"I realized about six weeks into law school that it was a mistake," he remembers. "There was pressure from my family that made me feel like I had to stick it out, so I did the minimum to get by, checked out mentally, and passed everything. I knew it wasn't what I wanted to do - I wanted to be in business."
Today, Bailey is where he dreamed of being five years ago: running his own business, a subscription company that supplies customers with regular deliveries of high-quality bacon from across the US. He named it Bacon Me Please.
Generally the company earns about $10,000 a month in revenue, although revenue reached nearly $25,000 in January. He says he can work on Bacon Me Please about seven hours a week and devote significant time to starting another venture.
So how did he get from reluctant lawyer to enthusiastic entrepreneur? He credits much of his success to one choice: surrounding himself with people who supported his plan.
After Bailey shut down his small-town Texas practice a year and a half in, he distanced himself from his family and friends who had always known him as and expected him to be a lawyer, both geographically and intellectually.
First, he moved to Colorado.
"In Texas, I set up my practice on property my family owned," Bailey says. 'There was a lot of visiting. They just expected me to be an attorney. You kind of live up to the expectations you set for yourself, but you base those expectations of yourself on what other people's expectations are. I had to remove myself from those influences, so I packed up from Texas and moved to Colorado to be far away from the influences I had around me."
Then, he stumbled across online entrepreneurship community The Foundation while seeking to learn more about skills like marketing, sales, and copy writing.
"I was surrounding myself every day, interacting with all these people who had businesses and were growing their businesses," he says. "You hear a lot in the entrepreneurship community that you're the average of your five closest friends. By surrounding myself with people who were doing things I wanted to do, it became inspiring, and I expected it of myself."
In Colorado, he was open to new ideas in a way he hadn't been before. "One night I had a craving for bacon around midnight, and the idea occurred to me: I wish someone would deliver me bacon!" he remembers. He put up a Facebook status to see if people would be interested in a service that did just that, and after many "likes" and some positive feedback, he set up a basic site and sold $3,000 worth of bacon before he even knew where he would get it. He used that money to road trip around the US for two months, finding the best local suppliers "and following leads from one town to the next."
Now, Bailey can spend the winter snowboarding and maintaining his business on his phone, from the ski lift. His best advice for others who want to make a drastic change? "Surround yourself with people who are going to hold you to the standard you want to be held to."
Have you walked away from a steady, high-paying job to create your own path? Email yourmoney[at]businessinsider[dot]com.