The problem with leaders
Welcome into my lair. It's pretty nice.
I’ve never had paying subscribers before, but here you are! I feel pressure to deliver. Fantastic! Horrifying & satisfying! And for our first paid issue I want to talk about leadership because I think we’ve lost track of what it is. I will frequently write about navigation through poor leadership, so we may as well start at the root.
Ed: Shared as Free post starting 3/22/26.
LEADERSHIP
Leadership (pushes her glasses down on her nose) is derived from the Old English word "laedere," meaning "one who leads," which itself comes from the verb "laedan," meaning "to guide" or "to bring forth". It connotes that you are, in fact, leading other people.
The “ship” concept is slightly different. Per the Google snippet, leadership as a word doesn’t show up until 18th century or so, but “the concept of leadership has been around for much longer, evident in religious, political, and military figures throughout history.” Well, that seems fraught with meaning already. Do we like the ship we’re on?
Also the word leadership itself is agnostic as to what we would consider good or bad leadership. I do have opinions on the quality of leadership and what drives actually positive outcomes for the world, but we can cover that another day.
WHAT IS IT FOR?
For now I want to focus on the “to guide” and “to bring forth” element of leadership. Because…author stares out in the distance in contemplation…
We are letting leaders wildly off the hook today. They get christened at some point as a ‘leader’ based on some element: their amazing product acumen, technical knowledge, charisma, or maybe even hypothetical knowledge of how to abuse the US loan and legal structure. Once labeled as a leader, they get unlimited power to do anything and everything. FULL BELIEF. They are LEADERS. Guide us forth any which way! Illegal or inappropriate behavior, be damn!
To receive this level of permission, they must meet our unconscious criteria of what a leader should look and sound like, including all of our internalized misogyny, racism, and other prejudices. They only, and especially, get FULL PERMISSION if they look and sound “right”. Sometimes we’ll give this to them before they’ve proven anything! He’s tall with a deep voice, and boom, he says important things! For everyone else, we doubt them and tear apart everything they say, but not the leaders.
But one second.
What are they guiding?
Who are they guiding?
What are they bringing forth?
Unfortunately, once we place our trust in leaders, we are slow to evaluate the vector of their leadership. Where are they leading us? Are they pushing us towards an outcome that only benefits them or the system? Even if we observe disturbing trends, we are likely to accept the behaviors as leadership once we think someone is a leader. Individually we don’t want to be wrong, and collectively we have chosen leaders whose primary talent is convincing us they are right. And there’s not really a plan B if a leader is heading astray; we are taught to follow.
THE RUB
Obviously I have the US government on my mind, but it isn’t just that. Capitalism is weighing on me heavily, and I’ve written about its impact on tech aspirations a lot in the new chapters for my book. Not that I don’t agree with the economical principles of capitalism, but the entire structure does depend on key leaders believing they have responsibility toward the larger population. The ‘free market’ requires self policing in the absence of control.
And herein lies my worry about leadership in modern times: it’s for personal profit and for benefiting other leaders. Even Congress! Even tenured professors! Even your boss’s boss’s boss! It’s both disturbingly separated from the everyday issues of people while also benefiting from their continued suppression. In other words, you need to have underlings to lead. Capitalism exacerbates this since the highest leaders, CEOs, answer to a self-calculated board and the demands of usually wealthy shareholders. So the system continues to turn with CEO salaries astronomically growing, profits soaring for shareholders, and minimum wage staying minimum.
WHAT CAN WE DO?
Despite this narrative being pretty meta and not the ilk of “what do I say to my boss”, I will always give some advice. We all need agency even if it’s hard to change the world. Please comment below if you have other ideas.
Don’t act like a follower.
Over time, leaders end up in a vacuum surrounded by ‘yes’ people. When they talk in front of crowds, everyone claps. They are rarely challenged because everyone near them is either a believer or paid. If they’re rich, they become divorced from everyday human problems: no lines, full access, everything catered. Gradually, the rest of us fade into background characters. We’re NPCs — in video game lingo — that’s the filler people that take up the space around the real players. They are meant to be passed by or killed. Leaders tell themselves lots of stories to make any of their behavior acceptable, most of it relies on their individual superiority. And often we act like leaders are right, acquiescing to what they want either to profit or survive.
So don’t. In whatever ways you feel comfortable or possible, remember that you have agency. You can vote with your feet, your money, your readership, your effort. And while those acts seem small, they add up. See: The Tesla stock price.
Don’t write a blank check.
Know why you like a leader and why you don’t. Take a real look at them. Know more about them. Read up on how they got to their position of power. Pay attention to the decisions they make and how they make them. See how they treat different people at different levels.
You can still like them, but know what you like them for. Are they a great speaker? Do they stand up for what’s right? Do they pay attention to the needs of others? Are they amazing at innovative ideas? Also know their weaknesses. Are they shitty to certain people? Are they awkward at speeches? Do they make impossible promises? Do they lack empathy?
Now, figure out where you will follow them and when. Decide. Don’t follow blindly. Help what you believe in, and don’t help what you don’t. Give feedback, if possible, where you don’t align.
Get off the ship.
My favorite thing about the word “leadership” is that it can imply two things: a physical ship and a relationship. Either way, a ship is something you can get off or out of. You can “consciously uncouple” from the ship. YOU CAN LEAVE.
(This metaphor works better for leaving a team or company than, say, easily leaving the country, but I’m sticking with it.)
You can leave if you don’t like where the ship is going. Or if you don’t like how the ship treats you. If you don’t believe the ship is being honest to you. If you are seeing the ship layoff your teammates. If you are simply tired of being on the ship, YOU CAN LEAVE.
It’s not that you couldn’t cut it. It’s not that better people than you can handle the ship. It’s not that if you were stronger, the ship wouldn’t bother you. It’s not that you need better strategic knowledge or political savvy to understand the ship. It’s none of that.
The ship didn’t work out for you. Period. And now it’s okay to start looking, in a discerning way, for another ship.
Next Up
I’m aiming for Tuesday each week for this newsletter. I plan to delve into aspects of leadership, digging into aspects both good and bad. I’ll also do an advice series on difficult feedback people have received. If you have requests, comment below or join the chat.
Until next time,
Alana