Good teachers can stay with you your entire life. For entrepreneur Charles Best, Mr. Buxton, his high school wrestling coach, inspired him to become a teacher. "I looked up to him. I wanted to have that same thing happen to me," says Best of his former coach, English teacher and assistant principal. Just like he planned, Best graduated from college, traveled the world and then returned to his home state of New York to be a teacher.

Teaching is a selfless career. For some educators, changing a student's life makes all the hard work worth it. But endless piles of papers, insufficient planning time and meager salaries can leave some teachers feeling helpless and unrewarded. A 2007 report from the U.S. Department of Education, National Center for Education Statistics found that half of teachers who left the classroom after the 2003-2004 school year found the workload at their new careers more manageable. Of those who left to pursue a career outside of education, 22 percent went on to become entrepreneurs.

Charles BestFor Best, 32, his decision to leave his teaching job at Wings Academy in the Bronx had nothing to do with not enjoying the job. He wanted to reach more children. "I knew I could reach a bazillion more children [with DonorsChoose.org] than I could have in the classroom," he says. He was right. Best's not-for-profit website allows teachers to submit project proposals for materials and experiences their students need to learn. Then donors fund projects of their choice. So far, his philanthropic marketplace has supplied 750,000 students with classroom materials and funded 33,000 classroom projects. Overall, DonorsChoose.org has raised more than $15 million worth of supplies, field trips, and other classroom items and projects.

But like other entrepreneurs transitioning from a day job to a full-time entrepreneurial venture, Best found himself working long days in the classroom and tiring nights at home. "By my fifth year of teaching, I risked not being as good a teacher," says Best. "I was on my cell phone in between classes, getting there right as the bell rang and not taking the time to prepare like I should have."

But one of the four classes he taught--virtual enterprise--actually helped him prepare for pursuing his own entrepreneurial dreams. "I had to teach myself how to write a business plan the night before I gave the lesson," he says. "Though I didn't have a real plan for DonorsChoose, the lesson came in handy when it was time for me to focus on my business."

Elizabeth WitengierOrganizing guru Elizabeth Witengier of Orlando, Florida, also has applied some of the skills she developed in the classroom to her business. "I wasn't patient until I became a teacher," she says. "Helping people organize their homes takes patience because many of them are emotionally attached to their stuff."

After attempting to make it as an ad executive in New York City, Witengier, 30, says her perspective on life changed after September 11. After re-assessing her goals and priorities, Witengier moved back to Orlando, where she took a position as a fifth-grade teacher at Wineguard Elementary. But it wasn't exactly what she had expected. "I was extremely overwhelmed, and one of my biggest concerns was that my students would catch on that I didn't know what I was doing," she says.

Around that time, Witengier began working on her first company on the side. Events by Elizabeth drew on her past event-planning experience in New York. She realized, however, there wasn't a strong demand for her services in Orlando. In the meantime, Witengier's fellow teachers began asking for her help organizing their classrooms thanks to her reputation for cleaning clutter. She began trading services with them; Witengier would help them organize, while they would help her with lesson planning and paperwork. Soon, they began asking her to help organize their home closets and garages--and they were willing to pay. By July 2005, Simply Organized was born.

Witengier left teaching in May 2006 to take on her business full time. But financial reasons recently forced her back in the classroom for the current 2007-2008 school year. "Looking back now, I think that my optimism overshadowed my fiscal reasoning. Now, I'm generating more capital to propel Simply Organized forward," says Witengier.

Monica Michelle
San Mateo, California-based photographer Monica Michelle can understand that financial struggle. But unlike Witengier, she found herself making more money in a weekend with her hobby, photography, than she did in a month of teaching. That's not to say teaching didn't help her transition into her new venture. In fact, the founder of White Rabbit Portrait Studios is best known for her work with children. Thanks to her time in the classroom, Michelle helps children feel at ease so she can capture them being themselves.

Though her family was appalled at the thought of her leaving her eight-year teaching career after spending so much time preparing for it, Michelle didn't let that stop her. She dabbled in jewelry-making before opening her own at-home photography studio. She became profitable within the first five or six months and thrived on setting her own schedule. "I do miss teaching literature," she says. "But now, I don't miss any time with my kids. I can still go on field trips with their school. I don't miss a beat."