A couple of weeks ago I posted a column on my FastCompany.com blog titled, Gen-Y, the Brazen Opportunist, and Curious Case of Penelope Trunk. It wasn’t until Nicole Crimaldi wrote about it on Ms. Career Girl that dialogue on the topic got interesting.

I just posted a comment on Nicole’s blog. Normally I wouldn’t reprint something here that I posted elsewhere, but I’d like to press this dialogue here, with this community. Ask The Headhunter is about advice, but you also know that I use this forum to critique the “career world,” which I believe is so out of hand and largely devoid of common sense that it does a massive disservice in the economy we’re living in.

I’d love to know your thoughts. Here’s my comment on Nicole’s blog:

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 obliquely takes on what David (citing Rebecca Thorman) tackles in his comment [on Crimaldi’s blog]: 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.

Like I said in my FastCompany.com posting — I think Gen Y deserves more credit. What do you think of all this?


  1. You nailed it right here, when you wrote, it’s “not a career advice site — at least not a credible or useful one.” If that is the case, well if “It’s a successful social club that takes its audience to a brink without warning them where they’re stepping.” Who cares? Let them fall where they may. Do adults really need a guide like THAT? That’s my two cents, or four on the floor on this matter.

  2. Nick, Once again, you rule. You cut right through the BS and nailed it. Being cool is just being cool. It canl win you lots of readers and fans but won’t get you a job.

  3. For the record I’m an engineer at Brazen Careerist. I just thought that I’d point out that we’re not trying to be a career advice site, but more of a virtual networking event. This is why we seem like a social club. When a young person gets out of college and doesn’t have a long list of professional achievements on their resume, their most valuable asset to a company is their ideas. A career focused social network like Brazen Careerist is just the place for these young professionals to share their ideas, meet like minded individuals and attract the kind of employers that will value their passion.

    As for Penelope’s advice. I’m 28 years old and after reading Penelope’s book last week, it seems like good advice based on my experiences. I’ve had 5 jobs over the last 7 years and each time I’ve moved on for a bigger better opportunity. I’m on very good terms with all but one of my past employers and still have a few trying to get me to come back to work for them. I did not achieve this by playing it safe or by following the rules the way my parents had to. I’m naturally brazen and it has worked out ridiculously well for me.

  4. It’s like I tell 8th graders every year, ultimately you choose how to dress, what to say and how you represent yourself on the web. Just don’t expect that every employer will offer you a job with open arms. Unless you are incredibly skilled, they won’t take a risk on you.

    You’ve nailed this one. I enjoy reading Penelope’s blog because she has a unique voice as a writer. I rarely would view anything shes says as career advice.

  5. Perhaps I’m missing a few details here but it would seem to me that Penelope Trunk is living her life on-line and airing a fair bit of dirty laundry that may work in her favor or against her. Some things in this world are still having their place developed in a sense, which may be the case for Brazen Careerist. Anyone who thinks that Facebook or LinkedIn won’t change a lot over the next 3-5 years, may well be in for a shock as I’d argue these sites will evolve as their users and community will shift in terms of what they want and what the sites provide to both users and advertisers as someone is paying the bills here but may not want to continue doing so indefinitely. Sometime we all have to pay the piper, and so will Penelope I’d think. Where I said that it may work for her is that if she is this open and honest person that her tweets imply, this may generate some buzz for her and people get interested in her and seeing if she is really doing what she says or if she is putting out there a double standard.

    As I said, I may be missing some details here, but it could be that Penelope lives her life in her own way which I’d think is commendable. Is it common for people to have that much freedom? Probably not, but then that’s part of the world we live in today.

    Just so it is stated here what my background is, I’m in Generation X which was supposed to be that slacker generation that exists between the baby boomers and Gen Y. I’m almost in my mid 30s and have been in my career for a while now and gone through a few different employers over the years.

  6. I have no idea who that person is, or what that blog is about, and IMHO I do not care. Yet, that stated across the board I do not like the terms Baby Boomer, or Gen (whatever.) Those terms to me are very irrelevant, especially since today there are 45 and 55 year olds that think and act like 12 year olds. As for the vast shift in this 21st century reality, this has been coming for some time. Involved in computers and tech since age 17 I saw this coming then in 1980. By the mid-1980s computers changed everything with the soon to be Internet revolution. Now, social networking and spots like Facebook and Twitter …they ARE the future. All big news is posted on Twitter first before any other format or venue. And with that in mind, the entire concept of being online anonymously is also a thing of the distant past. People out there with their full (verified) real names airing their views confidently are already in sophisticated circles considered the credible ones, (Amazon was one of the very first to verify the names of reviewers.) These mamke up the interesting people with nothing to hide and plenty to contribute. The idea of being online anon, living vicariously through anonymous IDs ofen are the same posting libel, lies and bullshit on sites such as Wikipedia, and are likely the same who feel big or important, using an anon to post against other people or defame their workplace. It is lame and antiquated. That whole mindset is not relevant today and swiftly being rejected. Therefore, my point is that intelligent tech savvy forward thinking people want to know what and whom they are dealing with and want a realistic view of character which is only exposed though open dialogue and open real and honest conversation, be it via a blog (blogs have already taken over magazines,) social networking, Twittering … or confident personal commentary. THAT is the future, like it or not …and it is that future that is changing the face of international business.

  7. Regarding the notion that to tell all, show all is evidence of authenticity, Voltaire said ‘The best way to be boring is to leave nothing out’.

  8. Yes, Voltaire is correct, and let us be clear, read between his words, boring is “to leave nothing out” which means disclosing personal issues and matters that for most people, outside of some authors and visionaries, do NOT belong in public in the first place. That is also different for different people. Voltaire, who is one who did disclose much himself in his lifetime is correct, and is speaking of highly personal and intimate matters, such matters of which would never be appropriate online or in job related blogging in my view. That is entirely different from creativity, authoring a work, an intellectual exercise that exemplifies one’s intellectual capabilities, or on the flip side as so many do just using an anon ID to libel people or bullshit online, or mislead people by virtue of attempting to hide. I have been reading Voltaire for many years and we must always remember that Voltaire held no respect for manipulators, cowards or frauds. I agree. I do not see the sense in any one showing all or telling all of one’s intimate life, online or off. That would be pure stupidity.

  9. I don’t know, a recurring argument across blogs is that Ms. Trunk “isn’t looking for a job” “doesn’t need to build a brand” – but that can change

  10. Dear Andrew,
    I read your post with interest and I’d like to comment on something you said about yourself personally. You said that you moved to the next job and former employers still seek to work with you. Congratulations. I’ll bet that wasn’t because you were ‘brazen’. I believe you developed an expertise and you were a good personality to work with.

  11. Bob,
    I think expertise and a good personality are required if you plan to be brazen. I’d figure out who in the company was important/influential and who wasn’t, I’d work on projects in secret that I knew would blow away those key people and then casually mention “Hey, check out what I threw together” and watch as they turned my side projects into official projects. I like to live by the saying that “It’s easier to ask forgiveness than it is to get permission”

  12. The most telling comment here is Andrew Shell’s, that Brazen Careerist is not a career advice site but a social network. From that standpoint, it might be a good listening site for those of us who don’t understand Gen Y. Those of us who have established careers and who need to attract and mentor those who don’t (we call them “emerging professionals” in my organization) have a real need to learn to speak their language.

    That being said, it sounds like Penelope Trunk is doing a great job of building a brand, if the brand she wants is “frank, emotional, controversial conversation starter.” Most of us don’t want or need that brand for our careers. Perhaps it’s not a lack of integrity, after all, on her part; perhaps it’s just extreme.

    When I advise people on using social media, I advise them to identify their audience and their objectives before they start, then to listen, and then to join the conversations to which they have the most to contribute. If Gen Y is your audience, then listening to Brazen Careerist might be important. (It might also be entertaining.) But if you take it as career advice, you’re missing the point.

  13. A few comments:

    @Vivian: I didn’t say Trunk lacks integrity. I said there’s a lack of integrity between Brazen Careerist and the image Trunk fosters for it. I also haven’t questioned Trunks’s ability to build her brand or her talent as a “diarist.”

    I’m talking about the website’s position as a “career” site. That’s what it calls itself.

    You also say, “But if you take it as career advice, you’re missing the point.” How is anyone missing the point? It’s called Brazen CAREERIST. And the articles on it provide advice about careers.

    @Andrew Shell: You say, “we’re not trying to be a career advice site” and then you refer to, “A career focused social network like Brazen Careerist…” The word career keeps coming up, and you can’t dispense with what it means to be a career advice site if you focus on career issues. Come on – I’ll say it again. There is no integrity when a thing behaves differently from the way it defines itself.

    Now I’ll go a step farther because in the end, this is about value and about quality. Robert Pirsig (author of Zen & the Art of Motorcycle Maintenance) would say (I think) that as a consequence of not having integrity, the site lacks quality. And I’d agree. I think the site trips all over itself.

    Back to Vivian: Why would I want to learn about Gen Y from a career site that lacks integrity and quality, as I’ve just defined them? (If you disagree with my definitions, I’d like to know why.) What I see is a lot of confused people trying to figure out their aspirations, jobs, careers and life. Nothing wrong with people dealing with their confusion, but Brazen Careerist seems to promote confusion.

  14. I’ve written about my complaints about Brazen Careerist in the past (here and here), and I continue to think that the site often does its readers a disservice, by presenting terrible career advice to people who might be inexperienced enough not to realize it.

    I suspect that it’s a function of some of the BC writers striving to be like Penelope — who has made a name for herself being provocative. But while Penelope can usually pull it off because she’s good at what she does, the BC writers generally don’t have the chops (or the experience) to.

    I think Penelope is a beautiful writer, whatever other beefs one may have with her. Her writing at times — particularly when she’s writing about personal things — has taken my breath away. In a good way.

  15. Andrew, You produce good work that speaks to the problems that the company has. What you do may be a bit rare, but it isn’t brazen. However the thought of doing work that speaks to problems the business has, is wonderful career advice.

  16. Nick, I share your sentiments completely. It’s ironic but I’ve been a little hesitant to put them out there in the past because of fears of destroying social capital. If you don’t ‘drink the kool-aid’, you might be shunned by certain community clusters. Sad, but true . . . as you know.
    My youngest sister was turning to the Brazen Careerist for ‘career advice’ . . . until it landed her out of a job. I warned her that the author(s) there wasn’t really trying to offer career advice – it was about being controversial enough to pull in lots of eyeballs, which can be monetized.
    Shock Jocks come and go – in this case, I wonder how many young people have destroyed their careers or regret that ‘great brazen advice’ about the benefits of sexually blackmailing the boss, etc.
    Entertainment and advice are two completely different things. Young people can’t always tell.

  17. Josh, come on, “If you don’t drink the Kool-Aid you might be shunned by certain community clusters?” Now let me be straight, I am not promoting or supporting that person’s site in question which I think is not worth my reading yet what you said above, ARE YOU SERIOUS? If anyone took that advice, I can certainly assure that person would never get anywhere in life, let alone a career. I am not 100% sure what you mean by that statement or what you view it as, but in my personal opinion, that statement to me spells LOSER.

  18. Just found this column via Ask A Manager’s recommendation regarding a question on job hopping and how it’s bad for your career. I have been attempting to find your original article on FastCompany, but it seems to be no longer live on the site. Does it exist somewhere else? I’d like to read it.

  19. @Kate: The FastCompany website seems to have gone crackers lately. I keep getting dead pages, including the one you’re looking for. Let me see if I can publish that column I wrote for them about Brazen Careerist. I’ll post a link here… if you don’t see it in a few days, ping me and complain!