Excerpts from

Winning the Game of Work:

Career Happiness and Success on Your Own Terms

by Terry Boyle McDougall | New Degree Press 2020



It would be so much easier if I could just be a student instead of always a pawn in a bigger game.

–Sarah K. L. Wilson

I was blindsided.

Okay, maybe I should have seen this coming, but I was just a babe in the woods at the time. Barely a year out of college, working my first job at a magazine publisher in Boston.

My boss, Dennis, got a new boss. It didn’t really impact him at first. Dennis continued to do what he’d always done—sell magazine advertising. When he had the chance to sell one more ad for the issue that had just closed, he did what had always worked in the past.

He threw his weight around with the head of production to get the ad into that issue. The only problem was that Dennis’s new boss, Pete, wasn’t budging on the new policy he’d put in place. Pete’s view was that once the book closed, it stayed closed.

What happened next is a matter of disagreement.

Dennis says he was fired.

Pete says he quit.

All I knew was that my happy little work family was suddenly missing one gregarious leader. As Dennis was escorted from the building, little did I know at the time, along with him went my promised promotion.

My earnest desire was to move up in the world of 1980s publishing . . . but a few weeks later, the dust of Dennis’s departure had settled and Mike, the new sales manager, had been hired and it was a whole new ball game.

Though I’d paid my dues as a bright and valued supporter of the sales team and been seen by Dennis as a rising associate ready to move to the next level, Mike saw me only as an administrative assistant with no tangible experience in marketing.

He interviewed me for the marketing coordinator role, but it soon became clear that he’d only been going through the motions. He hired an external candidate with an associate degree and one year working as a marketing coordinator for a local hotel.

In Mike’s estimation, my eighteen months of service at the firm and BA in Economics didn’t equate to the value his new marketing hire brought. I was incensed. To him I was nothing special—just someone who was already there when he started. Kind of like the office furniture. Even today I am still stunned, but no longer surprised, at how unfair his decision was. With many years of hindsight, I see a lot of things now that were invisible to me at the time.

Now I know I just hadn’t yet been initiated into how the game of work is played. It was the first of many lessons that would follow.


Why I Wrote This Book

Over the course of my career, it dawned on me that the rules I learned in school weren’t the same rules that governed the business world. Every time I expected things to be “fair” based on my read of the situations, I was disappointed.

It eventually occurred to me that something deeper was going on, and I was determined to figure out what it was. I hope you’ll find some insights to help make your path to your own career success and satisfaction a little smoother.


There’s More to Work Than You Realize

This book is for anyone who has experienced confusion about the mysterious things that happen at work—those days when you think you’re following the rules, but you don’t get the outcome you expect.

I bet you would prefer a career where you enjoy success and happiness rather than a grinding job that causes you nothing but stress and misery. You were drawn to the professional world because you like to solve complex problems and be rewarded for it. My guess is that you are smart and talented—after all, you picked up this book!

You probably figured, “Hey, this is America—the land of opportunity. I’m smart, hardworking, and ambitious. What else do I need to succeed?” Indeed, that’s the attitude I had more than thirty years ago when I first started my career. I’d been successful in school. What could be different in the workplace? It didn’t take long to realize I had a lot to learn.


This Is Not Turning Out How I Expected

I’ve learned many lessons the hard way. When I look back to the start of my career, it’s now easy to see how clueless I was. I was an earnest “good girl” who believed that if I studied the “rules” and followed them, was polite and cooperative, kept my head down and my nose clean, and didn’t complain, I’d get what was coming to me: advancement, raises, titles, growth opportunities—the works. I mean, that approach had worked for me throughout seventeen years of school and even for the first year or so after college.

But it was as if the business world said to me, “What a naive little thing you are. Keep bringing your best, and we’ll keep using you. And don’t think you’ll get any particular recognition for just doing your job.”


Where You’re Coming From

Maybe you’re a recent college graduate, and you’re learning the ropes in your first job. Or perhaps you’re a corporate veteran who has worked for many companies and has given up trying to make sense of the weird things that go on in your workplace. You may be committed to your company and want to be effective in your current role, or maybe you’re actively looking for a new job.

Regardless of where you are in your career, I’m certain of one thing: You’d like to be happy with the bargain of trading your time and talents for money, benefits, and if you’re lucky, fulfillment. You want to know that your work matters. You want to be seen and validated. You want to learn and grow.

It’s sometimes hard to understand what you can do to make that happen. Even when you follow the written rules, you may notice that things don’t always turn out as expected. You run into unforeseen obstacles. People who seem less talented than you move ahead, and you’re not sure why. It can be downright puzzling, even infuriating.


How Can Work Be a Game?

If you’re working hard, following the rules and not experiencing the outcomes you desire , it’s because of one thing: You are playing the game of work by the wrong rules! You may think, “Game of work? What is she smoking? Work is not a game. It’s serious business! My livelihood depends on this.”

Fair enough. Work is serious. But understanding how to navigate at work will help you achieve your professional goals. That’s precisely why I look at work as a game. Games, like work, have objectives, rules, and strategies you use when playing them.


Monopoly by the Rules of Twister

When people are confused by the results they are achieving at work, it’s usually because they don’t understand the objectives, are playing by the wrong rules, or have no strategy or one that takes the wrong factors into consideration.

So it’s no wonder they are frustrated. It’s like trying to win Monopoly when you’re playing with the rules from Twister.


Learning to Play the Game of Work

This book is about shifting your perspective and learning some of the unwritten rules that no one tells you. I’ll share new ways of looking at the things that go on at work so you can clearly see the whole “game board” and develop strategies for how to maneuver to win. This new set of rules will enable you to more effectively navigate your career in business.

The unwritten rules often seem counterintuitive. It took me years to make sense of this—to see that a whole other reality was beneath what I could see. I’d observed others who didn’t follow what seemed to be the most basic rules—they’d be late for meetings, turn in reports late, and be uncommunicative—yet they moved ahead. I was perplexed. It seemed unfair. What was going on? Well, the bottom line was that they knew the real rules and what to focus on, and I didn’t.


What’s in Store for You

In this book, I’ll tell my own stories and some from fascinating people who shared their hard-won career lessons with me. The thing to remember is that no one’s success is ever preordained. Though we see people who are currently successful, it’s important to acknowledge that along the way, they made mistakes and had moments of uncertainty and even failure.

They didn’t know which choices would result in the outcomes they got. It’s only in looking back on their careers that we see those pivotal moments that led them to their present success. In examining those moments, you can learn lessons to apply to your own journey.


Tenaciously Seeking the Why

I’ve always been drawn to complex challenges. When I was a kid, my mother compared me to a tenacious little terrier. Once I got ahold of something, I wouldn’t let it go until I figured it out. Indeed, even today my mind always runs through scenarios, observing and trying to understand the flow of information, the motivations of people, and how systems work. I always want to know why things happen. Frankly, it drives me crazy when I can’t puzzle something out.

To better understand how to be successful in the corporate world, I read scores of business and leadership books, countless articles, and white papers published by top business schools and consulting firms. I’ve gone to many training courses, absorbed the wisdom of experienced mentors, and worked with executive coaches to help me navigate and influence.

My interest in understanding systems and the factors that contribute to how they work is what drew me to economics as my major in college. The economy is driven by many factors—interest rates, consumer confidence, weather, the stock market, international trade, and even presidential tweets. It’s a mix of many components, influences, and forces.


Using the Influence That You Have

We all take part in this system, and no one really controls it. Though it may not feel like it, what each of us do impacts the economy in a small way. The same is true in the workplace. Whether you’re in the lowest entry-level position or you’re the CEO, what you do impacts the organization’s success. The trick is to recognize that and see the ripple effect you create, then learn how to control it.

If you’re not the CEO, I understand if you’re a little skeptical about how a book can help you make a bigger impact. However, keep an open mind. Recognize that maybe work is more than the rules you’ve believed until now and be willing to try some new things.

As you absorb the lessons in this book, I feel confident you’ll understand work in a new way. You’ll see the unwritten rules beneath the rules you’ve been taught. When you understand the extent of your own power, what motivates people around you, what you really want, and how you add value, you’ll see work in a whole new way.


The Purpose of This Book

I learned lessons during my career that helped me see the underlying dynamics of what happens at work and why. Once I could see the dynamics, I could understand how to influence the corporate ecosystems in which I worked. The purpose of this book is to shed light on these unwritten rules so you can maneuver and get the opportunities, rewards, and recognition you deserve.

Just a note about some of the language in the book: I worked for corporations for the majority of my career, but the lessons of this book can also be applied in other work environments such as education, government, and nonprofits.


Seeing the Whole Game Board

My goal is to shift your perspective on what happens at work so you can see the whole game board and understand what moves you have available. We usually have more options than we believe. Seeing hose additional options will give you courage to try different approaches to achieve the results you want out of your career. It can be natural to feel fear when trying unfamiliar approaches when deviating from what has worked in the past.

When faced with a leap of faith to try something different, I ask you, do you want to continue to ignore the unwritten rules and get the same outcome you’ve gotten in the past? Once again bypassed for a raise or promotion? Once again not getting the sorely needed extra resources? Or would you rather live by the unwritten rules and see your efforts pay off as you achieve the levels of success and rewards you’re capable of?


Get Off the Sidelines and into the Game

Many clients tell me that office politics is an area they find distasteful, inscrutable, and uncomfortable, and they want to avoid it. I can understand that; politics can feel unseemly. People who are good at it sometimes seem more influential without providing much value.

It is true that some players can use smoke and mirrors (and take credit for other people’s work) to move up the corporate ladder. But take a moment and focus on the key word here: influence. When you focus on the value you bring to your organization and learn how to play the game of work, you’ll have more influence and probably be more satisfied with your efforts.

The purpose of this book is to shed light on these unwritten rules so you can maneuver and get the opportunities, rewards, and recognition you deserve.

To keep reading, buy the book on Amazon or Barnes & Noble in paperbook or e-book format.

Audiobook coming this fall!



Are you ready for the next step?

If you're ready to step into your full potential to lead a happy and successful career, let's talk!

Or keep reading for more career wisdom from Winning the Game of Work. 



Chapter 1: Work is a Game


Nothing is like it seems, but everything is exactly like it is.

–Yogi Berra


How Can Work Be a Game?

After more than thirty years working and coaching hundreds of professionals on success, I know work is essentially a game. Work encompasses the activities you do to earn money to buy the stuff you and your loved ones need for survival—as well as enjoyment.

You may have worked hard to gain the education and experience required to do your job. In addition, part of your identity may be tied to what you do for a living.Think about how often “What do you do?” and “Who do you work for?” come up in casual conversations with acquaintances.

For better or worse, people rank and categorize our place in society based on our work.In contrast, games are activities we usually take part in for fun. If you lose a game, you might say, “No big deal. I’ll get ’em next time.” However, if you lose your job, that probably won’t be your reaction.

So I get it. It feels weird to frame work as a game, because work is such an important organizing force in your life. But that’s precisely why I propose that you look at it this way. It provides much-needed perspective.


Gaining Objectivity to be Strategic

We can get so attached to our work that we have a hard time being objective about it. It’s so personal. I see it all the time in my coaching practice when clients experience difficulty at work. It’s natural to get emotionally involved in what’s going on and feel helpless, hopeless, or angry and at a loss about how to make the situation better. This causes stress, which spills over and affects personal relationships and health—physically and mentally.If you think about it, work and games have many things in common.

Much like a game, work has an objective, which in for-profit businesses, is making money, and it has rules about how you play, as well as strategies that employees use to get ahead. The advantage of viewing work as a game is that it creates some distance between you as the “player” and the dynamics of the business. It enables you to see the larger game board and opportunities that would be impossible to see when you’re in the middle of the activity.

When you understand this, you can be more strategic and focus on achieving longer-term goals.When you fail to create this type of distance, you can’t see the whole board, and this can leave you feeling like a pawn. If you can’t see what’s going on around you, you can’t be strategic. When you leave yourself no moves, you are at the mercy of savvy players. That can leave you feeling helpless, and no one wants to feel that way.


There’s More to Work Than It Seems

I used to look at the workplace dynamic as a simplistic relationship between employer and employee. The business had an objective—to make money. The employer made up the rules of how that would happen, decided what the employees would do (or not do) to deliver the value that customers paid for.

The employees showed up, performed the activities associated with their roles, picked up a paycheck, and went home. Wash, rinse, repeat. The employees who did their jobs in a superlative way would naturally be recognized and promoted. It seemed simple.

Maybe you picked up this book because, in your career, it’s become apparent that it’s not that simple after all. You might feel a little lost, even cheated, if you’re not getting the results you expect from your efforts at work.Your frustration is understandable. If you’re confused about where you are and about the rules of unsuccess that you have to unlearn, your feelings are justified. Let’s work through it. The best revenge is success, right? So let the lessons begin.


Playing by the Wrong Rules

If you’re not getting the success and satisfaction from your job, it may be because work really is a game, and you don’t know the rules. After all, if you’re not achieving the objectives you desire, then something is not working.

Many factors can contribute to unattained goals. However, if you’re experienced, working hard on the right things, and still not getting the results you desire, you could be metaphorically playing Monopoly by Twister’s rules.


It’s Déjà Vu All Over Again

I started this chapter with a quote widely attributed to Yogi Berra. He was a catcher with the New York Yankees for eighteen seasons between the 1940s to the 1960s, and though he holds the record for the most World Series Championships as a player (ten), he is arguably best known nowadays for his quirky quotes.

Even if you’re not familiar with Berra, you’ve probably heard (or even repeated) some of his sayings, such as, “It ain’t over till it’s over,” “It’s déjà vu all over again,” and “When you come to a fork in the road, take it.” The fascinating thing about these “Yogisms,” and a large part of why his name is still brought up today, is the ironic wisdom they contain.

At face value, the sayings contradict themselves and make no sense, yet a deeper truth comes from them that isn’t perceived initially. Like the quote at the beginning of this chapter, there can be a big difference between what seems to be and what actually is.


Start Playing by the "Right" Rules

When you’re in the middle of your work and unable to recognize that you’re on a playing field, you may think you know what’s going on. You know the “rules” and are following them to the T. You’re working hard and expecting to earn the rewards, but then someone else gets the recognition or raise or promotion, and you’re left wondering what the heck went wrong.

You may feel robbed or cheated. You may want to blame those who received the reward you were expecting. After all, you are the one playing by the rules, and they aren’t.The reality is that they are playing Monopoly by the rules of Monopoly, and you’re playing by some other rules that you believe are the proper rules, but they may actually be the rules to Twister. Because you don’t understand the game, you’re twisting yourself into a pretzel trying to win Twister while your colleague is calmly putting hotels on Boardwalk and collecting all the rewards that go with it.

That’s where the wisdom of Berra’s saying comes in . . . Nothing is like it seems. Yet it is what it is. You can continue to operate based on what you think the rules are or what you think they should be, or you can take a step back, see the dynamic of what’s really going on at your work, and base your actions on what is.


On the Topic of Corporate “Playahs”

Another reason why some people have a hard time viewing work as a game is thanks to the “playahs” who exist in many workplaces. People who don’t seem to work as hard yet reap the rewards. Some people rise within organizations by manipulating those around them.

But others rise quickly for another reason that the rest of us should sit up and take note of: They simply understand the rules of the game of work. They show up equipped. They show up pretrained. They show up ready to play, rather than struggling to understand. Sometimes they may work shorter hours, but there’s nothing wrong with that. They work for impact.

Isn’t a baseball game that’s won 1-0  as much of a win as a game that’s 10–9? I might even argue that a game that’s 1–0 is more efficient and used fewer resources.


Inside Baseball

Many analogies in the sports world illustrate the differences between those who seem to rise effortlessly and those who toil away with little to show for it. When I was ten or eleven years old, I would play baseball with the kids in my neighborhood in an empty lot behind my house. We had no strategy. The team with the most runs when we were called home for dinner was the winning team.

Because I played sandlot baseball countless times, I thought I understood baseball. As I got older and began watching major league games, I noticed all the moves and substitutions that the managers made, and it dawned on me that baseball was a much deeper and more complex game than I’d understood as a child.


Trading Time for Money—Easy-Peasy

Do you remember your first job? I do. I scooped ice cream at a neighborhood store for $2 per hour. I traded my time for money. As long as I showed up for work on time, I got my paycheck every other Friday. Besides the minor drama that arises when a bunch of high school girls worked together, it was pretty simple. Show up, work, get paid. Easy-peasy.

Much the way I thought I knew the game of baseball because I played as a child, early in my post-college career, I thought I understood what it took to be successful at work because I held a few jobs between age fourteen and twenty-two.

Back then, I thought the key to success was as simple as working hard, showing my dedication, and letting my natural talent and intelligence wow my boss. I assumed I knew what to expect at my first real-world job at the publishing company. My boss liked me, I worked hard, and I figured in no time I’d be rewarded with a promotion.


Dennis Walks Out with My Promotion

As I shared in the introduction, I had a rude awakening at my first job when I realized that ambition and hard work weren’t enough to move ahead. I was so excited about the promotion that Dennis had promised me. It would be my first step out of administrative support. I would graduate from answering phones and typing letters to helping create the company’s marketing strategy.

When Dennis quit (or was fired), I was still optimistic that the hard work I’d put in would be recognized and rewarded by his successor. I saw myself as bright and dedicated and felt sure that was evident to everyone around me, including Dennis’s replacement, Mike. I realize now that Mike probably saw me as Dennis’s girl. He had no loyalty to me and was not under any obligation to follow through on Dennis’s promise to promote me.

I felt so cheated when Mike hired someone from outside to fill that role. At the time, I was naive and didn’t understand anything about office politics. I didn’t know that new leaders usually have their own ideas and don’t typically follow the playbook left behind by their predecessor—especially when the person they replaced was fired.

To say the least, that was an eye-opener, but a valuable lesson that has served me well in my career since then. It trained me to step back and look at the larger playing field—not just at the moves that I thought the other players were going to make. When circumstances change, everything else can change as well.


It Takes More Than Talent

You may believe that if you get educated, get a good job with a great company, and work hard that you’ll ascend the ranks of your organization, be recognized as a leader, and make lots of money. But as many smart, overachieving professionals have discovered, that’s not all there is to getting ahead at work.

It’s like a naturally gifted athlete thinking that if he got drafted by the New York Yankees, with some grit and hard work, he’d soon be wearing a World Series ring. The reality is that talent is only one factor required to achieve that goal.

Advancing at work also depends on:

  • What you do to improve your skills,
  • Who you surround yourself with,
  • Who you choose to follow,
  • How you perform in moments of crisis (or opportunity),
  • How you interact with team members,
  • The organization’s strategy,
  • Your own mind-set,
  • Timing,
  • And many other factors.


It’s Not Personal

I learned this lesson (and many others) the hard way. Too often, I was attached to the things that happened. I took the disappointments personally. I questioned why people didn’t think I was “good enough.”

I focused my anger in ways that had no productive results and did nothing but make me unhappy. At times, because of my reactions, I probably caused people to give me a wide berth when I could have used more friends.

As you’ll read in the chapters dedicated to telling other real career stories, it’s pretty common to take things that happen to us personally, when in reality, it’s “just business.” In some cases, employees are laid off not because they weren’t providing value, but because the company’s strategy changed or due to economic factors that negatively impacted business.


Accessing Your Power

When we step back from feeling like a change is personal, it enables us to have more access to the energy required to recover and move on. When we stay mired in feeling like a victim, not only are we wasting time we could be spending on what’s next, but we can also repel people who could help us find that next opportunity.

My objective with this book is to share my own stories and stories of some interesting and accomplished professionals—the funny ones, the depressing ones, the happy ones, and even the humiliating ones. If even one person learns something from my experiences and those of the people I interviewed, then the mishaps will have been worth it.


Waking Up to Find Your Job Isn’t a Fit

I’ve coached many mid-career professionals whose primary goal getting out of college was to get a job—really any job. They wanted to start making money and making a career for themselves without much thought about their passions and strengths. High-achieving people are typically able to do a lot of things, and often they just look for someone willing to exchange money for tasks that they can do. This is a common theme in several of the career stories in the book.

Fast forward ten or twenty years, and they can find themselves “successful” in a career that they actually didn’t consciously choose and may not be a great fit for them. Even if you don’t like your job, it can be tough to leave, especially if you’re highly compensated and your lifestyle is based on that income.

Several of the people I interviewed in the book had similar experiences and were able to reevaluate what they loved to do and were good at, then find a fit between those skills that they enjoyed using and the needs within the marketplace.


Understanding the Balance of Power

Workers sometimes feel that the employer holds all the cards and that they, as employees, have little control over the path of their careers. It can really depend on the situation, but often the employees have much more control than they recognize.

The reality is that employers need employees to create the value that their customers buy. While not every organization is this enlightened, the best employers recognize that aligning their employees’ skill sets and passions with the needs of the business increases employee engagement, productivity, and innovation, which benefits the company and their customers.


How Career Contributes to Identity

Though you might still have a hard time looking at work as a game, its distinct advantage has to do with how closely we associate our jobs with our identities. Much like when I didn’t get the promotion at my first job and felt betrayed, many people can get attached to things that happen at work. Our judgment can become clouded with emotion.

The actions and outcomes may or may not have anything to do with us personally, but nevertheless, we can take them that way. Strong emotions lead to all kinds of actions that can be a problem at work—from losing control (think crying or yelling) to holding grudges that don’t make for a happy or productive work environment.


Roll the Dice and Play the Game

When you think of your work situation as a game, it helps to remove you from the “day-to-day” as you gain a broader perspective and see the whole game board. Your boss, company leaders, peers, direct reports, and customers are the players.

You can observe the dynamics of how various players interact with each other and choose how you’d like to play. The goal is to recognize that it’s your perception of the events that give them meaning. When you see things from a different perspective, the meanings can begin to change as well.

Roll the dice and start playing the game of work!

Keep reading to:

  • Learn the "unwritten" rules of the game and how to become a savvy player, 
  • Be inspired by the career stories of 10 fascinating people,
  • Discover your own path to career happiness and success.

Available on Amazon or Barnes & Noble in paperback or e-book format. 

Audiobook coming this fall!



Are you ready for the next step?

If you're ready to step into your full potential to lead a happy and successful career, let's talk!