INTRODUCTION

When Expect to Win was published in 2009, we were at the beginning of a historic fiscal crisis. The real estate bubble had burst and we headed into one of the most severe downturns of consumer confidence that I have seen in my professional career, and began a period of labor unemployment not experienced since the seventies. Many people, across all industries, at all levels—entry, senior officer, exempt, nonexempt, from the boardroom to the post office—found themselves either without a job or restructured out of one, stagnating in their profession, or taking any position just to have an income. Rather than consider how a particular job might add to their skill set and prepare them for their dream job or career, many recent graduates accepted jobs to ease worries about paying off school loans or because they feared being out of the job market for too long. As a result, during my travels around the world, I have met many people who are having difficulty figuring out what career to pursue, how to make the most of the first few years of their career, and how to position themselves for success.

I have also spent time with people with five to ten years of work experience who are struggling with managing change, and are trying to figure out how to navigate the choppy waters of their careers, as their companies have downsized, they have been demoted, their job descriptions have changed, or their bosses have left or were fired. Some of these professionals are also in a quandary about why their careers haven’t progressed the way that they envisioned back when they finished their academic or experiential training. I’ve also found that many of these professionals are struggling to read the career signs, those subtle messages that are often communicated in behavior rather than words in most corporate environments. As a result, they are puzzled about what will fulfill them professionally and personally, and how to redirect and reposition themselves and their career successfully. Further, I have talked with people who are ten to fifteen years into their jobs who always wanted a meaningful career, but rather took a job just to have one, and now, because they have “put in so many years on the job” or have family or financial obligations, they don’t know how to decide what they really want to do for a career, or are afraid to take the leap to start something new.

Strategize to Win is a direct response to the people I’ve met and the questions they asked while I was on the road talking about Expect to Win. My hope for this book is that both young and mid-level professionals will find the answers and tools they need to get started in their career, to get “unstuck,” to redirect and crystallize their paths, and to position themselves to manage their career through any economic cycle or any corporate political environment and continue ascending toward success!

In this book, I will define a process of deciding on a career trajectory, and more important, define a process of positioning yourself for the opportunity that you want, no matter what stage of your working life. Whatever stage we are in, we all have to reposition ourselves for new opportunities. Whether you are looking for your first job, want to move up in your company, or leave it for a competitor or an entirely new industry, you will need these tools in order to enhance or insure your success. I will also address what you must do to be successful once you land a position. Because what got you there won’t be the thing that will keep you there: the skills that helped you land a position won’t be the same skills that will insure your success in that role. Last, I will also identify and clarify issues that are often murky for young and mid-career professionals and help them develop the key answers they need to create strategies for reaching the level of career success to which they aspire.

STARTING OUT

CHAPTER 1

Choosing a Career in Today’s Economy

“A journey of a thousand miles begins with a single step.”

—Chinese philosopher Lao Tzu

Congratulations! You’ve just graduated or are soon to graduate from college. Or maybe you’re just leaving the military. Whatever the case, you’ve worked hard and completed years of extensive education and training. You should be proud of yourself, what a wonderful accomplishment!

The problem is, you’re asking yourself: “Now what?”

After all of those years of hard work and dedication, you find that you have no real idea of what career you would like to pursue.

Or perhaps your situation is different. You’ve been out of college for a few years. After graduation you accepted a job because you needed one. You had student loans and bills to pay, perhaps a family to support, or other financial obligations. But now, a few years later, you find that this job, this company, or even this career is not for you. You’re frustrated, bored, and unenthusiastic. You’d like to make a move, but you have no idea what job, company, or career you are interested in. Worse, you have no clue how to begin to do anything to change it.

If any of these scenarios sounds familiar, you are not alone. Together, we are going to walk through a framework that will help you to sort out the appropriate next move in your career journey. Notice, I did not say that we are going to figure out what your entire career will look like.

Not yet.

That’s too ambitious and overwhelming. We’re going to start with the first step and determine the best next career move for you.

The End of the Ultimate Career Plan

It’s true that the quest for the “ultimate career plan” was once all the rage. But in today’s professional world, that kind of thinking is out-of-date. There was a time when advancing as a professional with one company, like IBM or Chase Manhattan Bank, over a twenty-five- or thirty-year period was the epitome of success. That kind of track record meant you had made it. You enjoyed the highest level of success and your financial and cultural status reflected that.

But today, aspiring to one career, with one company, doing one thing for two or three decades or more just doesn’t make sense. The environment we live in is dynamic and fast-paced. Technology has massively restructured, redefined, disrupted, and in some cases even destroyed industries and businesses. In the twentieth century, it was possible for a company to maintain its leadership position over decades; but today, given the fast pace of technological innovation and the leadership life cycle in most corporations, it is difficult for one company to maintain the number one, or even number two, position in its industry for even just ten years.

In fact, it was just a short time ago that moving from one company to another was considered a negative on one’s résumé. But today, success requires you to take a different approach to career planning. The new, more sensible, strategy is to consider your career in six to eight modules of five years each. And these modules could potentially be at five or six different companies. For example, you may choose to do two five-year modules with Company A in one type of role, leave to complete your third module at Company B, and then return to Company A in a more senior role. If you aspire to success and to working for a leading company in a leading industry, making changes like this is a given.

Here’s why.

To remain an industry leader, a company must continually reinvent and reposition itself by making significant and consistent financial, technological, and cultural investments. The truth is, most companies just don’t do that. If the company you work for isn’t constantly reinventing itself to remain at the forefront of innovation in its industry, and you are determined to work for the industry’s leading company, whatever the industry is, the leader will change over time.

Therefore, to pursue your objective, as the industry leader changes, you will have to change companies, too. Staying too long at a company, especially if you remain in the same role, will eventually begin to compromise your professional platform. That platform includes your compensation, influence, and ultimately your career success. If on the other hand, the company that you are working for does make the foregoing investments to maintain its industry leading position, then you may have an argument for working for the same company for several of the modules in your career journey. Not only is it unlikely that you will work for the same company your entire career, however, pursuing just one career is unlikely as well. It is more likely that you’ll have the chance to work at several companies and pursue a number of different careers in the same or different industries over your professional life.

How Do I Decide on What I Would Really Like to Do?

Finishing college and finding yourself unsure about what professional life you want to pursue and how to pursue it is common. Further, pursuing a career, and then deciding a few years later that you want to make a change, is fairly common, too.

It’s important to emphasize, particularly if you are just starting out, that there is no need to worry or feel pressured to make the exact right decision today about a career that could last thirty, forty, or even fifty years. It is pretty rare to stumble onto the job just out of school. Some people are lucky and have an internship they really enjoy, for example, and know from the start what they want to do. I actually was fortunate enough to fall into that category. From my very first internship at an investment bank, I knew I wanted to work on Wall Street.

Others might be driven by wanting to have a certain lifestyle and will choose a job they believe offers the salary to achieve that. Still others will finally decide upon a career through the process of elimination: trying a number of different jobs and experiences before deciding on the one to pursue.

Each of these strategies can help you to arrive at a career that you will find fulfilling and that will position you for success. You might, however, be someone who doesn’t know where to start; if this is you, there is an easier, less painful way to determine what you would like to do. You will find the answers to your career questions not in knowing the job itself, but in defining the content of your job.

Defining the Content

Think of the content as the building blocks. Content is not a specific job or career, but rather the components that make up a job or career. While you may not know exactly what you want to do at twenty-two or even thirty-two years old, you probably know what you like to do in life in general. Consider your hobbies. What do you find interesting, intriguing, stimulating, or challenging? What are you doing when hours go by and you barely notice? What would you do even if you weren’t paid for it? Asking yourself these kinds of questions is the first career move I want you to make. It will help you determine the content of your career.

This is an important exercise. No matter what stage of your career you find yourself at, you can always refer to the content you identify now for ideas and direction, as well as a reminder of your goals. It takes effort, but it’s an important first step, whether you are just graduating or you have fifteen years of work experience.

In fact, if you do the tough work now of figuring out what experiences you want to have, what skills you want to acquire, what kind of people you want to interact with, or what environment you want to work in, you can set yourself up for success, experience after experience. You’ll be able to make a job flow into a career, extend your success runway, and take off, ascending to the top. Keep in mind that sometimes that means taking the less popular path. No matter what path you choose, it is your path. This is your life and you are presumably going to work for a large part of it. So it is in your best interest to position yourself for success by pursuing something that you like or that is consistent with your life plan.

By developing the content for your career now, you can save yourself a lot of heartache, angst, and worry in ten years, when you realize that you need to change your job or career and doing so is a lot harder. As we go down the road of life, we tend to become more risk averse because we have financial and/or family obligations. Many of us become complacent, and even though we may not be happy, we stay in jobs because we fear change or think it’s too late to do something new. Doing the content work now will make it easier for you to chart your moves throughout your career, because you will know to pursue the jobs that contain the components that you enjoy, are good at, want to learn, or are motivated to do.

Start with three blank sheets of paper.

At the top of page one write: If money were no object, how would I spend my days? What would my job look like? This is your content.

On the top of the second sheet write: What jobs have this content?

And, on the top of the third sheet of paper, write: What skills, experiences, or education do I need in order to be eligible for these types of positions?

If Money Were No Object

Page one is designed to help you think through how you would like to spend your professional days if money were no object. Do you like sports, do you like entertainment? If you like entertainment as an industry, do you like music, film, theater, video, art? Do you want to perform, or do you want to manage other artists? Do you like working with things that involve numbers? Do you think you would like finance, or computers? Do you like figuring out how things work? Do you like science? If so, do you like biology, physiology, astronomy, or chemistry? These are some of the questions that you might ask yourself when trying to discern what you like.

Then you might ask yourself questions such as:

• Do I like working alone or in teams?

• Do I like problem solving or executing?

• Do I like building processes or developing solutions?

• Do I like things that require me to use my analytical or quantitative skills or am I more partial toward doing things that require me to use my writing and/or creative skills?

• Do I like convincing people to do things?

• Do I think that I would enjoy selling products or services that I like or would I simply like the challenge of trying to convince people to do/buy something, and what I’m trying to convince them to do/buy doesn’t matter?

• Do I want to do something where I am directly involved in helping people every day?

• Do I like figuring out puzzles?

• Do I think I would like spending my time in an open environment where everyone works together to solve problems?

• Do I like environments where everyone has their own assignment and we later come together to see how all of the pieces fit?

• Do I like working on things in a high-energy, fast-paced environment, under pressure?

• Do I prefer my assignments planned ahead of time or do I find the idea of new assignments each day exciting?

• Do I like to travel and want to get on a plane or train several days a week?

• Would I prefer to work in the same location each day with no travel?

• Do I like working with people of different ethnicities, backgrounds, etc.? Do I like working in an environment where I will be required to use different languages?

While considering these questions, I challenge you to think about things in your life that have always interested you, hobbies and other activities that you currently do or enjoy. For example, did you like playing sports as a student? Did you continue to pursue that sport in college? Are you committed to a life of constant practicing? Are you good enough to pursue that sport professionally? Then, dig a little further: Did you also like working on a team with others to pursue a goal? Would you like to coach others in the sport? Would you consider being a physical therapist treating professional athletes, or an orthopedist focusing on high school, collegiate, semiprofessional or professional athletes? Do you have strong communication and/or writing skills? Would you like writing or reporting on the sport? Could you report on sports on television or radio?

Alternatively, what was your best subject in high school? If it was art, for example, would you enjoy working for a museum, being an art critic, writing about art for a newspaper or magazine, or being an artist?

Especially early in your career, it is important that you focus more on content than a specific job. Why? Particularly in challenging economic times, the content of the job will be far more important than the specific job itself. In a difficult economy, when most companies typically cut back on personnel and try to conserve costs, the reality is that your dream job may not be available. If, however, you take an alternative position that allows you to acquire the basic skills necessary for your dream job, when the economic environment improves you will be well positioned to sell yourself into the job you really want. For example, suppose you are interested in working in ad sales at a magazine, but no matter how hard you try, those jobs remain few and far between, and the only people even getting interviews are the most experienced sales execs. You have very little, if any, experience.

So instead, you accept a job telemarketing and selling home security services over the phone. Not your dream position, but you’ll develop skills in getting prospective clients on the phone, keeping them engaged, and making sales. Later, you can use that experience to convince a hiring manager that your phone skills will translate to face-to-face sales for a product that you believe in, in this case the magazine. Now you can approach your dream job with not only aspiration but real sales experience.

It is understandable that many recent college grads focus on just getting a job, any job, figuring they can find their dream job once they have a foot in the door. I strongly advise you against taking this approach. It’s important to give careful consideration to the content of any job you take, even an entry-level one, to make sure it allows you the opportunity to develop the skills and experience you will need to land the job you really want.

During the financial crisis that began in 2008, I saw so many young professionals accepting whatever job they could find. They were afraid of the looming recession. I saw seasoned professionals who were laid off quickly jumping to any position without thought to how it would fit in with their future and overall career goals. As a result, when the economy began to improve a few years later, those same people had difficulty landing the jobs they really wanted. They could not explain how the jobs they took prepared them for a better position or fit into their overall career plan.

Content matters. It should be one of the key factors you focus on when deciding on a job or a career. Even if your primary reason for accepting a position is the money it will pay you, there should be something else about the job that’s consistent with your aspirations or the skills that you’d like to acquire. No prospective employer likes to hear that you took a position for the money. Focus on content first and you will be much better off.

There are usually several different jobs that can offer you the content you want. This is good news, because it expands your opportunities. Let’s assume the content of your dream job includes selling things. You like convincing people to make a decision to buy something. That means you could sell clothes, insurance, stocks, pharmaceuticals, consulting services, shoes, engineering services, industrial products, commercial ads, Internet ads, and the list goes on.

Ask yourself what kinds of things you might enjoy selling. What are your favorite products? What brands do you believe in? What would be challenging for you to sell, what would be a breeze? The content is the same, selling is selling. The question is which product is going to inspire, challenge, or excite you every day to sell it?

So many MBA candidates tell me they want to work in investment banking and mergers and acquisitions because they want to acquire valuation skills. But there are several jobs within the financial services industry that would expose them to valuation analysis. For example, as a sell side equity research analyst, the primary skill they would hone is the ability to value a company and make a comparative analysis of companies in an industry. In credit research, they would learn how to value a company and assess its comparative creditworthiness. As a private equity investment banker, they have to learn to value companies in order to make purchase or selling recommendations. While the overall job description and key success factors are markedly different for each role, each position would teach an MBA graduate the desired content: how to do valuation analysis. By focusing on the content and not just a specific job in mergers and acquisitions, these individuals could markedly expand the kinds of opportunities that are available to them.

It’s also important to note that, as you consider the content of the career you desire, you shouldn’t limit yourself to interests based on only the things that you have done before. Consider things that are intriguing or interesting to you for whatever reason, in the spirit of “you don’t know what you don’t know.” If it interests you, consider including it on your Content Page. You may not discover why it intrigues you until later. Have you always been fascinated by finance? Do you like the entertainment industry? If so, what part of the entertainment industry—recording arts, performance management, arts facility management, movies, Broadway theater, radio, videography?

The goal is to fill your Content Page with as many interests as possible. This will allow you to identify several jobs or careers that will position you to be successful. Your ultimate professional success is all about how you position yourself, and that starts with landing a position that engages you because you like doing it, are interested in it, and you want to learn it because you like the content.

Now, let’s turn to the second piece of paper in our exercise: what jobs have this type of content?

What Jobs Have This Content?

First, let me applaud you. Completing the Content Page is no easy task.

Admitting we don’t really know what we want to do is hard to do. If we’re younger, in college or graduate school, it can be difficult to admit. Society expects that we are in school pursuing something that will lead to a successful career. It is so easy to go with the flow and pursue jobs and opportunities that are popular or considered prestigious by the people who matter to you—peers and especially parents who have sacrificed to put you through college. You go along knowing, deep down, that even though you may have earned the credential, degree, or certificate, you still don’t have a clue about what to do next. Or worse, let’s say you have decided that after three years of law school you really don’t want to be a lawyer! As we continue to get older, we avoid the truth even more assiduously. We put our heads down and plow forward, rarely stopping to allow ourselves to ponder the question for very long.

When I was in college, all of the top economics students were flocking to Wall Street analyst positions, two-year internships with one of the top management consulting firms, or law school. While there were a few people going into brand management or on to other graduate programs, very few had the courage to consider becoming an entrepreneur or starting out in the mail room of an entertainment or artist management company to get a foot in the door somewhere they could pursue a personal passion and use their degree at the same time. My classmates who weren’t econ majors were also trying to pursue these types of jobs, even if they had an interest or passion to teach high school or become a book editor. Many of my colleagues and friends took at least ten years after college to figure out what they really wanted to do, losing valuable time that they have could have used to ascend in careers in which they were really interested.

So now you have done the hard work of thinking about the answers to questions like “How would I like to spend my day?” “What type of job content would have me excited about getting out of bed to go to work?” “What activities would I be happy doing for free?” Now you are ready to start considering the kind of jobs that contain that content—our Jobs Page. For example, if you like math or working with numbers, you might consider pursuing accounting or working in a commercial bank. If you like writing, you may think about working at a newspaper, writing columns for a magazine, or becoming a book editor.

In positioning yourself for success, however, I want to challenge you to go beyond the careers that you already know have the right content and consider opportunities that might not be within your current purview. Completing your Jobs Page also involves learning about jobs and careers that you currently know nothing about. This will require research. Choosing the right job or career means spending time talking to people and networking. People often miss opportunities that they might find professionally fulfilling simply because they don’t know they exist. Maximizing your options—and therefore your success—means understanding those options.

Begin by putting aside at least one week out of every month (or the equivalent of 100 hours), to do nothing but research and talking to people about what they do. If you’re already working, I don’t mean that you take a week off to pursue this activity. I am suggesting that over the course of one month, you find at least 100 hours to talk to others about what they do. You can do this by asking people out for coffee, lunch, or breakfast, or even when you are meeting new people through informal get-togethers with your friends. When you meet people, ask them questions about what preparation or experience they needed to do their jobs; what some of the key benefits or drawbacks of their specific job or career might be; or how they got to where they are. If you are not working, then you should be spending at least three days out of every week researching various opportunities and meeting with people. Use your network to get introduced to people who may be pursuing careers that you are interested in. For example, use your alumni network or make an appointment to talk with a former professor about their previous students and the jobs that they accepted after graduation. Ask if he or she would introduce you to a former student. Take the opportunity to have more in-depth discussions with your professors about the types of jobs they had before becoming educators or what type of work they considered. This will help to give you ideas about ways to leverage the intellectual content they have, and that you have now acquired through your studies.

As you research, make notes on your Jobs Page and keep track of all of the jobs that have content that you are interested in. It is important to do this research so that you can make an informed decision about what roles you want to pursue, instead of longing to do something and assuming you won’t be able to.

In today’s environment, it’s easy to do this kind of research because there is so much information on the Internet about people and what they do. If you don’t know anyone personally that you can network with, look to find information on the Internet that describes the opportunity that you are interested in. Read newspaper or magazine articles, blogs, or other sources about someone who does something similar to what you have interest in.

I find that often people don’t pursue things that have always interested them because for some reason they don’t believe they can find a job that they will enjoy and that will allow them to support themselves. Yet most of the time they have never done the research to determine if that were really true. I recently had a conversation with Gregory, a twenty-year-old college sophomore who was unsure what he wanted to do with his professional life. He did know that he wanted a career that would allow him to help his parents and siblings and the family that he hoped to build. During the course of our conversation, Gregory mentioned that he had been a terrific high school basketball player, but he constantly got hurt because he did not know how to properly care for his injuries. He spent most of his time on the team sidelined.

As a result, Gregory thought he might like to help high school athletes avoid spending as much time injured as he had. He also mentioned that he liked tinkering on his smartphone and was intrigued by technology. Gregory had never had a conversation with anyone about his interests in sports medicine and technology. He just assumed that there was no way for him to combine them. He also knew that his family was going to have a hard time helping him get through college to pursue one degree in four years, so he did not see how he would have enough money for the extra year necessary to complete another degree.

I suggested he could pair his interest in sports medicine with his interest in technology by considering biology, physiology, or industrial or mechanical engineering as areas of discipline in college. These majors would enable him to experience different types of courses within one discipline and have a wide range of career opportunities. Ultimately, he could work as an orthopedist; an engineer using technology to create orthopedic medical devices; or he might want to make mechanical limbs for veterans, athletes, and others. In just one conversation, Gregory went from articulating an interest in something to having five different career options!

Having as many conversations as possible with as many people you can about your career aspirations will help you expand your ideas and bring to light options you may never have considered. These valuable choices will help you craft a career over time that is built upon the content that excites and motivates you. Further, it will help you to reposition yourself later, if and when you decide you want to change or start a new career.

In addition to speaking to people about jobs that have the content you’re seeking, you can also start to crystallize what you want to do by spending time in an environment that interests you. For example, you can volunteer, or even take a job or internship that may not have the exact content that you want but puts you in the right environment and gives you exposure to jobs that may fulfill you.

You will be surprised by what you learn during this exercise. Let’s suppose that your Jobs Page analysis led you to conclude that you want to work in a hospital environment. While you’re not sure if you want to be a doctor or a nurse, you’ve determined from your Content Page that you like science and quantitative analysis, and that you want to help people each day. Why not then spend three to six months volunteering in a hospital? This would give you the opportunity to learn about the different jobs available there and would offer you the chance to speak to the various professionals you might encounter, in the elevator or over coffee.

If you don’t have time to volunteer, you could offer to take someone you know in that field to lunch. Even your own or a friend’s doctor would be a good candidate. Talk to them about the kind of people that typically work and do well in a hospital environment. Ask questions like: What are some of the key factors for a successful career in this field? In addition to patient care, what types of jobs are available? What relationships are necessary to be successful in their role? Who do they have to interact with in order to be successful? This last question might lead you to other people in the hospital or industry that you could also speak to.

Continuing with our hospital example, let’s say you notice that there is a hospital president whose job it is to make sure that the hospital not only services patients but that it also runs like a business. This person may or may not be a medical professional, but has most likely been trained in business or has held a series of management or operational jobs in medical institutions. They might have been the director of purchasing, the director of personnel, or the director of logistics at previous jobs. Combined, these previous positions make them the ideal candidate to efficiently run a hospital, making sure it has the resources it needs to attract top medical experts, the facilities necessary for an esteemed medical institution, and all with outstanding margins and profitability.