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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