Mentoring Students in Chicago: A Conversation with Jay Shah

Jocelyn TenorioMentors

Jay Shah recently joined WITS as a mentor in the Workplace Mentoring Program (WPM) at GCM Grosvenor. A 2024 graduate of the University of Texas at Austin, Jay moved to Chicago for work and was eager to find meaningful ways to connect with his new community. His passion for literacy and service quickly drew him to WITS, where he helps students build confidence and a love of reading through weekly sessions. In May 2025, Jay also joined the WITS Associates Board. 

What brought you to WITS? 

During my first month at work, one of my colleagues told me about WITS and shared that it was a way to connect with Chicago and the community without ever leaving the office. What also drew me in was the opportunity to make a direct impact and build community. Helping fourth- through sixth-grade students build their confidence through reading is such a powerful way to strengthen the foundational skills everyone needs to succeed and excel in life. It was so rewarding and fun to have that direct impact on a young person’s life and see their growth progress throughout the year. Being able to make that kind of connection from day one is really what brought me to WITS. 

Jay Shah and student at a Workplace Mentoring program.

Can you tell us about a favorite memory you have of reading with a student? 

When you first move to Chicago, everyone tells you about the Great Chicago Fire on those boat tours along the river. It just so happened that as I was learning about the fire, my mentee and I had also started reading a book from the I Survived series about how the characters lived through it. Making that connection with the city and imagining what it might have looked like, while we were looking out the office windows and picturing ourselves in that situation, was really fun. It was great to imagine ourselves in the city, place ourselves in that moment, and create that connection, even though we were just in an office pretending. It felt like we were building something greater than just reading a book; we were making the story our own. 

Could you please share any other challenges you’ve encountered while volunteering? 

It really was such a smooth process overall, and Jessica, our Program Coordinator, was always wonderful. But some days really depend on the student’s energy as well. It can vary throughout your time together, so sometimes you need to be a little extra creative to draw them into the activity or the book, since energy swings are typical for anyone. Sometimes they just want to talk, so it’s about finding that balance between chatting and reading. It definitely keeps me on my feet! 

What is your favorite book and why? 

My favorite book series is The Inheritance Cycle by Christopher Paolini. I’ve always loved world-building stories that start with an ordinary individual doing extraordinary things – it  always drew me in. The books were a real challenge to get through since each one was around 300-400 pages, but as a middle schooler reading them, I was completely enveloped. I loved them, and that world-building aspect kept me reading. 

What has your experience been like as a WITS Associates Board (AB) member? 

The first meeting I attended this past year was both fun and energizing. I was surrounded by a group of people united by one goal and one community, and it created an immediate sense of connection beyond just our work experiences.  

As a mentor, my perspective mostly came from my weekly interactions with my student and with Ms. Jess, who supported us through the activities and books. As an AB member, I gained exposure to the entire WITS organization – the logistics, fundraising, and different challenges that a nonprofit faces.  

That first meeting gave me a broader understanding of WITS and drew me in even further. It made me want to help strengthen what I already felt was an important goal: ensuring student literacy improvements. Seeing the hard work and community-building that goes into the entire organization has been great. 

What are you most looking forward to in this role? 

I’m hoping to further my impact in a tangible way beyond my hourly Tuesday sessions as a mentor. I’m also looking forward to deepening my connections to Chicago and the community. I’m from out of state, and this is my first full year here, so I’m excited to explore different ways to get involved and make a difference locally. 

I’m also excited to see how many more events we can organize. That’s always the fun part – drawing more people to WITS and welcoming new Associates Board members. I’m already thinking about asking my roommate to share the program at his workplace, just to start the conversation and see how that might benefit other communities. 

How has mentoring students in Chicago with WITS impacted your idea of what it means to be of service? 

While in college, I was involved in a charity organization called Seva. We organized fundraising events to support Akshaya Patra (AP), an organization in India that provides mid-day meals to children in need. My original idea of service was focused on planning and running these big events to raise funds. 

Coming to WITS, that perspective shifted. Here, you have a tangible weekly impact on one student, seeing their growth and deepening your connection. Those moments might feel small, but over the course of the year, they build up to be something bigger and more meaningful. You see the seed of wanting to read more and get deeper into books, which feels much more fulfilling.  

Get Involved 

Remember, mentoring students in Chicago isn’t just about giving; it’s about receiving fulfillment, connection, and purpose. Even simple acts of giving can have a significant impact on both others and yourself. Whether it’s a long-term commitment or a small contribution, volunteering can make a difference!