“It is impossible for a man to learn what he thinks he already knows.”
- Epictetus

Before you read another word, I want you to make a guess.

Do you think I'm a Democrat or a Republican?

For context, I grew up in California, and I live in San Francisco, one of the most Democratic-voting cities in the country.

I'm also a Black man, and 83% of Black voters identify with or lean toward the Democratic Party.

I have gay friends, believe in supporting social programs, and think many of our systems need serious reform.

If you guessed Democrat, that makes sense.

But, I'm also an entrepreneur who owns commercial real estate, stocks, and hold interests in oil and gas syndications.

I like tax breaks and am a registered gun owner.

I care deeply about the First Amendment, free speech, and generally limiting the powers of the federal government.

If you guessed Republican, I understand that too.

So here's my answer: I'm both.

To be clear: my political affiliation isn't the point of this email.

How I arrived at them is.

For most of my life I viewed politics felt like sports. You picked a team, and defended them no matter the score.

Then I read Nassim Nicholas Taleb's Skin in the Game, and one sentence blew my mind:

“I am, at the Fed level, libertarian; at the state level, Republican; at the local level, Democrat; and at the family and friends level, a socialist. If that saying doesn’t convince you of the fatuousness of left vs. right labels, nothing will.”

That sentence perfectly articulates how I view politics.

In my community, I donate to non-profits, I volunteer, and frequently give money to homeless people.

With family and friends, I share freely and never keep score. I host barbecues, dinners, and have never asked anyone for a dime.

Yes, I have a big heart, but, I also don’t trust career politicians; especially the one’s in D.C.

We’ve been burned too many times.

The data speaks for itself.

The farther a decision gets from the people it affects, the more carefully I want to watch who's making it.

Our policies, parties and news channels are too simplistic, and divisive.

They lack the necessary nuance to be effective; and nuance requires Intellectual Courage.

As we become dumber as a society, we become more politically polarized.

And there’s good reason for it.

F. Scott Fitzgerald wrote about it back in 1936:

“The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.”

Intellectual curiosity is the willingness to ask, "What else might be true that I am not considering?"

It asks us to hold our beliefs with an open hand, to be curious before we're certain, and to accept that two people can look at the same problem from different levels of life and both see something true.

And it starts with our own side. It's easy to list everything wrong with the other team.

The ego seeks to protect itself at all costs, and the ego is largely rooted in the fear of inadequacy and the fear of loss of control.

This is why it’s hard for people to admit they’ve been wrong, apologize or consider a perspective that challenges their existing beliefs.

It takes real courage to name what our own team gets wrong, and to say it out loud to people who agree with us.

I'm writing about it because voting season and the holidays are almost here, and this is when the divide stops being a headline and shows up at our own dinner tables.

We're already living through what the Surgeon General calls a loneliness epidemic, and part of the Daily Courage mission is to bring more healing into the world and more of us back together.

That can't happen if we only break bread with people who vote like we do.

To be clear: I won't tell you who to vote for, and I won't tell you which side is right, but I do plan on talking more about courage and politics in the coming episodes.

Epictetus warned that we can't learn what we think we already know.

So as the holidays come, let's try something braver than winning the argument.

Let’s focus on what connects us not separates us.

Let’s choose curiosity over condemnation.

Let’s practice respectful disagreement over disengagement.

The world needs more love, and love requires courage.

And that’s not something we can outsource to Washington.

Here's your reflection for the week:

When was the last time you changed your mind about something that mattered to you, and what made it possible?

Take the free Perception Gap quiz and see how well you predict what the other side believes.

With courage,

Jonathan