A Radical Concept: Starting Levels Based on Backstory

 This might not work at all.

One of the issues with creating a D&D character is how the concept for a character might not always match the mechanics.

Let's say that you want to play a character with a long backstory - maybe they're an older character who has spent a lot of time as, say, a soldier or a mercenary. Does it really make sense for you to start off at level 1? Surely, if you're some pirate who has sailed for twenty years, fighting royal marines and sahuagin, you'd for sure be beyond level 1 at this point.

On the other hand, let's take my new Wizard character. He's basically about six months out from having graduated from the Halls of Sagacity in Gwardan on the Menagerie Coast of Wildemount. He's 22, and very naive about the world. For him, level 1 makes perfect sense (and in fact, he's hit level 2 after our first session - still waiting to hear back from the other Wizard in the party before I pick my new spells).

Differing backstories would seem to lend a character different starting experience and thus levels.

So what if, as a DM, we just... let people do that.

Plenty of DMs start campaigns at higher levels. I think level 3 is often a good place to start a campaign because experienced players don't really need the "tutorial" that is level 1. Indeed, one of the big things about level 3 is that by then, every class has gotten its subclass. There are some character concepts that don't really start to make sense until you've got those subclass features. For example, I've often wanted to play a Path of the Beast Barbarian, flavoring it as his having been a mild-mannered bureaucrat (basically an insurance adjuster) who was bitten by a werewolf and has developed Barbarian-like qualities due to the curse.

Their "rage" would simply be their lycanthropic transformation.

But prior to getting that subclass... ok, I guess you could just skin it that way, but you wouldn't be able to use the claws or bite (the tail admittedly doesn't really fit with that idea).

Balancing encounters for such a party - especially with wide disparities in level - would be very difficult, though I'd suggest a DM could have a boss-type monster that focuses on the high-level characters with minions that will go toe-to-toe with the lower-level characters.

Again, I'm not sure it would really work. I think you'd want to stick to using XP to level characters up, as ideally the lower-level characters would level faster than the higher-level characters. Or, at the very least, you'd want to have a system that boosted the lower level characters more.

In terms of preparation, I'd say that the DM would have broad discretion to figure out the level a character should have based on their backstory. Of note, even a 4th- or 5th-level character would, in most worlds, be considered a truly remarkable individual by that point. The aforementioned pirate character could easily be only level 5 or so - unless you had a character who had faced down krakens and dragon turtles.

It'd be an interesting experiment. But I also think you'd only want to do this if you were committed to doing a longer campaign, as the development of those characters seems like a major part of making it fun for everyone.