Lives #5 – Lonely at the Top

[This is the fifth in a series of stories about interesting people I’ve known, a series I’m calling “Lives”. I don’t know whether you would call it non-fiction, or fiction. I’ve changed the names, and some of the details, so that the individuals are not easily identifiable. However, I think I’ve stayed true to the essence of what really happened. The point is what can be drawn from the story, and at least that part is 100% true.]

Try to picture this typical day for Brian in the office. He arrives without fanfare, and the receptionist sees him come in. Without a word, he goes into the corner office – the CEO’s office, his office – and shuts the door. There he works away at budgets and strategic plans, periodically sending emails to others in the company to join him for ten minutes, or an hour. When others are leaving in twos and threes to have lunch, he remains in his office, churning out a massive volume of work product. Sometime in the afternoon, he chairs a meeting of six key executives in the boardroom. He is all business, and does not participate in the good-natured banter amongst the others. Later, at some unknown time, he leaves the building, an event noted only by the receptionist.

Brian is the CEO of a software company. He didn’t start the company, and he has no vested interest in the products, or the technical foundations on which they were built, or even the customer base to which they are sold. He was brought in by the owners when the company reached a certain level, because, as they said, “Brian delivers”. He knows how to run things, and he achieves results.

This is not his first senior position. Now over fifty, Brian has a history of running things, and running things well, with two successful companies to his credit. He has delivered results for those previous company owners. There is an aura about him, a sense of an almost magical ability to get a company where it should go.

That history has also made him a sought-after speaker. He is cursed with a somewhat wooden speaking style, but that doesn’t stop software industry professionals, investors and others from hanging on his every word. His position means that what he says matters. His history says that maybe he knows some things other people don’t know. He is widely thought to be well-connected with financiers, government officials, and other software industry executives. The proof is that the financiers hire him, the government officials give his companies grants and other support, and executives speak of him with respect, even admiration.

Even his personal life appears charmed. Despite his notoriously long hours, he has been married to the same woman – herself a well-known writer – for more than twenty years, and has two teenaged sons whose pictures are the only personal touches in his otherwise austere office. His beautiful home was once featured on a local TV show, not because it is large or expensive (although it is both), but because it shows exquisitely good taste.

None of the outward appearance of Brian’s life, business or personal, is fraudulent or untrue. He didn’t build a Potemkin village to portray himself a certain way to the world. It’s all real.

Yet Brian knows that there are two other, more important, truths about his life. From his point of view, his life is not perfect. It is the opposite.

Those two other truths make him a deeply unhappy man.

The first truth is insecurity. Brian feels that he is walking on the knife edge of a high cliff. He is, indeed, a smart man. He has taken two companies and, in part through intelligent and timely decisions, made them successful. But he also knows that this is only his third company. He made good choices in his previous companies, but he also had fortune on his side. He knows he can’t rely on luck forever. At some point, he will roll the dice and it will come up craps. His decisions may be just as good, or not, but in either case he will be “exposed” as a failure.

In his heart, he doesn’t see this as “sometimes you win, sometimes you lose”. Like all of us, he is a mass of doubts and insecurities. He sees the reverence with which he is treated today as undeserved, and his reputation as a fraud (although of course he’ll never tell you that). His status as the man at the top is, in his mind, built on a teetering edifice of unreasonable expectations that he can’t possibly meet. Every moment of every day, he worries that the time has come when he will be found out. He will make a wrong decision, or he will even make a correct decision, but have bad luck. Either way, suddenly he will be just another guy: another guy who failed.

This constant fear that he will be exposed for what he really is makes him very sensitive to criticism.

When an industry publication trashes his new product, he is highly defensive. It doesn’t matter to him whether they are right or wrong. It matters that they have not understood his vision (and deep in his soul, he thinks maybe his vision is wrong, because he alone knows that he is not as good as they think he is). He has been known to deliver hard-hitting, almost vicious, responses to negative reviews.

Worse, over the years he has subconsciously preferred to hire and promote people who agree with him. Today, he is surrounded mostly by syncophants. Everyone in his company avoids disagreeing with him, on anything, for fear that it will be a career-limiting move. Brian feeds that fear by challenging all competing views, not just with intellectual intimidation, but also with the power of his position. Ask anyone who works for him: disagreeing with Brian is a very bad idea.

Brian is sufficiently experienced to understand that companies that stifle dissent are often destined to fail. He is also sufficiently self-aware to understand that he has too many yes-men, and not enough free thinkers, in his company. At the conscious level, he is trying to hire and promote more on the basis of creativity and independence. However, his subconscious need to build walls around his insecurities is fighting those attempts, and it’s winning.

The second truth is that Brian has no friends. None. Not one. Not even within his own family.

Brian’s isolation on his typical day in the office is not by chance. It is something that has built up over the years, a distance he has caused or allowed to evolve between himself and everyone around him. There was, perhaps, a time years ago when he would come out of his office and talk to others, treat them as people. Now, he doesn’t bother. He feels awkward trying to be sociable with his co-workers, all of whom are afraid of him. He is just as happy that they don’t approach him anymore, because he would always be second-guessing their motives.

It is almost sad to see Brian at a conference or other public event. Certainly, there will often be people talking to him, especially if he has been one of the speakers, but without exception they are trying to curry favour or generate influence. No-one wants to talk to Brian the person. No-one thinks they even know Brian the person, and to his mind they certainly don’t care about Brian the person. He can’t remember the last time someone he knew had a conversation with him about his family, or theirs.

This has been getting worse over the years. Now, it is probably fair to say that he is at least as fearful of social interactions with others, as they are of debating with him.

Even his family are not friends. His parents, alive and healthy, live on the other side of the continent. His busy schedule means that he rarely sees them. Family functions are often attended by Brian’s wife and kids, who know his parents and his siblings much better than Brian does. If you ask his mother, she will say, candidly, “Brian was always a bit of a loner, but we’re very proud of him”. She would have more to say about her daughter-in-law, and grandsons, since their lives are more entwined with hers.

Brian’s greatest angst is about his two sons. As teenagers, they are of course not likely to be his best buddies, true. On the other hand, he would expect them to have some strong feelings about their father, even if just anger or contempt or rebellion. Yet Brian knows that he has not been enough a part of their lives to deserve strong feelings.

It is not that he spent very little time with them. He did spend some time. He made a point of it, because he knew it mattered to him. No, it is, rather, that they perceive that they never really had enough of his mindshare, his attention, to be important to him. He wasn’t an absentee dad. He was a busy dad.

Brian knows that judgment isn’t true. He knows the visceral intensity with which he feels his love for his sons. There are days when he aches for a real connection with them. At the same time, he can step outside his head and see how seldom he has let them see the intensity of his feelings.

So he ends up feeling like a stranger at home. He watches the closeness between his sons and his wife, and he knows he is not a part of that. When they sit around the dinner table, or they watch a TV movie, or they hang out on the back deck, there is smiling and laughing, strong views and engagement. He wants to be a part of that, and he is, in a way. They don’t ignore him, and they do treat him with respect. But, Brian can see that it is the respect you give to an important visitor, not the respect you give to a father and husband you love.

Brian is, thus, deeply unhappy. Time and again he has played out in his mind the bleak future he assumes for himself. He will inevitably fall off his perch at the top of the corporate ladder, whether through his own fault or not. He will look around, and he will be totally alone.

In fact, in some ways he feels like he is already in that future. Amidst the continuing accolades and respect, he is isolated, surrounded by people but actually living by himself in a world where he doesn’t really matter to anyone. He knows he created this life, and can’t blame it on anyone else. But even if it’s his own fault, he still knows he doesn’t feel the way he desperately wants to feel – about life, about people, or about anything else.

The saddest thing about this is that he only knows one way to cope with this overwhelming sadness: bury himself in his work.

Sorry, no happy ending for Brian. Ask him. After he gets over his shock that someone wanted to know anything at all about Brian the person, he will tell you that he screwed up his life, and it’s too late to fix it.

Whether or not that’s true, that’s what he believes. And perhaps, as long as he believes it, it is true.

by Jay Shepherd, February 16, 2015

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About Jay Shepherd

Jay Shepherd is a Toronto lawyer and writer. This site includes a series on energy issues, plus some random non-fiction on matters of interest. More important, it includes the Lives series, which bridge the gap between fiction and non-fiction, and now some short stories. Fiction is where I'm going, but not everything you want to say fits one form. I am not spending any time actively marketing what I write, but by all means feel free to share if you think others would enjoy reading this stuff.
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