Shortly before it was time for me to come home from Austin on Sunday, my daughter Jennie and her 5-year-old daughter Zoe began going through Zoe’s things picking out items for next weekend’s garage sale. There were outgrown clothes, last year’s Halloween costume plus toys and books that weren’t being passed down to Zoe’s baby brother. By the time they finished, they had a formidable pile.

Zoe was inspired by hearing that her mother had once organized a garage sale when she was a kid who wanted to finance a trip to Disneyland. Zoe, too, has a specific project in mind and also plans to give part of her earnings to a cause she deems worthy.

What Zoe’s learning is something successful entrepreneurs have discovered for themselves and do all the time. The process goes something like this: 1) decide what you want to do or have, 2) determine what it will cost, 3) create a project to fund it. It’s a simple idea that’s quite foreign to the more conventional way salaried employees operate.  Shrinking your dreams to fit your budget may seem logical, but it’s a recipe for dullness. 

For most of us, becoming joyfully jobless requires that we examine our relationship to money and make a concerted effort to develop healthy attitudes and behaviors. Unlearning the scarcity thoughts of our elders, being willing to accept money for having fun with our work and a myriad of other unhelpful thoughts can keep us from moving ahead with our businesses and creating a life of abundance. Every dreambuilder gets ample opportunites to discard old approaches to money.

On my flight home from Austin, I saw another big example of what I’m talking about. I’m rereading Bill Strickland’s astonishing story, Make the Impossible Possible, and came across the story of how he financed his flying lessons in order to fulfill his dreams of becoming a flight engineer. He’d already gotten his private pilot’s license, but earning his commercial license was going to cost $50,000, an enormous sum for someone running an inner city arts’ program. 

Strickland writes that one night after leaving the flight school, he noticed a Beech Sundowner in a hangar with an “Airplane for Sale” sign on it. He writes, “As I looked it over an outrageous possibility occurred to me. When I got home, I called about the Sundowner. The asking price was $50,000. It struck me that my flight school might need another plane for training, so I called and asked the owner if he’d be interested in leasing a plane from me. The next day, I took his willingness to the bank—literally, I told the loan officer I wanted to buy an airplane, then lease it back to the flight school for a monthly fee that would cover my loan payments…Then I used the plane, when it wasn’t being rented out, to accumulate the flight time I needed. The flight school maintained the plane, and the money from the lease paid back my loan. My only expense was the cost of fuel.”

This month we’re exploring a new theme: Making Peace With Money. It’s a challenge that comes to all of us, but not everyone meets it with grace and poise. I’ll be sharing thoughts about this emotionally charged subject all month long. Hope you’ll visit often.