Founder Stories

The Risk-Averse 9-to-5er’s Guide to Quitting Your Day Job and Starting Up

Being ready isn’t about perfect timing or your feelings. It’s about preparation.

Amy Chan
Published in
5 min readJan 24, 2020


An illustration of a woman character stepping outside of a briefcase, in search of a new opportunity.
Illustration: Fran Caballero

WWhen I moved to New York, I hoped no one would notice that I was an imposter in an entrepreneurial world. It was as if I was plucked out of my proverbial fishbowl and dumped into an ocean of high-achieving entrepreneurs who were all busy growth hacking, microdosing, and fundraising their way into another seed round.

Back in Vancouver, my life goals had been to simply climb the corporate ladder, get married, and become a stay-at-home mom. But after reaching my professional goal of becoming a marketing executive, a messy breakup with my partner forced me to pivot my goals for the future. Goodbye, operation housewife. Determined to find another path, I took off to the city that never sleeps.

I gave myself a six-month timeline to transition. From the moment I made that decision, I started to think and act like an entrepreneur.

To meet new people, I joined communities such as Summit Series — — an organization that hosts events for “young entrepreneurs, artists, and activists.” None of my new friends had a regular 9-to-5 lifestyle. They were all startup founders, entrepreneurs, and even the ones who did have jobs had side hustles on side hustles! I envied their lives. While they could take off to Ibiza spontaneously, work remote from the beaches of Tulum, and go off-grid at Burning Man, I was stuck working at my desk. I felt pressure to start my own business, raise a seed round, do something — anything — that was cooler than having to report to a boss. But as much as my desire to join the new-rich was burning, there was one tiny problem: I had no savings or any idea what to do.

From hobby to business

I needed a business idea, so I took a look at what I loved doing. Despite my history of dabbling in different career paths and passion projects, there was one passion that persisted throughout: writing about relationships.