The Wrong Shoes

When style points don't exist

Dear Kids,

A lot of problems in life can be traced back to the wrong shoes.

Obviously, not all of them, but hear me out.

Some issues are bigger. Tragic. Structural. Caused by elected officials or tech bros. But a surprising amount of your more everyday hangnails can be traced back to the fact that you wore the wrong shoes for the thing you were doing.

You went with the cool pair instead of the comfortable ones.

You picked the squeaky ones on the day you spend walking through quiet, linoleum-laden hallways.

You believed “I think these might work” even though a deeper part of you knew you had no shot.

And for the rest of the day, you’re compensating.

You’re walking funny. You’re irritated. Distracted.

You’re trying to pretend you’re not thinking about this miserable choice you made every six seconds.

The older I get, the more often I realize that this applies to way more than shoes.

Sometimes, there are jobs that are the wrong shoes. Friends that are the wrong shoes. Versions of yourself you tried on because you thought you could pull it off that end up feeling terrible the moment you have to move around in them.

And humans have this incredible ability to endure discomfort because we’re committed to something. So for awhile, you can absolutely power through. But limping never looked good on anyone so why bother?

I have done this literally and (more) metaphorically more times than I can count.

Occasionally, you’ll receive wisdom that is big and dramatic. Accompanied by the sound of a Tibetan gong and a break in a wall of clouds. But sometimes wisdom is just finally saying, “These are the wrong shoes,” and putting them back in the cubby.

Again, nobody ever looked good limping and that’s not something you want to be the first to pull off.

Love you more than you’ll ever know,

Dad

P.S.

If this letter landed with you, would you forward it to someone who you think would like it too?

This letter is original work from The Unfinished Dad (© 2026). Feel free to share it, quote it, or forward it; just please credit the source and don’t present it as your own.