What I Wish I'd Known: 5 Hidden Tensions in Corporate Philanthropy

Justin hosting a film screening at the Castro Theatre in San Francisco

After two decades navigating Fortune 500 social impact and directing well over half a billion dollars in corporate philanthropy, I've come to realize a hard-earned truth: corporate philanthropy is a game of impossible tensions.

I didn't set out for this path. As an engineer, I dreamed of changing the world through product design. But somewhere between a student leadership role with the National Society of Black Engineers and studying capitalism at Harvard Business School, I found myself drawn to a bigger question: Can corporate resources truly drive meaningful social change?

Now, as I step into my next chapter, here are the five tensions that I've learned matter most - truths forged in the messy, high-stakes work of trying to “do well by doing good.”

1. The Win-Win Dilemma

The corporate world loves win-win solutions. But here's the uncomfortable truth: transformative social impact often challenges the very systems that benefit successful companies.

The consensus wins—education initiatives, disaster relief, employee volunteering—sell themselves. The real art lies in something harder: finding authentic ways to drive systemic change while advancing business interests.

The best corporate philanthropists I’ve seen are master translators—finding authentic ways to align bold, challenging initiatives with business interests without diluting their impact.

2. Generosity vs. Justice

Generosity eases immediate suffering. Justice asks why that suffering exists.

Supporting underserved students with learning resources matters deeply. But questioning why they're underserved in the first place? That's where conversations start to get uncomfortable.

As Bryan Stevenson taught me, "the opposite of poverty isn't wealth—it's justice." Both charity and justice matter, but confusing one for the other limits our impact.

3. The Measurement Mismatch

Corporate philanthropy operates like a school where only some classes are graded. We track business metrics—brand lift, influencer engagement, executive alignment—with rigor. Yet social impact often gets evaluated as a pass/fail.

The challenge? Demanding excellence in social impact when few people are checking that scorecard. This creates a subtle but powerful bias toward what's easily measured over what matters most.

4. The Innovation Obsession

As an engineer, I understand the allure: surely every social problem is just one clever innovation away from being solved. But technology is an amplifier, not a fix—it often makes good systems better and broken systems worse.

Many of our deepest challenges don't need another app or algorithm. They need the patient, deliberate work of shifting systems and changing minds. Innovation matters, but don't mistake new tools for social transformation.

5. The Power Paradox

Corporate philanthropy comes with immense privilege and power. The temptation is to wield that power like a savior or treat grantees like contractors rather than partners.

But real change requires proximity—deep relationships with affected communities and the humility to be both student and teacher. The most effective philanthropists I've seen leaned into discomfort, worked closely with grantees, and let their strategies be shaped by those most impacted.

A Note About Accountability

Want to ensure accountability to social impact? Hire people with lived experience in the issues you're addressing. When your team members are active participants in affected communities, excellence isn't abstract—it's personal.

Navigating Forward

Here's what I've learned about navigating these tensions:

• Build trust before pushing boundaries. Earn your "idiosyncrasy credits" through competence and reliability first.

• Separate role from self. When the heat gets high (and it will), remember that reactions to your role usually aren't personal—even when they feel deeply personal. Adjust your tactics, not your conviction.

• Find your outside anchors. For me, that's time in nature with family (hello Outdoorithm) and spiritual practice (sharing life with Rev. Sally Steele). The psychological toll of holding these tensions is real.

• Accept that you'll never fully resolve these tensions. The goal isn't to eliminate them—it's to navigate them thoughtfully, with humility and courage.

To my fellow corporate philanthropy practitioners: You have more power than you think. Use it wisely. Use it bravely. And never stop wrestling with the hard questions about how to use it better.