Exploring Freedom Through Unexpected Encounters

This is going to be an unusual blog post.

As a civil rights attorney living on one of the coasts, I often feel like I’m in a bubble. You wouldn’t be surprised to learn that I was taken aback by the results of the recent presidential election. My head knew it was possible. My heart, not so much.

In the weeks following the election, I’ve grappled with its impact on my clients, my practice, my family, and our collective future. I’ve always believed that the essential greatness of America lies in the idea that “the people rule.” I cannot support freedom and democracy only when I like the outcome; true freedom means accepting results with which we may not agree.

With that in mind, I decided my December blog post would focus on “freedom” and celebrate our ability to accept outcomes we dislike as a fundamental aspect of being free.

Then I met Ivan.

A Chance Encounter

While in New York City for meetings, I had some time between appointments and stopped at a well-known coffee shop in Chelsea for a cup of tea. Outside, I saw Ivan, a homeless man clearly cold and alone. 

I’ve long wrestled with the moral dilemma of giving money to the homeless, unsure if it would enable self-destructive behavior. Instead, I decided to offer him food.

“Hi,” I said. “Would you like something to eat?”

“What?” he replied.

I repeated myself. “Would you like something to eat? I’m happy to buy you something.”

Curiously, he asked, “What do they have?” This surprised me; it suggested he was exercising a level of autonomy over his next meal that I hadn’t expected. (To those who recognize my self-absorbed thoughts here, know that I cringe at my narrow-mindedness.)

“I don’t know,” I admitted, realizing that even at a ubiquitous coffee shop, I was unaware of its offerings.

“I’ll come in with you,” he said as he stood up.

This was not what I had intended. Panic set in as I recalled “New York Commuter Rule No. 1”: never engage with people!

Inside the Coffee Shop

As we entered together, we attracted some curious looks. The staff clearly recognized Ivan and understood our purpose there. They didn’t intervene or remind me of New York Commuter Rule No. 1.

I let Ivan order whatever he wanted: one small carton of chocolate milk, two white-chocolate raspberry tarts, and one small chocolate bundt cake. When he tried to order two lollipop cakes, I suggested he might want some protein instead.

That’s when it hit me: why should Ivan be limited by my assumptions? People with money indulge in sweets whenever they want—why shouldn’t he? My discomfort felt like an eternity as the staff treated Ivan’s order with the same care they would any customer.

Reflecting on Freedom

I realized Ivan’s choices were his own—not mine. Sure, some might be poor choices; I make bad choices all the time, too. 

As I reflected on this encounter and my planned blog about freedom, it dawned on me: perhaps I don’t fully understand what it means to be free.

That’s my experiment for 2025: to explore the contours of freedom.

It seems our society loves to proclaim freedom—until we see others’ choices. Suddenly, we’re not so sure they should have that freedom.

My encounter with Ivan inspired me to delve deeper into what it truly means to proclaim our freedom. Throughout 2025, I’ll read some books, attend some lectures, and dedicate several blog posts to this exploration. And since I don’t claim to have all the answers (my encounter with Ivan shows I may not have any), I invite readers to submit proposed “guest essays” on this topic.

Guest Blog Rules

– The Blog Publisher (me) reserves the right to accept, reject, or edit any proposed submission.

– Submissions that disparage or use profane or discriminatory language will not be accepted.

– Submissions should be fewer than 1,000 words.

– Rules can be modified based on experience.

– There are no prizes or payments for guest essays posted—after all, “beggars can’t be choosers.”

Please feel free to contact me here.