Three Valuable Lessons from the Infamous Leeroy Jenkins

Over the last 15 year, few moments have become as iconic in the gaming sphere as the infamous “Leeroy Jenkins” incident from the video game World of Warcraft. For those unfamiliar, Leeroy Jenkins is a character who, in a recorded raid planning session, abruptly charges into battle without waiting for his team’s strategy, resulting in a spectacular failure. While this moment is often remembered for its humor, it also holds valuable lessons that transcend gaming and apply to various aspects of life and teamwork. So what can we learn?

1. The Importance of Preparation

One of the most glaring takeaways from the Leeroy Jenkins saga is the significance of preparation. In the video, the team meticulously plans their strategy, calculating odds and discussing tactics. However, Leeroy’s unplanned charge into the fray completely derails their carefully laid plans, leading to most of the party being wiped out and their objective lost.

Lesson: Preparation is key to success, whether in gaming, work, or personal projects. Taking time to plan, understand the task at hand, and ensure everyone is on the same page can dramatically increase the chances of success. While spontaneity can sometimes lead to positive surprises, a lack of preparation often results in preventable failures. Think of the six Ps: Proper Planning Prevents Piss Poor Performance.

2. The Value of Teamwork and Communication

The Leeroy Jenkins moment underscores the importance of teamwork and clear communication. The rest of the team was engaged in a collaborative effort to strategize, yet Leeroy’s solo actions ignored this collective effort, leading to chaos. The actions of one, completely destroyed the goal of the group.

Lesson: Effective teamwork relies on every member contributing and adhering to the agreed-upon plan. Communication is crucial in ensuring that all team members understand their roles and responsibilities. Disregarding team dynamics can undermine the entire group’s efforts, leading to conflict and failure.

Although amusing, Leeroy Jenkins does highlight the issues of having a Lone Wolf on your team. As a leader you need to try and get everyone pulling together as a team. If an individual doesn’t want to do that, then perhaps it is time for them to work/play elsewhere.

Some great memes came from the Leeroy Jenkins incident.

3. Embracing Failure and Learning from It

Despite the catastrophic outcome, the Leeroy Jenkins incident has been embraced by the gaming community as a legendary moment of humor and learning. World of Warcraft now has a Leeroy Jenkins NPC for players to interact with and references have popped up in media ranging from Family Guy to serious military discourse. It highlights that failure, while sometimes embarrassing or frustrating, can also be an opportunity for growth and camaraderie.

Lesson: Failure is an inevitable part of any endeavor. The key is to embrace these moments, analyze what went wrong, and use the experience to improve future efforts. In both gaming and life, laughter and resilience in the face of failure can transform a setback into a memorable and educational experience.

Final Thoughts

The legend of Leeroy Jenkins is more than just a funny internet video; it’s a cautionary tale with lessons about preparation, teamwork, and the value of learning from failure. By taking these lessons to heart, we can approach our own challenges with greater foresight. So next time you’re about to charge into a situation, take a moment to plan, communicate, and remember the enduring cry: “Leeeeroy Jenkins!”

Start with Why: Running D&D with Purpose

Simon Sinek’s Start with Why has inspired countless leaders to dig deeper into their motivations and clarify their purpose. His message is simple but powerful: “People don’t buy what you do; they buy why you do it.” When applied to leadership, business, or creativity, this mindset can be transformative.

But what if we applied it to Dungeons & Dragons?

Whether you’re a Dungeon Master or a player, understanding your “Why” can elevate your game from a fun pastime to a truly memorable and meaningful experience—for yourself and everyone at the table.

Why are you playing?

Let’s start at the broadest level: why do you play D&D?

  • Is it to blow off steam and have a laugh with friends?
  • To experience epic, cinematic fantasy stories?
  • To scratch that creative itch—worldbuilding, improvisation, writing?
  • To connect more deeply with your friends, family, or coworkers?

Being honest about this can help you set expectations, choose the right tone, and avoid burnout. When you know your “Why,” you can shape your approach and make sure the game aligns with what you’re hoping to get from it.

As a Dungeon Master, this becomes even more important. You’re not just playing; you’re facilitating. So ask yourself:

Why am I running this game?

  • Is it to give new players a chance to fall in love with D&D?
  • To tell a dark, emotional story you’ve been imagining for years?
  • To create a low-pressure space where friends can just have fun together?

Your Why becomes the compass for your style of prep, how you run sessions, and even which rules you emphasize or ignore.

Simon Sinek’s Golden Circle applicable to business and D&D!

Why is this campaign happening?

Once you’ve got your own purpose clear, zoom in on the game you’re running. Every campaign needs a “Why” behind the story, or it risks feeling generic and forgettable.

You can ask:

  • Why is this world worth exploring?
  • Why are these characters central to what’s going on?
  • Why does this story need to be told now?

When your players understand the thematic or emotional core of the campaign—whether it’s rebellion, redemption, survival, legacy, or something else—it helps them buy in. They’re not just reacting to plot beats; they’re engaging with the story on a deeper level.

You don’t have to spell it out in a monologue. Just make sure your theme is present in the way you frame quests, describe NPCs, or react to player choices.

A campaign where “Why” is clear might look like:

“This land was conquered long ago, and the people are still suffering. You’re part of a fragile spark of rebellion. Will you fan the flames or protect what little peace remains?”

Now the game isn’t just about killing goblins. It’s about choosing between safety and justice.

Why is each character here?

Encourage your players to think about their Why too—not just backstory, but purpose.

Why did this character leave home? Why do they keep going after that near-death experience? Or even, why do they care about the group?

When players define their characters’ core motivations, they make better decisions in character, and the party becomes more than a random collection of murderhobos. Even better? Ask your players how their Why might evolve. Give them the space to change. Because just like in real life, a good “Why” can grow as your story deepens.

Running D&D like a Purpose-Driven Leader

If you’re a DM, you’re already leading a team—even if you don’t think of it that way. Applying Start with Why means you’re leading with intent.

  • Your prep becomes more focused.
  • Your storytelling has more depth.
  • Your players are more emotionally invested.
  • And your games—no matter how light-hearted or intense—feel more meaningful.

It doesn’t mean you need to be serious all the time. A campaign where the “Why” is “laugh until we cry every Wednesday night” is just as valid as “explore grief through fantasy allegory.”

The point is to know your Why. Share it. Revisit it when things start to drift.

Final thoughts on Start with Why

Simon Sinek’s idea isn’t just for boardrooms and brand strategists—it’s for anyone trying to create something with heart. In D&D, whether a DM or a player, knowing your “Why” can be the spark that takes your game from good to unforgettable.

So before your next session, pause and ask yourself:

Why are we sitting around this table?

Then build everything from there.

MartyCon 2025 Wrap Up

Last April saw a group of friends made their way to rural WA for MartyCon 2025, a weekend of gaming shenanigans. Getting away from everything and focusing on games and laughing with your mates is such a great thing to do. It didn’t take much to organize and let us all take turns running games and exploring systems that we hadn’t tried before.

Much like last time we had some incredibly creative sessions including:

  • New Zealand game inspired by the Peter Jackson film Bad Taste. Kiwi accents were mandatory.
  • Wild West Horror game involving pioneers finding that an evil cult has taken their refuge. Betrayal and sacrifices, holy guardians and gun fights. Very cinematic!
  • The Raid miniatures skirmish for 8 people. The Gangers thrashed the Enforcers. for a description of the game check out my post on the game design.
  • Harrowing submarine horror game based on the zine Crush Depth Apparition. Incredibly creepy and unsettling.
  • Paranoia, a game of dystopian future frustration and clone death…
Some of the crew getting ready for the first game of the weekend.

As you can see we had a broad variety of games. We also played board and card games throughout the weekend, went for walks and generally chilled out. The perfect mini break based on mates and gaming!

The Raid Synopsis

I was planning on running two miniature skirmish games, but unfortunately we only had time for one. So we ended up playing the Raid. This asymmetric wargame saw five underhive gangs take on three well disciplined Arbites (law) fire teams.

The game ended up being a real nail biter. The Arbites teams were dominating during the first half, basically trapping any over eager gangers. However, the gangs started working together pretty quickly and ended up swamping the Arbites patrol and winning by a huge margin.

The game was great fun and everyone stayed involved and engaged. However, having 8 players at the table was only just manageable and I think stretched the ruleset a little too much. If I have that many players next year I would split the battles over three separate boards with the outcomes all adding to the story of an overall conflict. I’m already thinking about a desperate siege. Battles could include, destroy the bridge to prevent reinforcement, silence the battery and break the line. Perhaps we need another MartyCon sooner rather than later.

An Arbites Enforcer keeps an eye out for the encroaching gangers.
The battleground
Gangers getting ready to rush the Law

Run Your Own Con

Why am I writing this you might ask? If you are part of a group of friends who enjoy playing games together why not run a mini con together. Grab an AirBnB, get everyone to chip in for food and you’re sorted.

Everyone has games that they want to play but have never had the chance to run. Well now’s your chance. Have a friend who’s always wanted to DM, give them a shot. As you can see above our games are very varied and all run by different people. It’s the perfect time to experiment.

Start small. The first MartyCon only had 5 attendees. But it was a great weekend that spawned a great tradition amongst our gaming groups. So grab some friends, plan some games and create a Con. I can almost guarantee you’ll have a great time!!

MartyCon 2025

All in all a fantastic weekend. So jam packed with games and laughter that I was absolutely exhausted by the time I got home on the Sunday afternoon.

Let me know if you are running your own mini Con. I’d love to hear what works for your group.