National Philanthropy Day: A Q&A with Sheila Cawley

Chief Philanthropy Officer Sheila Cawley joined the Trust in August with more than 30 years of experience in philanthropy and previous leadership roles at Chicago cultural institutions, including the Museum of Science and Industry and The Field Museum. On National Philanthropy Day, she shares her thoughts on her new role with the Trust, what it means to be a philanthropist, and what makes Chicago a uniquely philanthropic city.  

Talk a bit about your background working in philanthropy in Chicago.  

I started in philanthropy in my mid-twenties at a development consulting firm and was able to learn about philanthropy in real time, and directly from philanthropists. I decided at the time this was a path to marry my love for Chicago and for its cultural institutions, and work to make my hometown a better place.  

Later, I ended up living in Cleveland for a few years and eventually realized that it was time to move back home. Luckily, I saw a position posted for a major gift officer at The Field Museum, where I had previously volunteered for many years. I said to my husband: “We are going to move back to Chicago, and I am going to take this job.” I came back to the city and became much more entrenched in what was happening in the philanthropic landscape. I’ve been able to learn so much about the people who care for our region and why Chicago is an incredibly special place, especially when it comes to philanthropy.  

What makes Chicago special? How would you describe the spirit of philanthropy in Chicago? 

Chicago has such a unique place in the hearts of people who live not only in the city limits, but in our suburbs, our region, and across the country. I have met donors from everywhere who talk about childhood trips to Chicago that changed their life, and they talk about this place with such fond memories and love. People make a really conscious choice to be part of this culture. They’ve chosen to give back to Chicago because it’s an incredibly special place with so many assets that we have to care for and support for the next generation. There truly is a unique spirit among the people who understand that and want to be a part of it.  

What made you want to come to the Trust, and what do you hope to help achieve for the future of Chicago?  

What appealed to me about the Trust is that it has made an incredible commitment to the Chicago region, and it made that commitment decades and decades ago and has stayed true to that. All the philanthropic work being done in the region is fantastic and needs to keep growing, and the Trust is uniquely positioned to be at the center of that. Particularly with our commitment to closing the racial and ethnic wealth gap we can make Chicago a better place for everyone. And it’s an organization that appeals to donors who care about many diverse missions and who want to be part of many different initiatives. 

As for what I hope to achieve, with all humility, there have been a lot of people here before me who have done incredible work bringing together thousands of donors for the sake of the city. I hope that I’m able to carry that forward with integrity and think about who else can partner with us to continue to make Chicago even better. 

As someone who has worked in philanthropy most of your career, what does it mean to be a philanthropist?  

I define a philanthropist as someone who thinks outside of their own needs. Their care for and commitment to others can take many forms, including financial support for tangible things like comfort, basic human needs, helping people in the winter with hats and coats, doing whatever it is you can to help someone outside of yourself. That to me is philanthropy, and there’s no dollar barrier to that. We can all help make the world a better place. 

What is the best way for people who want to support the region and the Trust’s efforts to connect with us?  

The Trust has a wealth of knowledge and a huge breadth of ways people can help the region. The most essential component is someone’s individual urge and commitment to help. We’re here to serve as a partner to our donors and to help develop a giving strategy to shape the focus of their philanthropy.  

Some donors who want to support the region in perpetuity choose to make a bequest to the Trust’s endowment and say, “when I pass on, I’d like The Chicago Community Trust to take these funds and do the best thing for the city.” For an organization, an endowment gives you stability and the security to think about the future and make big bets. Thanks to the generosity of our donors over the years, we are incredibly fortunate to have a very strong endowment and the ability to think long term about the future of the region.