■ We lived in a nice neighborhood growing up in Omaha, but, like, our property was torn up. The roof was leaking. Our dishwasher didn’t work. The door to the oven wouldn’t close; we had to prop a chair up against it. But my parents founded their own business and worked super hard. Having that model was important to me.
■ I don’t know if money can buy happiness, but you can at least feel good about the impact you have in the world by how you employ your financial resources. Helping fund research on transgender women, being able to support queer women running for political office — that’s been incredibly rewarding.
■ My dad made it clear to us, from a very young age: “You’re going to have to go out and make your own way in the world. I’ll pay for your college and then you do the rest.” He invited all of us to come back and work for what was then Ameritrade, but not until we were 30. We had to go do something else first.
■ There was a life coach at a retreat I went on who suggested that at the end of every day, for 60 days, you write down 10 things that gave you joy that day. At the end of it all, you look back at what you wrote and let that inform what you should be doing with your life. Some of it was playing with Play-Doh with my kids or going to the beach — the small stuff. And some of it was more work-oriented things that help empower women. By going down that path and asking myself those questions, I feel like opportunities arose with the founding of Beyond Barriers, with the investment opportunities in the Chicago Sky and the Chicago Red Stars. Those are not things I set out to do in my head — they just kind of fell into place.
■ I love sports and have always followed sports. I was the best athlete in my family, as my mom will definitely tell you. I have three brothers, and I stand firmly by that.
■ Our family gets the media scrutiny any team owners would. In the early years with the Cubs, I was a lot more sensitive to that stuff. But you can’t live your life always worried about what other people think, because then you’re not really living your life. You’re living the life other people think you should. I’ve always just tried to focus on who I am and doing what I think is right.
■ I don’t think my family is different from others in terms of having divergent political views, but there are some things I might not talk to them in depth about. We know we have to agree to disagree and to respect each other because we love each other. If you want to be respected for who you are and the views you have, you’ve got to do the same for other people.
■ Winning the World Series was incredibly surreal. I played one small supporting role, but to me it’s one of the most important things I’ve done in my life, because it had such an impact on all these generations of fans. It was remarkable to witness the magnitude of that parade rally in Grant Park. I still don’t know how to place it, and I don’t know that I ever will. I do know that I want to do it again.