When we play a game, any kind of game – video, board, card – and it’s my 4-year-old son versus myself, I want to let him win all the time.

I don’t. I resist the urge to sit back and play passively. I don’t hold back.

It’s not like I just throw him into the water and expect him to swim (metaphorically, of course). I show him how to play and try to guide him, letting him know what’s right and wrong, before crushing him.

I remember my father not letting either my brother or I win at anything unless we legitimately won.

For instance, I didn’t beat my father in a one-on-one game of basketball until I was 18-years-old. He fouled me, trash talked, and generally gave me very little room to breathe. At the time I remember being pissed I couldn’t win. I also recall it making me work harder on my game. I practiced more, I worked harder.

Now, I’m not taking my son out to the court to rough him up just yet. It’s still a bit of a mismatch. Although I am grossly out of shape, but that’s beside the point.

The point of this post is that it’s hard to see how upset/frustrated/outright angry he gets at losing. Hell, he gets that way when it seems he’s going to lose. I have to explain to him that the game isn’t over and that you can’t stop when you think your effort will result in a loss.

Seeing him upset makes it hard for me to win. A part of me wants to let him win. I suppose it just boils down to seeing him fail.

I’ve gotten him to say, “never stop trying”. I’m trying to drill it into him now while he’s still mold-able.