The day I started at United Working Families, in August 2019, the first thing I did was go to a coalition meeting about the City of Chicago budget. I kind of was just thrown into it. Former executive director Emma Tai put a ton of trust in me, this young organizer, to create a coalition of labor, elected officials, and community groups to say, “Look, these are things that we specifically care about. How do we narrow that down to five key budget demands? How do we have elected officials who will hold the line on those demands? And how do we have a coalition of labor and community groups who will say, ‘Even if I win my demand, I’m going to stay at the table fighting for yours’?”

I can’t credit anything but my relationships and the time I spent. I had so many one-on-ones. I sat in every budget department meeting. It’s the ability to talk to everyone and see a middle ground. It’s the same model we used all the way through the very last budget coalition we pulled together for the fiscal year 2022. Any pride I take in my influence is because it’s used to bring the most good to the most people.

During COVID, when I was appointed president of the Blackhawks, I realized very quickly that I had to figure out what was happening in the organization. I had to navigate the pandemic. I had to keep the lights on. I had to keep us heading in the right direction. There were financial and structural decisions to make for the short term. We had to determine how we were going to restart our season in a bubble in Edmonton. At the same time, we had to reset the vision of the organization from a longer-term postpandemic standpoint and hire a leadership team to get us there.

Operating for most of my career in B2B businesses, I had made decisions and lived in a less public way. I’m in a position now that’s very public, so decisions are amplified. As someone who sometimes operates from an impostor syndrome standpoint, it was about realizing that I had both the influence and the support to do this. I feel comfortable that I don’t have to be Rocky 2.0. Hopefully, I’m taking all the great qualities of my dad and then bringing out the things that I’m good at uniquely.

After I graduated from law school, I ended up doing zoning law at a tiny five- or six-person law firm. I had gone over to City Hall to ask for something for a client. It was a small thing, but it meant a lot to them. When I went to the building department, the commissioner I needed to speak to wasn’t there. So I was like, “Well, call me if he comes back.” As I was walking through the lobby of City Hall, I ran into him. He looked at me and went, “Your boss has been calling me all day.” I reached in my bag and pulled out a sheet of application numbers and said, “These are stuck in your department. If we could get these out today before 4 o’clock, I’d really appreciate it.” And he was like, “Let me see what I can do.”

When I got back to my office, my phone was already ringing. It was him. He said, “Tell your boss you got this done, not him.”

I realized through that one instance that I had a lot more to give, and that my skill set wasn’t really measured by the billable hour.

In the summer of 2017, when I was 23, I was thrust into a position leading NBA coverage for Yahoo Sports as the main insider there. It put me in a situation and a spotlight that I didn’t know I was ready for. In the back of your mind, you always have this level of doubt. You’ve put in all this work and built these relationships. But will it pan out?

I felt the same way when I was covering games while I was in high school and college. I’m driving home from Milwaukee at like 3 or 4 in the morning, and I don’t know if what I’m doing is the right path. I’m just doing it out of sheer passion and will. You don’t leave that moment of self-doubt, but you just keep pushing through that and keep grinding.

That summer of 2017, I felt like I was at the forefront of a lot of reporting. I definitely got a lot of replies on social media. I saw a lot of memes. I had to turn a lot of it off, because it got overwhelming. That summer was big.