The deal closes on a Thursday. By Saturday the champagne is gone, and so is the sleep.
This is not the burnout story. Burnout follows depletion. This follows victory. The person finally has what he worked twenty years for, and something in him quietly refuses to accept it.
Most leadership advice treats this as a performance problem: rest more, delegate better, find the next goal. A century-old idea from psychoanalysis treats it as something else entirely. It is a verdict being carried out.
In 1916 Freud published a short essay with an unusual subject: people who fall ill not when they fail, but when they succeed. He called the section “Those Wrecked by Success.” It sits in Some Character-Types Met with in Psycho-Analytic Work, alongside two other studies, “The Exceptions” and “Criminals from a Sense of Guilt.”
His observation was uncomfortable. Some people, he wrote, “fall ill precisely when a deeply-rooted and long-cherished wish has come to fulfilment.” One of his cases reads like a board memo. A respected academic had wished for years to succeed his own mentor. When the post was finally offered to him, he hesitated, belittled his merits, declared himself unworthy, and sank into a melancholia that kept him from work for years.
Freud then turned to literature for the same pattern: Shakespeare’s Lady Macbeth, who collapses once the crown is won, and Rebecca West in Ibsen’s Rosmersholm, who rejects the happiness she schemed for.
His explanation was not exhaustion. A wish can be tolerated while it stays a fantasy; the mind defends against it once it becomes real. What forbids the enjoyment, he argued, are “forces of conscience,” largely unconscious, and he tied them to the oldest relationships of all, with father and mother. The success is felt as taken rather than earned. The mind then seeks relief through punishment. Illness, self-sabotage and misery become the sentence served for having won.
The moment of victory can be the moment the old verdict of conscience is carried out — Photo: konat umut budak / Pexels
How Is the Sentence Served at the Top?
In the executive suite the punishment rarely looks like punishment. It looks like character, strategy or bad luck. Typical forms:
The body: insomnia, a sudden illness, or a crash in the weeks after the win.
The decision: an unforced, oversized bet that puts the new position at risk.
The relationship: a picked fight with a co-founder, a board or a spouse, often with the person who made the success possible.
The appetite: a turn toward something that could end it all quietly, from an affair to a reckless trade.
None of these is proof of hidden guilt on its own. The pattern is the clue: the trouble arrives precisely when the wish comes true, and the person cannot explain why.
Freud’s companion study, “The Exceptions,” describes the mirror image. Some people carry an early injury and feel entitled, ever after, to privileges as compensation. In a leader this reads as boldness until it reads as a scandal. Boards meet both characters, often in the same person at different moments of a career.
Why Does Nobody Notice? The Room Gets Quieter as You Rise
The higher the seat, the fewer people will tell you what they see. A 2012 RHR International survey of 83 CEOs found that half reported loneliness in the role. Of those, 61% said the isolation hurt their performance. The report describes first-time CEOs as especially affected (Inc., reporting the RHR study).
The sample is small and the data are old, so read them as a signal, not a census. But the mechanism is clear. Unconscious guilt works best in silence. A leader with no one to hold up a mirror can mistake a self-inflicted wound for a market event, and so can everyone around him.
The higher the seat, the fewer people hold up a mirror — Photo: Shivansh Sharma / Pexels
Which Three Questions Are Worth More Than a Vacation?
If the win felt strangely empty, or the trouble started right after it, these questions go further than another retreat:
In my mind, who paid for this success? A partner pushed out, a parent outdone, a sibling left behind. Guilt keeps an older ledger than the balance sheet.
Whom would I be betraying if I simply enjoyed it? For some people, pleasure itself feels like disloyalty to where they came from.
Where does the bill arrive? Body, marriage, portfolio or board. The place the punishment lands is rarely random.
Coaching asks how to perform better. Analysis asks who is performing, and for whom. For a person who has already won, the second question is usually the one still open, and it is a question that can be answered.
Freud S. (1916). Some Character-Types Met with in Psycho-Analytic Work. Standard Edition, vol. 14, pp. 309–333. London: Hogarth Press (trans. J. Strachey). PEP-Web
Stillman J. Loneliness: An Under-Diagnosed Epidemic Among New CEOs. Inc., 20 January 2012 (reporting the RHR International CEO survey). Link
