Everyone says you need six months of savings before you quit your job. Ashley Caira left hers with $300 in the bank.

Ashley is a social media manager and content creator who built her business by meeting with James on her lunch breaks, in her car, while she was still working full time. In this conversation, she and James talk about what it actually took to make the leap — the fear of giving notice to people she genuinely liked, the friends and family who became her first clients before she even realized it, and the slump she hit a few months in after losing one of her closest friends, the same person who first encouraged her to start a business.

They get into setting boundaries so hustle doesn't turn into burnout, why having someone in your corner while you're still employed makes all the difference, and how Ashley's business evolved  ...