WINSday on Wednesday 07/16/2025

A thoughtful question to help you get over hump day and win the week!

The Psychology Hack that Works on Almost Everybody

Personality profiles are a dime a dozen, and I’ve taken them all: the Meyers Briggs, DISC, Strengths Finder, and Right Path. A few years ago, everybody was talking about the Enneagram, a profiling system that identifies a person’s core motivators, fears, and behavior patterns. So yeah, I signed up for that one, too. Meet anybody who knows anything about the Enneagram, and you’ll find a person who will talk your ear off about her assigned number.

1-Perfectionist

2-Helper

3-Achiever

4-Individualist

5-Investigator

6-Loyalist

7-Enthusiast

8-Challenger

9-Peacemaker

I’m a 5, by the way. Deep research is my love language.

While most people love their Enneagram number, Challengers elevate theirs to a whole ‘nother level. In a personality showdown, you can’t win against a challenger.

A challenger is fiercely competitive.

But I’ll tell you what I love about a challenger: She is not afraid to QUESTION EVERYTHING.

A challenger will bet her bottom dollar that she is more resourceful, decisive, and courageous than you.

And chances are good she’s right. Frustrating for sure.

Not an Enneagram 8? Here’s another kind of bet that works on those of us who weren’t designed to dominate the world.