Taking 20 Podcast - Ep 264 - Embracing Failure

Episode Date: November 2, 2025

This week, I talk about players’ and DMs’ relentless pursuit of perfection in tabletop RPGs.  I encourage both to embrace failures and give you some tips to help every roll and choice become a chance for exciting, unpredictable adventures.   #rpg #ttrpg #dnd #pathfinder #gmtips #playertips #tabletop #roleplaying #failure   Resources: Buy Me a Coffee! - ko-fi.com/taking20podcast www.taking20podcast.com  Instagram - https://www.instagram.com/taking20podcast  Facebook - https://www.facebook.com/taking20podcast  Bluesky - https://bsky.app/profile/taking20podcast.bsky.social

This week on the Taking 20 podcast. That quest to be perfect. That expectation that GMs and players never make mistakes, it's unhealthy. It's bullshit. And for your own mental health, you have to let it go. Thank you for listening to the Taking 20 podcast, episode 264. Some hard learned lessons I've been through about embracing face. failures while playing tabletop RPGs.

I want to thank this week's sponsor, Giants. Did you hear about the local giant who's had a stomach flu and keeps vomiting? Yeah, it's all over town. Owen Winkler was the generous donor of $70 to pay for the podcast expenses for the rest of the year. I didn't get a chance to thank him by name last episode, but I darn sure wanted to do it today. Thank you so much, Owen, for your amazing donation. To top it off, by the way, he had a great idea for a topic for the next episode. So stay tuned to the end to find out what that is.

Speaking of topics, by the way, it dawned on me this week that I didn't have any horror topics this year. I've been doing this podcast since early 2020, and this is the first year I didn't talk about scary games or topics or tips on running horror campaigns. If you're interested in that and you'd like me to add that kind of topic to the rotation, please hit me up on social media or via email, feedback at taking20podcast.com. It feels like there is a relentless pressure to be perfect, to be right, to get the best possible outcome in all scenarios. People put the best, most curated versions of their lives on social media, putting the picture of their amazing cooked food out there,

leaving out the fact that they almost cut the tip of their thumb off while making it. Not that I did that recently, but moving on. It's frankly an unreasonable expectation that we be perfect all the time. And by the way, yes, I did almost cut the top of my thumb off, making, I had to go to the ER, a bunch of fun stuff. I missed gaming that night, damn it. That's the thing I'm the most upset about the whole thing. By the way, why did I say that?

It has nothing to do with RPGs. I just want to let you know that I'm not perfect, and I don't care if the world views me as an idiot. I gave up on the quest for perfection long ago. More on that in a minute. But today, I want to encourage you to do the same thing, Join me here in the land of imperfection. Not just accept your failure, but embrace them.

It's pretty comfortable here, and it's a lot lower stress. Unfortunately, tabletop RPGs aren't immune from the pressure to be perfect. To always make that skill check, to always hit that attack roll, to always have the knowledge your character needs exactly when they need it. Players feel the pressure to be right and amazing at everything their characters do. Now, this is doubly true for DMs. There's this constant pressure that comes from the expectation that they know all the rules, have perfect knowledge of the world, never caught off guard by the adventure or decisions that the PCs make.

I am here to tell you right now that quest to be perfect, that expectation that GMs and players never make mistakes, it's unhealthy, it's bullshit. And for your own mental health, you have to let it go. I wouldn't have said that, by the way, 25 years ago. In my college days and immediately afterward, I was in a few games with new people and new groups. I mean, it's new people I didn't really know, and I wanted to always do things right, to be supportive, to be looked at as a valued member of the group. And it tempted me to commit cardinal sins at the table, like fudging die rolls and cutting through all the soft language that I wrote here, lying about what the dice says. said. I mean, my dice have been cold all night and I just want one roll to go right. Is that so wrong?

So what if I read that 11 as a 17 on the die and do my math accordingly? That's not good and not fair to the other players or to the DM. After I did it, I felt so much shame and embarrassment. I honestly thought, if I'm willing to lie like that, why don't we all just talk for a bit and then have the DM tell us we won and we go out for milkshakes. Here I sit, a quarter century later, and I still feel ashamed about doing it, especially when the time has given me the perspective

that when it comes to things that are high stakes in life, tabletop RPGs aren't one of them. We're going to fail and fumble at the table. Our characters could have flaws that we struggle to overcome. More on that in a future episode. And I am here to tell you, failure is

okay. Help, better than okay. It's normal. That's light. Our good enough, or pretty good, is just that. Pretty damn good, and we should learn to take the shortcomings with the successes. After all, what's a little success without failures that precede it? For players, this pressure to hide our failures comes from multiple places. There is the let's play or actual play standard. I imagine quite a few of you watch or listen to podcasts or actual plays of your favorite RPG games

from great sources like Critical Role or Glass Cannon or Venture Fourth or Dungeons and Daddies or so many others. Most of them show the flaws that their characters have, but sometimes they hide when they fail, the rules they flub up or misinterpret. Actual plays, whether they're put out on YouTube or podcast, are curated and they remove the times when they look up the rules or slow moments in the game. And while I love listening to them and I learn from them when I do, They do set an artificially high standard for expectations around the table. And for DMs, by the way, let me tell you, the death of happiness begins behind the screen when you start comparing yourself to the likes of Deborah Ann Wall and Matthew Mercer and Brennan and Troy LaValle or Matt Colville. These people are the best in the world at running games with years of experience, tons of acting talent, and none of us are them. You don't need to be the same as a professional DM to successfully run a game.

Matt Mercer has said on multiple occasions that he doesn't want you to be the second best him. He wants you to be like you. And being the best GM you can be, warts and all, is plenty good enough. Similarly, players out there, you don't have to be like the players in your favorite let's play. You won't need to have the skills of professional actor that plays a character that has a three-eastern, act arc, changing from drunken loner to member of a rag-tag group of adopted friends. Don't role play thinking you have to be Sydney Emanuel or Travis Willingham or who both had character moments in their games that made me audibly gasp and even tear up.

That's not the standard you should have for yourself. If you have the skills of an actor, then great. Find yourself a game where you can let that acting flag fly. But if not, that's okay. Don't think for a second that all games are like critical role or any of your other let's play that you listen to. Be you. Play the game in a way that you and your fellow players find fun, and that is plenty good enough. You are not a failure just because you're not Laura Bailey.

Another reason I advise all my beloved DMs and players out there to abandon this feeling, the need to be perfect, is because the vast majority of role-playing games have dice as part of their mechanics. And you know what dice means? Random, uncontrolled elements of the game. Games that have dice, dice means chaos, and chaos is part of the fun. Have you ever played a character that won against all the odds? Overcame every obstacle. At the end of the campaign, your character is standing over the Big Bad in triumphant, glorious victory.

You breathe a huge sigh of relief. Players are high-fiving and there's smiles and celebrations around the table. You know what causes that feeling? the possibility that it might not happen. The very real possibility of failure makes victory so much better. You might have made hundreds or even thousands of die rolls and choices throughout the campaign, each one of them with a chance to result in a failed check, a missed attack, a jump that you left just a little short, a tribe leader completely unimpressed with your words.

There are going to be combats or nights, weeks, months, hell, sometimes it feels like years, where the dice are just awful. They're not being good to you. They're just these little plastic pieces from Satan's butthole that seems all they want to do is make you completely miserable. You change the dice, you put some of the dice in dice jail, and still the low numbers are rolled again and again. No matter how desperately you want to succeed,

sometimes the dice won't cooperate. You may even be tempted to, like I mentioned in my earlier story, fudge your die rolls, lie about what they say, so you can get that taste of success, no matter how fleeting and unearned it is. If I didn't make it clear earlier, please don't lie about die rolls. It indicates you can't be trusted to be honest at the gaming table, and people wonder if you're dishonest about little things, can you be trusted with big ones? When it comes to failures, failed die rolls, and just general bad luck, one of the most important skills is to be able to accept and maybe even embrace your character's failures.

These missteps, big or small, probably aren't the end of your character and almost certainly not the end of your gaming career. Let these failures become character-defining moments where you can roleplay your character's tenacity, growth, and realistic humanity because we all fall down at times. The amazing part of the story will be how your character shakes off the failure and rises up, maybe even greater heights, especially when the failure is dramatic in nature. And DMs, you aren't immune to this either because sometimes the dice don't roll in a way

that you would make for the best story, or the most dramatic moments, or for your session to go as you plan. Again, that's okay. Embrace and adjust what you need to behind the screen. Now, should DMs fudge their dice rolls? For more on that topic, by the way, go all the way back to episode 31.

In short, unlike when players, do it. I don't think there's anything wrong with fudging secret roles a bit. Listen to that episode if you want more of my thoughts on that. But die rolls aren't the only way that we can fail. Sometimes we make the wrong choice at the wrong time and it leads to suboptimal outcomes. I want my characters to make the perfect choice at the perfect time in the campaign, so they eventually become a big damn hero to quote Firefly. At a critical moment, maybe you choose for your character to attack when they find out you probably should have fled, or you choose to cast a spell that the creature is partially or completely immune to.

Or you choose to go left at the intersection, leading to a huge fight with a beholder. You might get upset or even angry with yourself, maybe even berating yourself for making the wrong choice, using the wrong ability, or other decision you made that wasn't perfect. At a recent gaming session of mine, I was playing a barbarian who could take one attack of opportunity per round, and he threatened two opponents in melee. One was a front-line fighter, and the other was a spellcaster.

The way initiative shook out was that the enemy fighter went before the spellcaster and moved away from my barbarian on his turn. This meant that I could take my attack of opportunity on the fighter, but I chose not to. My hope was that the spellcaster would provoke an attack of opportunity, and I could use it to sink my claws into his rib cage and make that spellcaster rethink all of his life choices up until that moment. But the spellcaster didn't provoke an attack of opportunities, so my chance to damage an opponent for free was wasted by my choice. By the very nature of being a player in a campaign, we don't have perfect knowledge of the world, the opponents, or the tactics they're going to use. The term I've always heard for this is fog of war.

We know what we know, and we have to accept the fact that we won't have all the information, so we make the best decisions we can in the moment, and be ready to make the best decision we can, the next choice and the next choice, even if those choices wind up to being not ideal. DMs have choice struggles as well. We try to make decisions in the moment that might come back to haunt us. We give the wrong name for an NPC or give an incomplete description of an area

or leave out an important plot detail. Hell, one game I was running a long time ago had I'd only read half of it before the first session and the NPC I completely improvised wound up being described is completely different about a book later and was the ally of the big bad. I made a bad choice, A, to run the game before I fully understood the plot, and B, giving the PCs a trusted ally who had a major plot point later, antithetical to the way I was running them now. Sometimes your choices wind up being wrong,

and if you dwell on them, you might wind up berating yourself, getting upset with yourself, demanding that you do better, or thinking that you're a failure and a bad player and a bad DM, for making such a mistake. First off, please, don't be hard on yourself when choices turn out to be incorrect. This is a lesson I had to learn, and I was very hard on myself when I was younger. I thought that every time I made a mistake while mowing the yard or taking tests at school or playing sports, I was letting everyone around me down and making them disappointed in me.

Meanwhile, in the ultimate of double standards, I tried not to hold mistakes against my friends, family, teammates. When my teammate missed a literal layup on the basketball court, I would redouble my efforts to try to keep the negative repercussions from their mistake to a minimum. When I made a mistake, it was because I sucked. But when they did, it was because of bad circumstances. I tried my best to extend grace and forgiveness to others, but was not willing to give that same grace to myself. That is not a healthy mental state to have. Please, my beloved DMs and players out there. Give yourself permission to make mistakes and don't be too hard on yourself. Mistakes, failures, choices that lead to setbacks are not signs that you're a poor

player or a bad GM. It's a sign that you're human. A choice that leads to a setback, whether it's trusting the wrong NPC, splitting the party, or making a rash combat decision is not a sign of poor play except for possibly splitting the party. Never ever fucking split the party. Bad decisions and their outcomes are part of the game. Furthermore, the fear of making a wrong choice can lead to indecision, hesitancy, paralysis by analysis, and a bad experience at the table for everyone involved as everyone rings their hands in nervousness,

worrying that they're going to make the wrong call and make a mistake and everyone's going to hurt me. I want you to listen very carefully because it's something we all need to keep in mind. When it comes to gaming, very, very few choices we make at the table will seal the fate of permanent negative outcomes no matter how catastrophic the consequences and dramatic the failure is. There is almost always a way to come back from it.

You choose to fight the centaurs instead of negotiating and realize too late how powerful they really are. Okay, now you know. So run, hide, come back later with this new knowledge. in hand. Yes, okay, there are the occasional really strong negative consequences. If I take a swan dive out of a plane without a parachute, there's a pretty good chance of, well, death are probably worse. Hell, surviving in a field with broken everything of me. Yes, if I take a hammer to a nuclear bomb, chances are that's going to have some serious negative repercussions. But failures at the

gaming table aren't that consequential. Hell, I'd argue that failures, big or small, are powerful narrative catalysts. These moments of defeat, loss, complications added from bad die rolls or wrong choices, create dramatic tension and define your character's journey. Imagine a game where your character never fails, maybe even can't fail. The campaign is full of uninterrupted success after victory, after more success, after good outcome, after parade that's celebrating how great your characters are because they never made a bad. bad choice. Games like that would be just awful, stale. But games containing bad judgments, bad die rolls, and the consequences thereof are richer and more unpredictable. So yes,

you are going to make the wrong choice in a game, or before the game while you're building your character, or any of a thousand other choices we make while playing tabletop RPGs. When your character faces this failure, regardless of the cause, the right choice I think is to lean into it. There are going to be consequences. Embrace them. Don't try to instantly fix the problem out of character. No, no, I said I was going to do athletics, but I meant acrobatics. Calm down. If your cleric botches a saving throw and is now frightened,

rather than just lamenting the mechanical effect of being frightened, this is bullshit. No, no, have some fun with it. Describe how their weapons shakes in their hand or show their sudden doubts in their faith that haven't manifested before. These failures make your character feel real and allow your fellow players to react organically, offering support, stepping into salvage a situation,

or simply expressing disbelief or support. By owning the failure, you can create a more memorable, dynamic story, better time for everyone at the table, especially in role-play-heavy campaigns. I want to encourage you not only to allow yourself to make mistakes when you make decisions, but completely embrace the fallout from it. Not as an obstacle to bypass, but as a chance to role-play that difficult situation.

Ford's stronger relationships with allies in their resulting hardship and maybe make for a better game. In short, failure and bad decisions and bad die rolls can be narrative fuel that makes the game better, hotter, more fun. Now, to my beloved game masters out there, you need to encourage and support this mindset, not only in yourself, but in your players as well. Do not treat player failures from choices or die roles as opportunities to punish the players or automatically lead the character to a dead end from which there's no escape.

Use these failures as plot points, pivotal junctions that branch the narrative in surprising, maybe even exciting directions. When a player fails a critical check, be it on a lie detection role, against a deceptive NPC or an attempt to maybe repair a magical artifact. You should focus on the yes-but principle of gaming, where the failure happens, but it also creates a new and interesting problem,

or in the case of a failed attack role, demonstrates the skill of the opponent who parries the thrust or dives out of the way of the spell in the nick of time. The deceptive NPC now reports inaccurate intelligence to the king, complicating the next quest, door, the broken artifact now possesses unpredictable, volatile effects that the party must contain, or quest to seek help from a powerful NPC to repair.

The consequences of failure should be an opportunity to expand your campaign in new and exciting and fun ways. Rather than simply leaving a locked door impassable, use any setback as a source of immediate tension, character development, and maybe a set of compelling new challenges that require new and creative solutions from the players. Even in the worst of the worst consequences at the table where a character dies because they failed that climb check, attack the mayor, or stuck their finger in the whirling black orb of energy,

that's still okay. It's an opportunity to, A, learn something that didn't work, and B, maybe roll up that character you've been thinking about. Failure at the gaming table is rarely, if ever, permanent. So players, embrace the failures that will, inevitably crop up in every game. Let go of that pressure to be perfect. And this just end, by the way, you won't be perfect, and neither will I. Difficulties from players are not only normal, but drivers of memorable games and stories. DMs, whenever possible, give yourself

that grace to fail as well. And character failures, even dramatic ones, should not lead to permanent negative consequences, but instead opportunities for dramatic events. By doing that, you'll help your players reduce their fear of failure from bad die rolls or wrong choices. And if you do embrace that mindset, I'd be willing to bet that you and your players would have fun doing it. Thank you so much for listening. I'd like to get your feedback either via social media or email, feedback at taking 20podcast.com. What topics would you like to hear me cover? Is there a particular news item from Tabletop World that you'd like me to discuss? Please send me a message and let me know. Tune in next week when we're going to cover Owen's suggested topic, running high-level campaigns and high-level PCs.

I'm going to try to do both in one episode, but it might stretch to two. Honestly, I'm kind of stunned. I haven't talked about either of these topics before, so thank you again, Owen, for your very generous donation and for the topic idea. But before I go, I want to thank this week's sponsor, Giants. I was recently diagnosed with acute fear of giants. It's called V-5 phobia. Oh, yeah. This has been episode 264, encouraging players and DMs alike to embrace failure. My name is Jeremy Shelley, and I hope that your next game is your best game.

The Taking 20 podcast is Copyright 2025 by Jeremy Shelley. The opinions or views expressed by guests are their own, and do not necessarily reflect those of the host. References to game system content are copyright their respective publishers.