I have this friend, who is single, no kids, late 30s, kind of a mess. He’s overweight, drinks too much, smokes too much, only recently moved out of his mom’s basement. I’ve known him for years and am shocked again and again when you think his life is going to implode, only to watch him fall upwards.

He just always seems to skim the surface of disaster and land on his feet. I’m not sure why, but it drives me crazy. I don’t want him to fail, don’t misunderstand.

I think I’m just jealous of his good luck at every turn. How do I handle my feelings? Failing to Fail I think what’s bothering you is that your friend doesn’t seem to be following the “normal” path, and in its abnormality, he’s having some semblance of success. That’s upsetting to you because you (I surmise) have followed the path most paved, followed all the rules, and have only reached an average level of success thus far.

Get over yourself. If everyone followed the same path, life would be very, very dull. This guy’s doing the best he can with what he’s got and it’s working for him.

Perhaps it’s not the way you would do it, but he’s having some success. Be happy for him. Be proud of him.

And if anything, give him a leg up. It’s better to help each other along the way than to step on each other or push each other out of the way. That doesn’t feel good as either the pusher or the pushed.

Also, what goes around, comes around. You’d want him to root for you, give you a helping ha.