On Pirates And Management

[Editor’s note: mild spoilers ahead for Our Flag Means Death, a gay romantic comedy currently available on HBO Max.]

Early in my career, I wanted to be management. Director. Vice President. Chief Design Officer. From where I sat, down in a cubicle pushing pixels, that’s where the power lay, where the real work happened. (Never mind I was doing real work; it just wasn’t decision-making power.)

Being a manager requires managing people, and I was informed multiple times that you are not people management material. And that colored my career for a long time. “I can see you as a creative director, maybe. Or a principal/staff level. You’re a clear leader in this organization. But manager? Department director? That’s not in you.”

Like any good designer, though, I spent a lot of time observing and researching. Why was I so “not cut out to be a manager?” Surely I could watch my bosses and figure out what I was missing.

The problem: I had a number of terrible managers. One of the worst did their best to run me out of the organization with the grace of an elephant falling down stairs. Their management style was toxic, a combination of their own trauma-born insecurities and their emotional incapability to manage people as people, not as autonomous labor units. They weren’t the only managers like that. I saw a lot of managing through fear, managing through paternalistic “I know what’s best,” managing autocratically.

I also saw a lot of fear in doing the right thing and standing up to bullies. Often it was because the bully in question was so fundamentally important to the organization, supposedly, their behavior was tolerated.


One of the underlying themes of Our Flag Means Death how toxic masculinity has left men emotionally stunted and traumatized. The two main characters, Stede and Blackbeard, and their personal traumas provide the frame.

Stede Bonnet, the aristocrat bullied from youth and told he was a soft rich boy that would never matter, haunted by the abuse.

Ed Teach, who murdered his own abusive father, went to sea, and built the legend of Blackbeard around him to make himself strong in the face of his own trauma.

The pain inflicted on them came from society’s view of what a man, and a pirate, should be. Men should be manly, not soft. Pirates should be scary and bloodthirsty… not soft. There’s a zone you have to stay between, a standard deviation around society’s “normal.” Go outside this and you will be punished, at times violently.

Their traumas influence how they manage their own crews. Bonnet, emotionally traumatized by childhood bullying and plagued by feeling like a disappointment, leans hard into a “people-positive management style.” He centers on his crew and their needs, foregoing his own needs, telling them the best way to solve conflict is to “talk it out.” The result is a fairly confused crew… but also a crew that knows what to do and just does it. They don’t need to be “managed,” they just need to be left to take the initiative and do what they do best. They already knew how to pirate. By the end of the first series, a crew that wanted to mutiny against him in the first episode stands up for him when one of the chief antagonists insists he has not a pirate, just a weak little man.

On the other side, Teach, aka Blackbeard, cultivates a public persona so fearsome that people run at the sight of him. Internally, he’s an emotional mess who relies heavily on that perception to keep him going… to the point that he’s going through the motions at the start of the series. But his name has carried such cache he’s been able to build a traditional top-down culture of fear. It’s driven by his lieutenant, Israel “Izzy” Hands, by far the most competent pirate in the series. He’s so good Blackbeard’s ship is running with far less than a full complement of sailors. He’s just better at it.

In the tech industry we’d say he’s a “10x.”


The 10x developer, the 10x designer is supposedly as good as 10 developers or designers. They’re mythical, of course, but they’re the dream of every tech startup. Imagine the money savings of having someone that does the work of ten when you’re trying to bootstrap a business. They produce more work, faster, better than everyone else.

My experience with the mythical “10x” is different, though.

I met a lot of “10x” people who were terrible at collaboration. Some had zero people skills and zero tolerance for things not done their way. They’d see others as incompetents who, if they weren’t doing this his way, were clearly inferior. This would turn into abusing and bullying others on their team, or on the other end of the spectrum, pedantic micromanaging. 

Often they get put into managerial positions over these same people, which just exacerbates the problems.

Meanwhile, the rest of the team gets less productive. They have to tiptoe around the 10x’s behavior. The lack of agency drives the best of them to go elsewhere. The ones that remain are endlessly stifled, whether by the bullying or the demands from the 10x that everything must run through them. (One of my refrains is that a 10x person often means the rest of the team performs at less than 1x.)

Companies will tolerate all of it. I mean, they’re assholes, but they’re geniuses, and could you imagine where we would be without them? The companies felt the 10x was so fundamentally important to the organization, supposedly, their behavior needed to be tolerated, high turnover be damned.


Izzy is an asshole. First time he’s captain the crew mutinies within a matter of days — because he cannot manage people that do not fit his mold of what a pirate is. Bullying, toxic, and only tolerated by Blackbeard because of his competence, he sees piracy through the lens of being the “alpha wolf.” He wants Ed Teach to be Blackbeard, even though Blackbeard is a character on this stage, even though Blackbeard is not who Teach really is.

So Izzy becomes an enforcer, the one who insists Stede is a worthless pretty boy and Ed IS Blackbeard and not the mopey guy pining for his boyfriend. What he needs Ed to do is play the role society needs him to play, and Ed doesn’t, he’ll push him until he does. In light of a gay love affair, it codes as enforcing the norms expected of men (and pirates). This isn’t normal, and thus needs to be dealt with.


I was bullied pretty relentlessly as a kid because I was outside the normal. I was smart, gawky, unathletic. “Nerd” and “geek” were slurs back then, but they were the softer ones compared to the homophobic slurs. And mind you, I’m cishet, so none of this was about actually being “gay” as much as appearing what, in their minds, was “gay.”

Meanwhile, standing up to bullies was verboten. You didn’t want to become a target yourself. So you stayed inside the lines and kept quiet.

Masculinity, especially toxic masculinity, requires enforcement. The “right” way must be modeled, the “wrong” way must be pilloried, attacked, and treated as making someone “not a man.” It comes in so many forms, from the rise of pink-blue branding in the 80s to every suggestion a man is gay or a cuckold because he’s not in the bounds. Sometimes, it turns into physical attacks. And in between it all, there’s the Joe Rogans and the “real men” flogging testosterone boosting quack medicine. Strength is the virtue. Leadership is command. Aggressive action is what real men do; empathy and emotion are signs you have low T.

All that bullying left me with a lot of scars. I didn’t trust people and their motives; people being kind to me was just a setup for a cutdown. I struggled with self-esteem issues. And I struggled most of all with wondering if I’d just become another in the chain of bullies, of enforcers, who sprout from this unhappiness as they seek out someone to pour their own anger onto. Because that’s where the enforcers come from — the bullied kids who then need to make sure the next kid (or coworker, or sibling, or spouse, or person on Twitter) suffers as much as they did for being “different.”


I’d given up on the idea of leading a team. Clearly my powers came in strategy and systems thinking, so I could cruise along in a strategic role, like a principal or staff designer, for the rest of my UX career. It didn’t mean I didn’t have ideas for how you could manage a team — in fact, I’d keep getting asked to interview for management roles knowing full well the same things would always happen: They’d love my ideas, but I wasn’t a “people manager,” thanks but no thanks.

My ideas were anathema to what I’d watched in previous managers of mine. Trust but verify. You cannot be good at your job if you’re overworking yourself. Bullying and other forms of toxicity should be ruthlessly hunted and excised. Own your mistakes, don’t be ashamed of them. Try to do a better job today than you did yesterday. Log off at the end of the day. And most importantly, talk it out.

When I saw Stede Bonnet running his ship just like that, I understood what he was doing. When you’re raised in a system of cultural enforcement, you can choose to live within it, or you can choose to defend the culture and act harshly against the deviants… or you can choose to resist it. And I could have chosen either collaboration or enforcement — in fact, society would love for me to enforce — but like Stede, I looked at what happened and said, no, I’m not doing that.

So, I told the team to do what they believe is right for our customers — and ask them if they didn’t know. But I’m not here to give them work, nor am I here to micro-manage their work, so “Use your best judgment” at all times. And nothing we do is life-or-death, so: Show up, make good choices, and go home. No job is worth destroying yourself for.

Just, be an adult.

Something strange happened. They just did the work. Talked it out if they needed to. Came to me when they needed my voice or my director’s political power. Performance and throughput rose. The workload tripled during that time… and it got done.

Izzy Hands would have a conniption fit. I would have just tossed him off the ship.


I doubt I’ll ever be the manager that all those mentors and hiring managers wanted me to be. And I’m just fine with that. It has made me wonder, though, how much trauma and toxicity has woven its way into how we work and how we’re managed. We want to impress. We don’t want to get fired. We all work in fear. But what if we could step beyond those bounds, push back on the enforcers, and eschew the forces that tell us work is life and life is work? What if we shoved back at the trauma cycles and demanded something healthier in the third of our life we give to capitalism?

What if we treated people as people, not autonomous work units?

The Izzy Handses of the world — the enforcers, the 10x’ers, the ones who insist they know it all works — would question our sanity. But when Ed Teach looks around Stede Bonnet’s ship and his overwrought cabin, he says, “You’re a fucking lunatic, and I LIKE IT.” He sees someone going a different way, and he loves it.

Maybe it’s time we went a different way with managing people. Nothing new, maybe, but maybe for once we can get beyond the toxicity and trauma and redefine what running a pirate ship — and a design team — means.

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