Updated on 06.17.07

Review: Brazen Careerist

Trent Hamm

Each Sunday, The Simple Dollar reviews a personal productivity or personal development book.

Brazen CareeristI picked up a copy of Brazen Careerist after stumbling upon Penelope’s blog of the same name, reading through the archives, and thinking to myself that this is something like a What Color Is Your Parachute? (read my review) focusing on twenty- and thirtysomethings. When I saw the book at the bookstore shortly thereafter, I knew I had to pick it up and give it a shot. An hour later, I had read a good chunk of the book in the bookstore and I realized that I had already decided to buy it, take it home right now, and finish it. I’m glad I did.

Brazen Careerist is basically a guide written for modern twentysomethings on how to get ahead in the workplace. By focusing on that group (the late Generation Xers and the oldest of Generation Y) so tightly, it really provides a lot of very specific and useful advice for that group – assumptions about the social order in the workplace, the specific career desires of workers from Generation X and Y (not necessarily money), and the rather transient nature of modern white collar work are just assumed here. Here’s an analogy: I feel that What Color Is Your Parachute? (a standard career guide for the last twenty five years) is quite useful and applicable for both myself and my father, but that Brazen Careerist is very useful and applicable for me, but not much at all for my father.

What’s inside that makes it an interesting read for younger career-oriented workers? Let’s take a stroll through the book and find out.

Getting Inside Brazen Careerist

Brazen Careerist is broken into two distinct parts. Chapters one through six make up the first part, entitled Relish the Path From Starter Job to Dream Job; it focuses primarily on the intial steps of getting your foot in the door at a particular job. The second part, How to Get What You Want from the People You Work With, makes up the rest of the book and discusses a lot of the issues that arise once you’re actually in the door at a particular job. While the division is clear, the individual sub-topics all flow together well enough that the division probably isn’t necessary – if one part sounds interesting, the other part is well worth reading and serves as a nice complement.

Chapter 1 – Detours Are the Route to Happiness
Most people spend their twenties flailing. In fact, only about 12% of people did what I did – fall right into things they love doing right out of college. The others spend their twenties going through what is now commonly being called a “quarterlife crisis” where they try desperately to define themselves and figure out what they want to do with their lives. The average American college graduate now has 8.2 jobs before their thirty second birthday. The point is that if you find yourself doing this flailing about from position to position and don’t really know where you’re going, you’re normal. I would agree – many of my friends and relatives close to my age either went through or are going through this experience.

But it seems like such a waste, you might think. It’s not, and in fact it can serve several useful purposes: you can learn the corporate ropes from several different places and know how to navigate as soon as you find the place, you can continually add to your skill set, and without a lot of responsibility already set in stone, you can make choices that might not make any sense later on in life, like taking a job as a volunteer in Africa and using that as a basis to get started on a consulting career. One big point of advice: don’t use graduate school as a “bail out” because quite often it’s just postponing the inevitable. One should only go to grad school with a defined purpose beyond merely that of “getting a degree.”

Chapter 2 – A Resume Is a Sales Tool, Not a Work Summary
The average resume reader makes up his or her mind about a resume in about ten seconds, so when you’re writing a resume, you want to maximize those ten seconds by creating a resume that has the same attention-grabbing attributes of the best advertising copy so that you stand out from the pack. Penelope proposes some interesting ideas for achieving this, including limiting your resume to one page only. Why? This ensures that you include only the home run stuff and it all appears right in one place, making those ten seconds focus on a single page that highlights everything awesome about you. Another killer point: list everything you do as an achievement, not as a mere job duty. If you wrote some software for a company, mention that you wrote 50,000 lines of code for a project that made 8 million in sales (or whatever the quantifiable characteristic might be).

Just think of your resume as a sales tool, and that you’re trying to sell yourself to the potential employer. This doesn’t mean you should lie to get the job, but that you should accent every positive as nicely as you can. If you were at a company during a time of significant growth there, mention that growth on your resume. If you were a salesman while a company’s sales went up threefold, even if the sales boost was due to an awesome product that practically sold itself, mention that increase anyway. Use this same philosophy for your cover letter, too: keep it nice and short (under a page) and sell yourself from start to finish. This chapter has a ton of specific pointers on resume and cover letter writing that contrast quite a bit from the standard ideas floating around out there – not enough so that you look like a freak, but good ideas that adapt the logic of persuasive writing to resume and cover letter drafting.

Chapter 3 – Hunting for a Job Is Not a Task, It’s a Lifestyle
Most of the traditional advice about hunting for a job doesn’t make nearly as much sense in this modern era of people hopping from job to job rapidly during their twenties and early thirties. Instead of trying to find that perfect job right off the bat, you should just find jobs that match a few key needs for you. At this stage, you’re better off finding a job with a manager that’s a good fit for you than the perfect position – you can always find additional things that make you a more interesting candidate for future positions, like independent or consulting work.

Three more tips that interested me in this section:
+ Save up for a good-sized emergency fund, because you’ll often need one as you keep moving from position to position finding the right one for you;
+ Don’t be afraid to move back home, because it can provide a solid and safe base while you’re searching about for the right place; and
+ Learn how to cold call. This tip is really interesting, because it made me immediately think of the excellent book Never Eat Alone (read my detailed review) which talked about the art of cold-calling in detail – I never associated it with job hunting until I read Brazen Careerist.

Chapter 4 – An Interview Is a Test You Can Study For
This is easily one of the best chapters in the book – it sums up everything I’ve learned about good interviewing from both the side of being interviewed and from the side of conducting interviews. Most people go into an interview assigning far too much power to the person interviewing them – instead, you should view it as a meeting of equals where you’re both evaluating if the situation would be appropriate for you. For instance, if you come to the end of an interview and want the position, don’t hesitate to say that you really like the job and ask if they have any reservations in hiring you. Also, when the interviewer asks you if you have questions, have questions, especially ones that give the idea that you’re trying to find out more about this position.

So what can you do during the interview that will make you look great? First, know the company and the position. Research the organization extensively, know what they do, and know as best you can what role your position serves in this hierarchy. Try to tie what you would do in the position to the company’s bottom line. Second, dress the part – underdressing never impressed anyone. Third, practice some questions. Look for typical interview questions online, develop good answers, and practice them. Finally, have a few good stories about yourself. Polish them up in advance so that when you tell them, they not only entertain but also highlight the good features that you can bring to the company. In other words, you should actually prepare for an interview quite a bit.

Chapter 5 – Corporate Life Is Too Risky – Start Your Own Business
One option not often explored in typical career advice books is the option of going into business for yourself, particularly when you consider that corporate America often undervalues the young. While this is far from the focus of the book, this chapter gives a brief outline of some of the things to think about if this seems to be of interest to you.

Unfortunately, this chapter is perhaps the weakest part of the book, mostly because it is so detached from the rest of it. The really valuable idea from this chapter was, again, the value of networking. Over and over again, in various dimensions, this skill pops up as being useful as you build a career or build a business. Never Eat Alone is really a stellar guide for how to network with integrity and value.

Chapter 6 – First-time Managers Do Not Need to Suck
At some point, most people who are good at their work and display any natural social ability or leadership ability are put into some sort of management, and that first transition often shows whether you’re going to be stuck at this level for a long while or whether you’re headed up the food chain. Unfortunately for many, the skills that put you in place to get the promotion (getting the task at hand done and done well) aren’t the ones that will help you now.

The biggest skill shift will be the idea that your own work should now come last. Instead of getting tasks done, your primary goal should be maximizing the ability of the people under you to get their tasks done and then relating those tasks to what the people above you in the hierarchy want. This is a pretty significant transition, considering the people that usually shine and get promoted are effective at actually getting the tasks done. Another big tip is to toss out your preconceptions of what management actually is and actually learn the job for yourself. Quite often, an interview might give you one idea, but actually working the job will give you another – start the first day with a completely open mind and see what you learn.

Chapter 7 – Playing Office Politics and Other Acts of Kindness
Office poltics are reality – any group of people larger than two is going to eventually develop into a political situation no matter what you do. Because of that, if you refuse to play, you lose by default. So how do you play without being a scumbag?

First of all, learn how to interact well with others. Get rid of poor social skills – learn how to win friends and influence people. Also, always keep in mind that mudslinging is bad for everyone involved and that if there’s a problem, blame yourself first. Humility beats hubris any day of the week, but it takes a strong person to be able to actually do that. Basically, learn how to communicate well and if you find yourself doing anything that you wouldn’t respect in someone else, don’t do it.

Chapter 8 – Authenticity Is the Buzzword of the New Millennium
This is the point where the book started to get really interesting, because from here on out the ideas start really diverging from many career and business books. If you haven’t figured it out yet, the title of this chapter is basically a joke – real authenticity is about as far away from a buzzword as can possibly be. In fact, if at any point you find yourself using a buzzword in a non-ironic sense, stop. Just stop. Your authenticity is draining away from you.

What can you do instead? Practice reading things aloud and see if you can get others to pay attention (I actually do this to my wife and have learned many ways to speak well that work for me). Take a deep breath every once in a while when you speak (particularly after a deep point). Stop using all unnecessary words in writing and speaking, starting with adverbs. Write short paragraphs. Focus on action verbs.

Chapter 9 – Sex Discrimination Is Everywhere, So Don’t Try to Run
I applaud Penelope for tackling a really sensitive topic head on with straight talk here, even offering advice that might make many people gasp and call her a fool. First of all, she says that most harassment is subtle and unintentional (meaning that it’s usually done out of ignorance and not intended to belittle anyone) and that responding with an attack is very much the wrong tactic to use – in fact, she writes an entire subsection with the topic A Lawsuite Will Hurt You Worse Than Harassment.

Instead of freaking out over sexual harassment, Penelope basically encourages readers to instead use that harassment as career leverage. If you’re being harassed, don’t report it to HR or go to a lawyer, but instead look for a way to get out of the situation. She relates her own story of a harassing boss: instead of filing papers, instead she went to upper management, laid out the situation, said that she believed it was better for the company if she merely moved to another department, and she was rewarded for this move that was in the company’s overall best interest by getting a very nice placement elsewhere in the organization.

Chapter 10 – Electronic Communication Cannot Enhance Relationships You Don’t Have
Email is not a to-do list (get things done instead). Email is not a way to make a new friend. Email is nothing more than a way to exchange quick bits of information to someone. If you find yourself using it for deep discussions or using it to communicate serious emotional issues (breaking up, for example), you’re almost always going to find it backfiring on you. If you have something that serious to communicate, at least do it verbally or in the form of a handwritten letter.

On the other hand, electronic communication can be an effective networking tool, especially for the introverted (like myself). Basically, Penelope compresses several of the networking ideas from Never Eat Alone (particularly those appropriate for people who have a hard time being outgoing) onto a couple of pages. Most noteworthy (for me, anyway)? Send handwritten holiday cards to everyone you know (she refers to them as New Years cards). This is something I started doing two years ago and have been trying to build up ever since.

Chapter 11 – Get What You Want from Your Boss
Many people view their boss as an obstacle to greater success. I’ve read countless emails from friends who have complained loudly about their “stupid boss” and how that person is obviously getting in the way of their career. Penelope advises taking that same boss and using each other as assets. Take the thing that the group agrees irritates them most about the boss, dissolve that down into something you can help with, and then find ways to use that skill you’ve figured out to make things go smoother in the office. Rather than having the boss be an obstacle, you’ll be seen by the boss as a valuable asset – and eventually an invaluable one. Accentuate that by saying yes only to the things that are really important to the boss, and saying no to everything else – you’ll come off as a person with priorities, and good ones at that.

But what do you get in exchange for that? Look at your boss through new eyes – what are they good at that they can help you with? Maybe the boss is very skilled at negotiating and can show you how to do the same, or perhaps they have connections that you can utilize to further your own career. Whatever it is, there’s a reason your boss is your boss – find out what that skill or asset is and find ways to trade your assistance for those assets. In the end, you become a more complete and connected person because of it – so stop wasting time complaining about the boss and figure out how you can use that complaint.

Chapter 12 – Don’t Be the Hardest Worker
Don’t spend your time working your tail to the bone just to get what’s required of you finished – if you’re doing that, you’re just running on a treadmill that you’re bound to fall off of sooner or later. Instead, you should spend at least some of your time emptying your mind and thinking. This concept made me think of a friend of mine who got a job as an administrative assistant. The woman she took over for used to spend eight hours out of a ten hour day collating files in a giant file room. When my friend took over the job, she spent the first week filing as normal, then came in on Saturday and spent about three hours just going over things carefully, then she proceeded to spend the rest of the weekend (including an all night session on Saturday) overhauling the whole system. On Monday morning, she had her daily collating done in the first hour and was thus able to appear to have superhuman productivity while only working intently about half of the day – she spent the rest of her time networking and is now in upper management. Seriously.

So what can we learn from that story? Spend some time thinking about what you’re doing, particularly repetitive tasks like filing and collating. When you can make a breakthrough with these tasks, you often trim massive amounts of time out of your day, freeing you to follow other threads and appear really productive. Other ways to give the appearance of quality and efficiency are keeping a clean desk, focusing on producing quality results over a quantity of results, setting concrete limits on your work schedule, and simply having the willpower to say no sometimes.

Chapter 13 – Getting a Promotion Is So Last Century
Compensation is often a major issue for people following a career path. They continually dive for bigger salaries, but then continually find themselves going broke. They might be making $200,000 a year, but they know that not having a BMW to drive clients around in makes them look like they’re not serious and that they don’t respect the client, so suddenly that salary shrinks and shrinks. Be wise to this and realize that you only need $40,000 or so to cover necessities – the rest is just gravy. Think about it for a second – would you really have to give up any essentials if you only had $40,000 a year? You might have to downgrade the McMansion or something, but you could survive on that.

So when you’re thinking of asking for a raise, ask yourself honestly if you might not enjoy other job perks more instead. Would more vacation time or some flex time increase your quality of life more? What about training opportunities or the opportunity to work in a self-managed team environment instead? Look at these options instead of the bottom dollar and you may find some spectacular opportunities.

Chapter 14 – The New American Dream Is About Time, Not Money
Look around at most people in your environment. What do they really value the most? Almost all of them have all the money they actually need, so what is it that they truly seek? Often, in the end, it comes down to wanting more time, so if that’s the case, why are they miserable in the office all the time?

Rather than spending your time feeling miserable and chained to the office, be sure that you’re delegating plenty of time to yourself to follow whatever fulfills you. Don’t be afraid to do whatever it takes to make your inner self happy, whether it’s choosing to take a lower-paying job because it offers flexible time with your kids or it involves getting into a job that seems dead-end but really really brings you happiness. In the end, we all walk home and look at ourself in the mirror – what do you see when you look there?

Buy or Don’t Buy?
Over the last decade, I’ve read a big pile of books on jobs and careers, from how to write a resume to interviewing to getting a job to managing office politics and so on. During that time, I only found one book of that kind worth its salt: What Color Is Your Parachute? (read my review).

Until I read this one.

You know that feeling you get where a book takes conventional wisdom and tweaks it in several places, putting a whole new spin on the matter without tossing the fundamentals in the trash? Brazen Careerist does that in the career advice genre, particularly for those of us under the age of thirty five. It realizes that the late Generation X and Generation Y value structure is different than that of older generations and thus the conclusions sound quite a bit different than other books – but that’s what makes it interesting and in many places makes it ring so true.

In short, buy this book if you’re under thirty five and are trying to build a career. The advice is tremendously useful and it shows how advice from other books I’ve discussed (like Never Eat Alone, Getting Things Done, and so on) actually fit into the context of a young professional’s career. It’s not particularly strong if you’re already in the middle of a solid career or if you’re starting your own business, but for everyone else, this one’s a must-read.

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  1. 60 in 3 says:

    Hey Trent, great review. I’ve added this book to my Amazon list.

    You’re a computer engineer, right? Did you know this is what you wanted to do with your life even before you went to college?


  2. Trent Hamm Trent says:

    When I went to college, I wanted to be a writer. I wound up exploring other options in college. It’s somewhat amusing to me that I’ve wound up back with writing via The Simple Dollar.

  3. rhbee says:

    I agree, great and enthusiastic review. I actually am amazed every time I read one of yours because they are done in such depth. On the other hand, I’ve not had much success recommending books to people. It seems like the more I like one the more likely they are to let it sit. So I’ve kind of given that up. Still your review reads so well that I’m going to take a chance a buy one for my son. He’s 22 and just starting out of college.

  4. Adam says:

    Trent – THANK YOU for doing this review. I am 30 years old and in the middle of my own “Quarter Life Crisis”. I will be purchasing this book tonight. I am very relieved to know I’m not alone and that this is somewhat “normal” for twenty- and thirtysomethings living in the twenty-first century. I very much enjoy reading your blog each morning and wish you well.

  5. shawna says:

    Wow, great review. I eagerly looked it up on my local library’s site only to discover that all 9 copies are checked out :)

  6. MVP says:

    Thanks for reviewing this; sounds like it covers a lot of ground in a fresh way. Gotta say, I like that it’s written by a woman. We DO have a few different issues to deal with, no matter what any of you guys think. Another good one I just finished: “How to Work for an Idiot: Survive & Thrive-Without Killing Your Boss” by John Hoover. Gives solid suggestions for how to get ahead when you think your boss is what’s holding you back from reaching your potential. It also made me realize that many companies reward hard-working, talented employees by making them managers. Those hard-working, talented folks aren’t necessarily good leaders or managers, and the companies rarely train them to be qualified leaders. So, now I know if I’m ever offered a position of leadership, taking the position may mean saying goodbye to my passion.

  7. ejp in sd says:

    Wow, this sounds like an interesting read – I’ll definitely check it out. I’m almost 30, and have been at my current job (which thankfully, I actually LIKE… 95% of the time, at least) for almost five years. Right now, I’m being primed to take over my boss’ job when he eventually retires – most likely, within the next 2-3 years. That idea, to be honest, scares the total crap out of me – I’m not old enough to be someone’s boss… am I?! With that in mind, I’m especially intrigued by the “First-time Managers Do Not Need to Suck” title of chapter 6. :)

  8. BrianB says:

    I haven’t read the book, but from reading her blog archives (which I’m presuming to be of similar style), I’d be a little more cautious with the praise. I should fall right into the set of folks she’s talking to (26 year old nerd), but my career to date doesn’t match – I’ve been employed at the same company now for 3 1/2 years. There’s extenuating circumstances, but I dare you to find a person that doesn’t have those~ For me at least, the assumption that everyone in my generation goes through jobs like toilet paper just doesn’t stick, which cheapens much of the advice.

    That said, some of her writing has hit home with me in a very real way, which is why the book interests me. In particular, one of her articles on office politics has done more for my inter-personal skills at work than anything else has (http://blog.penelopetrunk.com/2007/01/25/office-politics-is-about-being-nice/). All I really needed to hear was “be nice”, and that clicked. “Politics” is a dirty word, but “be nice” isn’t.

  9. Rebecca says:

    Thanks for this review. I usually don’t pay much attention to career advice books, because I’m in the sciences, and we run by our own rules. I mean, really, in my discipline I go to undergrad, then spend another 6 years in grad school before I’m even actually looking for a “real” job, and even then it’s a postdoctoral position with a limited 2-3 year lifespan. THEN I look for a more permanent position either in a tenure-track academic job (where I can still loose that job if I don’t make tenure in a few years) or in industry, where…let’s face it…you don’t exactly stay at the same company for very long. And scientists…well…we’re out own brand of special a lot of times. More informal than a lot of other disciplines when it comes to interviewing, and with our own CV format to use and our own laundry list of publications and qualifications right up front to show an employer.

    I often don’t pay much attention to generalized career stuff because it always seems to be aiming towards the administrative corporate type of jobs. But this review actually made me want to read this book, just because it seems like it’s not just about getting a job and how to work the corporate ladder, but about how to deal with people and how to manage your LIFE around your job. There also did seem to be several sections that WOULD be good for me to read, as a scientist. For instance, how to be a good manager. The SAME thing happens in science, where you do a lot of good research, and your reward is to get your own lab or team…and suddenly you’re not a researcher anymore, but rather an administrator and manager and grant writer. I’m interested also in this author’s ideas on how to deal with things like sexual harassment. It’s a very practical suggestion to not make a fuss or report it to HR, but at the same time, it’s not a very moral one. After all, that will probably lead to that person just turning around and doing it to someone else, either thinking that they can get away with it or not even realizing that they did anything wrong. But then, life is never full of easy decisions.

    I’m going to have to look this book up. Thanks.

  10. Naomi says:

    Great review and totally agree with MVP on hardworking talented people becoming Managers. I have just left a position of GM for that very reason. Moved up the company ladder far too quicky with no mentoring or training. Great manager to everybody else but totally burnt out myself.
    After reading this review I would advise anybody wanting to climb the corporate ladder to buy this book.

  11. Cherise says:

    I have not read the book yet, but from reading your review I have found a new respect and pride for my generation. I’m 27 (right smack dab in the middle of all this) and I’m proud to say that my generation cares more about their fulfillment and are willing to “flail” to achieve the goals right for us. I see a shift in priority where others see a lack of priority. My father’s generation cared about providing; putting themselves aside until retirement or at least once the nest was empty. He didn’t feel free to reach for his ACTUAL dream until the age of 50 due to his family obligations. My generation has chosen to care about both and have the audacity to hope that it will work out. We have dreams that our career will fill our souls AND our wallets. Is that so bad? I think not.

    GO US is what I say!!

    Thanks for listening.

  12. Vincent Ma says:

    After reading you review about Brazen Careerist, I plan on purchasing the book (or hopefully winning it), because I own just able every other book on your list.

    I think your review is right on. Gen X and Gen Y is truly different than our parent’s generation and we value job satisfaction is a very different way. My parents wanted me to a good college, get a job at a large company, stay with them until retirement and collect my pension. I did what any good son would have done and I went to a top 25 University and joined a Fortune 500 company right out of school. It took me two years to realize that my parent’s advice is just not applicable.

    Jumping around from job to job not something that my parents would condone and I tried my best to stay with my first employer, but it was making me miserable. Had Penelope’s book been out earlier, I would have read it and left my job immediately.

    One thing that I have a different opinion is on is starting your own business. I think that is great, but I have tried to start my own business several times and not been successful. The reason that I started to read you blog is because I am in the hole with the failures of those businesses. I do view these experiences as a learning experience and the cost could be equated as tuition for graduate school. Instead of starting a business, I would suggest that we strive for multiple streams of income. For example, I have my day job as a medical device representative, I consultant on the side for medical device companies looking to source products from China and I have my blog which is geared toward medical device representatives.

    But all in all, I think this will be a great read. Thanks for all that you do in helping all of us save money.

    All the best,

  13. Nicholas the copywriter says:

    Hello all

    I agree with most of this book. I have been in career development for 2 years and our company helped hundreds of young people to find their career. The first chapter on job hopping I agree with completely, one is VERY lucky if you bounce into what you like. I hopped around a few times, but found my “calling” after about 5 hops.

    I do not agree with the suggestion of building your own business when you are still very young. In our vast experience we found that a career managed like a business is much more rewarding! And it comes with waaaay less stress.

    Building a business requires a very solid foundation. If you are a third generation successful business owner family, then by all means, build your business. Such young people will have a solid base and usually enough money in the family to afford failing and learning a few times.

    The books look good, and I will buy it just for the insights, but like all such career books, it tells you about the problem and not very much on the actual implementation of solutions. I am dying to see the day someone writes a book on careers that consists only of real life examples.

    Thanks for a great review and you taught me quite a bit on writing a reviews!


  14. Alicia says:

    As a 37-year old who has had one ‘adult’ job in her life (for the past twelve years), clearly I am not the target market for “The Brazen Careerist.” I haven’t read the book yet (hope to win it!), but Penelope’s blog has steadily moved up my daily blog priority list because what she says so consistently speaks to me. I wish I had had it sixteen years ago when I enrolled in graduate school just to ‘delay the inevitable’ reality of finding a job that suited my talents. I naively believed the same skills that made me successful in school would lead to success in a career, and that could not have been more wrong. Though I do disagree with a few of her points, Penelope’s blog and book should be required reading for every worker.

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