One of the biggest challenges for powerful white men who want to fight for social justice is unlearning much of what we’ve been taught about leadership.

That’s an insight I’ve gleaned from hundreds of conversations with people in the field about how white male elites like me can best contribute. Some urged me to stay on the sidelines. Others said I should just write a check and then get out of the way. A common fear was that if I got involved, I’d engage like a bull in a china shop, which I get, because, despite my best intentions, I’ve been that guy.

Throughout my life, I received messages that I had a responsibility to lead. When I arrived as a freshman at Stanford in 2006, I was taught that leadership meant controlling institutions, and that no form of leadership was more noble or effective than creating, and then controlling, an entrepreneurial venture.

I took those lessons to heart and, out of my dorm room, co-founded CollegeSpring, a national nonprofit that provides free college test prep to under-served students. For a decade, I led CollegeSpring as its founding CEO. I’m proud of the results: During my tenure, we served 19,000 students, raised $15 million, and were recognized by the Obama White House.

But leading CollegeSpring also exposed me to cracks in narratives I’d been taught. Our students faced multiple barriers, and their needs extended far beyond what CollegeSpring’s resources could provide. While fundraising, I met many ignorant philanthropists, such as a billionaire financier who refused to donate after he found out that we served all students at partner high schools. His reason: He didn’t want his money “going down the drain on the lazy kids.”

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I also started grappling with my own ignorance. More seasoned white women and people of color on CollegeSpring’s team helped me see that a 27-year-old white man running a nonprofit that served communities of color reproduced many of the same problematic dynamics as a billionaire assessing, from his corner office, which children deserved his resources.

His ignorance, and mine, were spilling onto the lives of the people and communities I was trying to support. So, in 2017, I stepped down and passed the baton to Yoon Choi, an experienced executive who has shored up the organization in many areas I’d come up short.

Since then, I’ve reassessed what role people like me are best positioned to play in the fight for social change. I’ve read dozens of books — about history, philanthropy, social movements, trauma, and more. I also wrote one of my own — “Rich White Men.” And I’ve tried my hand at leading differently as a co-creator of Liberation Ventures, where I supported Black co-founders in launching an organization that advocates for federal reparations.

Particularly valuable to me was discovering role models in other white male elites who have been successful partners for equity and justice. South African philanthropist Herman Kallenbach donated land for the Tolstoy Farm, where he lived with Gandhi and other leaders of the nonviolent resistance. John Palfrey, a descendant of Teddy Roosevelt, is leveraging his position at the helm of the MacArthur Foundation to champion justice, including funding the U.S. reparations movement. And the businessman and lawyer Stanley Levison, Dr. Martin Luther King Jr.'s closest white friend, was a key figure in the civil rights movement. (For more examples, check out a little known 2003 book called “White Men Challenging Racism.”)

(The John D. and Catherine T. MacArthur Foundation is a financial supporter of the Chronicle of Philanthropy.)

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I found Levison particularly inspiring. He supported King by drafting speeches, fundraising, organizing events, and hiring staff. Levison assessed his own value accurately: He knew he brought useful expertise, but he also didn’t hesitate to roll up his sleeves and work with the team. He didn’t demand that King solicit him at his office, write him a grant proposal, or coordinate a site visit. Nor did Levison insist on running the show, from a staff or board perch. He simply walked alongside King, and helped as needed. Levison was more than a colleague, ally, or co-conspirator; he was a true friend who loved King and his mission.

The social sector needs more wealthy white men who bring this sensibility — who see value in supporting, not controlling, yet also aren’t afraid to assert that they have something to offer.

No Quick Fixes

That isn’t easy. Every white man I know who is making a sincere effort to advance equity has struggled with the task. We read books that help us walk in the shoes of those whose lives are different than ours. We seek out and maintain friendships with people from diverse backgrounds. We join our organizations’ diversity, equity, and inclusion committees. But none of that seems sufficient.

Many of us want a to-do list to check off. This is such a popular request that I included one in my book. But quick fixes are inadequate because seeking social justice is a lifelong journey with no end point.

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I’ve found that showing up effectively requires something like a daily whole-body workout, which strengthens multiple muscle groups. There’s a relational aspect — nurturing relationships with diverse friends and colleagues. There’s an analytical aspect — studying the impact of culture and societal structures. There’s a messaging aspect — effectively communicating the need for justice to different audiences. There’s a change-management aspect — initiating change within families, institutions, and society. And there’s an emotional-intelligence aspect — understanding and healing our own trauma and recognizing emotions and bodily cues in others.

I don’t know any white men who are excelling in all these areas, including me.

One mistake I’ve made is prioritizing one muscle group over others. For instance, after reading extensively about equity and justice, I acted like a know-it-all and dominated conversations, which was poorly received because I was perpetuating patterns of dominance. However, before I had done that homework, my colleagues found my ignorant questions exhausting, regardless of how attentively I listened. Such situations can feel like a Catch-22 unless we learn to see personal growth as multi-dimensional.

Ill-Suited Behaviors

Another mistake I’ve made is misinterpreting “checking my privilege” as abandoning what I uniquely bring to the table. Levison’s effectiveness partly stemmed from skills his many advantages allowed him to develop, such as building lasting institutions and influencing those in charge. Even if rooted in unearned privileges, those skills are valuable. The task isn’t to disown them, but to share them humbly. At the same time, white men need to recognize that behavior patterns which served them well in other contexts might have the opposite effect in the social justice arena.

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I’ve also gotten into trouble by believing my role was merely to follow the lead of those from marginalized backgrounds. The limitations of that approach became clear when those I was following disagreed, or actions demanded of me didn’t feel right. I came to understand that I still needed to clarify and assert my own point of view.

Learning to express my needs and boundaries without being domineering has transformed my relationships and made me more comfortable with ambiguity. Being a perfect champion for equity, I’ve come to believe, is no more attainable than being a perfect spouse or parent.

Still, I’ve struggled to accept that I’m doing enough, a common dilemma among people like me who feel a responsibility to shoulder the world’s burdens in exchange for our privileged position.

Growing up, I was inspired by Steve Jobs’ call to action: “We’re here to put a dent in the universe. Otherwise, why else even be here?” Today, the arrogance of that statement troubles me. Humans are meant to be part of the universe, not masters of it. Letting go of that delusion has been more liberating than any power I’ve gained over others.

On a recent podcast, the host and I discussed how Americans often glorify financial greed, even though we know it frequently relies on privilege and exploitation. Then we talked about how social-change advocates can be greedy for impact — to aspire to leave a grand footprint and legacy. Gandhi went as far as to say that attachment to any outcome was a form of greed.

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If I’m honest, I’m still greedy for impact, but I’m starting to understand that if I’m contributing, learning, and growing, that just might be enough.