Why I’m Leaving LeadWise

Sunrise photo I took this weekend in Hualien County, Taiwan.

On a sunny spring day in early 2016, Rafael approached me about a team he was putting together. I had met Rafael a few years earlier through my work running a design thinking learning and consulting company.

“I think this really connects with your purpose,” Rafael said, and I agreed.

I left my New York-based finance career in May of 2013 with no idea what I would do next career-wise. I travelled to 20-something countries, and a year later, I moved back to my hometown of Miami, Florida to be closer to my family and participate in the startup and innovation scene blooming in town.

I felt attracted to startups because they were the opposite of what I was used to — highly structured, traditional businesses with rigid hierarchies that often lacked a clear purpose other than to make money. Soon, I learned that just because a startup was a startup, that didn’t mean it had good culture.

In my finance work, I had been a part of amazing, cohesive teams, especially during the financial crisis — everyone was stressed, but we had a common purpose and made things happen. Most of the people I worked with in my six years in finance were smart, honest, and great team members, with a few (very exceptional) exceptions (but that’s a post for another time).

While startups moved fast, got things done and weren’t hindered by hierarchy and a murky purpose, I missed some good aspects of corporate life, including skilled leaders and clear procedures to follow in the case of ethical conflicts.

By the time Rafael had approached me, I had started to view design thinking as a way to help companies improve the lives of their employees — as a way to help make work more creative and help employees connect with a greater sense of purpose.

Through my design thinking work, I learned that I cared deeply about company cultures. I noticed that people who burn out don’t feel creative and feel like they lack a purpose. I noticed that many of the ways we do things destroy souls for no good reason — that things don’t have to be the way they do.

Of course, I jumped head in into the team that would become LeadWise — through Ricardo Semler’s ideas, through this startup, I could be a part of spreading better cultures throughout the world. Also, I enjoyed being a part of a team that cared deeply about this purpose, about bringing meaning into work and reducing suffering in the workplace.

LeadWise has been an amazing school. I’ve met incredible people. I’ve had the opportunity to be a part of creating learning experiences that really transform leaders and how they think. I’ve met incredible folks creating amazing company cultures.

I’ve loved being a part of creating a 100% remote company, and I know that it’s possible to create meaningful work and sustain meaningful relationships with team members that you’ve never met in person.

All this has been incredible — but as everything in life, this chapter has not been without frustration.

My main frustration is that it’s been four years since I’ve left my finance career, and I still don’t have a stable financial footing, and I now find myself craving more financial stability than what an early stage startup is able to offer.

I’m now thinking about the different paths I could take and analyzing my options.

I still believe in creating positive employee cultures and reducing unnecessary suffering in the workplace.

A part of me thinks it would be really cool to rejoin an established company and apply everything I’ve learned with my design thinking work and LeadWise into practice; another part wants to become an academic and dive into research; another part wants to write about philosophy and the future all day; and I’m sure there are options I haven’t come across yet.

We’ll see how this next step goes.

If you’d like to to stay in touch, you can find me on LinkedIn here.

Thanks for everything and I look forward to continuing to change how work works with you!