5 Life Lessons from Succession

"You can't make a Tomlette without breaking some Gregs."

Previous generations drew inspiration and life lessons from classics such as “The Catcher in the Rye”, “The Great Gatsby” or “The Brothers Karamazov” maybe even Shakespeare. For those of us born after 1980, we had Succession.

When it comes to family drama, backstabbing, and the relentless pursuit of power, no show captures the chaotic essence of corporate ambition quite like HBO's "Succession." The series, centered around the Roy family and their global media empire, offers a masterclass in the complexities of business, leadership, and human nature. Much like attending an intensive MBA program with a front-row seat to a Shakespearean tragedy, "Succession" has plenty to teach us—if we can look past the dysfunction and focus on the underlying lessons.

Here are 5 life lessons, embedded with the series that we can learn from the Roy family and their associates.

(Here is your spoiler warning if you have not seen the Series in its entirety)

Lesson#1 “Sometimes it is a big dick contest” - Logan Roy

In the cutthroat world of Succession, power and dominance often overshadow collaboration and diplomacy. Logan Roy’s blunt declaration, “Sometimes it is a big dick contest,” encapsulates a harsh reality of both business and life: sometimes, brute force and sheer willpower are necessary to come out on top.

Logan says this line to Kendall during the premier as part of a discussion around naming Logan’s successor. Logan was not pleased that it was taking Ken so long to get a deal closed, even with all of the concessions Ken kept making. Logan told Ken that his inability to get the deal closed exemplified that he lacked the character needed to lead Waystar Royco. This declaration haunts Ken throughout the series.

It is fair to question Logan’s logic but his assessment of Ken is accurate; Ken lacks something. Despite all of his attempts, He is not a killer. This lesson is a stark reminder that in high-stakes environments, whether in the boardroom or beyond, assertiveness and confidence can be as crucial as strategy and intellect. It’s not just about having the best ideas; it’s about having the audacity to push them through against all odds. Logan’s ruthless approach might not always align with conventional wisdom about leadership, but it underscores a critical point: in a world where power dynamics are constantly at play, the ability to assert dominance can be a decisive factor.

Logan’s empire is a corporation, in corporations, even family owned ones, the oldest male is not the automatic heir. Even if the eldest boy is the heir apparent, they still need to convince others around them to vote for them. No matter how badly Kendall wants to be king, he cannot. Ken’s journey in Succession is a reminder that if you want to achieve your ambitions, knowledge, skill and desire is not enough. The more ambitious, the goal, the harder it will be to achieve. This is where strength of character is needed to fill in the remaining gaps. However, in Lesson # 2, you will see why you need to be careful of when you choose to demonstrate your character.

Logan Roy holds many similarities with another fictional character I wrote about recently, Tywin Lannister. (See 5 Business Lessons I learnt from Game of Thrones)

Lesson#2 “Don’t send d*ck pics to your father” - Roman Roy

In the chaotic world of Succession, Roman Roy’s infamous blunder—sending an explicit photo to his father, Logan, is a powerful reminder of how one impulsive act can instantly destroy credibility and goodwill, no matter how carefully it’s been built up. This is a perfect encapsulation of how it takes an entire lifetime to build a reputation but only a few seconds to ruin it.

Throughout the series but especially Season 3, Roman had been steadily proving himself within the Roy family empire. His sharp instincts, strategic moves, and unexpected displays of loyalty were earning him a significant amount of respect and positioning him as a serious contender in the family’s power dynamics. However, in one moment of poor judgment, all that progress was undone. The photo he accidently sent to Logan wasn’t just a personal embarrassment; it was a professional catastrophe that shattered the image Roman had worked so hard to cultivate.

Roman’s mistake underscores the importance of maintaining professionalism and discretion, especially when you’re on an upward trajectory. His loose and joking nature was an advantage in that it helped him connect with people such as Matheson, which earned his father’s trust. However, his nature along with his weird perversion with Jerry, led to his downfall. Starting off with joking flirtation (which you probably shouldn’t too with your company’s chief corporate legal council), before escalating to increasingly inappropriate behavior. This culminated in Roman, attempting to send a picture of his d**k to Jerry, but it instead went to his father.

Up until the picture was sent, it looked almost certain that Roman had finally shed his image of the court jester and would take over the empire. The repercussions of a single misstep can be swift and severe, as Roman’s downfall so vividly illustrates.

This is why, it is generally best not to send elicit photos, but especially not to people who do not want them. I would especially recommend not sending to family members unless it is for medical purposes. This can make people perceive you differently.

That is enough about phallus¹ (for now)

Lesson#3 "What the f*ck is this obsession with milk? You know who drinks milk? Kittens and perverts." — Roman Roy

In the world of Succession, Roman Roy’s irreverent quips often serve as comic relief, but they can also reveal deeper truths about the characters’ motivations and priorities. This particular line underscores a recurring theme in the show: Logan Roy’s intense concern for understanding the perspective of the average person. This differs greatly from most of the other characters, who are only concerned with elites.

Logan built his empire by meeting the average person where they were. The Roy family is based on the Murdoch’s, the owners of Fox News and other media brands. Fox News is largely criticized for its role in the public discourse, often being blamed for abandoning journalistic principals in exchange for brazen partisanship. Waystar owned ACN appears to fill the same role in the Succession universe. Logan might not agree with the positions taken by his media companies, but that does not matter to him. He wants his media companies to give the people what they want to hear in order to build trust and brand equity with their customers. This is why Logan is acutely aware that public opinion can make or break his business ventures; his obsession with the average person’s preferences is necessary to maintain his influence. If his company does not understand it’s audience, they won’t be able to cater to it. If they don’t cater to it, they will lose their customers.

Roman’s dismissive attitude toward seemingly trivial details like the obsession with milk contrasts sharply with Logan’s mindset. Logan knows that every detail, no matter how small, contributes to the larger picture of brand perception and market positioning. Roman’s irreverence shows the gap between Logan, who built the company and his children and the other executives at the company.

This demonstrates the difficulty with the succession. How can Logan entrust his company to people that know nothing about how the average person lives, when their whole business is predicated on exactly that? No matter what business you are in, you need to understand your customers, or you cannot give them what they want. Even outside of business contexts, you want to be empathetic, which will allow you to better understand situations you will find yourself in. Logan seems to be the only one at Waystar Rocyo that understands this.

Lesson#4 “Don’t be a boar on the floor” - Greg Hirsh, Tom Wambsgan & Logan Roy

In one of Succession's more memorable scenes, Logan Roy orchestrates a game called "Boar on the Floor" to expose disloyalty among his senior executives. The spectacle is humiliating, reducing powerful individuals to scrambling animals in a power play that underscores Logan’s ruthless control over his empire.

There was a consensus amongst the executive team that they disagreed with Logan’s desired acquisition target. Instead of bringing this up directly with him, the executives all tried to pawn off the uncomfortable conversation on somebody else, to not lose favor with Logan.

When Logan learns of this from Tom, his son-in law, he understands that his decisions are being undermined and everybody is too much of a coward to tell him. For Logan, this exercise is about establishing dominance, showing that to him loyalty is paramount and rooting out any threats to his authority.

"Boar on the Floor" is a vivid metaphor for the dangers of losing your autonomy and dignity in the pursuit of approval from those in power. It serves as a cautionary tale about the importance of maintaining self-respect and integrity, even in high-pressure environments. In the Roy family’s world, where power dynamics are constantly shifting, those who grovel and degrade themselves for favor are often the first to be trampled.

(Can skip to 2:45 if pressed for time)

For Tom and Greg, participants of the game, this scene illustrates the perils of complicity. Both characters are desperate to climb the corporate ladder and stay within the empire, they give up any sense of pride, morals or personal boundaries. The lesson here is about the cost of ambition: achieving success at the expense of your values and self-respect can lead to a hollow victory, one where you’re perpetually at the mercy of those more powerful.

Never find yourself in a position where you feel like you need to be a boar on the floor. Recognize your own self worth, and have some damn pride. At the end of the day, you need to be able to look at yourself in the mirror and have respect for the face that you see. The characters involved with what scene, have clearly forgone any sense of pride or agency, all in the pursuit of wealth and status and this scene was a perfect representation of that. This relates to our next lesson.

Lesson#5 "What am I gonna do with a soul anyways?" — Cousin Greg Hirsch

Cousin Greg Hirsch is the most relatable character in Succession. At the beginning of the series, the trappings of generational wealth are completely foreign to him, unlike his cousins Kendall, Roman and Shiv. We are introduced to Greg after he loses his entry level job, something his cousins likely never had.

Despite his upbringing and being new to the corporate world, he immediately exhibited a keen understanding of power dynamics and knew how to curry favor. He likely read the Prince by Machiavelli or a Kissinger biography. Greg’s air of goofy cluelessness, eliminated the chance of somebody viewing him as a threat, at the same time, his position in the family was just close enough that people could not entirely dismiss him. This is exactly why Tom, Shiv’s husband, took Greg under his wing, forming the purest relationship in the series, “The Disgusting Brothers”.

Neither of The Disgusting Brothers, are one of Logan’s children, therefore if they wanted power, they needed to get it through maneuvering. Tom was able to rise to at least middle management, without nepotism and from the start of the series, shown that he was willing to do whatever was needed to climb the corporate ladder. Hailing from Minnesota from a rich but not excessively wealthy family, Tom had to learn everything about the east coast corporate elite lifestyle himself. Even though, the Roy family, including Shiv all treat him like he is beneath them, he had engrained himself into their world. He clearly gave up his soul a long time ago. This is why he serves as the appropriate mentor to Greg².

This quote, delivered with his characteristic naivety, underscores a pivotal moment where Greg contemplates the value of his integrity versus the allure of power and wealth. This moment had been in the making for 3 seasons from the moment Greg appeared at Logan’s apartment. Greg had gradually became one of the Roy’s, learning how people of that financial standing behave and how and when to shift alliances etc.

By the time he had said the line, he had already sold out his beliefs. He was suing Greenpeace, abandoning a girl he recently coveted in exchange to try to date an Italian Contessa and had switched allegiances several times. The scene merely served as a confirmation of Greg’s descent (or ascent depending how you look at it). Either way, Greg ending up playing the game better than anybody, this is why by the end of the series, he found himself in a situation where he came out on top, regardless of whomever was named successor.

Greg showed how to climb quickly: You need to be cunning, adaptable and flexible with your allegiances, playing a fine line between being useful, but not so useful that people are worried that you will replace them.

Greg’s journey also serves as a cautionary tale about the slippery slope of ethical compromises. Each small concession can lead to larger, more significant sacrifices, ultimately resulting in a complete erosion of one’s moral foundation. By the time you realize the extent of your compromises, it might be too late to reclaim your integrity.

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1. Anyone know how to pluralize phallus?

2. You could even see Tom as a future version of Greg.