Why Good DMs Still Run Bad Sessions

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My goal as a game master is to run amazing games. I want my players to have fun, I want to have fun, and I want everyone leaving the table excited for the next session. But recently, one of my Ghosts of Saltmarsh sessions reinforced a simple truth that every game master eventually has to accept: sometimes, despite your best efforts, your best intentions, and your best laid plans, a session is still going to fall flat.

That does not automatically mean you are a bad game master. It means you had a bad session, and there is an important difference between the two.

The Session Started with Shopping

My group had just returned to town after slaying a dragon. I have been splicing adventures from Tales from the Yawning Portal into Ghosts of Saltmarsh to fill some of the level gaps, and this dragon came from The Forge of Fury. So the party returns with a dragon hoard full of gold and treasure, and naturally the first thing they want to do is go shopping. Who wouldn’t?

The problem is that shopping in D&D can take forever. The players were looking for specific magic items, which meant I was checking whether I would allow those items in the campaign, rolling to see whether they were available, figuring out prices, and then waiting while the group debated whether they actually wanted to buy them. Before I knew it, we had burned through about an hour.

If you have ever run one of these shopping sessions, you know exactly what I am talking about. In one of my Pathfinder 2 games, we once spent two hours shopping. It was miserable, and I basically begged my players to never make me do that again.

Why I Review Magic Items Before Allowing Them

Part of the reason the shopping took so long is that I do not automatically allow every magic item the players ask for. Magic items in D&D 5e are wildly inconsistent within their rarity categories. One uncommon item might be perfectly reasonable, while another feels powerful enough that it should probably be rare or even very rare.

The Pipes of Haunting are a good example. A DC 15 Wisdom save is no joke, and potentially imposing disadvantage on attacks from an entire group of enemies is extremely powerful, especially when you have a party that already takes Armor Class very seriously.

And game master fun matters, too. It is not terribly enjoyable when your monsters cannot do anything because they are constantly attacking with disadvantage or being shut down by one ability after another. These days, I try to take my own enjoyment into account when making rulings. If I know something is likely to make the game significantly less fun for me, I probably will not allow it.

That does not mean I need perfect balance. I do not. But things need to stay within reason.

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The Forgotten Magic Item Problem

During all this shopping, the group was also going through old loot and discovering magic items they had found months ago but completely forgotten about. Who has not seen that happen?

One player discovered an extra Wand of the War Mage and wanted to dual wield it alongside the one he already had. Fortunately, I was paying attention and pointed out that bonuses like that generally do not stack. It was an honest mistake, but it reinforced something important: game masters need to keep an eye on this stuff, particularly in campaigns with lots of magic items.

And yes, this is a fairly high-magic campaign. I allow my players to buy magic items within reason because I have enough experience with D&D 5e to adjust encounters when needed, players forget about half their magic items anyway, and published adventures do not always provide the exact kinds of items players want. It also gives them something useful to do with all that gold.

So maybe that was four reasons. Whatever.

The point is that the shopping made sense. The players were getting useful stuff. But from my perspective, it was tedious.

Why I Do Not Handle Shopping Outside the Session

A common solution is to say, “Why not just handle shopping outside the game on Discord?” I have tried that.

In my experience, it usually turns into a disjointed conversation where only some players participate, and it ends up consuming a bunch of my own time between sessions. I already have to find time to prepare the actual adventure. Adding a separate asynchronous shopping session on top of that is not exactly appealing.

So I generally prefer to handle this kind of thing during the game, even though sometimes that means accepting that part of the session may move more slowly.

Then the Players Blew Up My Downtime Scene

The players were also supposed to have downtime that session, and I had some backstory material prepared. One of the characters, Naeris, had previously hunted an infamous pirate captain. During downtime, I had one of that pirate’s representatives approach him with two goons.

My plan was simple. The representative would taunt Naeris a little, drop some foreshadowing, and remind him that this pirate was still out there and active. It was supposed to be a short social scene, maybe five or ten minutes.

Naturally, Naeris attacked him.

Now I suddenly had a three-on-one fight. To his credit, Naeris did pretty well at first. The party had just reached level 5, so he had two attacks and some additional abilities working in his favor. But almost immediately, I had a bigger problem than whether Naeris would survive.

D&D Is a Group Game

I was running a combat involving one player while the other five players were watching, and we all know D&D 5e combat is not exactly famous for being lightning fast. If this fight lasted thirty minutes, that would mean five players sitting around doing practically nothing for half an hour.

D&D is a group game. When the party splits up, some players are inevitably participating while others are waiting. Even if the game master switches between scenes, which you absolutely should, there is still a risk of leaving people sitting idle for too long. Combat makes this problem even worse because it tends to consume so much table time.

Fortunately, Naeris blew a horn of alarm that was keyed to another character. The dice ruled that another player character happened to be with her, so now I had two characters heading toward the fight. Even better, Naeris and the pirate representative were both using firearms, and firearms are loud. I ruled that the rest of the party could hear the shots and rush toward the scene.

Perfect. Now I could get everyone back together and turn this into a group encounter.

Sometimes You Have to Fix the Encounter on the Fly

Of course, that created another problem. By the time the rest of the party arrived, there was only one pirate left standing against an entire group of characters. That was not going to be much of a fight.

So I had the pirate call for reinforcements. Maybe those reinforcements were always supposed to be nearby. Maybe they were hiding on rooftops. Maybe I invented them five seconds earlier because I needed to fix the encounter. Who is to say?

As far as the players are concerned, the encounter was always designed that way. That is part of game mastering. Sometimes you need to adjust things in real time, and as long as you execute it well enough, the players usually do not need to know what was planned and what was improvised. Suspension of disbelief depends, in part, on the game master knowing when to keep his mouth shut.

Of course, now I am writing about it publicly, so maybe I have ruined the illusion anyway.

The Combat Still Turned into a Slog

Even though I managed to get the whole party involved and rescue the encounter from becoming a one-player combat, I still was not happy with how things played out. The fight lasted about an hour, and from my perspective, it felt like a slog.

You know the kind of combat I mean. It drags on, nothing particularly interesting happens, and eventually everyone is just waiting for the last few enemies to die. Now, it is entirely possible that my players loved the fight, and that is important to remember.

Game masters are often far more critical of their own games than players are. We see every awkward transition, every missed opportunity, every pacing problem, and every decision we wish we had handled differently. The players may just be thinking, “That was awesome.”

That self-criticism is not necessarily a bad thing, either. It can push us to improve. The important thing is not to let it turn into pointless self-punishment.

I Was So Busy Fixing Things That I Missed Something Important

After the battle, we were nearly at the end of our four-hour session, and that was when I realized something uncomfortable. I had spent so much attention dealing with the shopping slog, improvising the fight, getting the party reunited, and patching the encounter together that I had forgotten one of the most basic responsibilities of a game master: making sure everyone had a chance to participate.

I have some quieter players in this group. Usually, during non-combat scenes, I make a point of asking them what they want to do or say. During this session, though, I had not been doing that. I was too occupied with everything else going wrong.

That bothered me more than almost anything else that happened during the game.

Make Space for Quieter Players

Some quieter players are perfectly happy observing large portions of the game. They enjoy listening, watching the story unfold, and jumping in when they have something specific to contribute. Other quieter players, however, want to participate more and simply have trouble finding an opening.

That is where the game master needs to help. Sometimes you literally need to call on someone and say, “What is your character doing?” or “Is there anything you want to say here?” You are not forcing them to participate. You are giving them an opening.

At a table with more outspoken players, those openings can disappear quickly. And when I realized I had forgotten to do that during this session, I was pretty frustrated with myself.

Even the Quest Giver Felt Wrong

Near the end of the session, I introduced the NPC who would lead the party into the next adventure. That part was intentional. I wanted to end the session with the new quest already introduced so that next time we could jump straight into the adventure instead of spending thirty minutes figuring out what everyone was doing.

But even there, I found something to criticize. I had made the quest giver annoying and unlikeable. There is nothing wrong with an annoying NPC. They can create drama and tension. But I realized I had been doing that a lot lately, and when every other important NPC is abrasive, difficult, or obnoxious, it stops being interesting. It becomes repetitive.

So now that was one more thing I was thinking about after the session.

Bad Sessions Happen to Good Game Masters

At this point, you might think the lesson here is that I had a terrible session and needed someone to tell me everything was going to be okay. That is not the point. I am not looking for sympathy.

The point is that every game master runs bad sessions. I do. You do. The famous game masters you watch online do, too. Nobody consistently runs amazing games every single time.

Sometimes the pacing is wrong. Sometimes an encounter falls flat. Sometimes the players do something that derails half your preparation. Sometimes you make a bad ruling, forget about a player, or introduce an NPC and immediately wish you had handled him differently.

It happens.

What Matters Is What You Do Next

The important question is not whether you ever run a bad session. The important question is how you respond afterward.

If you simply beat yourself up, convince yourself you are terrible, and wallow in disappointment, nothing improves. But if you look back at the session and ask what went wrong, you can learn something.

Why did the shopping take so long? Why did the combat drag? Why did I forget to involve quieter players? Why did that NPC feel repetitive? What could I do differently next time?

That is where improvement happens. A bad session becomes useful when you treat it as information.

Continual Improvement Is the Secret

The difference between a mediocre game master and an excellent one is not that the excellent game master never screws up. The difference is that the excellent game master keeps learning.

After every session, there is something you can examine, refine, and do a little better next time. You are never going to reach some magical point where every session is perfect, and that is not the goal.

The goal is to keep improving.

Run the game. Pay attention. Be honest with yourself about what worked and what did not. Then make adjustments and come back better next time.

That is the secret sauce: continual improvement.