The people you lead are a reflection of your flaws.
Dream sequence
I recently had a dream. It’s not a new dream. I’m running away from something, trying to hide. Each place I’m trying to hide is extremely vivid. The staircase of a bell tower in a European church. Outside a snowy ski lodge, riding up the mountain in a gondola. The outskirts of a shadow-filled Norwegian city on the beach of a lake in the evening.
Each time I reach a new, niche location, I think: This is the most unique place I’ve ever been. I’ll never be found. But, somehow, always, I’m discovered. It’s like I have a GPS chip hidden in my arm. I don’t get it. It’s a pattern. I’m found, then, I run to the next specific place and try to blend in. Then, I’m found again.
Funnily enough, I can’t seem to place what I’m running from. It’s a vague shape or physical thing. I can’t even describe it.
Family patterns
I recently moved back to the United States. I have been living in Europe for just shy of 10 years. My first stop has been to make up time with my immediate family in the Midwest. I haven’t been home for three years. And, I wanted everything to be the same, but it’s not.
Since I was last home, my little (baby) brother became an adult. We were pretty close when he was young but I haven’t been here. More importantly, I wasn’t here when he needed me. He doesn’t open up to me anymore and it makes me miserable.
My mom has a strange attachment style. Sometimes she’s so close that I can’t breathe and sometimes she’s so far that I feel completely isolated. I’ve noticed that I’m the same. In fact, I probably learned it from her.
Neoplatonism speaks of created things containing an expressed principle, which is a rational principle within each of us that forms our actions.1 In nature, it guides the growth of a tree from an acorn to a tall maple. In art, it guides the hands of a potter to create beautiful and well-formed pottery,
There should be something static within [crafters], that it is according to what is static that they will produce their works with their hands” (3. 8. 2. 13).
The expressed principle originates from the creator of the creation. It’s like a light inside of every being, guiding it toward its actualization.
"Still Life with Wild Strawberries". Adriaen Coorte, 1705.
But the piece can be a curse.
The Danish philosopher Søren Kierkegaard believed that he was cursed due to the sins of his father—his infidelity—which led to much suffering in Kierkegaard’s life. In his writing, Kierkegaard refers to this concept as hereditary sin.2 In my own behavior, I can see many inherited vices from my parents.
Hereditary sin does not only pass down in your family, but in other groups you lead, especially in startups.
Founder issues
In Naval’s podcast, Spearhead, David Sacks points out the fact that the psychological tendencies of founders become the mantras of their startups:
The simplest way to understand company culture is a macrocosm of the founder’s psychology. If there is a founder’s psychology problem, it’s going to be writ large across the company. This happens even if the founder has a reasonably balanced psychology. Their strengths, weaknesses, internal struggles—whatever is playing out in the founder’s head—will percolate into the culture. This is true of good company cultures as well as bad ones, and sometimes there’s a mix of both. Whatever the founder’s traits are, the culture will take on those traits.
This phenomenon is caused by two features: first, the founder’s behavior is constantly being role-modeled through subtle cues, creating a cult around the founder.
This is the way the founder behaves, so this is the way things are done.
Second, the behavior is reinforced by rewards and codified into catchphrases, including ones that are clear vices. Famous startup mantras include “Move fast, break things” (Mark Zuckerberg), “Strong opinions, weakly held” (Marc Andreessen), and “Forgiveness over permission” (Admiral Grace Hopper).
The concept of inheriting sin may sound preposterous, however, when we suffer greatly due to the culture of a work environment, we only can truly blame the head.
Blowing off some steam
Once upon a time, I worked in a startup where everyone was extremely cautious. The first day I was told, “It’s already risky being a startup, why should we do something that would take on even more risk?” Considering that the startup was operating in a highly-regulated industry, it made sense that the people working it were also very careful.
But, a culture of caution doesn’t necessarily make for a good startup. This mixed poorly with the CEO, who was insecure and perfectionistic. The startup itself stagnated often, which made investors unhappy. The CEO was overcome with decision fatigue; he thought obsessively about all his decisions, trying to choose the perfect option as if there were a rulebook he needed to meticulously follow.
When I came in as risk-taking, truth-telling, and guns-a-blazing, we butted heads and created a ton of friction. You can imagine how that ended.
On the other hand, I also worked very closely with another startup founder who viewed himself as diplomatic. He recognized the advantage gained from signaling, especially in corporate culture, but he knew deep down that it was hollow. At the start, I was impressed by that. But, he wasn’t without his own struggles. He was adamant about the greatness of his own creative ideas; he couldn’t kill his darlings.
A deeper problem concerned the authenticity of company values. My role involved speaking to people in confidence. I often heard frustrations about the founder being inconsistent with his own ideals. When I confronted him, he presented his own view on how to interpret the values, refusing to listen to any other voices. His version of diplomacy. But, to be frank, he just didn’t consider it important enough.
A while after I left, I spoke with an employee over coffee. Eventually, I asked about the company, and he repeated verbatim the same problems we had when I decided to leave. I remember feeling vindicated but left with a bad taste in my mouth.
Getting unstuck
The MIT System Dynamics group did a study on corporate modeling, which examined the forces that lie behind high-technology growth. They wanted to discover the most important factors in the success of a high-tech business.
It turns out, there are only two factors that matter in sustained growth: how fast you grow and the founders themselves. Every other factor had a negligible influence on the outcome of the business.
Okay, then.
If being a leader means vices always follow you and being a follower means you don't get to have an impact, then, what the fuck is the point of trying so hard?
Kazu. Herb Ritts, 1995.
Hol' up. The team is there for a vital reason: to actually execute the project. In order for the team to execute well, the leader needs to step up their game.
A good team executes the intent of the leader. This requires the leader to convey their intent in a way that is clear, simple, and not overly descriptive so as to be stifling. This method of execution allows as much autonomy as possible while remaining true to the original vision of the leader.
But why should we care about autonomy? More autonomy means more buy-in from the team, “Nothing happens unless the key people involved in it want it too, and if the top team does not stand four-squarely behind the strategy, it is doomed.”3 The team must participate of their own free will, which relies on your ability as a leader to convey intent and give space for freedom to execute that intent.
Not only does free choice matter but choosing the right people from the very start determines the culture of the company in saecula saeculorum. In Zero to One, Peter Thiel says that the first 20 hires in your startup will set the company culture into place. For instance, the Paypal Mafia (including Peter Thiel, Reid Hoffman, Keith Rabois, Elon Musk, etc.) were all the same type of nerd, with Cryptonomicon as required reading and preferring Star Wars over Star Trek. A unifying set of ideas needs to bring people together, “Everyone at your company should be different in the same way—a tribe of like-minded people fiercely devoted to the company’s mission.”4
For a similar reason, when you hire at the start of a venture, be picky. When someone leaves, they'll leave a person-shaped hole when they go.
An interior of Venaria Palace in Turin, Italy. Massimo Listri, 2016.
For those on the job market: there’s a very good reason why you aren’t a good fit for every company. People are not cookie-cutter shaped. For the same reason, your family is not going to get along with every other family you meet. Moreover, it’s impossible for startups to be value-neutral unless the founder is saying nothing.
Learnings
But remember: you cannot escape yourself. Your sins will always be there, following you, knowing exactly where you are.
Introspection is necessary. Action isn’t the only success factor and neither is speed. You need to understand how your weaknesses are influencing the behavior around you. Be aware of them. Be biased towards believing that those weaknesses may be causing something to be blocked or even sabotaged.
It’s possible to embrace your flaws and have a fighting chance.
Jessica Stam in John Galliano for Dior Couture. Corinne Day for Vogue, 2004.
One of my founder friends told me he used to be overly optimistic. He would read signs when other people wouldn’t see them. But, once he became aware of his inclination, he was careful to double-check his intuition. He would check with others to make sure they read the room in a similar way, especially in high-stakes situations.
But, despite the need to develop a clear view of your vices, remember to give yourself some credit. Your strengths are the unique features that are a vital contribution to the success of your enterprise, your family, or the group you’re leading. You are the hero in someone’s story, whether you want to accept it or not.
Conclusion
I can’t change the fact that I’ve been away from home for so long. But that doesn’t stop me from embracing and understanding my weaknesses, rather than hiding from them.
I used to study philosophy in (very) eastern Poland. Once, when I was riding a bus with a classmate, she told me:
Why should I compare myself with someone else? I don’t want to be them. I want to be me. Besides, I’m the best person in the world to do it.
1 Plotinus. Enneads. Edited by T. E. Page et al. Translated by A. H. Armstrong. 7 vols. The Loeb Classical Library. London: Harvard University Press, 1966.
2 Kierkegaard, Søren, and Alastair Hannay. The Concept of Anxiety: A Simple Psychologically Oriented Deliberation in View of the Dogmatic Problem of Hereditary Sin. Liveright Publishing Corporation, 2015.
3 Bungay, Stephen. The Art of Action: How Leaders Close the Gaps between Plans, Actions and Results. Nicholas Brealey Publishing, 2021.
4 Thiel, Peter, and Blake Masters. “What's Under Silicon Valley's Hoodies.” Zero to One Notes on Startups, or How to Build the Future, Virgin Books, London, 2015.
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