Inclusive Impact

“Say More” with Tulaine Montgomery and Jeff Livingston

In the final episode of “Say More: Live Conversations with Tulaine,” Tulaine and Jeff Livingston brought radical truths to light. The pair spoke of perfectionism and the difference between mentorship and sponsorship, as well as ways in which to cultivate self-care during this time.

October 14, 2020

To close out Season 1 of “Say More,” Tulaine Montgomery’s Instagram live interview series, Tulaine spoke with Jeff Livingston, Founder and CEO of EdSolutions, a strategy and consulting firm focused on generating social impact in educational markets. The EdSolutions team works with non-profit organizations, social enterprises, and investors to help build scale, bolster sustainability, and ensure lasting impact within education—all with an ultimate goal of driving innovation and change to underserved students. 

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Tulaine and Jeff focused their conversion on the dynamics of career and mentorship opportunities for communities of color. Both Tulaine and Jeff noted a heightened standard of excellence that people of color are asked to meet—a message of perfectionism—that carries a responsibility to uphold the future generations. Tulaine described that, if mistakes are made, this pressure to succeed and achieve can inflict immense shame. In order to combat this crippling sense of shame, Jeff argued that mentors have a responsibility to check in with their mentees— a task he took on when he established a summer internship program at McGraw Hill for students of color. “I said to each of the interns ‘you will mess up, everybody messes up. When you’re in the hole and up to your ankles, call me and I can pull you out.’ I had to make sure that the students knew that I wanted to hear them, that I was on their side. I had to lean in and do what my grandmother would call ‘going to see about people.’” In addition, Jeff described the responsibility that mentees have—that they must remember to check in with their mentors at work and establish a relationship of trust.

I said to each of them ‘you will mess up, everybody messes up. When you’re in the hole and up to your ankles, call me and I can pull you out.’

— Jeff Livingston, Founder and CEO of EdSolutions

In expanding on this notion of mentorship, Jeff compared the ideas of mentorship and sponsorship. For Jeff, mentorship entails giving someone advice and encouraging them to follow that advice. Sponsorship, however, entails working hard to get mentees in the decision-making room, so that they become accustomed to being a part of the decision-making process. “Sponsorship is about extending trust to a mentee. It’s about giving them opportunity. You don’t wake up one day and have a significant impact. It’s a struggle and it takes work. It takes opening up a door to another.” Sponsorship requires a level of letting go of competition and scarcity and welcoming people onto your team, of looking out for one another. Jeff has taken the role of a sponsor frequently throughout his life, and encouraged audience members to think critically about the ways in which they could practice sponsorship, too.

We are operating in oppressive systems and contexts; however, there is a degree to which we have more power than we imagined when we think of doing internal work. How do we internalize competition and scarcity, and how does this get in our way? We need to have conversations about this. We have to name and heal and transform those things.

— Tulaine Montgomery

To end their conversation, Tulaine and Jeff shifted to discussing self-care in the context of this tumultuous societal moment. Jeff has been reaching back into history to stay steady during this time. He has been reading the works of James Baldwin, including Begin Again: James Baldwin’s America and Its Urgent Lessons for Our Own by Eddie S. Glaude Jr. and Uncollected Writings edited by Randall Kenan, and has begun to understand the depths of Baldwin and his wisdom of the Black experience. There is a profound sense of comfort and belonging in drawing from people who you may not know intimately, but who inform your reality.

For updates and announcements of future “Say More” show dates and guests, follow Tulaine’s Instagram at @tulainemarie.

To read more about James Baldwin, here’s a list: