Be a Part of the Conversation!
Conversations with Cara is our ongoing series of insightful, inspiring, and spirited discussions around Cara Collective’s work to eradicate poverty – and the topics and issues we face as we build a more inclusive economy for all. A rotating panel of experts joins Cara leadership in conversation on topics ranging from health equity to education access to unlocking opportunities for fair chance job seekers and more. This is a free, virtual discussion series held three times a year.
Previous Conversations
From Poverty to Prosperity
We partnered with Robinhood CEO Vlad Tenev for a special live-streamed conversation around how we can create more opportunities for financial independence for our often-overlooked communities.
From Poverty to Prosperity
We partnered with Robinhood CEO Vlad Tenev for a special live-streamed conversation around how we can create more opportunities for financial independence for our often-overlooked communities.
Trauma Informed Mental Health
In honor of Black History Month, join us for an important conversation on trauma-informed mental health care that honors lived experiences of the Black community.
Celebrating Hispanic Heritage Month 2025
In honor of National Hispanic Heritage Month, we celebrate the essential contributions of the Hispanic and Latino communities to our economy, workforce, and culture.
Unlocking Opportunity Through Fair Chance Hiring
In honor of National Fair Chance Month, join Cara Collective for a virtual discussion on the importance of creating job opportunities for justice-impacted individuals.
The Business of Profit & Purpose
In honor of Black History Month, we discuss how employment social enterprises fuel economic mobility on Chicago’s South and West Sides. Hear directly from leaders who work at the intersection of profit and purpose to create opportunity for job seekers facing barriers to employment
Investing in the Workforce
Employers can pull one of the most powerful levers for economic and social change: supporting and advancing their frontline workers. Our panelists will share the “why” and the “how” behind meeting the needs of historically untapped talent, whether that be job seekers impacted by the justice system or those who have faced systemic barriers and the effects of poverty.
The Intersection of Education and Workforce Development
As the workforce continues to evolve, so must the ways we prepare current and future generations of workers. We were joined by civic and philanthropic leaders to explore how education and workforce development institutions are working together to build more inclusive pathways to gainful employment.
Building Economic Vibrancy Across the Latine Community
In honor of National Hispanic Heritage Month, we were joined by a panel of civic and philanthropic leaders to discuss the role policy plays in creating equity, and how we are addressing and removing the barriers faced in the pursuit of meaningful employment opportunities.
Writing My Legacy
In honor of Black History Month, Kathleen St. Louis Caliento, Suzet McKinney, and Nicole Robinson take part in a discussion on creating change, inspiring others, and building a legacy.
Appetite for Hope
Because gainful employment and food security go hand in hand, Kathleen St. Louis Caliento and Kellie O’Connell, CEO of Nourishing Hope, discuss the barriers to food and job access and our collective hunger for a poverty-free Chicago.
Beyond the Shecession
In celebration of Women’s History Month, Kathleen St. Louis Caliento and Felicia Davis Blakley reflect on this moment in history and its impact on women in the workforce.
Finding My Voice
In celebration of Black History Month, Kathleen St. Louis Caliento and Dominique Jordan Turner discuss how they found their voices as Black women, impactful leaders, devoted mothers, and so much more.