The Boss Battle Principle

The Boss Battle Principle

I loved video games as a kid, which is a polite way of saying I was an "indoor kid."

I'd spend hours in our back room playing Space Invaders on an Atari hooked up to a TV that weighed approximately 400 pounds.

Then I got a Nintendo, and my fate was sealed. I spent years hunched over a controller while my mom yelled things like "ARE YOU EVER GOING TO GO OUTSIDE?"

I can't tell you how many hours I played those games, but I can tell you that playing video games taught me something no business book ever did:

Every time you encounter enemies, you're making progress and heading in the right direction.

I call it the Boss Battle Principle.

Think about it. In games, empty hallways mean you've wandered off the main quest.

The hardest boss battles? They come right before you level up.

Smooth, easy paths rarely lead anywhere interesting.

Looking back on my own life, I could never have predicted where I'd end up. I've built careers that didn't exist when I graduated college. Life has had more twists and turns than I expected. But what made it hard is also what made it worth it.

But what made it hard is also what helped make it worth it. If I'd turned away from my fears and never pursued the things that scared me, I shudder to think of where I'd be today. Probably still in that back room, controllers in hand, my mom still yelling about going outside.

The treasure is the reward for not giving up.

This doesn't mean all resistance is good or that you should ignore feedback. (If everyone says your idea sounds like it was conceived by someone who ate paint chips as a child, maybe listen.)

It just means opposition isn't automatically a red light. It's often a sign you're pushing boundaries that need pushing.

In a world where we're primed for instant gratification, and everything takes longer than you want, the treasure is the reward for not giving up.

Seth Godin talks a lot about this in his book, The Dip, (affiliate) about when to keep going and when to give up. He actually writes you have to realize that the bigger the barrier, the bigger the reward for getting past it. (thanks Seth, I'm glad we agree!)

At Once Upon a Roll, we use tabletop RPGs to help people learn the mindset of D&D to better handle whatever comes your way. We teach you how to communicate more confidently, make sharp choices, and take smarter risks – everywhere it counts.

Because sometimes the best way to level up in life is to remember: you're on the main quest, and if you get sidetracked, you can always turn around and come back.

Nothing worth fighting for is easy. But it is always worth it.

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At Once Upon a Roll, we design games that unlock team trust and collaboration. Whether you need a 2-hour spark or a full-day transformation, we tailor every adventure to your goals. Email us to learn more: hello@onceuponaroll.com