Tell a story about learning that you retroactively were less prepared than you thought.

You mean "Every game I've ever played"?

My first time with an At-Will Feather Fall. This means I can jump down and scout ahead while my companions are climbing down soooo slowly. Brilliant, right? Not if you can't ensure your safety against whatever you find down there. Oops.

Game over.

I've learned to underprepare rather than overprepare. If you underprepare, you wind up fighting plant monsters. If you overprepare, you wind up fighting Tarrasques and kobolds.

Try having been over-prepared as a BARD, just by ROLLING YOUR CHARACTER.

My group was captured by a band of Berserker/Bard Orcs, who set four of the six of us up on stage along with one of the orcs, and we got to play Whose Line, except the points did matter! The better we entertained the audience, the faster we were released.

They wanted to laugh at us being stupid, not having actual comedy to our acts, and since everyone else had no levels in Bard, they were able to bumble their way to freedom in only a few short rolls. In order to get free, I literally had to crit-fail a roll, twice. Thank all that is lovely in this world that it wasn't "twice in a row," but I'd rolled too well the entire time there that it took three 4s, two 1s, and a 2 on a d20 to finally get me off the stage.

That sounds like a realy weird adventure. I like the idea... I guess I'll try it one of these days. Let's see, what my players think.

DM wanted to make a game where we gained X-Men like powers as we went through the story, we started with no powers... I had the 3.0 Psionics book and wanted a chara with telekinetic powers using one of the class's from it. DM said I could take the class once I had my powers awakened... At the points where we would have gained powers we had to make fort saves against mutation (to gain them), I kept resisting it. I barely had to roll, the class I wanted had powers using con so I set that as high as I could and I took fighter as my first class...

I actually don't have anything for this one; my neurotically optimized selection of spells and inventory tends to leave me ready for whatever a DM's thrown at me so far. I've never taken a ten-foot pole or straight ladder before, just because my need for a modicum of realism means I'm not gonna carry those without some form of extradimensional storage, but weighted ropes coupled with a good DEX score have worked just as well to date.
As Dexter, Boy Genius, said in one of the Cartoon Network comics, "Be Overprepared."

Alright, back to trawling through Pixel Crew to today's date.

thinking of it, i rarely am prepared enough for anything.

When we played the beta for dnd 5 i actually went full circle. Playing a monster of a man, and some insane rolls during creation, me and my friend where Arnold from predator, only larger and stronger. it was the first game where i actually bought the portable ram as a starting equipment, partially since i could do it while staying on light load. Combined with rations for weeks, and our collection of weapons, we where a two pieces of walking armory, with any tool any task could ask form. We even had good hygiene.

Then we came to a bridge, and realized that while we could carry our gear easily while remaining on light load, most bridges and indeed, some roads, could not