What My Failures in D&D Taught Me About Life

I spent months preparing to be a Dungeon Master.

I wasn’t just excited—I was obsessed.

Every free moment, I dove into the Player’s Handbook, dissecting it like it held the meaning of life. I read it eight times, then started on the Dungeon Master’s Guide.

If you looked at my desk back then, it was a war zone of notebooks, maps, and scraps of paper scribbled with NPC stats and world-building ideas. I even had a binder filled with random questlines and character arcs. My campaign map looked like something straight out of Tolkien’s notes.

I thought I was doing everything right.

But the truth is, I wasn’t getting closer to running a game. I didn't even know what made a good session good.

I was stuck in tutorial hell.

I convinced myself I wasn’t "ready." That I needed to know more. That I had to memorize every rule, anticipate every player decision, and prepare for every possible outcome before I sat behind the DM screen.

I only had one chance to make that first impression, or my career as a DM would be doomed.

I wasn't good enough. I could never be as good as him.

Perfectionism Feeds Anxiety

If you’ve ever struggled with perfectionism, you know the cycle.

It starts with a goal: "I want to run my first game of D&D." The goal feels exciting at first. Inspiring.

Then, perfectionism steps in.

You tell yourself that to achieve the goal, everything has to be perfect. You imagine everything that could go wrong and start over-preparing. You focus on details that don’t really matter (things like memorizing obscure rules or crafting NPCs with ridiculously deep backstories.)

And the longer you spend preparing, the more anxious you feel.

Instead of building confidence, all that "preparation" amplifies your fear. You get stuck in a loop: prepare, overthink, avoid.

At this point, you feel overwhelmed, and your enthusiasm is gone. You forgot why you were excited in the first place.

I spent months building the perfect campaign setting. I created NPCs with tragic pasts, complex motivations, and intricate connections to the world I’d created. I planned out quests, conflicts, and big dramatic moments that would make my players feel like they were in an epic fantasy novel.

I had no idea then that when I would finally run my first session, not a single bit of it mattered.

The Fear of Starting

All that preparation turned running the game into a high-stakes performance.

I joined other campaigns as a player, thinking, Maybe if I watch enough other DMs, I’ll figure out what they’re doing right. At one point, I was playing in four different campaigns a week.

I became a rules lawyer, obsessively correcting other players or even the DM when something wasn’t "by the book." I found reasons to hate my fellow players for their choices. I had lists of reasons to hate every DM: their house rules, their NPC's lore, their combat pacing.

I became that asshole. It didn't take long before I would leave a group or be asked to leave. Fine, fuck them. They're not Matt Mercer.

The Breaking Point

Eventually, I hit a breaking point.

I convinced myself that I wasn’t "good enough" to run a game. It turned out that nobody else was good enough either. I had become a D&D wretch. My attitude was so bad I could've ruined even the best session with the coolest people.

One night, on my way to a session, I stopped in the restroom.

I washed my hands and checked my hair—normal stuff, right? I caught a glimpse of myself in that reflection. I saw my face: tight-lipped, exhausted, and just… miserable. And that’s when the thought hit me like a crit from a half-orc's greataxe:

I'm Gollum.

Not Smeagol, the pitiful but redeemable creature from the start of The Lord of the Rings. No, I was like the dude at his worst—consumed by his insatiable obsession, driven mad by his own endless grasping.

I had become the kind of person I've always avoided. The type of nerd who sucked the joy out of every game and fandom with constant nitpicking.

At that moment, the truth was undeniable: I wasn’t the hero of my story. I wasn’t calling shots like a Dungeon Master. I was the monster.

For months, I had blamed everyone else for my misery:

• The players who just wanted to chat instead of "taking the game seriously."
• The DMs who didn’t run by the book.
• The world itself for not giving me the talent and confidence to run my own games like the pros I idolized (Matt Mercer)

But staring into that mirror, I couldn’t hide from the truth anymore.

I wasn’t angry at them. I was angry at myself.

Angry that I’d wasted so much time preparing instead of playing. Angry that I’d let my fear of failure keep me from even trying. Angry that I had turned my love for D&D into something miserable, bitter, and suffocating.

It wasn’t just about D&D anymore. It was about the story of me. How many other parts of my life had I avoided because I didn’t feel “ready?” How many other opportunities had I let slip by because I couldn't accept failure?

I had to do it—I had to break that mirror. (just kidding)

The Decision to Start Anyway

I had two choices:

1. Keep walking down the road I was on—hoarding knowledge, avoiding risks, and letting perfectionism hollow me out from the inside.
2. Turn around. Take a step into the unknown. Roll the dice.

It was clear which path I had to take.

That was the day I set up my first game. Not my “perfect” game. Not the one I’d spent months dreaming about. Just a messy, chaotic, imperfect game that changed everything.

I threw my 100-page campaign prep out the window. I stopped obsessing over the rules and storylines.

I recruited players for an impromptu session, starting that night. I grabbed the first published campaign module I found.

I wasn’t ready—not even close. I hadn't even read the adventure hooks. I sat behind the DM screen with a racing heart, double fisting coffee and whiskey to get my energy right.

It SUCKED.

I forgot half the rules. My players immediately killed off key story NPCs. I rolled a d8 instead of a d10 for about 20 minutes before one of my players called me out. Embarrassing.

But here’s the thing:

My players had the time of their lives. Nine years later they still talk about that session.

A Spark of Realization

That first session taught me something I wish I’d understood months earlier: The goal of a creator isn’t perfection.

It’s connection.

My players didn’t care that I forgot a rule or stumbled over my words. They didn't care that the story fell apart and I had to make up a bunch of random shit to get us back on track. Players don't even care about the plot!

All they care about is rolling dice and having a shared world to play in.

I had failed at everything except for the few things that actually mattered:

• I showed up
• I took the first steps (running the game)
• I said go

I thought being a Dungeon Master meant never making mistakes. They're not called "Dungeon Journeyman that fucks up everything half the time."

Dungeon Master. It's in the name.

Here’s the truth: You can't improve on something that you've never started. You have to walk before you can run, and if you can't walk, you have to crawl. You have to be a little baby beginner who fails a lot before you can become the Master.

Why Failure Is Your Greatest Teacher

“The greatest teacher, failure is.”– Yoda (from some movie I didn't see)

That first session as DM was full of "failures."

But every single one of those failures taught me something I needed to know:

1. You Can’t Plan for Everything. Players ignore the important NPCs who add to the storyline and hyper-focus on the guards and minions who are put there to die. They don't care about your story. Failure forces you to let go of control and embrace the unexpected. Creativity thrives in chaos.
2. The Rules Are Just Guidelines. I forgot rules, misinterpreted others, and made up a few on the spot. My players didn’t care. My players were better players than I ever was. They weren’t there for rules. They were there for a good time. Failure taught me that I was focused on the wrong things. I learned that I didn't suck at my job, I was just doing the wrong job.
3. Other People (Players) Don’t See What You See. You're hyper-aware of every mistake you make but others aren't. They're focused on their perspective. Most people don't want to see behind the screen. "Nobody wants to see how the sausage gets made." They just want to eat. Keep your mistakes to yourself and instead of pointless complaints, they become opportunities for you to see the gaps in your skills or knowledge.

The Mindset Shift That Changed Everything

Failure isn’t the opposite of success. It’s part of the process.

Every time I made a mistake, I learned something that made me a better Dungeon Master. Because I didn't quit, each "fail" taught me how to prepare, improvise, and connect with my players. Every stumble was actually a stepping stone toward becoming the DM I wanted to be. Matt fucking Mercer.

It also taught me that most of the shit I was worried about didn't even matter. I had robbed myself of the opportunity to develop the skills and knowledge that made the game better. I hadn't failed enough to know which 20% of my work would account for 80% of my success.

This isn’t just true for D&D—it’s true for everything.

Whether you’re learning a new skill, starting a creative project, or chasing a big goal, failure is inevitable.

And that’s a good thing.

Failure is what forces you to grow. It shows you where your gaps are. It pushes you out of your comfort zone and into the realm of progress.

You just have to start the game.

A Universal Truth

One of my favorite quotes is from The Well of Ascension by Brandon Sanderson:

"A man can only stumble for so long before he either falls or stands up straight." -Tindwyl

Stumbling isn’t a sign of weakness—it’s a sign that you’re moving forward.

Every stumble, every mistake, every "failure" is an opportunity to learn, adjust, and keep going. The only real failure is quitting.

I used to think the noble path was to create the perfect game. To follow the rules. To control the story. To eliminate mistakes.

But now I know the truth: it's to create a space where everyone—including yourself—can have fun, be creative, and build.

It’s not about perfection. It’s about connection.

How to Fail Forward and Turn Mistakes into Growth

By now, you already know that failure is inevitable.

But here’s the part no one tells you: Failure is also your biggest advantage.

Think about it. Every mistake you make is an opportunity to learn, adapt, and improve. It’s like getting EXP in a game—you’re leveling up with every stumble.

But there’s a catch.

You only get the EXP if you stick with it.

If you can reframe your goals as EXP bars, you can power level yourself to completing them. "I only have to fail 30 more times to hit next level, let's fucking go!"

Most people will dread something for 10 days that they could be done with in 10 minutes.

Action conquers fear. Take action.

The Magic of Failure

Failure is terrible in the moment. It’s frustrating. Embarrassing. Soul-crushing.

But when you zoom out and look at failure for what it really is, you realize it’s a gift. Failure can be your best friend.

Because failure forces you to do things that success never will:

• It Forces You to Take Action. You can’t learn the game by just reading the rulebook. You can’t get good by binge-watching Critical Role. You have to play—and yes, fail miserably—before you actually gain any knowledge or valuable experience. Failure is the price of action, and action is the price of growth.
• It Shines a Light on Your Weaknesses. A failed check in D&D shows the party’s lack of planning, a gap in their skills, or knowledge. A failure in life does the same thing. Treat it like a part of the game.
• It Builds Resilience. The first time I bombed as a Dungeon Master, it felt like the end of the world. The second time, it stung a little less. By the third or fourth time, I realized something: I survived. Now I don't even notice mistakes. Everything becomes a part of the game.

Every failure you endure makes you stronger. It thickens your skin and builds your confidence. Eventually, the fear of failing fades, and you start seeing failure as just another step in the process.

Don't fear failure—fear a life hiding from your own shadow. A life of ignorance, devoid of value and purpose, scurrying around in the dark like a rat while hungry cats stalk your every move.

People Don’t See Your Mistakes

Behind the DM screen, I saw my sessions as disasters. I saw the plans that fell apart, the rules I forgot, the moments I froze.

But my players? They didn’t see any of that.

They saw a hilarious, memorable session full of laughter and surprises.

This is one of the most important lessons I’ve learned as a Dungeon Master—and in life:

The mistakes you notice aren’t the ones other people remember.

You’re hyper-aware of your flaws because you’re living them in real time. Ignore them and focus on the outcome you desire.

As long as you stay in the game, your mistakes won’t define you. They'll inevitably become part of your success story.

Skill > Luck

Here’s another truth I had to learn the hard way: Luck is bullshit.

In D&D, a bad dice roll can feel like the end of the world. But when you zoom out, you realize that most "bad luck" comes down to skill issue or lazy thinking.

• Did your rogue fail the stealth check because the dice rolled low? Or because the hinges weren't greased, the guards weren't distracted by a clever ploy, or your boots weren't padded to reduce noise?
• Did your campaign stall because of bad luck? Or because you weren’t ready to improvise when your players derailed the story? Players always derail the story. Roll with it.

The same is true in life. If you’re relying on chance to succeed, your plan sucks.

The solution? Level up your skills.

• Study. Practice. Experiment.
• Build competence so that even when things don’t go your way, you can adapt and recover.
• Turn every failure into a stepping stone for growth.

You don’t grow by avoiding failure. You grow by embracing it.

As James Joyce said:

"Mistakes are the portals of discovery."

How to Embrace Failure and Level Up

Failure isn’t something you fix. It’s something you use.

In D&D, you don’t stop playing just because the rogue failed a stealth roll or the fighter missed an attack. You keep rolling. You adapt. You let the story unfold.

Life works the same way.

The trick is to gamify the process—to turn every mistake, every setback, and every failure into a half-step forward.

Step 1: Start Before You’re Ready

You'll never know you're ready for something until after it's happened. Stop waiting for the perfect moment.

Stop telling yourself you need to know more, plan better, or be more prepared.

You'll never feel ready, because ready doesn't feel like anything. If you felt ready you wouldn't even be thinking, you'd be halfway toward your goals already.

Read this carefully: The only way to get ready is to start.

Step 2: When You Fail, Fail Forward

When things go wrong—and they will—don’t see it as a dead end.

Instead, ask yourself:

• What’s the opportunity here?
• What is the lesson?
• How can I adapt and keep moving forward?

In D&D, failure often leads to unexpected fun. A failed persuasion check might create a hilarious misunderstanding. A botched stealth roll might spark an awkward but memorable scene that presents new opportunities.

The same is true in life.

Every failure is a chance to pivot. To improvise. To find a new path forward.

Remember: if you don't lose sight of your goal, you can't fail. Even a misstep can move you closer to success.

Step 3: Keep Your Mistakes Behind the Screen

Here’s a secret I wish I’d learned sooner: Nobody cares about your mistakes. At all. Nobody.

The only people who notice your mistakes are trolls and dickheads. Don't give your power to trolls and dickheads. Nobody who has ever actually created anything in their lives is going to call you out.

Your audience, your customers, your friends don’t see the chaos in your head. They don't want to hear you go on about how you messed this or that up. They just want the experience you create for them.

Step 4: Replace Luck with Skill

In the game, a bad roll of the dice can completely mess you up. If you’re relying on the dice to save you, you’re playing the game wrong.

The same goes for life.

If you’re putting your fate in the hands of "luck," you’re setting yourself up for the greatest failure of all—not owning your outcome and leveling up.

Here’s what you need to do instead:

• Take responsibility.
• Focus on the things that matter to you.
• Develop the courage to embrace challenges—no matter how the dice land.

The dice are just a tool, not a crutch.

Luck is unreliable. Skill is not.

Step 5: Iterate, iterate, iterate

Here’s the golden rule for leveling up: Reflect. Adjust. Improve.

After every game you run—or every challenge you face in life—take time to review.

Ask yourself:

• What worked?
• What didn’t?
• What lessons can I take into the next session?

For example:

• Did your players get bored during a certain part of the game? Cut it or raise the stakes.
• Did you struggle to improvise when things went off-script? Write down three go-to encounters that you can pull out at any time.
• Did your players love a particular moment? Double down on what made it great.

Cut out the shit that doesn't work, unless you enjoy it. If you enjoy it, figure out how to make others enjoy it too.

Iteration is how you transform failure into progress. There's no limit to the amount of progress you can make with incremental, iterative improvements.

Why This Matters

Gamifying failure isn’t just about D&D. It’s a framework for life.

• Every mistake is potential EXP.
• Every failure is the interesting part of a story.
• Every setback is a chance to pivot and grow.

You don’t need to be perfect to succeed. You just need to stay in the game.

As Théoden said (kind of):

"Courage is not the absence of fear, but the decision that something else is more important."

The question is: what’s more important to you?

Your Next Quest

Pick the thing you’ve been putting off because you don't "feel ready"—you're done with that.

1. Take one small step forward. Today. Right now. Set a date. Make a plan. Roll the dice.
2. Prepare to fail.
3. Learn from every mistake.

And most importantly—stay in the game.

Your epic adventure is waiting.

- Rex