SM: What were some of the jobs you had when you started out as a freelance makeup artist?
Brown: After college, I did two things. I tried to begin my career as a makeup artist and I waited on tables at a local seafood restaurant on the waterfront. The latter is important because it [enabled me] to pay rent and eat! I did makeup for one film while in Boston—a very low budget one. That four-week production was enough for me to realize that the film business was not for me.

One year after graduation, I moved to New York. I was able to begin freelancing at soap operas from time to time. I also did makeup on both men and women anchors at local news shows.

I also worked with Linda Mason on fashion shows. She taught me to take a chance, and much of my early work was a mixture of natural and bolts of color. I got to work with Bonnie Maller, both on fashion shoots and shows. Her makeup was the most instrumental in helping my style emerge. It was clean, natural and always beautiful.

While Bobbi is sentimental about her twenties, she is also keenly aware of the beauty woes felt by many 20-somethings. In Bobbi Brown Beauty Evolution: A Guide to a Lifetime of Beauty, one of her three bestselling books, Bobbi writes, “Coming to New York in my twenties as a young makeup artist, I worked all day surrounded by models and mirrors. That was hard. No matter how good I thought I looked when I left the house in the morning, I’d get to the studio and feel like I didn’t have it together. Every day I experimented with my clothes and hair and makeup, trying to figure out who I was and how I wanted to look…. I promise that you will one day look back to your twenties and say, ‘I shouldn’t have been so critical of myself. I really looked good!’"