When Lindsay Feldstein first considered becoming a mentor, she worried that her technical expertise might not be enough to make an impact. Now, as a longtime Break Through Tech AI Program mentor, Lindsay proves that effective mentorship isn’t about knowing everything, it’s about listening, encouraging, and guiding fellows as they explore new opportunities.
Published
09/22/2025
Written By
Fatima Asif
From Mentee to Mentor
Lindsay’s journey as a Break Through Tech mentor began with Yvonne Wong, another AI Program mentor and former colleague. Yvonne not only introduced Lindsay to Break Through Tech, but also inspired her to grow her career by taking on roles outside of her comfort zone.
Lindsay has now mentored three cohorts of AI Program fellows and still draws inspiration from her own experience. “Mentoring is my way of making sure I continue to pay forward what Yvonne gave me – the belief that your interest to learn and your confidence in yourself matters a lot,” she says.
Through Break Through Tech, she has been able to help fellows grow their confidence and reframe their career stories by understanding the importance of maximizing your transferrable skills and tapping into your network. She recalls one mentee who was struggling to land an internship but felt confident enough through Lindsay’s mentorship to reach out for help: “We practiced her interview, and she ended up getting that internship. And I kept in touch with her past the program.”
Stories like these reaffirm Lindsay’s commitment. “Having mentors in my life has given me the confidence that I need to make sure I feel like I deserve to go into every room,” she says. Now she wants to do the same for her fellows.
A Mentorship Program That Changes Lives
For Lindsay, this isn’t a typical mentorship program. Break Through Tech fellows gain access to structured resources, career guidance, and opportunities to practice real-world skills, while mentors like Lindsay provide guidance and support to help fellows navigate every step of their journey.
The program is transformative for mentors too. Lindsay credits it with improving her communication skills, leadership abilities, and confidence. “My time is maximized with the [undergraduate] students because of the support, materials, and guidance that the program gives,” she says. “I’m very busy, but this mentorship, the structure of it, definitely makes it a hundred percent worth the time because I know I’m having an impact.”
Learning Goes Both Ways
Lindsay approaches mentorship with the mindset that her mentees can teach her something. “Everyone you meet – personal, professional – has something important to teach you. Building a two-way relationship with my mentees is essential. I’m also there to learn from them,” she explains.
This shapes her mentorship style, blending empathy with accountability. Lindsay encourages fellows to reflect, prepare, and hold themselves to high standards while creating a safe space to discuss challenges and setbacks. One of her proudest moments was helping a mentee reframe her interview experience, resulting in a successful internship placement, and an ongoing connection beyond the program.
Why You Should Mentor
Time and time again, mentorship has been proven to help open doors and broaden who gets to succeed in tech, regardless of technical experience. Lindsay’s story embodies that perfectly: “If anyone is even somewhat interested in paying their time forward, they shouldn’t be concerned that it’s Break Through Tech’s AI Program,” she says. “This program gives you a channel to have such a strong impact on [undergraduate] students who want to break into tech, without needing subject matter expertise. It’s about dedicating your time, giving [undergraduate] students confidence, and helping them build their ability to go after their roles and hold themselves to a high standard.”
After three years of mentoring, Lindsay is certain of one thing: mentorship transforms both fellows and mentors. For her, it is about paying it forward. Every conversation and moment of guidance strengthens the bond between mentor and fellow, allowing mentors to grow alongside their mentees while helping them see their own potential and the possibilities ahead.