Chapter One
THE TOSS
Two years out of college, unaware of the good fortune heading my way, I moved to Seattle with my best friend, Donna, and began looking for a job. I scoured the want ads and sent out resumes, serious about a career. My hope was to land an entry-level position in advertising. But I couldn’t even get an interview. All the downtown agencies had long lines at the door.
After weeks of looking, I began to do temp work, handling customer complaint calls and alphabetizing files. Every evening, when I returned to my apartment, my fingers were crossed in anticipation. Maybe there’d be a message from a potential employer waiting for me on my answering machine. But the light on my phone was rarely blinking. The only calls I got were from my mother.
“How’s the job search?” she asked.
“Okay,” I lied.
“And the apartment?”
“It’s fine. A bit empty. I saw a sofa I like, but I’m not going to buy it until I have a job.”
“Sounds wise,” she said with approval. “How’s Donna doing?”
“She’s fine. She’s always busy,” I said. “She loves her job.”
Hanging up, I sat back in the wooden chair at my desk, alone. Best friends since high school, Donna and I had moved to Seattle together, but when she started her new job at a computer company, Donna had disappeared. We rarely saw one another.
Finally, after months of sending resumes and making follow-up calls, I got an informational interview at a small agency downtown. Hoping for my big break, I arrived early and walked around the block several times before entering the building. After only a few minutes in the lobby, I saw a man in a flannel shirt and corduroy pants sauntering toward me, looking as though he’d just dropped by the office to water his favorite plant. I couldn’t have conjured up someone more approachable. He introduced himself as Dave and gave me a tour of the agency, nodding as I pitched myself as a hard worker, eager to learn.
“I’m afraid we just don’t have any openings,” he said. “But let me introduce you to our HR guy, Jan. Maybe he knows something I don’t.”
Dave took me downstairs, stopping outside an office where a woman in her early twenties was slapping high fives with a man wearing a silky black tie covered in bubblegum machines.
“So, you want to work in advertising,” Jan said after Dave introduced us.
“I have a resume with me,” I said. “Would you like to see it?”
“Sure, why not?”
Bobbing his head at my resume, Jan asked about my summer work experience, then told me there were only three entry-level account coordinator positions at the agency. All of them were taken.
“I just don’t have anything,” he said.
“Could you use extra help? I’ll work for free.”
My mouth made the proclamation before my head had the chance to approve the material. But I wasn’t sorry. Working in advertising had been a dream of mine for years. I was finally inside an agency and wanted to stay.
Jan didn’t seem the type often at a loss for words, but he froze for a moment.
“Okay,” he finally said. “I like the attitude. The Nordstrom team could use your help. We’ll see you Monday morning.”
The next week, I began showing up early and doing whatever was needed, excited to experience the inner workings of advertising. I also started to make work friends. And after more than a month of helping full-time, when one of my new friends told me about an opening at McCann Erickson, the big agency across the street, I rushed my resume over and landed the job. Finally! I had a paid position. My goal had been accomplished. My career was underway.
My days at McCann Erickson were spent running between the account management and creative departments, shepherding projects through production. I did a lot of grunt work too, making photocopies and serving coffee to clients. I came in early, left late, and worked on the weekends, keeping the job files up to date and making sure everything was in order. Meanwhile, earning $19,500 a year, it was tough to get through the month with enough left to pay rent. I rarely went out, cut coupons, rode the bus, brought my lunch to the office, and rationed my coffee. At a time when Seattle’s very own Starbucks was becoming a national phenomenon, I only allowed myself a $1.65 drink once a week. It felt important to watch every dollar. Managing my money made me feel responsible.
One day, after nearly a year at the agency, as I sat on the floor, sorting photocopies in a skirt and heels, dressed for the job I hoped to earn, not the one I had, I got an important phone call. Seemingly out of the blue, this call was a peace offering of sorts. Two years earlier, before arriving in Seattle, Donna and I had planned a move to San Francisco. We’d talked about sharing an apartment and looking for jobs together. Then, a week before our move, Donna broke the news that she’d accepted a position at a computer company in Seattle. Initially, I’d been crushed but ended up moving to Seattle with her.
“Hi. It’s me,” Donna said. “Do you have a minute?”
“Sure,” I told her. “But I can’t talk long.”
A rule follower, I felt uncomfortable taking personal calls during work hours.
“There’s an opening here in campus recruiting,” Donna said. “I know you don’t want to work in HR, but I thought you should know about the job. Are you interested?”
Unaware of the gold coin floating into the air, I took a few moments to think. The photocopying was getting old, but I didn’t want to leave advertising. There was so much still to be learned about targeting customers and positioning products. An HR job hiring business school graduates into marketing positions didn’t sound that appealing. But I missed Donna’s friendship and imagined we’d be more connected if we worked at the same company. I was also intrigued by Microsoft, the company where she worked. After nearly two years in Seattle, I knew Microsoft represented challenge and opportunity. There were great perks too: free soft drinks, cafeterias with latte stands, and a membership to the health club right down the street. Maybe if I got in the door, I could wrangle myself a marketing job from the inside. With that thought, I told Donna I was interested in an interview—and the gold coin landed. One moment, one answer, and the trajectory of my life was about to change.
Unlike the sleek, image-conscious world of advertising where we dressed to impress clients, Microsoft was full of boys in T-shirts practically living in their offices, spending days and nights writing code. It was 1991. While the rest of the country was recovering from a minor recession, Microsoft was booming. The workforce had outgrown its original pod of six white ’80s-style structures, and several new brick buildings were under construction. The halls buzzed with energy, and inside each office, employees stared intently into computer screens or scribbled furiously on whiteboards, on a mission to put a computer on every desktop. Windows 3.0, the newest version of the company’s operating system, had launched a year earlier to huge success, and with the average age of thirty, employees were out to change the world. It was an exciting time to be at the company.
After several long, demanding interviews, I got a call with an offer, and accepted immediately, excited about becoming part of the action. My starting salary was $26,000, a big step up from what I’d been making, and I barely listened as my new manager, Jane, explained the biannual reviews, bonuses, salary increases, and stock options.
At the time, employee stock options were a complete unknown. Even within Microsoft, no one truly understood what options were or how they worked. No other company had ever granted so many options to so many employees, and without history as a reference, it was impossible to know what to expect. Certainly, no one at Microsoft was talking about their compensation. Everyone prided themselves on being nothing like the brokers and bankers of Wall Street who were making money with money and bragging about their bonuses. Intelligence, hard work, and a passion for technology were currency at Microsoft. While it was clear that options were a benefit, they were viewed as a bunch of numbers on paper, completely unrelated to everyday life.
But in time, options began making us rich.
Midway through my second year at Microsoft, as a quarter of my options vested, I took a closer look—and was astonished. The Microsoft stock price had been moving steadily upwards since my first day, and after eighteen months at the company, I had tens of thousands of dollars of free money in my future. I couldn’t believe it. If the stock price continued to climb, in another three years, my options would be worth as much as $300,000. Three hundred thousand dollars!
Four years earlier, after graduating from college and before moving to Seattle, I’d worked at a steel company in Tokyo teaching English to executives. I thought of my time in Japan as a final hurrah, a chance to follow my heart and have one last adventure before settling down and starting a career. I’d known nothing about Japan, and loved my time in Tokyo. Living in company housing and benefitting from the power of the yen, I unexpectedly returned home feeling rich, not only from the experience, but from the money I’d saved.
“I can buy a new car,” I’d bragged to my father.
“You think you have a lot,” he’d cautioned. “You need to be careful with your money.”
As usual, my dad had been right. Twenty-four thousand dollars had sounded like a fortune, but after buying a car and working for free, I’d depleted my savings. But Microsoft stock options were different. My fortune was so much bigger. In fact, $300,000 was an uncomfortably large sum. I never considered telling my parents. If they knew, I was worried they’d look at me differently. I didn’t want my options to create a distance between us, my place in our family at risk. Where would I fit in if I had more money than my father? My mother wouldn’t approve of me having so much either. She wasn’t comfortable with wealth or the wealthy.
July 15, 1991, my first day at Microsoft, Donna introduced me to Lynn, another campus recruiter who fast became a friend. Lynn’s sharp wit and strong opinions made her fun to be around. Many mornings, the two of us walked to the cafeteria together, Lynn giving me the scoop on the heroes and villains within each department and offering advice on how to create effective interview questions. We laughed about Bill Clinton’s failure to inhale and scrutinized the relationship she was beginning with a man named Adam, a program manager at Microsoft.
At the end of August, campus recruiters were required to attend farewell parties for the interns who’d been working at the company for the summer. Lynn and Donna had gone to these events in the past and weren’t excited. But I couldn’t wait. The parties were being held at the home of Bill Gates. Not only was Bill highly respected throughout the company, he was practically a billionaire. Going to his house meant seeing how he lived.
On the evening of the first party, I drove into the upper-class neighborhood of Laurelhurst and searched for the address, which was right on Lake Washington. Spotting the house, I pulled forward, parked, and felt disappointed. The dark green Craftsman looked like any other large home. It didn’t scream rich or have a special aura of sophistication. There was no Bentley in the driveway, no butler at the door. I walked up the front path, was directed down the stairs, and my disappointment grew. The rooms were not grand. Gorgeous artwork did not grace the walls. There were no fine pieces of furniture or elegant antiques. Nothing about Bill’s home was flashy or glamorous. With its worn leather sofas, wood-paneled walls, and pool table, the basement, from which we gained access to the backyard where dinner was served, looked like a bachelor pad stuck in the 1970s.
After a perfectly nice evening talking with interns and their managers, while the view of the water was beautiful and the food delicious, I remained baffled. I’d hoped to see inside the life of the rich, and nothing about the evening came close to fulfilling my expectations. I didn’t understand why Bill wasn’t living in one of those spectacular mansions I’d seen in movies and on TV. I thought the wealthy lived stylish lives in rambling manors and enjoyed showing off their success. What was Bill doing with all his money?
In the fall, our team of twelve campus recruiters traveled the country, giving presentations at top colleges and universities. In the winter, we conducted interviews at Microsoft in Redmond, looking for people who were smart, hardworking, and could get things done. As each candidate talked with employees doing the jobs they would do if hired, campus recruiters read feedback over email and made sure the best and the brightest met with key decision makers. Those failing to reach the bar returned to our offices to wrap up the day. No one at Microsoft wanted to waste precious time with someone who wasn’t a good fit for the company.
Lynn and Donna handled the recruiting process for college undergraduates applying for test and development positions, while I worked with the MBA candidates interested in product management and marketing. In the early 1990s, most business school graduates were out to land high-paying jobs in corporate banking, consumer products companies, and consulting firms like Goldman Sachs, Procter & Gamble, and Deloitte & Touche. Since Microsoft was relatively unknown—way out in the boonies of Washington State—and offered salaries below industry standard and the unfamiliar benefit of employee stock options, the MBAs who interviewed were entrepreneurial in spirit, not necessarily looking to get rich.
In the spring, making offers over the phone, I did my best to explain how stock options worked: the strike price of an option was set the first week on the job and each option was worth the difference between that strike price and the stock’s current market value. After eighteen months at the company, a quarter of an employee’s stock option grant was vested, which meant it was available for cash. Every six months after that, another eighth of the grant vested and the full amount could be cashed-in after four-and-a-half years.
“If you work hard, you’ll help drive the stock price up,” I said. “If the price goes up $50 in the next four-and-a-half years, your grant of 2,000 options will be worth $100,000. If the stock goes up $100, you’ll have twice as much.”
Even though I understood stock options in theory, I’d had no idea what they really meant until I’d been at Microsoft for eighteen months and my own options began vesting. Then, seeing a potential $300,000 in my future, I ran into the office next door and took my usual seat in the chair opposite my co-worker, Stephen.
Stephen and I had started the same day, were doing the same job, and spent many hours together, discussing candidates and interview strategies. We’d shared company gossip, savored juicy anecdotes about our love interests, discussed religion, and argued politics. Although we’d never talked about money, it seemed reasonable to slap a private high five in acknowledgment of our mutual good fortune.
“Do you realize what we have?” I asked. “Our options are worth $300,000.”
Stephen stared at me in silence.
“I’m not comfortable talking about this,” he murmured, glancing at the open door. He then lowered his voice and confided, “You know, I accepted my job offer earlier than you did, right before a stock split. I have more. You can’t say anything, but I have over a half-million dollars.”
It was my turn to stare. We had started the same day. We were doing the same job. I couldn’t believe Stephen had twice as much as I did.
I leaned back in my chair and looked out the window at the construction across the street. Attempting to appear casual, I asked Stephen about his girlfriend. We talked about the positions we both needed to fill. And as soon as enough time had elapsed, I excused myself and headed down the hall.
“Can two people who started the same day, who are doing the same job have vastly different stock option grants?” I asked Jane, our manager, as I burst into her office.
Jane turned from her desk.
“Are you thinking about a specific case?”
“I know it’s not something I should be talking about, but does Stephen really have twice as many stock options as I do?”
The words hung in the air. Blood rushed to my face. What was I doing? It wasn’t any of my business. I shouldn’t be talking about Stephen behind his back. I shouldn’t be so interested in money either. The Microsoft culture scorned a focus on personal financial reward. It was cool to be smart, technical, and strategic, to be creating cutting-edge software and outpacing the competition. Talking about money was evidence of misplaced values and greed. I wasn’t being the responsible woman my mother had raised.
At ten years old, when I asked how much my father made, my mother frowned and turned away. His salary was none of my business. On those special occasions, when our family went out for dinner, my mother scolded me for peering at the check at the end of the meal. It was improper and unladylike to care about cost. I needed to avert my eyes and let my father handle the finances.
“I shouldn’t be talking about this,” I mumbled to Jane.
“You’re right. It’s not up for discussion,” Jane said.
But my concern wasn’t about money alone. Stephen and I were doing the same work. Our goals were identical. We were both good employees. Where was the justice in him having so much more?
“Aren’t Stephen and I both doing a good job?” I asked.
“Yes,” Jane said. “But he accepted his offer in May, before he graduated. With the three-for-two stock split in June, he had more when he started. Your offer came after that split.”
“That’s not fair!” I exclaimed. “Our start date was the same.”
“That’s true.”
“Isn’t there something you can do?”
“Look, we’re all lucky. Just appreciate what you have. Stop looking around at other people.”
“I’m not. It’s just . . .”
“It’s just the way things are,” Jane said, turning in her chair and ending the conversation.
Back in the safety of my office, I closed the door and sat down. Gazing at my computer screen, frustrated and upset by the inequity, I moved the cursor in small angry circles. Then, letting out my breath, I slumped back in my chair. I wanted to crawl under my desk. I couldn’t believe I’d just stormed into my boss’s office and betrayed a friend’s trust.
From within the small world of recruiting at Microsoft, surrounded by friends and co-workers who were benefitting from employee stock options, and without much experience in the workforce, I lacked perspective on money and life. Looking back, I still see the unfairness of Stephen’s compensation being higher than mine, but there was unfairness in everything happening with stock options at Microsoft in the 1990s. A bunch of employees in their late twenties and early thirties were becoming wildly rich. We may have made some smart decisions along the way and were helping put a computer on every desktop, working eighty-hour weeks but the amount of money we were gaining was way out of proportion to anything any of us were doing or had done. As a twenty-something kid, wrapped up in the moment and in myself, I didn’t yet understand my own crazy good luck, let alone comprehend the reality of having so much money.
Though it was upsetting that Stephen had more money than I did, in a matter of weeks, stock options faded back into the future where they’d been hiding for the previous eighteen months, more an abstraction than part of everyday life. For Stephen and me, it was work as usual. We never spoke of our options again.
Two years after starting at Microsoft, I began contemplating a move from recruiting to marketing, and when a product manager from the Consumer Division contacted campus recruiting in search of an entry-level marketer to help launch a new software product code-named Utopia, I walked my resume to his office and told him I wanted the job.
“If you join a product group, you’ll be at the bottom of the pay scale,” Donna warned. “You won’t get an increase. I doubt you’ll get more stock.”
I appreciated Donna’s counsel but didn’t care about a raise or additional options. I was hoping to learn more about marketing and contribute directly to Microsoft’s bottom line. Utopia was intriguing too. It was such a creative product, offering an intuitive way to work on a home computer. In fact, Utopia’s revolutionary social interface was attracting attention within the company. There was even talk of Melinda French heading up the project.
Melinda had gone on a recruiting trip with me to UCLA the previous fall and was already my idol. Smart and straightforward, she was one of the best interviewers at the company and a big-deal manager. Even at the time, it wouldn’t have been a stretch to imagine the impact she would have on philanthropy, focusing on improving the lives of underserved women and girls across the globe. But as I thought about working for Melinda and considered the notoriously tough questions that were asked during the interview process, I got nervous. Was I up for the challenge? Was I smart enough for the job? How would I answer all those questions? Why were manhole covers round? What animal did I want to be? How would I market a car to someone in a wheelchair? How could I get my grandmother to buy Excel? I didn’t know much about marketing and was worried about not having good ideas or the right thing to say. Then, I thought of David.
On my first day, at orientation, he had been standing behind me in line, wearing shockingly bright blue shorts. He told me about being an intern the previous summer, and about the job he was starting as a product manager for the company’s first database. Later, by email, a mode of communication unknown to me and most of the world but ubiquitous at Microsoft, David had asked me out.
It sounded like a bad idea to date someone at work, but the company was big, he was cute, and soon we were spending a couple of hours together in the dark, watching Terminator 2: Judgment Day. Over dinner afterward, David told me his favorite joke about a duck. He also laughed at my favorite about an orange and a banana, and grinned when I mentioned my favorite quote from Joseph Conrad’s Heart of Darkness.
“You mean, ‘I don’t like work—no man does, but I like what is in the work, the chance to find yourself’?” he said.
“That’s the one!”
“That was the quote I put in my college yearbook,” he told me.
Believing, as Conrad suggested, that work helped me connect with myself, I’d copied that same quote into my journal during college. Whenever truly engrossed in an activity, I felt self-consciousness fall away and time disappear, allowing me to get in touch with an essential part of my being. Did David see and understand that? Was he someone with whom I could truly connect?
For our second date, he invited me to dinner at his apartment. Answering the door wearing an apron and holding a knife, he swept his arm wide to usher me into his living room. Two brown plaid loveseats sat opposite one another, and piles of books and unpacked cardboard boxes were spread across the floor. An old TV was perched in one corner, its rabbit-ear antennae leaning against the window as though seeking fresh air. Several intriguing items sat proudly on an otherwise empty bookshelf: a tiny blue-wire bicycle, a yellow rubber duck in a sailor’s hat, a green plastic crocodile, and a glass bottle of blue ink. I wanted to walk over to get a closer look at these treasures, in search of additional information about the man who had invited me to dinner, but propriety compelled me to follow David to the kitchen.
“How can I help?” I asked.
He leaned over a cookbook and frowned down at a recipe, assuring me everything was under control. The mess of wooden spoons and mixing bowls didn’t seem to bother him. He reached for a spice jar and plastic measuring spoons. Then, crouching slightly, holding a teaspoon, he extracted just the right amount of thyme, which he sprinkled carefully into a small glass bowl.
“To taste,” he read aloud, his finger on the recipe. “How do you measure that?”
His goofy humor was endearing. So was his methodical approach. Watching him attempt to wrap a flattened pork loin around a filling of prunes and apricots, pushing at the dried fruit with his fingers and fumbling with a piece of string clearly dug up from somewhere far from the kitchen and cut way too short, I wanted to give him a hug. He was so earnest. So sweet.
Over dinner, we talked about our experiences at college. Both of us had graduated in 1987 with liberal arts degrees, me with a BA from Connecticut College where I’d majored in art history and minored in philosophy, David with a degree from Princeton University where he studied French and comparative literature. He seemed impressed by the two years I’d worked in Tokyo. I found him impressive too. After Princeton, he’d worked in consulting for two years, spent three months biking across the country with a friend, and had then gone to Harvard Business School. But he hadn’t gotten an MBA as a matter of course. He’d applied to Harvard on a whim and, when he got in, decided to go.
In the months that followed, David and I met after work for late dinners and watched a lot of movies. As we took long walks around our neighborhood, we discovered we shared a similarly open, liberal perspective on life and the world. Many weekends, we got together with Donna and Lynn from recruiting and their boyfriends, Matt and Adam, the six of us talking non-stop about Microsoft.
But while we got along well and had fun together, when I tried to get close, David pulled away. I’d suggest spending a night at the coast and he claimed to need “alone time.” He didn’t want to hang out all weekend either. He needed space. Although it was becoming painfully clear he didn’t want the same intimacy I craved, I couldn’t walk away. He was so smart, so funny, so easy to be around. He gave me a sense of belonging. I felt understood. Then, one evening, when I answered the phone in his apartment, his former girlfriend was on the other end of the line. I handed him the receiver and walked out the door in tears.
It turned out David had moved from Boston to Seattle without completely letting go of a four-year relationship. When he revealed his old girlfriend was going to visit for a weekend, I told him I didn’t want to see him anymore. It was too difficult to know he cared for someone else.
But our breakup had been months in the past and, eager to get help preparing for interviews, I steeled myself and gave him a call. Right away, he agreed to meet and suggested Victrola, a coffee shop the two of us had frequented as a couple. Walking in the door, and seeing him at our table, wearing one of his many striped T-shirts, I wanted to run over and jump into his lap. Instead, I waved and strolled to the counter where I ordered a nonfat latte. I then pulled up a chair opposite my old boyfriend and thanked him in advance for sharing his knowledge about marketing.
The following week, I had my first interview with Karen, the visionary behind Utopia. Afterward, I met with Melinda, who had just taken the position as group product manager. Quickly putting me at ease, Melinda sat casually on a table in front of a white board. Rather than peppering me with questions, as I’d anticipated, she posed hypothetical marketing problems that we contemplated together. We debated how to position a product and considered the best way to reach customers. The discussion was fun. When the conversation ended, I skipped back to my office.
The next day, I was skipping again—right across campus and into the building where David worked.
“I got the job!” I shouted.
Bringing my arms down around David’s neck, I forgot we weren’t a couple. With a kiss, we were together again. Well, almost. He told me he’d been confused, that his old girlfriend had been going through a hard time, but that her visit to Seattle had been the end of their relationship. He then told me he’d been thinking about me, surprised at how much he missed me. I too was surprised. I’d never broken up and gotten back together with anyone before and didn’t want to be that person who wasn’t clear about her feelings. But I wanted to be with David. The two of us were in sync. We found the same things funny and shared a similar view of life. We complemented one another too, me helping him get in touch with his emotions and him helping me find words for my feelings.
For our official second-time-around first date, David and I spent an afternoon at Green Lake, the best place in Seattle to enjoy a sunny afternoon. At first, as we walked the perimeter of the lake, I felt myself talking way too much. When we sat down together on the grass and watched people walking by, he couldn’t sit still. He jumped up and pulled me up with him.
“Let’s rent a paddle boat,” he said, heading to the dock.
Sitting side by side, cruising through the lily pads past the ducks, we raced from the shore, challenging one another to see who could pedal faster and who would tire first. Finally, we let the boat drift. I leaned back and closed my eyes, happy to be next to David.
“Hey, stop!” I said as sprinkles of water hit my face. “Who knows what’s in that lake water?”
David smiled. He stood up, pulled his shirt over his head, and let his pants drop. Wearing nothing but boxers, as if to prove he wouldn’t splash anything on me that he wouldn’t mind being submerged in himself, he dove into the water.
“Feels great. Want to join me?” he asked, popping up seconds later, his skin shining green through the murk. “I love you,” he added.
His words took me by surprise, filling me with joy and opening me up to how much I cared about him too. I’d missed his smarts and goofiness. Could he be my forever partner? I smiled, imagining a future together.
“I love you too,” I said.
Contemplation & Conversation
•Was it good luck or good decisions that helped Jennifer land the Microsoft job? Do you attribute your successes and failures to circumstances, luck, choices, or talent?
•Jennifer had preconceived ideas about the way the rich live. What do you believe about people who have a lot of money?
•Was Jennifer wrong to talk to her boss about her stock options? Do you talk about money or your salary with co-workers?