“Why are you looking for help? Do you believe help will come from outside? What is to come will be created in you and from you. Hence look into yourself. Do not compare, do not measure. No other way is like yours. All other ways deceive and tempt you. You must fulfill the way that is in you.” – Carl Jung

Ambition. “I’m going to be a successful entrepreneur by 30.” I’d say.  With my future already written, it was sure to be better than everybody else’s. 

For the ambitious, the urge to “get ahead” compresses our timeline and narrows our focus. We fill our days with cluttered productive goals. We get to tell our Mom’s friends how well we’re doing. We are “winning,” after all, and it feels damn good to be ahead.

When the ambitious person finds an admirable teacher who says, “I have an esteemed opportunity for you,” nothing more must be said. The ambitious person becomes a teacher’s pet, a follower. In the job interview, she makes everything appear perfect to protect her structured future. A rejection letter is a painful loss. She thought the future was something real.

The dropout personality, on the other hand, throws paper airplanes at the teacher. He drinks 2% milk out of a champagne glass and is completely himself in a job interview. He cares little about the future your ambitious self is attached to. He is a lesson in saying, “fuck your structure, that ain’t me.” He’s fine with rejection from square establishments that don’t fit his groove. It’s his defiance that allows a criticism of the structured path.

It’s a balance, the dropout will overdo freedom by refusing to choose a path and develop himself. He’s the artist with an unpracticed hand, the writer with a story and no form, and the entrepreneur with ideas and no execution. Pure freedom without discipline isn’t useful. But the ambitious person can learn to rebel from structure and the rebel dropout can learn to approach things.

The voice of society tells us to be suspect of those who pursue a plurality of paths– accused of incompetence, at risk of falling sinfully behind. The police knock on the underground fort of those who deviate. And a to-do list becomes the prison to tyrannize the unattended aspects of ourselves. We become slaves to a golden future mistaken for love and self-acceptance.

The ambitious winner is the one stuck in a cubicle making $180k with mortgage payments in the wrong city, a hated spouse, and a life meant for someone else. Failing to escape a winner’s mentality means ending up miserably stuck despite “having it all.”

Winners clench the known narrative of past wins. This makes it painful to lose moments in time we’ll never be back to. I’ll never make sandcastles with my ex-girlfriend again. Winners struggle to let go of wins.

To give up games we’ve been winning at is to become a loser. It takes a bit of courage and rebellion, but only a loser can break out of the known to find new paths and adventures. Losers can laugh off loss.

When feeling lost– appreciate the opportunity to search for a better narrative. When feeling stuck– saying “fuck it” to lose your idea of the only winning future is incredibly refreshing.