When You've Had Enough—Have You?


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Alex was in New York City real estate, a cut-throat game where politics, high finance, and the encroaching nemesis of climate change were eating most players alive. “You know,” he told me, “between the City Council and the unions, let alone the banks and the flood zones, it’s amazing that anything gets built.”

But it does. Billions of dollars of it, every year. Guys like Alex made it happen—deft, sophisticated operators who know the law (and some good lawyers) and can manage projects with multiple intricate moving parts. Did he love it? Sure. But he came to see me because he was ready to kill.

Okay, figuratively ready. For years, Alex had worked in a firm run by his father, which he’d joined straight out of business school. He’d started in accounting but, over the course of twenty-five years, had taken over operations—acquiring property, dealing with contractors, ensuring compliance with city regulations. His problem was that his father, now approaching eighty, still wouldn’t make him a partner.

“Look,” Alex said, “I brought our firm into the 21st century. My father was old-school, a back-slapper. I made him rich.”

Alex tried several times to be made a partner, but his father just insisted that the firm was his. “He said that when he died, I’d inherit it.” But Alex didn’t feel that he should have to wait.

He felt he was getting nowhere in being reasonable with his father. Couldn’t the Old Man see why it was advantageous to allow Alex greater prominence in the firm, even apart from the ethics involved? Most people thought of the firm as Alex’s in all but name, anyway, and were surprised when his father still had to sign off on every deal.

Alex suspected that his father’s self-esteem was tied up with the firm and that admitting his son to partnership would, in his mind, dilute his sense of self. “I actually feel sorry for him,” Alex said. “He’s always run the firm, it’s always been known as his, and he’s afraid what might happen if anything changes.” Alex didn’t want to hurt his father. But still, he thought he was looking out for the firm’s best interests and that he deserved a share in the profits. “What am I supposed to do,” he asked?

Family can be a source of happiness, but internal conflicts can be bitter, exhausting, and intractable. People don’t always see the issues as based on disinterested concerns of practicality and ethics. They bring in personal considerations like gratitude, and looking out for your parents, and preserving harmony for the sake of harmony. Long-simmering resentments can just keep simmering. Alex felt he was up against a father whom he never intended to antagonize but antagonized nonetheless by simply outperforming him. “It’s like there’s this wall,” he said, “and no amount of logic, or even appeal to their own self-interest, will ever breach it.” He felt trapped.

At one point, Alex thought he’d quit and start his own firm. But he thought there was a lot of goodwill associated with the firm and that it would be hard to replicate right out of the box. He also thought that if he quit, the firm would implode, and he couldn’t bring himself to do that to his father. Alex was furious with his father but still loved him. He couldn’t hurt him.

So, what could he do?

One problem of living in a family, as we all do –

is that we’re expected to balance our own interests with those of other people. Of course, we want to achieve that balance and we work hard at it, even making sacrifices. But just as often, tensions develop. The interests of one person, however misperceived, collide with those of other people. When love and history and obligation complicate all these tensions, it can seem impossible to sort through them.

So, I suggested that perhaps Alex could talk with his father again, this time deploying a different, less assertive strategy. Instead of asking outright to be made a partner, maybe he could ask for a raise. Maybe his father wouldn’t have to sign off on every deal. The point was not to seem threatening, not to suggest that Alex meant to become his father’s counterpart and then move to replace him. His father was afraid that letting go in any way might mean he’d be kicked upstairs.

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But maybe if Alex assured him that sharing some of the profits was no threat to his status, he would acquiesce. The point was to let the world know that his father, and hence the firm, acknowledged Alex’s worth and was going to maintain continuity. It wasn’t all that Alex wanted, but it made business sense while it would keep his father from fretting.

When I most recently spoke with Alex, he told me “I’ve got to convince my father that’s it’s in everyone’s interest to show that we’re planning for transition. I’ll say, ‘Look, we can’t just keep people guessing.’” This seemed smart.

TV has reminded us, through the drama Succession, that family cross-currents can get in the way of a smooth transition. We have to work within the constraints that love and practicality impose. “In families,” I commented, “it can be a high-wire act. You’re trying to balance competing forces.” We should expect that any such act will, at times, seem fraught. We just have to keep going and keep up the balancing act. If family means anything to us, we may have to compromise. Happiness won’t be everything all at once. But we can keep trying.

We balance self-interest with love. But when we finally must square the circle and make progress in resolving problems, we realize that it’s in our self-interest to love. We can’t function in a family setting unless, at least to a degree, our actions have a substrate of love. So, the point is to determine how much love we have at our disposal and then act accordingly.

Alex realized that he could never act in ways detrimental to the family, so—despite his exasperation—he found workarounds that accommodated his father and brother. Not total accommodation, but enough so that he felt good about himself. He had to balance his need for independence and success with a desire not to disrupt the family.

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