How I reinvented my day job (and became an accidental intrapreneur)

Sheena Livingston
Doable
Published in
5 min readJan 18, 2017

It was a fall day in 2014 and I was about to quit my job. Usually when I decide to do something, I’m at least marginally successful at it. But that day, I totally failed at quitting.

A little backstory. I had spent the last eighteen months working at co: collective, a secretive strategy and innovation company on Park Avenue. Behind the curtain, things were exciting. We were dreaming up the future with the likes of Google, GE and Infiniti. As one of the few designers at the company, I was in high-demand and spread thin across many projects. I said yes to everything, because everything sounded cool and I didn’t want to miss any opportunities. Cue slew of articles about the virtues of saying “no.”

On top of client work, I had been asked to pitch in on a new product idea that had been bouncing around the office. It eventually became Doable, but at the time, it was nameless and mostly shapeless. We were given autonomy — permission to make it what we wanted. More than just an assignment, I felt a sense of ownership, and it quickly became a passion project. After a few weeks of work, our small team pitched our concept and prototype to the co: leadership team. They believed in our vision of what Doable could be, gave us a pile of money and said “Go build it.”

We were elated. Success feels good. Validation feels good (I guess I really am a millennial?). But it didn’t fix my problem. Like many young urban professionals, I was waist-deep in a simmering vat of burnout. Intellectually and creatively, I felt like I was hitting a wall. My body was in a shambles: I had gained weight and developed carpal tunnel in both wrists. I knew something big needed to change.

And I decided that the “something big” was my job. It needed to go away.* I had nothing lined up except a small savings account and a healthy tolerance for risk. But I needed to take ownership over something: my projects, my life, my destiny. I needed a break. Maybe I just needed a really long nap. I was confused; my brain wasn’t working very well. Like I said… burnout.

Back to the day I “quit.” In the midst of working up the courage to put in my notice, something unexpected happened. Ty Montague, the CEO of co:, asked to meet with me. He told me he was excited about the Doable project and that he wanted me to be the creative lead as we moved into developing an MVP. I was astonished by his timing. I was flattered. I was intrigued. But I also knew I intended to quit later that day.

This put me in an awkward position, but my mind was made up. So I “quit” right then and there. Ty looked surprised. He listened intently and seemed to empathize. Then I saw the expression on his face transform into something like determination. He laid out a case for me to stay. He spoke convincingly about our rare opportunity to build something innovative from the ground up.

I knew he was right. But I also knew things couldn’t just continue the same way. What would have to change for me to stick around? We agreed I would take some time to think. Even though I had until the end of the week, I made up my mind that night and asked to meet the next day.

Here’s what I proposed. I would stay if I could work on Doable 100% of the time, no other projects. I would want some flexibility in my schedule, like the ability to work from home some days. I didn’t ask for more money; it was more important to me that I work on something I was passionate about. Ty agreed and we hit the ground running.

Everything changed for me after that. I could actually focus on one thing. My brain got a chance to clear up. I felt more energized, creative and productive than ever. Six months later, Doable became its own company and I became the creative director. We were building a product for intrapreneurs – employees who create new products, services or businesses within the walls of an existing company–but it was only around this time that I realized that word applied to me too.

I admit I had it easy. I didn’t work at ACME Giant Corporation. I worked at co:collective, a place known for its willingness to experiment with new ways of working. Not everyone is so lucky. Many companies don’t yet value intrapreneurship as a way to innovate from within and keep valuable talent from leaving.*

The conventional wisdom on the internet nowadays is that your day job and your passion are separate entities. But we don’t all have to ditch the security that comes with a steady paycheck. I was an accidental intrapreneur. I hope my story (and the product I’m building) can help more people become intentional ones. If you think you have to leave your job to do meaningful work, first try asking for what you really want. Or better yet, just start doing it.

* Not everyone can just up and quit their jobs. I understand that I was in a privileged class where this is concerned. I had no dependents (besides two lazy cats), a loving partner who could, in a pinch, support both of us, and a coveted rent-stabilized apartment. I lived in NYC, a place where freelance jobs for designers like me are abundant. I was going to be ok. The solution to this isn’t everyone quitting (or threatening to quit) to get what they want. It’s companies being open to different ways of approaching employment, like intrapreneurship.

** I read a study that said intrapreneurs need to be ok with the prospect of getting fired. That’s how frowned upon not “staying in your lane” still is in corporate America. :(

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Sheena Livingston
Doable
Editor for

animals, swimming holes, product designer at Mado