CHAPTER 1Beyond Good Intentions

I thought 2016 was going to be a year for the underdogs. The Cubs were having their moment. It had been 108 years since they had won a World Series.

Yes, Cleveland had home field advantage. Yes, the Cubs were coming back from a 3–1 deficit, and only five teams in history had come back from that far behind to win. But when I deplaned in O'Hare, I believed the fanaticism surrounding me could beat any odds. I hadn't felt that kind of energy since Seattle's “Refuse to Lose” euphoria in '95.

I wasn't in town specifically for the Series, but I came from a baseball-loving family, and my parents had Chicago roots, so I was going to soak it up while I had the chance. Everywhere I went, I was seeing either Cubs signs or Hillary signs. #ImWithHer banners peeked out from under End the Curse! flags. All around, history seemed to be in the making.

I was in Chicago for work, and at the time, I had what I thought was a corporate do-gooder's dream job, overseeing DEI programming for a large financial company. I had spent the first part of my career advocating for equity from the other side, either in nonprofits and international NGOs, or through the lens of public policy. I had seen the limits of working on systemic problems from the outside, and I wanted to drive change from within. So, I had made the leap to the financial sector, determined to diversify the original old boys' club.

At the time, I felt optimistic. My employer had invested both time and budget. ...

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