In the train wreck of Eliot Spitzer's political career, there are many workplace lessons. And lots of people are talking about Spitzer's career. But what about the call girl?

Ashley Dupre, who was Kristen in bed, was no slouch in the career management department. Sure, her breasts are plastered all over the Internet, but don't be so ignorant as to think you can't learn from someone like her. Here are three lessons.

1. Invest money in your career.
I write a lot about how when you don't have disposable income, you still need to spend money on your career so you can earn more money. I have paid for career coaching with my last dollar. I have bought clothes on credit to look like I belong in the position I was interviewing for. All good investments.

But when I wrote about how I got my teeth whitened for TV even though I was unemployed, so many money mavens complained to me that it was irresponsible spending. People constantly undervalue the return on investment you get from taking risks to invest in your own career.

So, Ashley goes to New York with basically no money, and the first big money she makes, what does she do with it? Breast implants! How smart of her! The implants cost about $3000, but after that, she can make $4000 an hour from guys like Spitzer. She made back her investment in an hour, everything else is profit.

2. Know what you are really selling.
You know why most people have terrible resumes? They can't figure out what they really bring to the table. If you really know what you are selling, then most of your resume is not going to be relevant. But people get mixed up about what they are selling. And they start just selling what they think they should be selling that second instead of analyzing the situation.

So Ashley figured out that she was having sex with the Governor of New York. In fact, a few women in her prostitution ring knew. They could have sold their story to the New York Post, but you know what? They make more money as call girls. It's not uncommon for a call girl to bring in $200,000 a year, and the perks are great—trips to Paris with billionaires, for example.

Once a call girl tells on a client, her career is over. Because, as Melissa Gira Grant points out, call girls aren't selling sex, they are selling discretion. Of course a guy like Spitzer could get a mistress, no problem. He's not great looking, but being the Governor of New York makes up for that. But the mistress is dangerous—she could talk. In a call girl, you buy discretion.

3. If you have two careers, make sure they have synergy.
A lot of people have two careers. It's a way to earn money and do what you love. It's a way to hedge your bets. It's just that you need two careers that somehow make sense together. If you want to be a lawyer, side work as a hooker is not a good idea. But Dupre wants to be a singer. And it's expensive to live in New York to build a singing career. So the hooker/singer combination is a decent idea just on that alone.

But look at the synergy after the Spitzer fallout: everyone goes to her MySpace page to see what she looks like, and then they notice she has music. More than four million people have heard her singing. And at this point, she's earned $200,000 in a month from downloads.

So look, it's not great that Dupre is stuck in court right now. But she did a lot of things right when it came to her career, and to be honest, Spitzer's political aspirations will tank from the call-girl-brouhaha. But Dupre's dreams of a singing career will probably be fine. If she had any talent to begin with.

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  1. anon
    anon says:

    How could you further idolize Ashley and the call-girl industry? This is plain rubbish. Good way to market your blog, but in a totally inappropriate light.

  2. Healthy Amelia
    Healthy Amelia says:

    I could not disagree with the first commenter more. If I manage to step back from my judgments for one moment and look at the situation in a somewhat objective manner, it's clear to me that Penelope has a point. I love how people get so indignant about prostitution, especially when so many of the holier than thou types have vices of their own. We're all human and imperfect. "Let he who is without sin cast the first stone – " and all that.

  3. Mark W.
    Mark W. says:

    While reading your March 11 post on ‘The best career tool is self-knowledge’ at that time, Eliott Spitzer was on my mind. You ended your post with the following – “Identity changes as life changes And it's hard to know what's true to us at any given point. It takes a lot of vigilance and honesty and a willingness to shift when we're totally off base.”
    He was off base in more than one way and now he’s lost. I think he’ll find his way somehow though. Hopefully others will learn from the misguided path he chose to take.

  4. Joselle Palacios
    Joselle Palacios says:

    Sorry but I’m firmly with I Blame the Patriarchy on this. Cutifying prostitution and nelgecting the fact that the many pimps around Ashley Dupre are getting way more money from her pictures than she will (just like all pimps get a greater cut of any prostitute’s money) is something I am just not down with. I used to be all rah-rah strippers are so empowering!!!! WOOT! All you have to do is shop to make yourself powerful YAY! But, nah. The way this story has been covered in the media has been really gross. I’m not judging Ashley Dupre at all and I don’t blame her for what she’s done. But believing her story is anything but a fluke or that she’s somehow representative of most prostitutes, let alone most career trajectories, is just too gimmicky for me. I guess I’ll just be the humorless feminist on this one.

  5. Sakoro
    Sakoro says:

    The only problem with her career is that prostitutes tend to have much higher rates of depression and other mental health disorders. It sucks having to behave sexually for people you aren’t attracted to and who probably don’t respect you.

    * * * * * * *

    I am not sure it’s fair to lump depression statistics of high end prostitutes and crack-addict prostitutes and everyone in between. Not really informative. And, as a side note, lawyers have a very high rate of depression and I think if you compared lawyers and prostitutes with similar yearly incomes, the lawyers might be more depressed, on average, than the prostitutes.

    I’m not saying prostitution is a great career choice, I’m just saying that it’s a complicated discussion.


  6. Neuromancer
    Neuromancer says:

    well depends if you want to trade a good income for maybe 10 years vs trying to make it in the music biz where theres a tone of competition who are just as good looking and probaly can sing better and dont have the whole ex hooker tag.

  7. Jim C
    Jim C says:

    Okay, let’s all agree that prostitution is a horrible career choice. Now let’s stop the bitching about it already.

    Penelope is using a call girl’s job as an excellent (though bizarre) example of three important career strategies. All of them apply, and the points are well made.

  8. HR Wench
    HR Wench says:

    Not only was she selling discretion, she was selling a sense of power to an arrogant SOB. He ended up taking it up the pipe, big time. Poetic, really.

  9. Matt Bingham
    Matt Bingham says:

    Believe it or not, we are all prostitutes in some way or form – we just have to decide who the madaam is – ourselves or someone else. We are putting ourselves out there everyday for someone to hire us, to build our network, to advance monetarily – sound familiar. Great post, it really grabbed my attention and stated it’s relevance very clearly.

    * * * * * *

    Matt, great comment. We each have to decide who our madame is. Great.

    Also, I want to point out that even as a supposedly self-employed business owner, I work for someone else — I mean, I have investors, and they will make a lot of money off of me (hopefully) for doing much less day-to-day work than I’m doing. And I actually feel lucky to have the investors.

    So (to Matt’s point) it’s not like the issues of prostitution are all completely unique to prostitution.


  10. Phil
    Phil says:

    Wow…that is all I can really say. To analyze a prostitute and “attempt” to make it career advice is just beyond me. You seemed to have left off the tax evasion advice part of it.

  11. Ruth
    Ruth says:

    People need to stop reporting that she made a ton of money selling her songs so far. She hasn’t. You can listen to them for free and that number is simply based on IF all of those people who listened to her songs had bought them. Sure, she made some money, but that IF is very important when it comes to the actual figure.

    Guess what? I listened to some of the songs out of curiosity. And I didn’t pay Ashley Dupre a dime from my pocket.

    * * * * * * *

    Hm. Well, this does seem to be a debatable point. The New York Post reported the income, but you can see that in the link I have at $200,000 Valleywag has a whole analysis of whether or not the number is right, and what it means if it’s not the right number.

    Sidenote about the future of journalism: This, by the way, is why online media is, in some ways, more accountable than print media. Online media is having a real-time discussion of the truth of numbers. Print media prints and moves on.


  12. Robert W.
    Robert W. says:


    In the future, when you write something so hilarious, perhaps you could provide a warning near the top?! If I hadn’t finished my coffee, I would have sprayed it all over my keyboard as I burst out laughing! Practical advice yes, but most funny. Great job!


  13. Joselle Palacios
    Joselle Palacios says:

    Yes, we all have to work. But having to work in an office isn’t the same as being a prostitute. Office workers and entrepreneurs and waitresses are protected by labor laws. Prostitutes–high class or otherwise–aren’t. And receptionists aren’t trafficked into the profession as 13 year olds. Those are the facts. Lighten it up all you want but being a prostitute isn’t just like opening up your very own hipster cupcake bakery.

  14. bill martineau
    bill martineau says:

    Great analogy! As a blogger for IT professionals I’m constantly stressing the first two lessons, and unfortunately everyone doesn’t see the forest through the trees. So if you have to use an example of a call girl to get their attention than I say go for it.

  15. Todd
    Todd says:

    Great post Penelope.

    And I’ll wonder if she paid anything to get those tracks produced. A lot of the time, it’s just getting yourself in the game and then waiting for your time to come around and for you to receive your pay back. If you do have a small disposable income, then investing it in your career could lead to a larger one.

  16. Scott Williamson
    Scott Williamson says:

    If you take prostitution out the equation, this is excellent advice. Adding it in makes the topic all the more juicy, no matter what side you land on the topic.

    Way to keep the discussion lively!

  17. Dan
    Dan says:

    And with this post, I have unsubscribed from your blog in my RSS reader.

    I’m sure this is sensationally entertaining for some people — but you need to take your own advice: Know what you’re selling. I originally thought you had good (tasteful) advice for careers and job hunting. Apparently, I was misinformed.

  18. Mark W.
    Mark W. says:

    Ruth and Penelope – regarding dollars earned by Ashley Dupre thanks to her career management now begs the question how much the lawyers are going to make!

  19. PunditMom
    PunditMom says:

    This post is why I love you! Now teach me to see the political world with the same lens you use to view the working world! Pretty please? ;)

  20. Chris
    Chris says:


    Looking at your post from a marketing perspective…I think there is some great advice here – re product offering. I will definitely be revisiting my resume. Leveraging off current news is great.
    Well Done!

  21. Mark
    Mark says:

    Wow,Elliot has empowered women of all ages to step out of their comfort zones. Why just the other day when I was at a Bagel shop to order a tray for delivery to a brunch I was attending. A girl at the counter spoke up and said she would be more than happy to deliver the bagels for the owner since he was to busy. Her Price? $4,500. Go fiqure. I’m Justa saying!

  22. Dale
    Dale says:

    You forgot one bit of career advice, always leave your potential employer, wanting to see, hear, or know more!

    Yes, hookers sell discretion, but that's really very incidental to their allure. Business would be great even if they had diarrhea of the mouth – we men are such pigs:)

    They sell the forbidden, fantasy, mystery, adventure… SEX. If we can add these components to our resumes – sans the sex part – we would be unstoppable careerists. As you've said before, the resume should be a sales/marketing document, not a CV. To get that interview invitation, we need to have the recruiter wanting to see, hear and experience more of us. And that is a major lesson to be learned from hookers.
    Additionally you said and I agree,

    "And, as a side note, lawyers have a very high rate of depression and I think if you compared lawyers and prostitutes with similar yearly incomes, the lawyers might be more depressed, on average, than the prostitutes."

    This is likely true because whereas prostitutes sell their bodies, lawyers must occasionally sell their souls in defending the undefendable. We as human can easily rationalize the damage we do to ourselves, but it is really difficult to defend inflicting financial, emotional, or societal damage on the undeserving. One truly needs to be sociopathic to do this without there being an emotional toll.
    Just my two cents worth.

  23. Rich
    Rich says:

    Penelope, I often wonder if just anyone could creat a blog and make money with their random thoughts. You are making me realize that the answer is ‘no’. This post is really creative.

    When I went to Dupree’s MySpace page (guilty!) I was expecting the site to be taken down, or a message from her asking for privacy and sympathy. Instead I found somewhat modest pictures of her, her music and had a chance to see her as a normal person and disconnect her from Spitzer. She should be running a PR firm somewhere!

    Thanks for the insight

  24. Dale
    Dale says:


    You forgot one bit of career advice from all this, always leave your potential employer, wanting to see, hear, or know more!

    Yes, prostitutes sell discretion, but that's largely incidental to their allure. Even if they suffered from diarrhea of the mouth, business would be great – €“ we men are such pigs.
    No, prostitutes sell the forbidden, fantasy, mystery, adventure… SEX. If we could add these components to our resumes – sans the sex part – we would be unstoppable careerists. As you've said before, the resume should be a sales document, not a CV. To get that interview invitation, we need to have the recruiter wanting to see, hear and experience more. And that is a major lesson to be learned from prostitutes.

    Additionally you said and I agree,

    "And, as a side note, lawyers have a very high rate of depression and I think if you compared lawyers and prostitutes with similar yearly incomes, the lawyers might be more depressed, on average, than the prostitutes."

    This is probably true because whereas prostitutes sell their bodies, lawyers must occasionally sell their souls in defending the undefendable. We as people can easily rationalize the damage we do to ourselves, but it is really difficult to defend inflicting financial, emotional, or societal damage on the undeserving. Even if consciously we can use logic to abate our guilt, one truly needs to be sociopathic to do what some lawyers do without there being an emotional toll.
    Just my two cents worth.

  25. Kate Hutchinson
    Kate Hutchinson says:

    Penelope, while I admire your creativity in trying to find the silver lining for this woman, I really have to say that you’re championing in this case the objectification of women and the idea that a woman’s body (looks, image, sexual organs) are the best ways to boost one’s career.

    The real solution here is to provide women with training and opportunities to create careers without having to sell sex for money. It’s a sad society where a woman with a master’s degree and a serious work ethic like myself worries about keeping a roof over her head, while a high school dropout is making over 4x what I make for having sex. I am disgusted by Eliot Spitzer’s hypocrisy in working to create legislation to fault johns more than prostitutes while he is at the same time using women as disposable sex.

  26. Mushroom Factor
    Mushroom Factor says:

    Perhaps Spitzer’s wife needs to read Penelope Trunk. Wait…maybe she already does. Standing up there on the podium beside her cheating husband is, in a sense, investing in her career, which in this case is life with a political figure.

    Career, or no career, as long as women stand by and tolerate this behavior, it says to the world it’s okay. It says they support it. Spitzer’s not the only hypocrite here.

  27. Jennifer Lynn
    Jennifer Lynn says:

    I'm new to the blog, but this compelling conversation is exactly what's kept me coming back.

    On the topic of prostitution itself, I agree with Penelope – it's complicated. Just the other day, a girlfriend of mine asked me why paying a woman to use her body for sex is different than paying a woman to use her body for modeling (assuming there is real consent – whatever that means – in both cases). In both situations, she's reduced to her physical form, and then disposed of. When I couldn't think of any intrinsic differences (other than "it just is"), we realized how difficult it is to get enough of a handle on this, uh, slippery topic to fashion a consistent policy. Yes, prostitution feels different, but how, exactly? Kate- I wonder if you have any thoughts.

    That said, Penelope, I can't believe how perfect this example is! "Know what you're really selling" is probably the best piece of advice I've heard. It's one of those things that should be obvious but often isn't.

    This (fabulous!) post isn't a defense of prostitution – it just goes to show that certain career truths transcend any particular…um…industry.
    * * * * * *

    Jennifer. Your friend asks a great question: Why is modeling any different than prostitution?

    I can’t believe I haven’t heard this before. But I see that there’s a big problem with it. Because if modeling is selling your body in the same way that sex is selling your body, then every time you pick up Vogue, you are a john. But I love Vogue.



  28. chris
    chris says:

    So this rich guy is dancing with this beautiful woman. “Will you sleep with me for a million dollars?”, he asks. “Sure”, she replies. “Will you sleep with me for a dollar?”, he asks. “What do you think I am?”, she replies. “We’ve already established what you are. Now we’re just haggling over price.”

    Oh, and a more relevant point: ‘Kristen’ followed another one of your career suggestions – she is a specialist.

  29. Randy
    Randy says:

    I’m not a fan of breast implants; Real are so much nicer. Although Ashley’s look pretty nice.

    Anyone considering breast implants should watch the surgery. It is gross.

    You have one thing in common with Ashley. Both of you have changed your legal name and also have a work pseudonym.

  30. katie
    katie says:

    RIGHT ON. this is hysterical – and, sadly, rings rather true. thanks for the lessons and an afternoon laugh.

  31. Ann
    Ann says:

    Dan, you need to lighten up. Oh that’s right, you unsubscribed…. And why? Because you couldn’t take the wonderful sense of humor that the BRAZEN CAREERIST has!

    This post was hilarious. I agree with Robert — it was a coffee-spurting, yet insightful, piece. Humorous and meaningful. I’ve been subscribing to your blog before the word blog was created — and this one tops the sarcasm list. Right on!

  32. *DJ FunkyGrrL*
    *DJ FunkyGrrL* says:

    Ciao Penelope,

    Long time since we chatted. I think too mnay people are confusing the morality with the actual situation. You have two adults who decide to engage in this business transaction.

    I think some of the men who are offended isn’t due to the sex. It’s to do with the fact, they can’t get a women like Ashley. I hope she makes alot of money

    By the way, there are alot of women having sex after 1st, 2nd and third dates constantly, only difference they are doing it (sex) for free….

  33. Sydney
    Sydney says:

    Reading the comments on this one was almost as enjoyable as reading the original post! I think some have missed the point. You write to entertain me, and you succeed!

    I don’t actually need career advice (I’m retired) and yet this is my favorite of all the blogs I read. Why–I can certainly identify with the topic (because I did, after all work at one time.) But mostly because it ENTERTAINS me–and this one surely did.

  34. Meg
    Meg says:

    I was aghast to see your latest post on the Spitzer girl. First you give an impression that she has a legitimate “profession”, just like us accountants, lawyers and doctors. Then you go on to discuss the gory details of her “career management” and laud her “career moves”. If that was not enough, you also mention her “salary and “perks”. One would think that you are trying to glorify her profession.

    Dear Ms. Trunk, please remember that career/profession should also be something dignified. Quoting your own example, that girl aspired to be a singer, though she might have more money as a call girl.

  35. Leonard Klaatu
    Leonard Klaatu says:

    Kudos, Penny for creating lively discussion. Nothing sells like sex!

    It’s all about VISIBILITY. Ashley Dupre went from anonymity (discretion) to broad daylight exposure. We’ll see what she makes of it.

    To me the irony is how the tables are now turned. Spitzer wanted the spotlight as Gov. Now he wants to find a cave in Afghanistan. Ms. Dupre was discreet (as you point out), but now she’s looking for all the spotlights. I suppose their futures will be determined now by how successful they each are their new respective objectives.


  36. Kate Hutchinson
    Kate Hutchinson says:


    I can see where the line blurs, but the difference is that models are on the page, and do not engage directly with those who are exploiting their image. They can choose who and what to have sex with. They still have an image, and can still become business women (like Tyra Banks) or have acting careers (Milla Jovovich) or simply be respected (think Cindy Crawford).

    A prostitute must engage sexually with those who exploit her, and because it is illegal and unregulated, she is more likely to become a victim of violence. Look through the annals of serial killers and murderers, and you’ll find an overwhelming number of victims are prostitutes. Models are idols, prostitutes are disposable.


  37. MJ
    MJ says:

    I’m enjoying the irony here of the “you can’t do what you love, because I’ve been writing stories since I was a child and we love sex but don’t get paid for it” story and the fact that, at least in NYC, some people sure do get paid for having sex. So maybe we should follow our passions at work after all?

  38. Neil Pursey
    Neil Pursey says:

    Hi Penelope

    I was referred by a mate to start reading your blog. Wow, some really good advice by him. I love the layout to your blog, simplicity is key!


  39. Ryssee
    Ryssee says:

    This post did make me laugh, and the whole situation is kind of sad, but the points are well made.
    Sakoro-what do you have to say about professional athletes or models? About the same career span, if they’re lucky! Singers too.

  40. Sam Harold
    Sam Harold says:

    Great idea about spending money on your career! There are tons of professional organizations that offer the equivalent of advance degrees through certifications. If people are interested in spending money on their career, they should join a professional organization in their field and see if the organization offers any type of certification. Most of the time it will be cheaper than school and be widely recognized in the field.

  41. Sue
    Sue says:

    I actually think this post is pretty tasteless. Seems like a desperate appeal for hits from all the people searching on her name.

    I’m not a prude, and I have a sense of humor. I just think this is cheap.

  42. Adunate
    Adunate says:

    I’ve been following this post for a couple days. It’s absolutely hilarious! The comments add as much humor as the article itself.

    What I find so funny is people’s failure to see the ironic comparison between our legitimate professions and the notoriously less legitimate. Jennifer Lynn, above, said it right when she wrote “This (fabulous!) post isn't a defense of prostitution – it just goes to show that certain career truths transcend any particular – um – industry.”

    The comparisons between prostitution and modeling are also right on. That can extend further to the sports world, as well. Athletes get paid big money for the way they use their bodies. Team owners are their johns and reap millions themselves.

    By the way, I do not condone prostitution in any way! But, we better look at the whole picture here before we climb onto our high horse.

  43. Mark W.
    Mark W. says:

    This is for the what it’s worth – Eliot Spitzer’s new career is financial commentator for Slate. His first column can be found at . There’s also an interesting post from Henry Blodget who currently works for Slate. Henry was a high-profile Internet stock analyst who was banished from Wall Street in 2001 by Eliot Spitzer, the then New York attorney general. Now Henry and Eliot both work for Slate. Henry Blodget’s post is titled “A Very Warm Welcome To My New Slate Colleague” and can be found at . Too funny.

  44. YSI
    YSI says:

    Jennifer Lynn and Penelope,

    I suppose there is no difference between a model vs. a prostitute in the same way as…say, the wife vs. the mistress.

    Fair enough?

  45. Michael Ross
    Michael Ross says:

    I think your observation is misplaced. Ashley got luckly and from that followed the publicity. Without it, should would have been nothing but a pretty girl with white teeth and great tits. Many times it has been said that it is better to be lucky than smart.

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