In the summer of 2012 I was a bike commuter, hauling my groceries, gym clothes, art supplies, and everything else in an army surplus black canvas messenger bag. And that bag tore from repeated use- the strap, the corners, the strap again, until it was no longer useable.
Ever resourceful, I pulled out the Kenmore sewing machine gifted to me when I turned 18 and headed off to college. I had been sewing since a very young age- doll blankets and clothes, repurposing thrifted clothes, a pencil mini skirt sewn from an old Vogue pattern so my friend and I could dress like Britney in Baby One More Time, and sewing together t-shirts into dresses and rock and roll outfits to wear when my band had a gig. So I figured, why not, I can make a new messenger bag to match this, easy.
Of course, it wasn't so easy, it never is when you blindly throw yourself into a project without any research or plan. The fabric I chose was awful, too light and flimsy to hold the heavy load it needed to bear while on my back. The straps pulled and ripped. And it just looked handmade (in a bad way).
So I made another one.
I rode my bike to the Joann Fabrics that was *just* a smidge too far to bike to. Bought heavyweight canvas, cotton webbing for straps, new needles for my sewing machine, and rode home to get started.
That same day my bike was stolen from my garage, fitting.
But the bag was better, the improvements I made off the first messenger bag had made the second bag functional and not quite as crafty looking. I took a leap and photographed that bag on my porch, submitting it as a part of my application to vend at Hover Craft, a Milwaukee show that highlighted small creative businesses, makers, artists, and people with good ideas they want to create (and still does). 
Somehow, the kind humans behind Hover Craft, accepted me to vend that December. I had three months to figure out how I was going to make it work.