Leadership in The Trump 2.0 Era: Resist or Influence?

Part 1: When Principles and Power Collide

I am fascinated by how history repeats itself—not in a perfect loop, but more like echoes that bounce through time. Leaders today deal with dilemmas eerily similar to those faced centuries ago. While the names and contexts change, the core conflicts remain stubbornly consistent. Recently, as I’ve watched the shifting sands of political and social change, particularly in the turbulence created by the second Trump administration and Elon Musk's Department of Government Efficiency (DOGE), I found myself turning to two historical figures for insight: Marcus Porcius Cato and Lucius Annaeus Seneca.

These two Romans lived during times of enormous change and deep crisis—when principles collided dramatically with power. Their reactions couldn’t have been more different. Cato was famously uncompromising, staunchly resisting the changes he saw as threats to Rome's Republic. Seneca, on the other hand, sought to influence power from within, becoming advisor and tutor to Emperor Nero, trying to mitigate the chaos and guide the empire from behind the scenes.

Photo by Elijah Macleod on Unsplash

Today, leaders across industries face a similar tension. The Trump administration, alongside Elon Musk’s DOGE initiative, is currently dismantling longstanding programs and federal agencies, fundamentally reshaping the relationship between the American government and the business community. Leaders in sectors deeply reliant on these traditional government frameworks—such as SBA lending, impact investing, and beyond—are navigating a rapidly evolving landscape. They're challenged to decide whether to stand firm against these sweeping changes, resisting what they perceive as harmful disruption, or to step into the uncertainty and attempt to shape the outcomes constructively.

Why Ancient Rome?

I get it—Ancient Rome seems distant. But here's the thing: Rome wasn't just powerful. It was messy, political, contradictory, and very human. It felt chaos deeply. Rome's politics swung wildly between lofty ideals and gritty pragmatism. And that’s exactly why leaders today can learn so much from it.

Take Cato, for example. He stood for principle over pragmatism, believing the Republic's traditional values were non-negotiable. His stubborn refusal to yield to Julius Caesar’s rising influence has made him a legendary figure of principled resistance. He became the gold standard for leaders who prioritize ideals above political convenience.

Then consider Seneca. He had high ideals, too. But he chose a different path. He entered Nero’s inner circle, hoping his guidance could tame the emperor’s impulses. Seneca believed he could do more good influencing from within, even if it meant occasionally turning a blind eye to moral ambiguity.

A Modern Parallel: Ambition and Chaos

The current era of Trump 2.0 and Elon Musk's DOGE initiative has become a contemporary backdrop for these ancient leadership dilemmas. Whatever your political stance, it’s undeniable that the administration is executing radical changes with unprecedented ambition and unpredictability. Longstanding federal agencies and programs are being dismantled, and the relationship between government and business is fundamentally shifting. Many sectors—including SBA lending and impact investing, fields I know intimately—are caught in the turbulence, grappling with a stark reality: adapt rapidly to these drastic, sometimes chaotic changes or firmly oppose them.

For leaders across all sectors, this chaotic governance poses tough questions: Do you stand by your principles, resist vigorously, and risk isolation or irrelevance? Or do you engage, stepping into the confusion to guide or at least moderate the outcomes, potentially at the cost of complicity? The stakes feel high, and clarity is hard to come by.

This dilemma goes far beyond SBA loans or impact investing—it echoes throughout modern leadership. Whether you lead a team, run a small business, or manage a large organization, you've probably faced a situation where you had to choose between uncompromising resistance and pragmatic influence.

The Uncompromising Path: Cato’s Example

Cato didn’t compromise. He saw any surrender as moral weakness. He believed that once you start compromising your core principles, you’ve already lost. This rigidity cost him dearly—ultimately, his life. Yet, paradoxically, history remembers Cato precisely because of his refusal to bend.

In modern terms, we might say Cato's style is "brand integrity" taken to an extreme. It's powerful and clear. It rallies your base, inspires loyalty, and gives your stance unquestionable moral clarity. But it can also isolate you, limit your impact, and sometimes make you a martyr rather than a change-maker.

The Influence Path: Seneca’s Example

Seneca chose differently. He worked closely with Nero, who was notoriously unpredictable and cruel. Seneca attempted to steer Nero towards moderation, and at first, it seemed to work. But the longer Seneca stayed, the more he compromised. Gradually, Nero's excesses became worse, and Seneca's ability to moderate him diminished. Seneca eventually found himself complicit in acts he would never have condoned earlier in his life.

Seneca's approach illustrates the risks inherent in compromise. It's the idea that if you're not careful, "working within the system" can subtly transform into compliance with it. Still, his early years showed the power of influence from within. Sometimes, being in the room—however uncomfortable—can make a genuine difference.

Leadership's Timeless Dilemma

Every leader faces moments of principle vs. pragmatism. It’s easy to romanticize Cato’s purity or Seneca’s practical engagement. But leadership is rarely that simple. The truth is messy. It involves difficult trade-offs and careful calculations. Real leadership usually requires elements of both resistance and influence.

This five-part series will explore the complexity of these choices:

• Part 2: The Integrity Trap – Cato’s Uncompromising Stand

• Part 3: The Cost of Compromise – Seneca’s Risky Influence

• Part 4: The Limits of Influence – Knowing When to Leave

• Part 5: Balancing Resistance and Influence – A Path Forward for Leaders

My hope is to share lessons from history that are useful to modern leaders facing their own turbulent times. We’ll look at when to stand firm, when to engage, how to know when it's time to step away, and how to navigate those choices strategically.

Cato and Seneca show us that these choices are timeless—and that there's wisdom to be found whether you resist or engage. The key, as always, is to know the difference. Stay tuned for part two, where we dive deeper into the integrity trap and what happens when we choose never to bend.