Backstory

I might have already mentioned that I played a lot of D&D as an adolescent. In doing so, I created a handful of characters, but most of my focus went to running the campaigns.

This time around, it’s all about creating some depth. Sure, you still have the whole idea of selecting from a menu of classes and species, and you still roll for character attributes like strength, wisdom, and dexterity—but beyond the stats, people who play these days are encouraged to make a much more detailed backstory for their characters.

I love this. I think it really helps folks immerse, and good storytelling requires immersion. It also gives you a really good direction for decision-making, and it makes the improv aspect of the game much smoother if everyone has a good idea of their character’s underlying motivations, traumas, and triggers.

I thought it might be fun to share my current (draft version) backstory with you here. This won’t be particularly flowery language, but I hope you can sort of immerse yourself into my character’s shoes with me for a few moments.

And no, I don’t have a name yet. Let’s use Flip for now, which may just stick.

My little man (literally a little person) is a halfling rogue, if you have to pigeonhole him. Flip is so much more than a mere rogue, though.

With two parents who were traveling circus performers, Flip was a true circus nepo-baby, destined for a life under the big tent. By the age of adolescence—a bit older for halflings than for us humans—he was among the elite acrobat performers anywhere in the realm. Both of his parents were huge stars, but Flip understood from an early age that they were treated like property, not like people.

Flip is a legit Big-Top Pee Wee, but don’t ever call him that

Flip’s resentment grew as he became more of a focus for the show, headlining event after event and being recognized by people no matter where he went.

The circus guild was a very powerful institution, not to be trifled with. The guild claimed to help entertainers everywhere to be able to learn a valuable skill, and—most importantly of all—the guild would negotiate on your behalf, virtually guaranteeing that you’d have enough to eat and a place to sleep at night.

In theory, this would work in the best interests of the guild participants. In reality, the circus guild operated much more like an organized crime syndicate than advertised, and Flip saw all this from the inside. He saw how little power his parents (and he) really had behind the scenes. Sure, they got to eat good food, but they were performing monkeys as far as Flip was concerned, and the high intensity life of a daily performer left little time or energy for anything else.

Most of this bubbled under the surface for Flip, until he watched his mom fall to her death. There was supposed to be more time to practice the routine, but the tentrunners had insisted on adding a new move to impress an important lord who was making a surprise visit that day.

This moment changed everything. All of the rage that had been quiet before was now unleashed. Flip’s better angels wrestled with vengeance and only kept them down for long enough for Flip to make a hasty exit from the circus. All he knew for sure was that he didn’t want to have anything to do with the event, ever.

He penned a quick note to his father and made his escape at nightfall. Out on his own and with just enough coin to survive for a few days, Flip found himself among some pretty shady characters. This really suited his mood, though—and besides, he had grown up in the circus, for crying out loud. Flip found himself feeling comfortable among the seamy underbelly of society.

He felt a real kinship for the first time, viewing these rapscallions as compatriots in a similar position, under the thumb of the rich and powerful who seemed to dictate so much of their lives.

Flip liked being anonymous. The last thing he wanted to do was climb up a rope and start flipping around for people, so he kept his experience on the DL everywhere he went. Having a shady past was okay among the rogues’ guild here in this small town, and Flip became involved.

The rogues’ guild was no ordinary guild, though. This was for elite assassins, trained to kill rich and powerful targets.

Okay, maybe Flip didn’t stumble into this particular guild entirely by accident, but it was truly fortuitous that the first town where Flip settled in after traveling was the home of the most elite training grounds for killers within a thousand miles. How could Flip get into such an elite institution if he was intent on keeping his superpower (acrobatic mastery) secret?

By getting drunk one night and showing off, of course.

That little display nearly got Flip and his drinking buddies killed, but it also got him into the assassins’ guild, where Flip swore vengeance on the circus owners and the rich lord who had come to town that one fateful day.

Flip grew his hair long, and now he has a few scars from fighting. It’s pretty easy for him to blend in and be anonymous—the one thing he craves most in life.

Did I stick the landing with Flip here? Is the little dude rolling his eyes at me every time he hears me tell an acrobat joke or call him “the little dude”?