Gamemaster like a Pirate: Wisdom from Teach Like a Pirate by Dave Brugess


The game master wears a lot of hats—that of group leader to storyteller to rules adjudicator, and so on—but it surprised even me how much overlap there was running a game and teaching a class. When I was prepping to run my “Agency and Narrative in Games” workshop with Bree Kaiser-Powers for the Glitch Immersion Program, I wanted to learn more about being a teacher and connecting with students. Though I’m no certified educator, I found the recommendations in Dave Brugess’s Teach Like a Pirate book to be invaluable, not only for teaching workshops, but also for gamemastering for kids and adults.

Here are five takeaways from teaching (like a pirate)—five “pieces of plunder,” if you like—that you can apply to your game to better engage your players and boost everyone’s creativity.

Takeaway #1: Share ALL THE ENTHUSIASM

The very first chapter in Burgess’s book is on the topic of passion, and his own passion for teaching practically vibrates off the page. Later, he touches on this topic again and again, discussing the importance of always being “on” (or “bringing it”) and doing that by lighting your inner fire (exploring what interests you). From my own experience, the number one thing you can do to engage your players and change the vibe is to showcase your excitement and energy for your game. You’ve likely taken a class or listened to a lecture about something that hadn’t interested you before, but the enthusiasm of the speaker or leader becomes infectious, and suddenly you want to know what exactly they’re so pumped about. Conversely, even a topic you’re super fascinated by can become a slog if the teacher is quiet and lethargic, or worse, doesn’t seem to care about what they’re talking about.

At your game table, it’s the same thing. Make sure you’re well rested, well fed, and have the (caffeinated) beverage of your choice to keep your energy up throughout the length of the session. Make your voices animated, whether you’re narrating the description of a location or speaking as if you were a non-player character. Stand up and gesticulate at your table if that helps, and vary the volume level to keep everyone on their toes and paying attention. You’ve probably passed by GMs running games in this manner at convention before and stopped to see what was going on—it’s arresting. Your curiosity is piqued, and you want to find out what is just so damn cool or interesting about the game or scenario that makes the GM that enthusiastic.

Besides radiating energy, it’s also important for you to actually be excited about the game you’re running. If you find yourself beginning to burn out, or if the campaign just isn’t interesting to you anymore, find a way to bring in a cool new element that does interest you, or take a break and run some one-shots for a game you are interested in. If your group isn’t interested in playing different games (a complaint I hear a lot from GMs), there are lots of possibilities for finding other games who do want to try out the systems and setting you’re excited about. As the GM, you should be having fun too, and if you’re not, you deserve to make the changes you need to in order to enjoy your games.

Takeaway #2: Encourage Outside-the-Box Thinking

How many of us have had classes we wanted to—or did—skip because they consisted of copying notes from an overhead projector or powerpoint, or the professor simply reviewed the same exact material that was covered in the previous night’s reading? How much imagination was required to engage with the class content? Zero. What was your engagement level with these types of classes? Probably also zero.

One of the main points of Burgess’s book is how this style of teaching is problematic:

“We need risk-takers, outside-the-box thinkers, and entrepreneurs; our school systems do the next generation of leaders a disservice by discouraging these very skills and attitudes. Instead of helping and encouraging them to find and develop their unique strengths, they’re told to shut up, sit down, put the cell phone away, memorize these facts and fill in the bubbles.”

His answer is to provide hooks to engage with the students’ imaginations and problem-solving power by having them learn through doing. Several of these hooks allow students to have some agency in their own learning (see Takeaway #4). The thinking is that students are more engaged when they get to come up with their own answers instead of simply looking up the answer in a book.

Imagine an RPG adventure that consisted of a series of pre-determined checks loosely strung together by a quest, and all you had to do to succeed was roll high enough each time? That probably sounds pretty boring—it’s the equivalent of checking to see if you’ve memorized a fact or not. It’s a binary outcome: Are you correct or incorrect? Did you pass or fail?

When the answers to the questions aren’t determined in advance, when the players have real agency to decide how they want to tackle a problem or solve a mystery, the players’ imagination gets to come out to play. “Can I use this spell in this unexpected way?” “Can we evade this obstacle instead of losing precious resources by confronting it directly?” They get a chance to think outside the box. And because the characters get to choose how they want to approach a given encounter, the players themselves have to engage with the game.

Takeaway #3: Make that Space Safe and Fun For Everyone

The big caveat when encouraging people to think outside the box (read: be creative) is that they need to feel safe while expressing their creativity, knowing that not everyone is going to create gold from nothing on the very first try. In Burgess’s classrooms, he knows that “all of the fun will come grinding to a stop” if the environment stops being safe and supportive, especially if people are only just (re)learning to use their imagination.

As the GM, it usually falls to you to keep the game fun for everyone and recruit the rest of the players to support you in that goal. Safe space means making sure no one feels uncomfortable or excluded during the game because of the content or the way the game is run—everyone’s here to have fun, after all. If it’s a home campaign, this can be done by discussing the social contract. For home games as well as convention games, resources like the X-card, “lines and veils”, the support flower, and others can help your group navigate around potentially difficult topics.

Another challenge to making games feel like a space people can express themselves is to create and enforce what Burgess calls a “no meanness zone.” I’ve seen bullying at the table take place among kids as well as adults, and previously I haven’t known how to intervene and get everyone back to the same page of having fun together. One way to help deal with this is to set the expectation of a “No Meanness Zone” from the get-go and explain what that means. For kids, this means they’re not allowed to say or do things to one another to intentionally hurt another person’s feelings or put someone down. If it happens unintentionally, kids should speak up and talk it out (“sorry” is often a term kids are learning to use appropriately). For adults, the ground rules to lay down are: make sure everyone gets a turn, don’t speak over each other, and give everyone your full attention and respect. By setting expectations early, you won’t feel awkward about enforcing those expectations later.

Takeaway #4: Engage with Multiple Gaming Styles

The entire second half of Burgess’s book includes hooks for engaging with different styles of learners and keeping things interesting. Whether that means developing props or creating avenues for artistic expression from art to writing to acting—or even taking the lesson outside or getting students physically moving—teachers can benefit tremendously from getting to know their pupils and what interests them in particular, and then catering to those interests. Burgess likens it to hosting people for dinner—wouldn’t you make sure your guests like steak before offering it as the main course?

For roleplaying games, there are two dimensions to engaging with different players’ tastes. The first is fairly straightforward: does your group prefer combat encounters, social intrigues, investigative mysteries, or a combination of all three? Examine the choices players make in regards to their characters, and you’ll be able to fine-tune the adventure to highlight the skills they’ve chosen to take ranks in, as well as the particular abilities their characters possess. You can use a player survey to help gauge what kinds of playstyles your group prefers, and then use that data to plan game sessions.

The second dimension is to look at the players’ interests outside of the game. Do you have a group of minis gamers on your hands? Artists? Writers? Crocheters? How can you bring in this external hobby into the game and let them enjoy two of their favorite pasttimes at once? I know some groups who put a lot of emphasis on miniatures combat during the game, and when they aren’t playing in a session they get together to assemble and paint those miniatures. When they finally get to see a set piece battle happen with the minis they labored over for hours, there’s an even greater sense of accomplishment.

When artists have a chance to compose character portraits and post them on a group website, or when writers get to chronicle the sessions through journal entries, you’re engaging those players on a whole ’nother level. When the climactic session is run as a live-action roleplay instead of a regular session, you’re giving the actors and improvisers a chance to truly shine. If you have crafters in your group, be it calligraphers or crocheters or woodworkers, you have an amazing resource at your disposal for creating props! The rest of the group will be blown away when you bring in a physical representation of a cue or plot point for them to interact with.

Takeaway #5: Showcase How Failure isn’t the End, but the Beginning

While I was initially reading teach like a pirate, this quote really hit home for me (especially because I struggle with perfectionism): “Do you want a guaranteed formula for disappointment in life? Set up the rules of your life so that you have to win every time or have one hundred percent success in order to feel fulfilled.” For students, it’s unhealthy to derive all their self-worth from their grades. As an adult, expecting success all the time means you can feel sidelined when something is hard and failure happens again and again—or god forbid, you have to compromise.

In roleplaying games, this mindset can crop up when players are confronted with bad things happening to their characters, particularly permanent penalties in the form of “corruption” or “insanity” or whatever they’re called in the system. Other times, this arises when the dice just don’t cooperate or poor choices were made, and the group is on the verge of a total party kill (TPK) or letting the win condition slip through their fingers. I’ve struggled with this myself in cases—it isn’t fun to lose. But in RPGs, if you’re having fun, you can’t lose.

One thing I want to try to show in my games is that if you don’t win the combat or catch the villain, you don’t lose the game entirely—or at least, you don’t have to stop playing. The GM just has to figure out how to adapt the story. It helps to consider that not every enemy wants to slay the PCs outright, and so the villain might leave the PCs incapacitated or, better yet, capture them. If a villain gets away or an investigation stalls out, that might mean that the situation and stakes get escalated. When planning adventures, brainstorm a couple of avenues that the group could venture down should they “fail” their main objectives.

One of my favorite campaigns of all time featured an accidental TPK very early on in the story, courtesy of the group staying in character. Rather than punish the group, the GM let us keep our XP to spend on new characters, and the very first mission we had to confront after we rolled new characters was to clean up the mess our previous characters left behind. This meant that the story itself continued, even if it was told through a different point of view.

It helps everyone cope better during games—as well as in life—if failure isn’t treated as an insurmountable defeat. It’s an essential part of learning and growing, after all.

Are you an educator, and if so, what lessons have you learned from teaching that can apply to roleplaying games? If you’re a game master, which of these takeaways are most helpful or even surprising to you? Leave a comment below!

If you want to check out the rest of the book for yourself, you can purchase the book on Amazon. As an Amazon affiliate, I get a portion of the sale price if you use the above link, which helps me offset the costs of TripleCrit like hosting and the domain. Thanks for reading!

Image Credit: Amazon.com, Canva

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