The Growth Season Challenge—Activity 1: Own your money story

Riley got a lead from a friend to power wash an expensive home in an upscale neighborhood. The friend assured her that the owner didn’t care about price—they’d 
pay “anything” if someone could get the knotted tendrils of an old vine off the side of 
the house.

On the drive up the hill and past the guardhouse, Riley rehearsed how much she would charge—how much she knew she could charge. After doing a superb job with her crew, she meekly asked the owner for … her usual rate.

Driving home she got a lump in her throat; embarrassment welled up. Riley was behind on her loan. The money would have been meaningful. Why’d she do that? Why didn’t she ask for more?

Riley was acting out her personal money story

Many of us are operating on unspoken beliefs about what we deserve and what it feels reasonable to earn. Rarely do we think about these beliefs. But these hidden ideas shape how we interact with money—especially in business, where the stakes are high.

We’ve probably all felt some version of Riley’s story.

Ever find yourself acting like your own worst counter-negotiator, knocking down prices before anyone even asks? Or ghosting a vendor because you’re embarrassed you can’t afford them? Or saying yes to purchasing an expensive new device while thinking, “No don't do it!”

Sometimes we feel like a spectator in our own lives, watching as we make poor money decisions. If you have felt that, congratulations! You are human.

We all have money stories. We often carry them from childhood. And the beautiful thing is you can rewrite yours—if you just write it down.

Riley’s money story is about not feeling worthy. This causes her to leave money on the table. But if she can name it, speak it aloud, and realize that she’s doing it, over time, she can rewrite it to do the opposite. She can have a money story that tells her to always ask for more.

This isn’t easy. But you didn’t come here because you want to take the easy way out. You signed up for a reason.

Your one action today:
Complete this prompt

If this feels hard, it means you need it. Keep the rewritten story in your office or truck where you can see it.

Think it’s hokey? Prove us wrong. This is based on decades of psychological research. Do not leave this article without pulling out a pen and giving it a shot. You will be shocked at how clear you feel tomorrow.

On the other side of this exercise is a world free of worry.

Until tomorrow,
The Pilot Team