This as-told-to essay is based on a conversation with Mallory Contois, a 35-year-old founder and CEO based in Los Angeles. It’s been edited for length and clarity.
By 2019, my life was comfortable. I had a lovely fiancé, a lovely home by the ocean, and I knew how to do my tech job very well. It felt like I had full control over everything, but I reached a point in my life where I went from wanting stability to wanting to see what I was capable of.
That same year, all in short succession, I quit my job, called off my wedding, and moved back to LA from San Diego.
I spent the next two years focused on chasing my dream of becoming a COO, only to reach it and realize I still wasn’t fulfilled — so I quit again. Now I run a six-figure business and a portfolio career that fulfills me.
My career changes have been the reason for my success.
I worried I was delusional for leaving behind a lovely partnership and stable job
I knew my relationship in 2019 wasn’t the right one for me, and I didn’t feel as though my tech role was allowing me enough insight into how decisions were being made, but I questioned if I was crazy for leaving it and thinking I could have something more or better.
To walk away from a comfortable situation felt very selfish, like gambling. I still look back and can’t believe I made that decision. I think, “Who was that girl?”
I was also fearful of disappointing myself. What if I didn’t succeed in this “era of expansiveness” and I ended up in a worse position? All of those fears were very real, but I was diagnosed with cancer years prior and had reached a pivotal moment in my healing journey after finishing chemo in 2016. Having gone through that, the risk felt very worth taking.
Healing is a funny thing, and sometimes you wake up one day, and it feels like the clouds have lifted, and suddenly you’re in a new mental space. I think that’s what happened.
I worked to achieve my dream of becoming a COO — only to realize how unfulfilled I felt
I moved to Los Angeles and jumped almost immediately into a new role as chief of staff at Cameo. Suddenly, I had what I was looking for: I was in the room where decisions were being made, and I had the opportunity to influence the direction of a high-growth company.
My goal, or what I thought was my career goal, was to become a COO at a Series A startup, and this role was an amazing first step toward that. In 2021, I reached my dream. I thought it would be a moment of achievement, but all I felt was unrest and dissatisfaction. I didn’t feel excited about the problems I was solving.
To spend years in pursuit of something, only to have it and feel dissatisfied, was very confusing.
I quit my COO job without another lined up and felt lost
I thought about quitting, and all of the same fears I had in 2019 came right back up. However, this time the fears were primarily identity-based. I had always defined myself by the industry I was in. I was always an operator, so I thought becoming a COO was what I was supposed to do.
I stepped down from that role in 2022 without another role set up.
At the time, I had been doing some consulting work on the side, and I was about a year into starting The Old Girls Club — OGC — a private membership club for mid- to late-career accomplished women who prioritize their career as part of their identity. I was making some money. This was the origin of the portfolio career I have now.
I’ve built a portfolio career alongside full-time work, and I finally feel fulfilled
I got hired for a head of community role at a fintech company, and continued doing consulting and running the OGC on the side. I realized I could build a really cool ecosystem of projects that felt complementary and actually added value to one another.
When most people think of portfolio careers, they picture it as entirely freelance, but I’ve worked full-time, across two different companies, for four years now, while doing side gigs like consulting, writing on Substack, and running OGC. It all kind of blends together in a way that allows me to exercise my brain.
I jump around all day. Most people would really stress out watching me work, but it never feels like I’m switching into another project because everything is so values-aligned and topically similar.
The biggest challenge of a portfolio career is resource allocation. It’s always a challenge to determine which projects require my brain power, time, and/or resources at any given point. However, it allows me to learn and accelerate quickly, and gives me more control over my financial situation than if I were reliant on a single source of income.
My advice is to treat your career as an experiment
My career changes have given me a much clearer understanding of myself, what I care about, and what I enjoy.
The pace of acceleration toward what I would call my dream life has gotten much faster as I’ve gotten clearer on who I am and what I care about. Making all these big life changes and experimentations has not been all sunshine and rainbows. Just like any experiment, I learned cause and effect, pattern matching, and clarity about myself.
Do you have a story to share about quitting your dream job? If so, please reach out to the reporter at [email protected].
