Wisdom Wednesday (On a Thursday?): When I Roll a Natural 1 on Initiative

December 4, 2025

Before we start today, shall we we will start off on an Insight check, and address the elephant, or rather the Mind Flayer, in the room?

Don’t worry, you have not failed your Saving Throw against the Bard’s Enthrall spell, you did not spend too much time in the Upside Down and lose a day, and you certainly did not magically draw a Time Warp card from your Dimir deck in MTG. You are absolutely finding this blog post on a Thursday. But this is Wisdom Wednesday! I know, I know. You’re confused. You’re checking your calendar. You’re wondering if a DeLorean ran 88 miles per hour past your house and messed with the timeline.

Sadly, none of that happened. This is the truth: I rolled a Natural 1 on my Initiative check this week.

I had a high Dexterity modifier. I even had the Alert feat to give me Advantage. I was ready to launch this post. But sometimes, the universe (or the Dice) decides that life gets the better of you. I was caught flat-footed, surprised, and by the time I unsheathed my keyboard, the turn order had already moved to Thursday.

But, in the spirit of the game, we play the hand, or the initiative count, we are dealt. So, let’s talk about that very mechanic: Initiative and Surprise!

Initiative Is More Than Just Rolling Dice

At the D&D table, our group casually treats Initiative as a mechanical but necessary step before jumping in and slaying that dragon or battling those orcs. "Roll Initiative." It's like a swirly administrative loading screen before the fun combat starts.

But here at Giants of the North, we believe Initiative should be a storytelling moment! A standoff of heroes and villains (or sometimes villains and villains) standing there, frozen in time like The Good, The Bad and The Ugly - Final Duel, waiting for someone to go first. And who goes first depends on what comes out of the 20-sided magic rock + math.

The Natural 20: Damn that’s luck!

Hyper Aware! You aren't just fast—you were expecting this. When you crit that Initiative roll, it's not just about speed; it's about anticipation. You aren't reacting to the threat; you are the threat.

The Story: You noticed the kobold's hand twitch toward his dagger before he even touched it. You smelled the sulfur in the air before the Wizard started his fireball incantation. You saw the blood on the leaves before the invisible stalker struck.

The Feeling: You are the samurai (or ronin) who already beheaded the drug lord before your katana left its sheath. Time itself slows down just enough that you can act Matrix-style before others know you're even there. You are the shadow in a sea of darkness. You are Han shooting first.

The Natural 1 (Me, this week):

What is going on? You aren't just slow…you're distracted.

The Story: Maybe you were adjusting your armour straps, or perhaps you were confidently explaining why this dungeon is definitely safe right before the ceiling collapsed with giant spiders.

The Feeling: This time, you are the comic relief in the opening scene of an action movie. You're studying the map upside down while the ambush triggers. You're caught flat-footed, scrambling to drop your backpack and draw your weapon while the enemy is already mid-swing. You've made a fantastic sandwich and are about to take the first bite when goblin fire arrows have already crossed your vision.

Surprise Rounds: Now vs. Then (5e vs. 2024)

Since I'm a day late, let's talk about why I'm late. Was I procrastinating? Was I working too much on my actual career? Was I caught Surprised? The answer depends entirely on which Player's Handbook you're holding for your game!

The Old School "Surprise Round" (2014 Rules)

(I cannot believe I just wrote "Old School" when I've played Dungeons and Dragons since AD&D. #oldschooldnd.)

In the 2014 rules, being surprised was brutal and really to be avoided at all costs. If the DM determined you were surprised, you couldn't move or take an action on your first turn, and you couldn't take a reaction until that turn ended. A free attack on those who cannot fight back.

The Story: You're basically stunned. You're caught unawares with your proverbial pants down. You're looking at the calendar, realizing it's Thursday, and your brain completely shuts down. You lose your turn entirely. You're literally the sitting duck.

The Feeling: The enemies (or deadlines) get a full round of beating you up before you can even blink, act, run, or take a bite of that delicious sandwich.

The New School "Disadvantage" (2024 Rules)

The 2024 update changes the game. There are no "Surprise Rounds." Instead, if you're surprised, you simply have Disadvantage on your Initiative roll.

The Story: You're caught off guard, fumbling for your weapon (or laptop), but you're still in the fight. You aren't paralyzed; you're just slow on the uptake. Like living without coffee for an online meeting that's sure to last too long.

The Feeling: You might go last in the turn order (like posting a Wednesday blog on a Thursday), but you still get to act! Or heck, you may even go first if the magic dice roll in your favour!

The Verdict: Clearly, I'm operating on the 2024 Ruleset, and I think this is the better way to go. I was surprised by the midweek rush, rolled with Disadvantage, and ended up at the bottom of the Initiative count. But hey, at least I didn't lose my turn entirely!

Recovering from a Bad Initiative Roll

So what do you do when you roll a 1 or a really low roll? What do you do when you're last in the turn order…or when your blog post is a day late?

You hold your action. You assess the battlefield. You let the enemies commit to their movement. You see where the party needs you the most. Sometimes, going last is a tactical advantage. You get to be the "closer." You get to fix the mistakes made by those who went early. Think of it as an advantage…not a failure. The magic rocks giveth and the dice taketh away…but only if you let them!

DM's Wisdom of the Week: Initiative dictates when you act, not how well you act. A delayed Fireball does the same damage as an early one.

So, to my loyal readers: I apologize for the delay. I failed my perception check on the calendar. But now that it's my turn? I would like to Rage and possibly go Reckless on my enemies. But, as you know if you know me, I'm more the Bard or Thief character…so I'll likely just skulk in the darkness and wait for my opportunity to strike or sing a really bad song. :)