01/09/2026
Happy Friday, and welcome back to Tabletop Thoughts!
Today I want to talk about something that comes up every single time Shadowdark hits the table: getting new players—and new GMs—up to speed without scaring them off. Shadowdark is fast, deadly, and very “old school” in spirit, which can be a shock if your group is coming from D&D 5e or other crunchy, rules-heavy systems. The good news? It’s way easier to teach than most people expect… as long as you frame it right.
What New Players Actually Need to Know
One of the biggest mistakes I see is trying to explain everything up front. Shadowdark shines when you keep the rules light and let play do the teaching.
For brand-new players, I focus on just a few core ideas.
The Core Loop
Explain the game like this:
You explore dangerous places.
You manage light, time, and risk.
You try not to die (and probably fail sometimes).
That’s it. If players understand that, the rest will click quickly.
Ability Checks & Saves Are Simple
No skill lists. No long explanations.
Roll a d20.
Add the relevant stat.
Meet or beat the target number.
For players coming from 5e, this feels strange at first—but it’s incredibly freeing once they realize they don’t need to hunt for the “right” button on their character sheet.
Combat Is Fast and Risky
Make this crystal clear right away.
Combat is not balanced.
Running away is valid—and often smart.
Enemies don’t exist to be “fair.”
Once players accept this, Shadowdark suddenly makes a lot more sense.
Common Pitfalls (Especially for 5e Veterans)
This is where most friction happens, so it’s worth calling out directly.
Expecting the Character Sheet to Solve Problems
In Shadowdark, there’s no Perception safety net. No Investigation skill to lean on. If you don’t describe it, it probably doesn’t happen.
Encourage players to ask questions, poke at the environment, and interact with the fiction—not just their stats.
Overvaluing Backstories
This one surprises a lot of people. Level 1 characters are fragile, and long, detailed backstories often die with them.
My usual advice is simple:
“Write one sentence about who you were before adventuring. We’ll discover the rest in play.”
Treating Death as Failure
Shadowdark assumes characters will die. Replacement characters are fast. The story keeps going because of those losses.
Once players stop viewing death as a campaign-ending disaster, the game becomes much more enjoyable.
How I Teach the Rules at the Table
This is my go-to approach, whether I’m teaching players or helping a brand-new GM.
Teach in Layers
Start with the basics: rolls, combat, and light.
Add rules only when they come up.
Don’t front-load things like spell mishaps or special abilities.
Shadowdark is designed to be learned this way.
Use a Short, Dangerous Intro
I love starting with a small dungeon, tight corridors, and limited torches.
Nothing teaches Shadowdark faster than watching the torch timer tick down while something growls in the dark.
Say “Yes” (Then Roll)
When a player wants to try something weird, say yes. Call for a roll. Let the outcome shape the story.
This reinforces that creativity matters more than system mastery.
Helping New GMs Make the Jump
Shadowdark is honestly easier to run than most modern games—but it does ask GMs to unlearn a few habits.
You Don’t Need Perfect Balance
Stop worrying about encounter math, CR equivalents, or whether something is “too hard.”
Instead, focus on clear danger signals, meaningful choices, and consequences that make sense in the fiction.
Rulings Over Rules
If you’re unsure, make a quick ruling and keep the game moving. You can always look it up after the session.
Your players will thank you.
Embrace the Empty Space
Shadowdark leaves room for interpretation—and that’s intentional. Not everything is defined, and not every outcome is predictable.
Let the table fill in the gaps. That’s where the magic happens.
Easing Players into the Old-School Mindset
If your group is coming straight from 5e, I recommend easing them in rather than ripping the band-aid off.
A few tricks that work well:
Start with a one-shot.
Use pre-generated characters for the first session.
Explicitly tell them, “This game rewards caution and clever thinking.”
Once they survive (or don’t), most players get it.
Final Thoughts
Shadowdark isn’t about memorizing rules or building perfect characters. It’s about tension, momentum, and meaningful risk. When you teach it that way—especially to players and GMs coming from heavier systems—it stops feeling harsh and starts feeling liberating.
If you’ve been on the fence about introducing Shadowdark to your group, my advice is simple: keep it light, keep it dangerous, and let the dungeon do the teaching.
Keep on gaming!
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