essay
Teaching My Kid to Lose on Purpose
2026-03-18 · 3 min read
My daughter is old enough now to sit through a real game, not a candy land style roll and move thing but something with actual decisions in it, and I’ve been slowly working her through Gloomhaven’s Jaws of the Lion box on weekend afternoons when Renae takes her brother to his thing across town. It’s gone well overall, better than I expected honestly, the tutorial scenarios really are built for exactly this, easing a new player in a scenario at a time without making them feel dumb for not knowing the combat system yet.
Two weekends ago we hit a scenario that just went badly. Bad card draws, a monster that got two activations in a row somehow, and about forty minutes in she was down to almost no health and visibly frustrated in the specific way an eight year old gets frustrated, not crying exactly but close enough that I could see it building. She wanted to stop. Not pause, stop, put it away and not come back to it. And I had this whole internal debate in about four seconds, do I let her quit because it’s her call and forcing her to finish a game she’s not enjoying teaches the wrong lesson, or do I push through it because bailing every time something goes badly is its own bad habit to build early.
I told her we’d play three more rounds and then decide, which is a compromise I’m not sure I’d defend under cross examination, it’s not really her choice at that point, it’s mine dressed up as one. She agreed, mostly I think because eight year olds will agree to almost anything that gets an adult to stop talking. Round two of those three, her character landed a hit that turned the whole fight, one of those swings where a single good roll changes the entire shape of what happens next, and by round three she was leaning over the table again instead of slumped back in her chair.
We won that scenario, barely, and I don’t actually know what the lesson was, if there was one. Maybe it’s that things turn around more often than they feel like they will in the moment, which is a real thing worth learning young. Maybe it’s just that I got lucky with the timing of a good die roll and I’m building a whole parenting narrative around something that could just as easily have gone the other way and left her more frustrated than before. I don’t have a clean answer. I do know she asked to play again the next weekend without me bringing it up first, which I’m choosing to take as a good sign.