Home Work Penelope Trunk’s Interesting Personal Branding Strategy

What is the first thing you think of when I say Penelope Trunk?

A very interesting article by Fast Company points out the obvious, yet interesting, personal branding strategy of Gen Y career “expert” and founder of brazencareerist.com, Penelope Trunk.

If you’ve ever read Penelope’s personal blog you can find out just about every detail of her personal life, including her abortions and divorce.

I get that she’s branding herself as “BRAZEN,” but honestly what is her strategy here? From a business perspective, it’s hard for me to understand why she would want to talk about her Brazilian wax on Twitter one minute, then turn around and tell people in her “About Brazen Careerist” comments that everything they do online becomes an important part of their career.

Penelope Trunk is a smart and successful entrepreneur.  In fact, I respect her career, I love her entrepreneurial spirit, I’m a huge fan of brazencareerist.com and- although occasionally painful to read- I subscribe to her blog as well. Therefore, I’m assuming her choice of contradicting her own advice is intentional but I just can’t figure it out.  What do you think?  If it is intentional, what is her goal or purpose?

Despite the public details of her personal life, companies continue to pay her a lot of money to consult with them on career issues.  Is this the kind of person we want representing Gen Y?  Is this what Gen Y is? A “share-all-and-still-expect-to-be-paid-a-lot-of-money” kind of generation?

Why do you think Penelope Trunk has chosen this personal branding strategy for her own career?  Should Gen Y and beyond listen to someone who contradicts her own advice?

Penelope and Dan Schawbel- I hope you can give us your feedback too!

55 replies to this post
  1. When I think of Penelope Trunk I think of someone who has no fear and is willing to be transparent about her life. She attracts attention by being herself, which is very special.

    If you analyze Gen-Y, we (I’m 26) share a lot of our lives online just like Penelope. The only difference is that Penelope’s personal brand is more visible and her life is more interesting (at some level). You could be writing this about other Gen-Y’ers, but her brand stands out for better or worse.

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  2. This one is interesting. I had some similar reactions to the Fast Company article. I know as a Gen-Yer, I’m pretty open, but again, I have that little rule: Don’t put anything up that would embarrass my mother. Some people just don’t care, though. And the thing is, Penelope represents one side. I think what they may want to explore is further broadcasting the diversity of Gen-Y and the bloggers in the community. We aren’t always fans of mass generalizations, so what better way combat issues than to not depend on one?

  3. Dan,

    I agree that we (as Gen Y’ers) share a lot about ourselves online. But should someone who gets paid to give career advice be sharing to the level that Penelope is? Should we listen to someone who says to watch what you say, and then spills all?

    Yes she has built a brand, but I’m not sure if it will ultimately be one that survives the test of time, or one that people like.


  4. You’ll probably think I’m living in a nuclear shelter, yet I had no idea who Penelope Trunk was until this very day.

    I felt compelled by your article, simply because I could relate the matter to a short blog essay about the “corruption of authenticity” by author Modite (Rebecca Thorman) (http://modite.com/blog/2009/12/08/the-corruption-of-authenticity/) — an article which I definitely recommend — where she mentions off the bat that “we instinctively know that insistent self-actualization is an incredibly banal form of entertainment, it remains so vast in its infectiousness, and so strong in its self-referential feeding, that navel-gazing is now suffocating in its empire(…)”. She has a point.

    The thing is, when you reach a certain level of personal fame or notoriety, the divide between your personal life and your personal brand begins to (unfortunately) fade. Some socialites take this to their advantage because a celebrity’s casual deeds of garbage-throwing and shopping activities, let alone abortions and divorces, have now become a form of cheap micro-entertainement for Mr and Mrs Average Joe. Should this be part of one’s personal branding strategy? Well, my answer is that “it’s a strategy, period”. Some people might respond well to this form of “authenticity”, while some others might deem it boring at best.

    Self-comparison is a form of personal validation. French author Talleyrand said it best: “When I look at myself, I’m devastated; when I compare myself with others, I’m consoled”.

    Self-publishing is a tool that gives us better access to our right of opinion; but is it also an open door to personal validation? Is the feedback we receive from this self-publishing a necessary step in the evolution of our personal branding process?

  5. Also – A brand’s is engineered is to become a public product, and can only be successful using an efficient communication strategy. When someone’s personal brand reaches this success, some companies invest money to keep it alive — disregarding the reason behind the strategy, but encouraging only the success.

    Is that blatant irresponsible capitalism by the companies, or simply what the market is nowadays?

    For some people, its all about makin’ moneeey.

  6. I didn’t really see this mentioned at all–I sort of had to skim while at work–but I wanted to bring up the point that Penelope randomly shares personal insight into her life without providing some sort of career-related lesson. I think it’s sort of refreshing that she uses examples of everyday life that nearly everyone (gen Y, gen x, men, women, etc.) can relate to. I think to understand what it really takes to be successful, you have to get into the personal realm as well as the work realm. The two are hardly ever mutually exclusive. I know I learn more from her posts than I do from those “Top 10″ lists that most other blogs use.

    Therefore, her type of branding may be different from the type of branding that you or I might seek. I don’t think she’s contradicting herself at all. The audience she’s after is going to be different from the audience at your job. She’s giving us perspective on what a successful business woman is from all angles. You’d never get the same understanding if she only talked about business.

    At least that’s how I feel.

  7. Cassandra,

    You make very good points. I agree that sometimes incorporating personal stories can help clarify professional lessons and that personal events and success are intertwined. And yes, she does dig deeper than the top ten lists which is great.

    Her branding has definitely worked (evidence is all of us talking about it right now!) and does give us deeper insight into her life.

    It has been hard for me to determine just HOW personal I should get on this very blog. I’ve tried both ways- and my posts which have more “Penelope” in them are by far more popular then the posts which I take myself out of.

  8. David,

    I read Rebecca’s article and it is fantastic and definitely relates to this topic. I like the idea of keeping some things to yourself as a writer.

    A modern (and wildly popular)form of self-publishing is reality television. If someone lands a reality show by revealing their personal lives to the world, they’ve “made it” in today’s society. When, truth be told, half the time we are just laughing at their ridiculousness (for example, MTV’s newest disaster Jersey Shore). Are we boosting our confidence and being validated by self-publishing, even if disasterous?

  9. Hi Nicole – great discussion here. Let me preface by saying you should check out this article (and ridiculously good discussion following) that I wrote after Penelope reacted in what I think was a ridiculous way to someone who criticized her parenting skills (in passing on Twitter)


    To your point – she has created a persona for herself – and for better or for worse, people know her because she is VERY open to sharing VERY personal things about her life. I am all for transparency but I think that a lot of what she does is for the sake of controversy – done simply to create a buzz and get traffic. Not my style, but to each his, or her own. She’s been very successful with her approach. If nothing else, she gets people talking.

    More thoughts on Penelope & transparency:


  10. Nicole – that’s a good precision to the question. I think that, for people “following” anyone who’s self-publishing, the consumption of these new “Me-media”, these new personal brands, comes down to the same thing: Quality vs.Popularity. Just like TV right now.

    What’s coming on the web: A competition of personal brands. That (still isolated) fact that companies can actually pay to contribute to the most powerful bloggers and tweeters will not be a social media strategy anymore, it will become an industry…

  11. First thing I think of with PT: TMI, controversial to be controversial, but obviously good at getting attention.

    I would guess that the majority of her readers (myself included) are simply there to read what’s going on in her life not so much for career advice. I’ve seen several commenters echo that sentiment over the last few years.

    Her business isn’t selling career advice. She’s selling access to a network of bright young professionals and advice on how to deal with them. Is she the best person to represent GenY’s wants/needs? I don’t think so. While she is the founder, the network is made up of a lot of very bright people, which is why I’m still there!

  12. I definitely agree that she’s going for the authentic angle, although with how open she is, it is suspect to interpretation.

    Some think she’s just stirring the pot to seem authentic and real, like twittering about her wax.

    She also gives some pretty solid advice at times, but regardless of who it is, I take everything that everyone says with a grain of salt.

    Without a doubt, she is more of a character to read, with occasional career advice than she is an actual career advisor to many.

    I just don’t read her blog, but people pass along her best articles, so I consider that a win win.

  13. I have spent days trying to decide if I should comment here.

    Here is something to think about. I’m 42 years old. I have had a very successful career, and I can be judged on my track record. So I don’t need a personal brand. Also, I have switched careers in a big way, and very successfully, four times — professional volleyball, Fortune 500 marketing, journalist, founder of three Internet startups. As you can imagine, the utility of a single, defined personal brand becomes less and less the more radically you successfully change careers.

    So, newsflash, you never hear me writing about my personal brand because I don’t need one. I am not at the beginning of my career, I am not trying to figure out what I stand for. I am not trying to explain to people how they should view me.

    Younger people need to do that stuff. Because they don’t have a track record. I can just write my blog because I love my blog. I love the collaboration of figuring out life together. I also love that I can show people really what it is like to be a woman at the top of her field. People don’t know. Because it’s very risky for other women in my position to show what it’s really like. I love that I can show people, and they can like it or not like it, but at least someone is talking about it.

    I don’t need a lot of traffic for my blog. I don’t sell ads. I don’t get paid based on traffic. There would be no reason for me to write something just to shock people. I have a lot on my plate right now. If it’s not helping me grow, I don’t do it.


  14. Penelope,

    Thanks for your comment. That makes a lot of sense. Thanks for clarifying.

    I’ve been following your career for quite a while and look to you as a role model in what I’d like to accomplish in my own career. I’m looking forward to building my own track record so I too don’t need to screen everything I write!

    Thanks for your response,


  15. “Don’t do what I do, do what I say.” Ever heard that before?

    I like Ms. Trunk. She’s an excellent writer and what might work for her won’t work for most folks. While she is successful, she may be her own worst enemy, or like many people, the good things she does wouldn’t happen if the not so good things didn’t. From reading her, I gather she does what she has to do for good, or for bad. She just has to do it.

  16. Penelope’s advice to be careful how much you reveal about yourself in a professional setting does not contradict her blog. The difference is that she is known for her brazen behavior and for boldly disclosing intimate details of her personal life. She is also the creator of her own company.

    Most of Gen-Y does not own their own company, although, many of us aspire to do so. Disclosing very detailed personal information may not be the best strategy as we attract investors or while we are trying to climb the corporate later. So, Penelope is saying that we should conservatively disclose the details of our personal lives until we are in a place where doing so will not negatively impact our employment options. Being totally open works for her, but she is fully aware that that strategy does not work for everyone. Good advice.

    Plus, we are all intelligent enough to know that one cannot judge an entire generation by the acts of one individual. Gen-Y is no different.

  17. >> I also love that I can show people really what it is like to be a woman at the top of her field.

    You know, it’s interesting, after following PT for the better part of two years, I have never once thought that she was a woman at the top of her field. I suppose it’s true, given the exposure that she enjoys, but there isn’t anything inspirational or legacy-leaving about the blog or the work. Like many others, I read what she has to say because so many of her choices and issues are like a giant train wreck; one can’t help but gawking. It’s kind of like reading the Enquirer in the grocery store checkout line. There is no particular redeeming value, but the pictures are interesting. Her posts have had me shaking my head in disbelief, a few have made me sad- for herself and her children, but if someone were to ask what value I get from engaging… I really couldn’t answer.

  18. ‘Same thing applies to Penelope. How can she write about and give “Brazen” advice to ‘Gen Y’ on their careers and work life, when she isn’t even living that ‘Gen Y’ life or working in a ‘Gen Y’ career’.


    The point you’re missing is that Gen Y isn’t so different from any other generation. I know we all like to think that we’re individuals, and different to our parents, but the truth is, we all want the same things. The differences are just detail.

    Everyone starts at the bottom of the pile looking up. Including Penelope. So why isn’t her advice relevant? Are you suggesting that the only people who can advise Gen Y are…other Gen Yers?

  19. Others have noted that PT runs her own company and so has a little more leeway to say what she thinks. It’s also worth pointing out that she’s a woman, which means she can get away with being vulnerable and especially talking about sex, whereas a man would come across as a whiner or creepy. That’s they the most popular blogs of men talking about sex are anonymous (and generally called misogynist), and there are no male escort blogs.

    I imagine some women will take umbrage to this, but just because I say this doesn’t mean I think the workplace is tilted toward women. Only that in this one area there is a slight edge to women being able to share their deeper thoughts and feelings.

  20. I found her blog recently because a friend shared a post from it on Google Reader. She really seems to be a person who puts her career far ahead of her personal connections, and I think that is not a lesson that I, as a Gen-Yer want to take to heart. While she is clearly intelligent, she has made a lot of mistakes, and sabotaged a lot of opportunities, which is something most people will not get away with. She is successful partially because she was able to harness an emerging medium at the right time. Her advice tends towards the brutal. She seems to treat life like a train headed on the path to success with no regard for what could be in its path.

    She says she can be exceptionally honest in her blog because she has reached success. She blogs this way because she knows it drives traffic, and because she has no filter. Really all this tactic, and the contents of her blog reflect is a complete lack of regard for an appropriate work-life balance. She will meet her life duties, but she seems to see her and her career as #1 always.

  21. I wrote the column in FastCompany that you’re commenting on, Nicole. You’ve stimulated a far better dialogue than my post did on FC.

    As the title of the column suggests, its main topic is Gen Y – which is easily defined as people in their 20’s starting out on their careers. I closed the column with my point: I see a lot of pandering to an image of Gen Y’ers. Lots of businesses capitalize on that image. (But hell, people in their 20’s have always been a target of the media – the demographic spends a lot of money and pandering to it is a business unto itself.) I think people in their 20’s (no matter when in time we’re talking about them) deserve more credit than the advertising world – and Brazen Careerist – gives them.

    Second in the title is Brazen Careerist, which behaves more like a social club than anything having to do with careers. (Nothing wrong with social clubs, but someone branded this one a career site.) Every generation of people in their 20’s needs and wants to reflect on itself. Brazen Careerist is a fun, if not rocky, place to do that. My point is that Brazen Careerist is a social clubhouse masquerading as a career-advice website.

    The reference to Penelope Trunk points out that today no company can stand apart from the image and reputation of its boss. Brazen Careerist misrepresents itself: No matter how “authentic” people want to be, or how authentic they insist an employer must permit them to be, the reality is that most emlpoyers will eject a job candidate whose online persona is brazen and risky to the employer. I don’t care if someone doesn’t want to face reality; but don’t tell me employers don’t care, or that you’re likely to find an employer who’ll let you bring your dog to work and embrace your embellishments of brazilian waxes and board-room miscarriages. Good for you if that’s your objective. But good luck. You will need it.

    Though some argue that the contradictions between the website and the boss make it all very interesting and instructive in a cool sort of way, there is no escaping the fundamental contradictions. They are fatal to most people’s careers because few will cultivate the successful brand and following that Trunk has cultivated. (You could also strive to be Britney Spears, Paris Hilton or Tiger Woods. You’d better have a backup plan, including someone who will clean up after you online.) Being brassy is fun and cool and it sometimes enables a person to develop a complex, compelling character that serves them well. But teaching, across the board, that being brazen while trying to establish a career is irresponsible.

    “Living the authentic life” is an idea cultivated most simply and clearly by Aleister Crowley. His dictum was, “Do as thou wilt” and it’s very interesting. But Crowley did not hide the risks that walking on the edge of life posed. Hedonism, authenticity, personal branding – there isn’t even a debate today, because for the most part it’s all been reduced to b.s., with the apology that it’s up to you to figure out which is which. Crowley would puke. It’s a lot of fun to tell all in public forums, when you don’t have to worry about being ejected from a job interview (or from a venture capitalist’s office).

    What anyone makes of Brazen Careerist or how they choose to use the site is up to them. My compliments to those who point out that they know how to separate shit from shine-ola. It’s been said again and again in this dialogue, on this forum, on the FC website and elsewhere: Beware of people who tell you to do as they say, not as they do. Asperger’s, hedonism, naivete – none of these are excuses OR explanations for giving self-contradictory advice to an audience that’s looking for legitimate guidance. Perhaps the worst of all the pandering and the gutless claims of “authenticity” is the use of Asperger’s Syndrome to foil criticism. Authenticity does not make anything and everything okay.

    In a song titled, “An Indistinct Notion of Cool,” John Cale takes on what David (citing Rebecca Thorman) tackles in his comment: self-indulgence. Cool is still a challenge to pull off, if it really is authentic. The character of the Brazen Careerist is mostly indistinct.

    All of which tells me that Brazen Careerist is not a career advice site – at least not a credible or useful one. It’s a successful social club that takes its audience to a brink without warning them where they’re stepping. The message of my FC column: Gen Y’ers who want a chance to do work they aspire to should reflect on that.

  22. Chad,

    I learned pretty early on that “blogging takes balls!” Thanks for the compliment.

    You make valid points about Penelope being almost 20 years older than most of us Gen Y’ers. I’m fascinated by her career in that I don’t think many others could follow her path successfully. Yes, those of us who are in our twenties (I’m currently 25) are living it and talking about the struggles every day w/ their friends whether it is about career uncertainty, living independently, debt, student loans, crappy first jobs etc. A LOT has changed in 20 years.

    I don’t look down on Penelope’s career changes as I think she probably has gained many perspectives along with a well rounded experience that allow her to see things differently than most of us. I think a lot of us wish we could try different things but don’t because of fear.

    Thanks for reading Chad,


  23. Derek,

    I disagree with you when you say that maybe women can get away with saying more about these topics. I think when women voice their opinion in a career-related realm they are quickly looked at as weak, emotionally unstable, or perhaps even promiscuous. Whereas men may be given a high five or even seen as bad asses.


  24. i must be the worst Gen-Y-er in the universe, because i’ve had jobs in at least 10 different career fields in the last 10 years.

    oh wait… i now own my own successful photography business, which i just started last year after discovering i love to photograph weddings, and now i’m too busy to have a home office.

    guess i’m not so crappy after all.

    penelope does give Gen-y advice, because she was there once. her experiences apply to everyone, across the board, specifically women. just because she’s giving the advice 20 years late doesn’t mean squat. hindsight is 20/20.

  25. btw… giving contradicting advice… she’s talking about us youngsters. i wouldn’t dare speak as openly about my life right now, right in the middle of building my reputation as a photographer. when you’ve earned that right, you’ll feel liberated in doing it just like she does. and you forget… there’s a reason she despises secrecy.

  26. Read Nick’s Fast Company blog and found my way here,

    Here’s my deal (and everyone has one=): I don’t think you can tell the person from the persona… so I’m skeptical of anyone who wants to know if she’s authentic, because these days who you are online is who you are.

    In regards to should she be giving career advice or not: who knows, it depends on what kind of advice you’re looking for. If you’d like to be CEO of a Fortune 500 company than maybe not. But there are a lot of options out there these days, not all of which require the piety of a nun or a monk.

    Nice point made by Marisa “We’re not supposed to want to be like Penelope, we’re supposed to be as much ourselves as she is herself.”

    Also people forget the scrutiny high profile professional women are under. Boys club is still very much in effect, frankly talking about a Brazilian wax job is pretty small stuff compared to some of the things men have said in public forums. From what I gather Penelope is interested in being herself in all of her online communications, that seems to point out the need for balance between being who you truly are personally and representing yourself professionally.

    Gen Y is more and more interested in being themselves, while still being able to pursue professional ambitions. Nothing wrong with that, but as Nick mentioned companies might not be so hot on it (to varying degrees). Most companies want to be able to attract the talent, but the reality is that the yoga classes, gyms, and “health advocate programs” are there as dressing, they know what they have to do and look like to get the right people in the door. But “the talent” in turn has to know that it’s reciprocal.

    I wouldn’t promote one at the expense of the other, it’s a balance. Otherwise you could be the person who says embarrassing outrageous things that probably hurt your career….. or you could be the plain professional who people think of as a corporate cardboard cutout.

    Both sound unappealing to me!

  27. Hey Chad,

    “Same thing applies to Penelope. How can she write about and give “Brazen” advice to ‘Gen Y’ on their careers and work life, when she isn’t even living that ‘Gen Y’ life or working in a ‘Gen Y’ career ?”

    I’m always amazed at the apparent bottomless naivete of some people. What do you think advertisers have been doing for over 50 years? And believe me, Gen Y is probably the easiest generation to figure out (and to fool) since the early 60s.

    “On top of that, she has switched 4 CAREERS and proudly states touts that as a positive notch on her personal brand. I, however, look at this as a negative blotch on her personal brand.”

    I’m sure you’ve got your agenda all planned out for the next 20 years, but anyway, just make a note to look back at this, on Dec. 23, 2029.

  28. Trunk’s famous for being famous (among dozens, but still.) Her notion of a successful career doesn’t really stack up against Meg Whitman, Mary Wells, Mary Kay Ash or hundreds of other women.

    Her pro volleyball career was pretty short (6 tournaments, career record 3 &12.) I’m surprised she even mentions it anymore.

    The start-ups she was involved with are solid achievements, but she didn’t work alone (and she has trouble giving credit.)

    I often wonder if she’s writing stuff in hopes it will be true.

  29. Chad stated “If someone is going from
    professional volleyball to Fortune 500 marketing
    to journalist to
    ‘founder of three Internet startups’

    all in the space of roughly 20 years (assuming she started working at 21) it tells me that the person has a muddled brain, and is really not clear on what they want to do with their career life.”

    Well, like many things in this Gen-Y era, it’s all subject to interpretation.

    Nowadays, we hear that this is NOT our father’s career era any more, that we must expect to hold way beyond 10 jobs in 5 to 7 careers during our lifetimes. So in the above citing, Ms. Trunk has had 4 careers in 20 years.

    So what is muddled to one person is VERSATILITY to another.

    This is both irritating and invigorating. Why? It’s irritating that some employers insist a person has to have chosen the right career at age 22 and stay with it until age 65 while at the same time saying candidates of today MUST embrace lifelong learning. (Ever try telling today’s frazzled employer that you are willing to learn on the job, to which s/he exclaims, “Next!”?)

    It’s invigorating and exciting that someone has actually switched careers, either by choice or by necessity. Brazenly, or otherwise, hopefully each careerist decides to what extent they choose to do so. (And smart employers can prosper, especially with so few viewing their employees as a resource to develop.)

  30. I understand where everyone is coming from. Alot of times when people Tweet or update their Facebook status, they don’t think about what they’re saying. I’ve tweeted some things then deleted them! Sometimes people don’ t realize certain things until they get called out or someone criticizes them. That’s how we learn, right?! Unfortunately.

    Penelope seems like a smart woman, sharing her life with us and pretending that it’s a “how to” guide (as she said herself) is what has made her successful. Using situations in her personal life for her career. I can’t hate on her. I think everyone has their faults. She’s done a great thing with Brazen, but I think people can learn from her: 1.) don’t tweet about your Brazilian wax, and 2.) keep really personal things private :)

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  32. PT is easy to understand. Just look up Narcissistic Personality Disorder. She’s a textbook case. It’s really, truly no more complicated than that, but today’s youngsters, who have a sense of history that stretches back exactly fifteen minutes, think she is something special. She is Sarah Palin with a blog.

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