Amy Chan, 42, always envisioned herself in marketing, and she spent the first decade of her career establishing herself in that industry. However, her true passion lay elsewhere. At 25, Chan wrote about a breakup on Myspace, which resonated deeply with others. “I had so many people reach out to me,” she recalls. This was in 2007, a time when sharing intimate personal details online was still uncommon.
Chan continued to write about relationships, contributing to her local newspaper, her own blog, and national publications like the Huffington Post, all while maintaining her marketing career. During this time, she conceived the idea of a breakup bootcamp—a sanctuary for those recently heartbroken to find support and solace. She wondered, “What happens to people who don’t have friends to lean on or don’t know which books to read?”
Despite outlining her vision for the bootcamp in 2015, fear held her back from acting immediately. “I was too scared,” she admits. Looking back, she sees that hesitation as misplaced and advises others to seize their passions without delay. “Just launch it,” she urges, noting that the mind often creates unnecessary obstacles.
Realizing she needed to act, Chan began breaking down her daunting vision into manageable steps. “Just like what a writer does,” she explains, focusing initially on small tasks rather than the entire project. For anyone contemplating a career change, this could mean reading an article or speaking to someone in the field. For a new venture, it might involve creating a social media presence.
To maintain momentum, Chan found an accountability partner and took concrete steps like booking a space and collaborating with a psychologist. This preparation culminated in the launch of her first breakup bootcamp in February 2017—a three-day, two-night retreat in upstate New York featuring yoga and sessions with Chan and the psychologist.
Reflecting on the inaugural event, which had only seven participants (including two from the media and two friends), Chan felt an overwhelming sense of accomplishment: “I f------ did it.” The modest start empowered her to continue organizing bootcamps regularly.
Testing her idea helped Chan refine her approach and set a clear direction. Coverage in publications such as Fortune and The Cut garnered the attention of a major talent agency, which outlined a potential career as a breakup coach. In August 2017, Chan left her marketing job to pursue her passion full-time. Her transition culminated in a six-figure book deal, solidifying her new career.