Letting the hoop roll...

When I was at Wellesley College, we had this very odd tradition of hoop rolling.  You had to roll a wooden hoop down a bumpy road, and if you won, as tradition went, you’d be thrown into Lake Waban and get some kinda prize in life. In the late 1800s, it was you’d be the first to be married, in the 1980s you’d be the first to be a CEO, then some time in the 90s or the aughts you’d be the first to find happiness and success however you define it. That was the trajectory of prizes. But you’d definitely be first. Competition was baked into happiness. Woah. 

I haven’t been first in anything. A few gold medals from regional YMCA gymnastics competitions, a couple plaques for academic achievement in 1997, but I’ve never made a 30 under 30 list. A 40 under 40 list. Maybe I’ll make the 50 over 50 list. To be sure, I didn’t win hoop rolling or even participate in it because I was likely hungover. (Sidebar: it would take me almost 25 years to realize that I’d lost a lot of hours of my life to hangovers.) 

I’m not saying that I haven’t been successful. I have. I have also wondered if there was more. A bigger prize. A chance to be first. And it had always eaten away at me. 

However in the course of my career, I worked on a world-changing election to get the first Black president elected to the United States of America. I helped elevate menstrual equity to the mainstream. I told Big Food to Bite Me in the New York Times. I was on the frontlines of some of the biggest issues our country has had to contend with and helped brands and NGOs alike make an impact on those issues. I’ve also had the honor of leading fitness classes that go beyond getting your butt toned and have had students cry in my arms because they finally have the space to be seen, heard, grieve, and feel. It’s work and an honor I don’t take lightly. 

I recently posted on LinkedIn that I reached a career milestone in co-hosting my first retreat in Tuscany. Hosting a retreat, teaching a method I love, in a country I love, was a career milestone that wasn’t even in my realm of possibility when I graduated in 2002. 

I’ve been doing a lot of reflecting since I left my job at Daily Harvest in September. I’ve gone to Florence not once but twice. I’ve invested in hosting a retreat. I didn’t get one job because it wasn’t in alignment with my career. I got another consulting client that did and that has opened a door to more. 

Maybe going for success has actually meant letting go a little. Letting go of the expectation that doing one thing will lead to another. Like rolling a hoop means I’ll find happiness and success however I define it. Maybe blowing up the playbook in favor of choosing my own adventure will lead to more interesting milestones. Like joy. Like learning Italian. Like not playing the startup game in hope that one acquisition, will lead to another IPO, will lead to a better apartment and will lead to “better” happiness. 

Maybe hoop rolling wasn’t about being first. Maybe it was about letting the hoop roll and embracing the absurdity of the game and more so embracing the absurdity of the journey.