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Life Lessons: Stormy Simon starts again

If the thought of having to reinvent yourself after having one successful career scares you, you need to meet Stormy Simon. She willingly talks about being a teenage mom and being on welfare in her early 20s.

She worked her way up from being a temp to being president of online giant OverStock.com.

But true to her entrepreneurial spirit, Simon left that job a year ago to try something new and unproven. In that is a lesson for all of us.

Simon traded her corporate office for a home work base with all her animals.

"It’s having all these life events happen," Simon said. "You lose your mom, you get a grandbaby, your boys move out. You’re like, 'Oh my god, it’s really happening. I’m getting older.'"

She loved growing overstock.com into a huge success. She wants to do it again in the cannabis industry.

“I really believe in it as a medicinal product," Simon said. "Passionate about it being a more organic way to heal.”

She’s also passionate about her 5000 club. She puts up $5,000, challenging women entrepreneurs to turn it into $10,000.

Julie Bellon, a 5000 Club Member, said “I thought, 'Oh, I have to do this first, I have to do this.' And then I thought, 'I was just going to build the website. I’m just going to find a company that will help me build it and start somewhere.'"

Simon is happy to share tips on reinventing a career. First, know that you take your talent with you.

“Your innate abilities stick with you," she said. "The performance you have at the job you’re at currently gets to go with you. You don’t lose any of that.”

Number two: Answer only to yourself.

“When I started talking about this, a lot of people were like, 'What? You’ve got to be crazy. You can’t go. You’re e-commerce. You’ve got to go to a big company,'" Simon said.

Number three: Make it a positive move.

“Make sure you’re not running from something, but you’re walking toward something.” she said.

Simon can’t wait to see where her new trajectory takes her.

Simon makes herself a part owner in 5000 Club projects. As they become successful, her share will shrink or grow. Right now it’s limited to her friends, but she says some day she hopes to help more women start new businesses.


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