After graduating from Harvard Business School she skipped the Wall Street route and headed instead for Viacom, where she eventually developed shows for Spike TV, VH1, and MTV.
From there she dove into digital media at YouTube, where she helped transform the company from its early days as a cat-video host to the brand name video-sharing website and major media partner it is today.
And most recently Lee signed on as Margaritaville Enterprises' president of media and chief digital officer.
Through all her leaps of faith, Lee tells Business Insider she's always let her passion lead her career.
Here she shares her five steps for making a smooth career transition:
1. Filter through and follow through.
First things first, Lee says you need to stay focused, take a breath, and really think about the direction of your career - where it is now and where you want it to be. Based on that, she suggests you create a detailed list of goals and a corresponding timeline. Throughout your career you'll need to be diligent and honest about following through.
Lee says she's always been fascinated with the entertainment industry and how it connected consumers to brands so intimately. "I saw the big picture and knew I wanted to be involved in the developmental process so I laid out my own action plan," she says. Through all her career transitions she kept the action plan in mind.
2. Become an expert.
"When thinking about a career change or embarking on a new professional direction, get involved and do your research," Lee says. This means immersing yourself in the terminology, culture, and news of the industry. Lee suggests joining professional networks, attending events, and meeting people in the field. "You need to have intricate knowledge of an industry to understand if the industry is truly right for you," she says.
3. Be patient.
Transitioning to a new job or career can be a long process, Lee says, and you need to be realistic about the time it will take to succeed in the role. "It takes a lot of work and even more humility," she says.
As Lee got further along in her career and began to hone in on what she loved to do and what she had a knack for, she recalls digital media was also beginning to emerge in the industry, which added another layer to brand development.
"Because digital media was such a new concept, I knew I had to work even harder to break into the space," she recalls. "I took a position at Viacom, answering phones, to get my foot in the door."
"With patience and persistence, you can advance your career steadily," Lee says.
4. Never stop learning.
In career transitions, as with any circumstance, we need to make every experience count.
"There are days when we make the wrong decision - and that's okay," Lee says. "Making mistakes is when we do the most learning."
5. Take a leap of faith.
"Change can be scary, but often that fear of change or failure is actually what will keep you from succeeding," Lee says. "Instead of spending your time thinking, start doing - experiment and take a leap of faith."
Many of Lees colleagues, friends, and family members thought she was crazy for jumping into digital media when is was so new and unknown. Lee was vice president and head of business development and operations at MTV, an established company, when she left for YouTube, which at the time was a startup "that seemingly only produced cat videos. But I knew I had to keep to my vision and stick to what I believed in," Lee says.
The same is true of her move from the now huge entity that is YouTube to Margaritaville. "If my career path has taught me anything, it's that you should always have faith in your intuition," she says.