Your Ego Can Kill Your Career
A quick audit of CEOs sleeping with subordinates reveals how your ego is working against you.
If you follow business news, there appears to be an uptick in the trend of chief executives losing their jobs over romantic dalliances at work. What was so commonplace and accepted that it was more or less a sitcom trope of bosses sleeping with secretaries is now not only costing CEOs their jobs, but those sweet sweet golden parachutes they typically enjoy on the way out, led by the light of the bridges they burning behind them.
While many factors go into an affair, one of the main ones - especially for those with power - is their ego. As one rises through the corporate or political ranks, their ego grows like a psychological muscle that is constantly worked out by yes-men and other sycophants looking to please the ascending individual. When their ego grows too large, the individual essentially loses control of it, which makes leading (and impulse control) a difficult exercise.
Das Ech, Ich, und Uber-Ich
While literally translated to “the it,” “I,” and “over-I,” Freud’s concept of the structural model of the human psyche is most commonly known by its Latinized translations of the id, ego, and super-ego (to the consternation of some linguists, but I digress.)
To poorly paraphrase decades of Freud’s research, the ego is more or less the mediator between the id - whose only guiding framework is the pleasure principle - and reality, where things like decorum and societal expectations dictate that we can’t simply indulge our instinctual urges at the drop of a hat. The superego plays a part in trying to help the ego out by providing a structure against which the ego must play - more or less an individual’s moral compass, but this tends to remain static and is set much earlier throughout childhood.

When these three psychological players cooperate with each other, one’s individual world is in balance. Freud likened the role of the ego to a human riding a metaphorical id as a horse - they must use the power of the animal wisely and appropriately, while also tending to its needs enough to keep it satisfied with a person on top of it.
Ride Away
If we think of it through the Irish sense, the metaphor of riding is even more apt. And let’s be clear: no matter how accepted it has been in the past, sleeping with those at work with whom you share an unequal power dynamic is wrong. Full stop. And when you’re the chief executive, everyone at your office is on the wrong side of the power dynamic. But that hasn’t stopped high-profile CEOs from losing control of their id thanks to a faulty ego.
To name a few recent examples, CBOE Global Markets CEO Edward Tilly had to resign due to “personal relationships.” McDonald’s CEO Steve Easterbrook not only had to resign, but had his 9-figure compensation clawed back when it came to light that he didn’t just sleep with one subordinate (for which he was canned), but was cosplaying Austin Powers when it came to his randiness in the corporation. BP’s Bernard Looney had a bit too much energy when it came to his relations with employees. NBC Universal CEO Jeff Shell torpedoed an extremely promising career thanks to sleeping with a subordinate, years after having to fire an executive for doing the very same thing. And most recently, Norfolk Southern CEO Alan Shaw - who had just survived a very public and difficult proxy battle with an activist investor group - was finally fired at the group’s behest when it came to light that he and NS’s general counsel Nabanita Chaterjee Nag were brazenly carrying on an affair at the company (Nag was also fired.)
It would be so easy to point to the philanderers and say “Well, they’re just crappy people doing crappy things.” And that might explain some of the situation if a solid pattern can be established, but the reality - as it usually is - tends to be a lot more complex.
Reality’s Relationship with the Ego
With great power, comes great responsibility. And in the corporate world, a huge part of that responsibility is controlling one’s ego so it can continue to guide us properly in a world where reality becomes warped simply through one’s success.
Powerful people are much more susceptible to ego inflation because as they climb the corporate ladder they are often interacting with people whose goal is to gain the powerful person’s favor. That tends to lead to people pleasing of the successful individual - confirming their judgement is correct, or their ideas are awesome, or simply agreeing with them constantly.
If executives aren’t careful, this can begin to distort their reality - if all you are told is you’re crushing it, you begin to think that’s simply an innate skill you have. You begin to think you are King Midas and you are where you are solely because of your ability to do things others just can’t. Through that reasoning, if you’re always right, why shouldn’t you indulge your id? When your reality becomes that distorted, the ego has less ability to regulate because it’s working on bad information.
You begin to fall prey to “hubris syndrome” - a condition undetectable until someone has held power for a number of years. What is fascinating about this is that this is not something easily identified in anyone outside of a power structure; it only becomes apparent after power acquisition. It’s essentially the culmination of power’s corrupting properties on the psyche.
Maintain Your Reality
Hubris syndrome - and ruining your career and marriage - aren’t inevitable outcomes of climbing the corporate ladder. And while the examples are voluminous, they certainly aren’t the majority. That doesn’t mean we all couldn’t use a refresher on how to keep our egos in check and ensure a proper relationship with reality (and, crucially, those around us.) There’s a couple of good ways to do this:
Say no to the yes-men: Surrounding yourself with sycophants is a losing equation and has taken down many a powerful person. Not only do you need the right people, but you also need the right environment that allows for dissent. If you’re pushing back against every piece of criticism, you’re encouraging a “yes man” environment that will begin to mess with reality and your ego.
Evaluate your journey: Think about the people and circumstances that have helped you get where you are today. Realizing that success is not a solo journey will help ground you in understanding your power is not ex nihilo but a culmination of your efforts and of those around you. Take time to show gratitude - it will keep your feet in better contact with the ground.
Sample some humble tart: In 1986 Richard Dreyfuss was making a Hollywood comeback after wrapping his Benz around a tree while high as a kite on cocaine. The resultant film was the wacky but sentimental Down and Out in Beverly Hills. I’ll save you the full synopsis, but the movie is about a successful but dysfunctional family snapping out of their problems thanks to a homeless Nick Nolte trying to drown himself in their family pool. In it, Dreyfuss has a moment where he is reflecting on his success, looking at Nolte and saying “There but for the grace of God, go I.” Dreyfuss was able to course correct his own ego’s relationship with reality through rehab and - eventually - this movie, firmly turning his career around. Humility is one of the best medicines for an outsized ego. Take it in small doses before being force-fed the pie version by your bosses or board.
These concepts of Freud’s are philosophical, not necessarily scientific, but they make sense intuitively. The id is what it is, your super ego is likely already set, so the best thing to do is to maintain your reality, to make sure your ego is working off of the best signals it can to maintain the balance required for life in society and at the office.
Grab Bag Sections
WTF MKE: I had the absolute privilege of spending the weekend with some of the best degenerates I know in a tucked-away little jewel of the midwest in Milwaukee, Wisconsin. I know typically the WTF section is for rants and complaints, but honestly the MKE was delightful. Friendly folks, classic German lagers, taverns galore, and a damn nice baseball stadium, to boot. All of that said, I do have some notes.
Boy is this a car city. Said group of degenerates are classic northeasterners and we like to walk places in a city. The morning walk from the AirBnB to the closest Dunks was devoid of anything resembling greenery and was an expanse of concrete as far as the eye could see. It also included one of the most accidentally (?) imposing police buildings this newsletter’s author has come across.
We also need to talk about the official abbreviation of MKE for Milwaukee when MWK is the clear and obvious answer to the question “How should we abbreviate this town?” Also, who set the policy at American Family Field that the pitching section to see how fast you can throw a baseball has an age cap of 14? Reverse ageism at its worst, folks.
But despite these things, Milwaukee was a great time and we appreciated the midwestern hospitality for a half dozen 30-somethings who still think they’re in their early 20s when they end up in the same geographical location for multiple nights. But whatever, it was frickin’ awesome.
Album of the Week: I’m heading to London this week. While it may look like I am there to work out of the London office, I’m really there for some sneaky pints and to scope out Oasis tickets for next year because seeing that band play at Wembley would be a top 5 life experience. So it’s only natural we deep dive into their debut album Definitely Maybe.
In a surprise to very likely no one, the making of this album was a drama-filled disaster. The album was recorded twice and mixed three separate times (the final cut being a desperation play that worked out quite well for the group.) Noel had to talk his way into the band (and insisted on complete control.) The first producer was canned and the group barely got the album to market. It’s a microcosm of what Oasis is.
Despite the final mix not being the perfection the Gallaghers and Co. expect out of themselves, the album is excellent. “Live Forever” is an absolute banger and the best track on an album full of good ones. “Slide Away” is that classic Oasis sound (and the only song kept from the original, ill-fated first recording sessions.) In the same vain of this newsletter’s love of “She’s Electric” from the very first album of the week, “Married with Children” is an excellent deep cut, if not a mellow outro.
Now let’s see how long next year’s tour lasts.
Quote of the Week: “The first half of life is devoted to forming a healthy ego, the second half is going inward and letting go of it.” - Carl Jung
See you next week!