WIN OR LEARN

WEEK OF 9/14/2026

 

“You either win, or you learn.”

This expression is so ubiquitous, it may as well end up on a piece of wall art you can buy from Target on the shelf next to “Live, Laugh, Love” or something.  And there are plenty like it: “if you’re going through hell, keep going,” “fall down seven times, stand up eight” etc etc etc.

This conventional wisdom is everywhere, and often comes off as sappy and cliche.  Which, I suppose, it kind of is.

But for the people who are out there actually taking risks, actually working to get to the top, and actually dealing with significant loss, it’s all true.

Well, sort of.

I propose we change the eponymous quote, though.  “You either win, or you learn” is misleading.  Learning isn’t something you do by default.  In fact, many people never learn from their mistakes (we all have that one friend who dates the same type of person that’s absolutely terrible for them) and are thus doomed to repeat them.

“You either win, or you can learn” is a little more apt.  Losses present the opportunity to learn.  An opportunity to reflect, analyze, re-motivate, and re-orient.  An opportunity to demonstrate character.

The point here is that learning is an active choice, an active pursuit.  It’s not passive.  It’s not a byproduct of losing.  It’s more work, and it’s hard work, but it can be mined for some of the most valuable insight and perspective there is.