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Yesterday is not like today

May 07, 2016


This morning I woke up for the first time in nearly three years without something that had become a core part of my identity.

Yesterday, I was an Oaky. I worked for one of the most innovative health care start ups in the country. More than that, it was an integral part of my self-definition for nearly three years. I define myself by my work. Possibly too much. But during my time at Oak Street, that was a blessing.

It’s not that everything was roses. Any company that grows from 10 to 600 in 36 months is going to experience growing pains. But when you have that team around you, a team that’s dedicated to helping — our patients and one another, it’s easy to have faith that it’s going work out.

I am leaving Oak Street filled with fond memories, incredible friendships, and stretch experiences which will continue to shape me for years to come.

Today, I’m self-employed. I’m realizing a dream years in the making. This past week was one of the most surreal of my life. Nearly every conversation I had was about what life was going to be like after leaving Oak Street. The outpouring of support that I received from friends and colleagues was amazing. I have had so many people offer help.

I learned so much at Oak Street, from the nitty gritty of running a business to leading teams and so much more. I found mentors and role models. I soaked up everything I could. Now, I have the opportunity to put into practice what I’ve learned and continue to grow.


A few of the wonderful friends I’ve made at Oak Street

Stephen Weiss

Written by Stephen Weiss who lives in Chicago with his wife, Kate, and dog, Finn. Follow him on Twitter!