Three workplace lessons from HBO’s Our Flag Means Death (Spoiler warning)

“What the heck do a bunch of gay pirates have to do with succeeding at work?” you’re probably thinking. Or maybe, “What the heck is Our Flag Means Death?”

In case you haven’t already jumped feet-first into this hilarious imagining of a very odd moment in the Golden Age of Piracy, let’s take a step back and recap. One day, show creator David Jenkins’ wife showed him the story of Stede Bonnet, the Gentleman Pirate. In 1717, the wealthy landowner had one seriously epic midlife crisis; abandoned his entire life, wife, and children; and ran away to be a pirate captain on a ship called Revenge.

And, of course, he sucked at it.

He somehow made it to Nassau without dying, and crossed paths with the one and only Blackbeard, Edward Teach. Blackbeard didn’t go the likely route of exploiting the man’s incompetence to steal his (beautiful, luxurious, custom-built) ship and leave him stranded or worse. He took him on as some kind of companion! The two sailed together for months.?

So when David Jenkins’ wife showed him the story and said, “Wouldn’t this make an interesting show?” he said something akin to, “hell yes, and also, there’s no heterosexual explanation for this.”

He proceeded to find a cast and crew, get legendary actor/filmmaker Taika Waititi on board as executive producer, and create a five-hour romp of beautifully designed, impressively shot, incredibly written television. (Taika dithered in casting Edward Teach until Jenkins just gave him the role.)?

Real-life besties Rhys and Taika (and the whole ensemble cast) took viewers through an incredible range of emotions as Stede and Edward met, bonded, and fell head over heels in love. A huge, rabidly-devoted fanbase quickly formed. It was the most in-demand streaming show - not just on HBO, on all networks - for three solid months.

It’s not exaggerating to say I’m a little obsessed with this show. It isn’t “just good queer television.” Our Flag Means Death is one of 2022’s best shows, period.

So… What the heck does all this have to do with work advice? If you’ve seen the show, you’re probably already following where I’m going. If not, you should go watch it and then come back.?

That’s your warning, sailor. There be spoilers ahead.?

Here are three real takeaways from watching fictional pirates:

1. Alignment and respect are life-or-death important!?

When Stede (played by Rhys Darby, pronouns he/him) was out of sync with what motivated the Revenge crew, they started plotting to end his life in a mutiny. By the end of Season 1, they literally saved his life. How’d he pull that off??

He never ran things like a tyrant. In fact, coming onboard the ship Revenge was the first time this misfit crew had ever had a captain who paid them a salary, gave work perks, and generally cared about their well-being. But he was fully out of touch with their motivations and expectations, and they got bored.

Fortunately, his first mate tipped him off to the mutiny plot: “The general impression is that you’re weak. Soft bellied, yellow. Ill-equipped to lead men.”

Somewhat hurt that they hadn’t appreciated his efforts, Stede organized his first real raid. Of course this immediately went sideways, but thanks to some accidental violence and really good advice, he turned the tables and started to win their respect.

If you don’t have the right dynamic of aligned motivation and trust, as a boss or employee, the end result probably won’t kill you. But it won’t be pleasant.

2. Get really good at providing attractive options!

The polyandrist Spanish Jackie (Leslie Jones, she/her) was on the business end of Jim’s (Vico Ortiz, they/their) wrath, seconds from consigning her 18 surviving husbands to widowhood. But she turned the tables. How? She knew the psychology behind Jim’s actions.

The whole Revenge crew was nearly killed by the Spanish Navy in an earlier episode, because Jackie sold them out in retaliation for Jim stabbing her favorite husband, Alfeo (Fernando Frias, he/him.) But Jim only did that because Alfeo and his gang murdered their whole family when they were a child. Jackie knew she had a shot at survival, because 1) Jim didn’t know where the rest of the gang was. And 2) vengeance alone hadn’t been enough to soothe her own past misery. So she offered something else. Drinks, and information.?

So don’t just throw paint at the wall or offer cookie-cutter solutions without strategically listening to the prospect, coworker, or manager you’re talking to. Sales staff may find this especially resonant, but it’s useful in any field. Persuasion is a versatile skill.

3. If the status quo isn’t working, give yourself permission to try something radically new!

I definitely don’t recommend running away from your whole life and family in the dead of night, but there are healthy ways to get away from what’s no longer serving you.

One of the coolest things about being in this fandom is seeing all the real people in their 30s, 40s, and up being so inspired by Stede’s wild leap of faith, they started making their own. I can honestly say this show is why I was brave enough to quit my job in my own time of burnout and exhaustion. (My body wouldn’t have given me a choice eventually, but this way I didn’t land in the hospital.)

People are creating art, launching music careers, switching jobs, leaving toxic partners and homes, and more - at ages when the overwhelming societal message is that we should just have been settled already.?

I spent the first ten years of my career in awful, low-paying jobs, with micromanaged schedules, toxic cultures, and abusive customers that left me traumatized. Finally, I took one more chance at something different. And it was awesome. I started making more money than I ever have, my input was valued, my “coworkers aren’t your friends” rule got enthusiastically broken, and I got to contribute in ways that will last far beyond my time there.?

For two years, that company was exactly where I needed to be. And then it wasn’t. The trauma caught up to me. I wasn’t being actively abused anymore, but I wasn’t healing. It was time to do that.?

It wasn’t just this show, but seeing the cast and crew truly enjoying their lives - living their best lives in both work and leisure - that made me long to know what that’s like. And, finally, I felt like I had the permission I needed to start that journey.

If you’re in a position where you feel like you need permission to make a change in your work, consider this your permission slip from the Captain. You're allowed.

Was a goofy crew of questionably-competent, misfit pirates an unlikely source for a LinkedIn article? Probably. Was it worth the read? You tell me.