounded by a bunch of girls as he told stories about his incredible success and wealth. I sat next to a quiet looking girl who appeared to be around my age in her 30s, and we talked on the ride up. She was a graphic designer originally from Russia, who currently lived in San Francisco, and who had come down to Los Angeles for the party. She was really mellow and was dressed like a prostitute in an old Western movie. We talked about where she went to school, the difference between good graphic design and outsourcing. It was a very professional sort of chat and she seemed like a nice person.

When we pulled up to the mansion I saw one of Heff’s girlfriends standing in the front yard playing with a puppy. Everyone on the opposite side of the bus stood up so they could see her too as the bus drove by. I could not help but think how sad it was that all of these people were literally enamored and clamoring to get a glimpse of one of Heff’s girlfriends because they had seen her on television.

“Wow!! That’s really her!”

“Oh my God! Look!”

It was kind of annoying because people were pushing up against me, trying to get a glimpse of her. We were the first bus to arrive at the party and when we got there a bunch of playboy bunnies were wandering around. The entire bus I was on, all walked towards the bar and the girls started ordering all sorts of drinks I had never heard of, and the guys mainly were ordering Coronas, and another group of guys were doing shots of Jagermeister. As the guys looked around, I heard several of them say things like “Fuck Yeah!!” and so forth to express their enthusiasm. I saw a couple of other guys do headbutts.

Within an hour of getting there, stuff started to get out of control. There is a manmade cave there called “the Grotto” that has a bunch of Jacuzzis and manmade waterfalls inside of it. I walked in there and saw a bunch of people with their clothes off jumping around. I also saw various women with their shirts off kissing multiple men. It was unlike anything I had ever seen before. Within two hours the situation got so out of control, I am not even sure if I should be writing about it. In addition to a large crowd forming in the Grotto, people were now starting to walk around the entire area naked. There were some clear small platforms set up over the pool and women were dancing on top of the platforms naked. Meanwhile, men were swimming under these Plexiglas things and looking up.

My friend had brought a couple of other guys and they had begun swimming around completely naked in the pool. When they started yelling at me to join them, I decided that it was time to get the hell out of there. I had experienced enough of the party. By the time I left the party, it appeared that more people were naked than not. With more people naked than not, I determined that I probably should leave right then and there. I have no immediate plans to run for public office; however, I decided that this was something that was simply too risky to be a part of. It would not be a good thing.

I think I was probably the first person to leave the party that night. As I got on the bus (its only passenger), I could hear the screaming from the party and it sounded like people were positively having a good time. What occurred to me, however, was that people were having an incredible time and here I was leaving due to my concern about perceptions and so forth. However, inside the party, people were living, and many appeared to be having the time of their lives. Deep down I realized that the strangest thing about all of this was that for many of these people, getting drunk, getting naked, and hanging out in such a famous place was the culmination of many of their greatest dreams and aspirations. However, for many more, they were just “letting loose” and having a really good time.

I had always wondered what the Playboy Mansion represents to people and now I think I understand: It represents living and forgetting about what society thinks, and having fun in the process. Throughout the world people are afraid to do this, or afraid of what other people think.

• We are always expected to act in a certain way and behave in a certain way.
• We have reputations to defend and ways of looking to others that are considered incredibly important.
• We want to look like a certain kind of person and be “serious”.

However, when it comes right down to it, I am not sure how much all of this matters. People try and maintain appearances and look a certain way because they are trying to protect things and keep them a certain way. I think trying to keep things a certain way is something that is incredibly dangerous in many respects. It is generally the people who challenge convention, are the ones that really make an impression.

Speaking of pajamas, in the 1980s Madonna made women wearing underwear on the outside of their clothes an “in style”. This is a challenge to convention. Today, companies are starting up challenging established automobile companies by manufacturing battery powered cars more cheaply than large companies can. This is what Henry Ford did with the assembly line a long, long time ago and what most modern companies do: They challenge convention.

Bill Gates dropped out of Harvard College. That’s challenging convention. I know a guy who was an investment banker on Wall Street and quit his job to try and become an actor in New York and succeeded, he has been a lead character in many important roles. Over and over, you will find some of the most successful people out there are those who challenged convention.

People will surely remember Hugh Hefner when he dies and talk about him for probably hundreds of years. Will they do the same with you? If you were single at the age of 77, do you think you would have four girlfriends in their early 20s living with you in a big mansion and own a huge magazine and media empire?

He is someone who challenges convention and he has been rewarded for it. In fact, by the looks of the party I saw, he downright sets an example that hundreds of people aspire to.

Over and over you will find that there is a huge lesson in challenging convention and most of society’s heroes are those who challenge convention. I think what Hefner ultimately has done for men, women, and the world is, show us that it is acceptable to challenge convention.

As I got into my truck in my pajamas and started driving home that night, I realized I was missing out on something because I was afraid to live, and what I was really afraid of was challenging convention.

What the people in the party were doing was living and they were living with gusto and the way they wanted to. I had been incredibly self conscious the entire night and had ultimately been the first person to leave because I was worried what people, who were not even there, would think of me in the future. I was afraid to challenge convention. The reason Hefner has made such an impact on the world is precisely because he is able to bring just the sort of reaction in guys like me. What was so meaningful to me about that night was that I was pushed to such an uncomfortable state which showed me my own limits. Showing people their limits is not an easy thing to do.


Most people assume that those around them are more interested in what they are doing than is the case, and focus on themselves rather than on what the people around them are doing. Rather than worrying about what others think of you, focus on your own forward momentum in whatever you are doing. Do not try to keep things a certain way and protect a norm, but instead challenge conventions to find career and life success.

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About Harrison Barnes

Harrison Barnes is the Founder of BCG Attorney Search and a successful legal recruiter himself. Harrison is extremely committed to and passionate about the profession of legal placement. His firm BCG Attorney Search has placed thousands of attorneys. BCG Attorney Search works with attorneys to dramatically improve their careers by leaving no stone unturned in a search and bringing out the very best in them. Harrison has placed the leaders of the nation’s top law firms, and countless associates who have gone on to lead the nation’s top law firms. There are very few firms Harrison has not made placements with. Harrison’s writings about attorney careers and placements attract millions of reads each year. He coaches and consults with law firms about how to dramatically improve their recruiting and retention efforts. His company LawCrossing has been ranked on the Inc. 500 twice. For more information, please visit Harrison Barnes’ bio.

About BCG Attorney Search

BCG Attorney Search matches attorneys and law firms with unparalleled expertise and drive that gets results. Known globally for its success in locating and placing attorneys in law firms of all sizes, BCG Attorney Search has placed thousands of attorneys in law firms in thousands of different law firms around the country. Unlike other legal placement firms, BCG Attorney Search brings massive resources of over 150 employees to its placement efforts locating positions and opportunities that its competitors simply cannot. Every legal recruiter at BCG Attorney Search is a former successful attorney who attended a top law school, worked in top law firms and brought massive drive and commitment to their work. BCG Attorney Search legal recruiters take your legal career seriously and understand attorneys. For more information, please visit www.BCGSearch.com.

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9 Responses to “ My Trip to the Playboy Mansion: The Importance of Challenging Convention”
  1. Avatar Daniel Spielman says:

    You could of at least taken pictures.

  2. Avatar George says:

    Hey nicely written!
    Well your story resemble to each and every person who is not getting time to find some relax. Well Playboy Mansion is a great place, I would also have an urge to go and enjoy a day at Playboy Mansion.

  3. Avatar Wesley Carnahan says:

    Wow. I actually saw you in the lobby that day. I was there with some girlfriends and they surmised that someone dressed like that probably oversees a bunch of companies and has a net worth in the nine figures. The disregard for convention was the giveaway.

  4. Avatar Lindsay Blake says:

    I love this story and remember that day well. :) Memories!!! Thanks for the shout out!

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