“Tell me this, Andy. What was the best day of your career?”

Andrew considered asking the old man not to call him Andy, a nickname he’d worked hard to kill since business school, but then decided it wasn’t worth the trouble. “What do you mean—”

Charlie held up his hand to interrupt Andrew, like a kind parent. “Try not to make it complicated. Just tell me what your best day was.”

Andrew considered it for a few seconds. “I’d have to say the day I was promoted to CEO. One year ago tomorrow.”

Charlie seemed disappointed by the answer. Not judgmental. Just disappointed. “Why?”

Andrew was surprised by the question. “Gee, Charlie. Being CEO is a pretty big step in a person’s career. I worked for twenty years to get where I am.”

Charlie seemed to disregard Andrew’s answer. “Okay, then, what about the second-best day?”

Andrew took a breath and described his first promotion to vice president, and about how it was the first time his salary “cracked six figures.”

Charlie was slowly nodding his head as though he had figured something out. “Okay, Andy. I don’t want to be too critical, but—”

Andrew interrupted. “Feel free to be as critical as you like, Charlie. Everyone else is.” He smiled in a tired kind of way.

The old man leaned forward and put his hand on Andrew’s knee. “I think you’ve given in to temptation number one. And it’s the toughest one to fix.”

As much as he wanted to dismiss it with a laugh, Andrew felt a sense of authenticity in the old man that wouldn’t let him discount his advice completely. Not wanting Charlie to sense his concern, he responded jovially: “What is this, Charlie? Right off the bat I’m not fixable?”

Andrew’s attempt at humor did not diminish Charlie’s concern. “Possibly. Some people are just not cut out to be a CEO.”

With less humor now, Andrew asked: “Okay, what makes you think I’ve given in to temptation number one? What is temptation number one, anyway?”

Charlie paused like a bedside doctor about to give his patient a diagnosis of cancer. “Well, I can’t be certain, but it seems to me that you may be more interested in protecting your career status than you are in making sure your company achieves results.”

Andrew looked puzzled, so Charlie went on.

“Let’s use an example.” Charlie looked at the ceiling of the train for a moment. “Okay. Here’s one. Think about a politician, maybe even the president of the United States. Imagine that I were to ask him the same question I just asked you. ‘Mr. President, what was the biggest day of your career?’ What would a great president say?”

Andrew shrugged.

“Or think about the head of a nonprofit agency. Or even the coach of a professional basketball team.”

Andrew was growing a little tired of the old man’s elusiveness. “What are you getting at, Charlie?”

“Well, imagine the president of the United States saying that the greatest day of his career was election day, or inauguration day.” Charlie hesitated, but nothing registered on Andrew’s face, so he went on. “Or imagine the head of the nonprofit agency saying that her proudest moment was when she received a grant from the government. Or imagine the basketball coach saying his greatest day was signing a big contract with a team.”

Andrew frowned. “To tell you the truth, those sound like pretty realistic answers to me.”

“They’re extremely realistic. And that’s the problem.”

Andrew still seemed confused, so Charlie lowered his voice to a gentler level. “You know what my father said when I asked him about the best day of his career?”

Andrew shook his head.

“He said it was a toss-up between the day the railroad opened its first passenger line west of the Mississippi and the day the company first turned a profit.”

Charlie sensed that something seemed to be sinking in with Andrew now, so he went on.

“You see, a great president of the United States wouldn’t be as proud of being elected as he would of actually accomplishing something. And a nonprofit agency shouldn’t feel good about getting funding unless they did something meaningful with the money. And there isn’t a great coach alive who would say that his best day was getting hired. Winning games and championships is what great coaching is all about.”

Andrew decided to fight Charlie a little. “So you’re saying that people shouldn’t be proud to reach personal milestones in their careers?”

Charlie smiled. “Of course they can be proud of milestones. But not as proud as they are of actually doing something with their status. In fact, great CEOs should be almost overwhelmed by the need to achieve something. That is what drives them. Achievement. Not ego.”

Andrew decided to ask a question of his own. “Why couldn’t a person be so motivated by his ego that he would drive for results? Lots of CEOs have big egos.”

Charlie seemed stumped, but just for a moment. “That’s true, I suppose a CEO could be driven by ego.” Andrew was relieved to be agreed with for once—until Charlie clarified, “But it wouldn’t last for long.”

“Why not?”

“Because once a person’s ego is initially satisfied, they turn their efforts toward enjoying the fruits of their new status. They work less hours. They worry less about the company’s performance than they do about their own level of comfort and status.”

Andrew nodded his head just slightly to allow Charlie’s point. The janitor pressed on.

“Of course, when the company shows signs of failure and the CEO’s status is in jeopardy, then he might work hard again, but not because he’s concerned about the company. He’s really only concerned about his image.”

Charlie then asked a leading question, as politely as he could: “Why is it again that you’re working so late tonight? I can’t imagine that you usually work these hours.”

Andrew responded without making the connection to Charlie’s point. “Oh no. I’m usually home by seven. But there’s a board meeting tomorrow, and things aren’t looking too good.”

Suddenly Andrew made the connection. He sat in silence, contemplating the point, and seemed unaware of Charlie’s presence.

Deciding it was time to change the subject, Andrew relented. “Okay, Charlie. I can buy this. I can admit that it’s sometimes tempting for a CEO to put his career, his status, even his ego a little too high on the list of priorities. That’s good advice. I could probably work on that one myself.” Andrew felt a sense of charitable satisfaction at conceding the point to Charlie, who didn’t seem so crazy anymore.

His satisfaction was short-lived when Charlie explained: “But don’t get me wrong. It’s very hard to overcome this one. It’s part of who you are sometimes. And even if you are able to resist the first temptation, there are still four more that can sink you.”