Episode 137: Wildly important questions with Trudi Lebron

Hey, everybody, welcome to today’s episode of Beyond the Shadow of Doubt. I’m thrilled to have my guest, Trudy Lebron, with me here today. Welcome, Trudy.

Thank you for having me. Hello, everyone!

Oh my goodness, I admire Trudy so very much, and I know you will too after you listen to all the wisdom she has to offer. Trudy, I want to give the floor to you. Can you share a bit of your origin story—where you’re from, your family, upbringing, faith of origin if you have one, your education, profession, all of those things?

Okay, I’ll give you the whole. I grew up in central Connecticut, in the inner cities of New Britain and Hartford. We were a lower middle class or upper lower-class family. My parents divorced when I was around 10 or 11, and that really impacted me and my sister. I come from a big, blended family with siblings on both my mom’s and dad’s sides.

My mom is a white woman who also grew up in poverty in an inner city in Connecticut. My dad is a dark-skinned Puerto Rican man who moved to the mainland United States at 18 without speaking any English. So I grew up in very diverse communities and in a very diverse family.

One of the best things about my childhood was how diverse my schools and neighborhoods were. My classmates were Black, brown, white, Asian, African immigrants—people from all over the world. At the time, I didn’t realize how unique that was. It wasn’t until I was older, meeting people who told me they didn’t meet a Black person until college, that I understood how different my experience had been.

I really struggled in school. Looking back, I had undiagnosed learning disabilities and ADHD. Those challenges turned into behavioral problems. By middle school, I was disengaged and couldn’t wait to drop out. At 15, I left school in 9th grade, seven months pregnant with my first child. By 16, I had two kids, no high school education, and no money. My mom worked hard, but life was a struggle.

Faith wasn’t a strong influence in my upbringing. My grandparents in Puerto Rico were Catholic, but my father wasn’t practicing. We went to church sometimes, but not regularly. Throughout my life, I’ve visited different churches with friends or family, but nothing stuck. From a young age, I rebelled against anything that felt contradictory. Ideas about punishment, sin, or labeling certain behaviors as evil didn’t add up when I compared them to people’s actual behavior.

On the other hand, I’ve always been deeply moved by a sense of purpose and calling. I often describe it as getting “downloads from the universe”—guidance that doesn’t fit neatly into religion but feels true for me. I believe we all have gifts and a purpose, and that we are connected to the universe around us.

I see my work and the way I live as a practice of faith. I try to make decisions aligned with how I believe people should be treated, how relationships should work, and how my goals affect the larger world. To me, that’s an expression of faith.

By nature, I rebel against contradictions—whether in religion, school, or life. For example, certain faith groups reject things I believe in as true, particularly around sexuality, gender, and bodily autonomy. Their teachings felt inconsistent with their professed values of love and justice. Similarly, in school, rules often didn’t make sense or weren’t set up for kids like me to thrive. Being held to arbitrary standards felt impossible and unjust.

My background gave me a front-row seat to contradictions. Exposure to different religions and diverse communities made it obvious when teachings didn’t align with lived experiences. For people who’ve never encountered that diversity, contradictions may not be as visible.

Later in life, I began exploring concepts of race, diversity, equity, and inclusion more deeply. Equality and equity are not the same. Equality gives everyone the same thing; equity ensures people get what they actually need. The classic image is three kids trying to see over a fence at a baseball game: equality gives them all the same size box, but only equity gives them the right-sized box so they can all see.

This applies to religion too. A faith might say, “Everyone can participate if you do XYZ,” but the requirements themselves may exclude people, ignoring their real circumstances and needs. Equity challenges us to ask: is the goal to make people conform to our way, or to build healthy, humane relationships?

For example, in my host’s faith tradition, until the late 1970s, Black men couldn’t hold the priesthood. That exclusion harmed people. The change came after the civil rights movement and broader cultural awareness. But was it made because leaders realized it was wrong, or because of external pressure? Questions like that are uncomfortable, but essential. True transformation requires honesty about motivations, harm, and whether decisions were humane.

When we measure harm, the simplest test is this: would I want this decision enacted upon me? If not, it’s likely inhumane.

In my work, I’ve seen that when people are given structured, safe environments to have difficult conversations, they often discover they agree on far more than they realized. They may disagree on solutions or paths forward, but they usually share core values. The problem is, most conversations never happen because we rush into character judgments. We hear someone say “Republican” or “Democrat” and instantly assume an entire story about them. We disconnect before asking, “Tell me why you believe that.”

When we do talk, we often discover we agree on 70–80% of what we want for the world. We disagree on how to get there, but the shared vision is there. That’s powerful.

Boundaries are essential in these conversations. A boundary is simply saying, “Here’s what’s acceptable in my space and what isn’t.” It doesn’t require agreement from others—you set it, and you enforce it. Boundaries protect relationships by clarifying limits. They’re not judgments of character.

Resistance to equity work often comes from the desire to be right. The more tightly someone clings to being certain, the less open they are to growth. Sometimes that certainty protects privilege; sometimes it’s because people have built their entire lives around beliefs and find it too destabilizing to question them. But transformation requires loosening that grip and admitting, “I don’t know everything.”

For me, living beyond the shadow of doubt means embracing that I don’t know anything for certain. It means letting go of the need to be right, and choosing to live aligned with my values of connection, purpose, and humanity.

Listeners can learn more about this work through my community, The Exchange, a professional association for coaches and leaders committed to equity in their practice, and through my book, The Antiracist Business Book.

Before we close, a few quick questions.

Favorite book right now? The Sum of Us.
Introvert or extrovert? Introvert.
Favorite artist? Lauryn Hill—she’s timeless.
Night owl or morning lark? Depends on the time of the month.
Celebrity crush? Idris Elba.
Still water, carbonated water, or diet soda? Carbonated water.
Furthest place traveled? Indonesia.

Thank you so much for having me. This has been wonderful.

And thank you for being here. This was an incredible conversation.