How does your business evolve with you? Have you outgrown it? Is it time to start another one with a different direction, so it aligns with who you are today?

These were the tough questions Jessica Zweig, founder of the SimplyBe Agency, was faced with when she decided to end her first business, Cheeky Chicago, that had been running for 7 years. Launching in 2008, Cheeky Chicago was an online lifestyle magazine for women, and was of Chicago's first online destinations for the hottest socialite venues. It soon evolved to include content about dating, fashion, restaurants, buying your first home, and more.