Optionality: Our Origin Story

Entrepreneur? Fractional Executive? Caregiver? Multi-hyphenate? Career Questioning? In Transition? Yes to all of it.

Our conversation around Optionality started in a nondescript vegan Indian restaurant toward the back of a strip mall two blocks off one of the many freeways in the Bay Area. That’s where we had been meeting every few months for a check-in, usually on a Friday, when there were the fewest afternoon meetings, doctor appointments, business trips, and after-school activities. It was also an approximate midway point between our homes with the added benefit of being delightfully removed from the Silicon Valley scene.

Our conversations usually consisted of updates on people we used to work with or see at our BlogHer events. Having worked together (along with our third #forevercofounder) for 10 years building and exiting a startup that supported a community of mostly women creators, there were always dynamic updates…a book deal here, a new baby there, a big glow-up over there. We also briefed each other on our own latest gigs, new roles, challenges with those roles, and advised each other on navigating those challenges.

Conversationality this Week: Hustle & Flow: Hear Optionality Co-Founders Elisa Camahort Page and Jory Des Jardins talk about the elements of Occupational Nirvana, and how to achieve it.

There were recurring themes. 

• We still seek the ideal Occupational Nirvana. We knew what it was like to be in the zone in our career. For 10 years we worked together closely and even though it was intense, yes stressful, we never burned out or walked away.  We know it was because we had a similar work ethic, complementary skills, shared purpose, and a mission that mattered. 

• Work feels broken. Since 2016 we have experienced leadership roles in startups, media companies, and a corporate behemoth, consulted for and advised dozens of teams, evangelized important causes and bleeding edge technology, and created content across an ever-changing media and publishing landscape. We also talked to hundreds of our peers in experience, ambition, achievement, and in the search for our best selves. We keep coming back to the conclusion that it is harder than it should be to find a path that feels best, right, or sustainable.

• Work feels broken because trust is broken. There have been a solid 20 years of disruption to the way we were led to think about work, from the dot.com bust to the Great Recession to the gig economy to overnight remote work transformation, the subsequent Great Resignation, and the current Return-to-Office push-and-pull. When we created a community and disruptive business model for bloggers, we had to invite organizations and brand marketers into the community to be an equal part of the ecosystem. We needed to establish trust between constituencies. The push-and-pull we are now witnessing between organizations and talent is also about trust.

• We are older and wiser. We’ve weathered deaths, family illnesses, and pandemics, and we’ve asked existential questions, just like everyone else. We know our value, but we also know our priorities. We have read great work by friends and colleagues about the future of work, and for us that future is now. We feel galvanized, like back in 2005. Back then we saw blogging as more than an online trend; it was a movement of autonomy and expression that resulted in a new creator economy. Similarly, the movement for Optionality is happening right now. When we support each other in questioning the status quo – and instilling trust and best practices into alternative pathways – we will again create a better way – together.

From recurring themes to new initiative

Small-case optionality swirled around our conversations, but it became Optionality with a capital O on a phone call that followed one of our lunch dates. We were talking about transitions. Elisa had been to a 2023 planning retreat and had listed things she wanted to accomplish this year. We both had other calls to take, so Elisa got right to the point and shared her last bullet point.

“I think we should work together on something.”

That’s really all she needed to say. 

From here we followed a playbook we wrote many years ago, forged a vision, and started crafting an operating plan. We also looked head on at what we wanted to do differently.

One thing we could not shake, our love of creating spaces for connecting with and elevating others. We can’t think of a better business model.  

We hope you’ll join us — or let us tag along — on this next big adventure.

—Jory + Elisa