🤞 A Skeptic’s Hope

It’s Fourth of July in the year 2025, and I’m conflicted.

On Skepticism

I am, by nature, a skeptic. At times, I’ve leaned too deeply into that skepticism, allowing it to poison the possibilities of better outcomes. In other cases, it has served me well, allowing me to approach things with a cautious curiosity.

I heard Maryland Governor Wes Moore (an Army vet who cut his teeth on the enlisted side, by the way) speak about this a couple years ago. He said he doesn’t consider his inherent skepticism to be a bad thing. The trick, he opined, is to let skepticism be your companion, not your captor. I like that framing.

It’s easy to be skeptical these days. Hell, it’s easy and understandable to be cynical right now, even angry.

In the lead up to today, where we celebrate independence and what this country is supposed to stand for, I’ve sometimes let the skeptical dial tilt toward the negative. Serving as my captor instead of a useful companion.

On Hope

The counterbalance, I’ve found, is hope.

The governor’s framework for skepticism is also instructive here: let hope be a companion, not a captor. It does little good to walk around with your head in the clouds, so hopeful that you ignore the real-world circumstances on the ground beneath your feet.

But if you let it be your companion, buoying you in hard times and helping you connect with sources of light and motivation and positivity and forward movement, well, that’s the good stuff.

I’m in a unique place in life where I have direct, constant access to folks that can and do give me hope.

Last week, I wrote about my experience teaching the Declaration of Independence to a group of fired up enlisted veterans at Harvard. Reading and processing that document together gives me hope, resolve, and inspiration, I wrote.

In a very real sense, the entirety of Warrior-Scholar Project is about hope. Through the lens of academics, we foster hope with those in the midst of wildly difficult transitions.

Importantly, it’s not just about the experience of individuals; it’s also about the connection of individuals to community. Hope in transition derives from a growing confidence that you don’t have to go it alone. That each person is part of a group committed to supporting each other, in the easy times and the hard.

When I taught that session on the foundations of American democracy, I looked around the room at this group of 12 enlisted veterans who had all raised their right hand while they swore to uphold and defend the Constitution. Who better to examine what it means to serve this complex country of ours in this particular time in history? We examined the twin pillars of liberty and equality, and how the latter is much harder to uphold. No simple topic.

On Skeptical Hope

The hope, then, isn’t simply a desperate, even naive, belief that things will automatically get better. It’s a skeptic’s hope, where we acknowledge how vigilant and intentional we must be to preserve a liberty explicitly grounded in equality, clear-eyed about how difficult the task before us actually is.

My skeptic’s hope is similarly reinforced through my engagements at the Union League Club of Chicago, where I have the wild privilege of chairing the club’s historic Public Affairs Committee. This club was founded in the 19th century in bold defense of the Union and in explicit opposition to an insidious movement to preserve slavery. The Public Affairs Committee oversees the club’s advocacy and positions on issues like the rule of law, immigration, and civic reform.

A fellow club leader recently shared that he views public affairs as the committee of hope. I think he’s onto something. In this work, we’re surrounded by civic servants who are committed to making our country ever better. Yes please.

I am not, to use Putnam’s phrase, Bowling Alone. Democracy is a team sport. Community building takes work. The community I’ve found in Warrior-Scholar Project and at the Union League Club are worth the work ten times over, as it gives me a type of reinforced and grounded hope on this Independence Day 2025.

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Ricky Holder, a stellar Warrior Scholar Project alumnus and Marshall Scholar at Oxford, shared a speech he gave recently to his graduating class. It is well worth the read, but here I’ll just share the concluding challenge. We must “not despair when we look out at the world and notice all that’s broken, but rather draw strength from everything that must be fixed.”

Yes.

Hope! Manifestly challenging work, but hope.

This skeptic, for one, will not lose sight of the fact that our country was founded not just on the pillar of freedom, but also that of equality. I will not stop fighting for that, and I hope you will join me.

-Rye

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