I had the idea for this post at least a year ago. I have a list of post ideas for days when I can’t think of any. This post idea has been on it as long as I can remember. When I think to write it, it makes me feel vulnerable.

Does writing about me crying related to what I usually post about? Will I be sharing weaknesses? Will people see patterns I don’t notice and make me feel awkward? What might people I don’t know think of me?

I also know the pattern of feelings like this: I feel awkward writing it, people respond that they love learning more about me for sharing, people share their similar stories and we connect more, I learn more than I expected about myself and humanity, and other life lessons. Many will congratulate me from sharing something vulnerable and say I should do it more.

Still, for all of people proclaiming the value of sharing such things, I don’t hear them doing it first. They like when other people do it. I guess part of the pattern is that some people describe it as brave.

After all that preamble, I’m just going to mention the times and say a few words about them, not tell stories about them. I don’t remember that many times I seriously cried. I’ve shed many tears, but when I read The Choice, for example, tears were streaming down my face and my body heaved. The other times too.

• September 11, 2021: On the twenty year anniversary of the attacks, I watched the firefighters at the firehouse across the street from me muster in their dress blues. On my way from watching them out the window to recording a podcast episode, I started crying. Some days or weeks later I shared with a friend how, besides people who died, suffered injury, or their family members, I didn’t know anyone whose life was affected as much as mine. Since those who did suffered so much more, I didn’t feel it was my place to complain. His response liberated me from twenty years of limbo. He said, “Just because others suffered more doesn’t mean you can’t grieve.”
• High school girlfriend breakup: My high school girlfriend, also my first girlfriend and romantic love, and I tried to stay together into college, despite her attending a school outside Boston and mine being in New York City. Things didn’t last long. We broke up and got back together a few times, but one time when I visited her was particularly final. When I left her in Boston I was fine. When I got back to my dorm in New York, I lost it.
• Breakup in Shanghai: I lived a year in Shanghai around 2010-11. I don’t remember the details, but my girlfriend in New York and I agreed to some freedom to date. We were open to the relationship not lasting. A year is a long time so who knew. Still, we talked nearly daily with a regular time set for a call. We kept growing closer despite the distance, but at some point a breakup seemed inevitable. I cried and cried like a child in the room I was renting, lying on the bed. I realized I cared for her more than I thought. I resolved to restore the relationship. On my next trip home I took her to the top of the Empire State Building as part of a big romantic night. I had also bought her a Tiffany pendant that I had shipped to her. I’d never sent someone Tiffany before, nor had she received anything like it. She told me later that as she unwrapped the big box she wasn’t sure if she glimpsed the trademark blue through the packing paper. When she confirmed it, it took her breath away.
• As a baby: Speaking of feeling like a child, I have vague memories, probably made up by now, of crying in infancy, before I had acquired language. I just felt “I want!” and all I could to do get what I wanted was to scream. I suppose that motivation remains in all humans, maybe all mammals.
• My grandmother’s funeral: At the funeral for my dad’s mother, I approached the open casket, not thinking of what I would see. Until a certain distance, I could only see the exterior, but as I approached, I saw her face, as far as I remember, the first dead body I’d ever seen. I had only remembered her as one of the most vivacious, energetic people I’d known. Seeing her lifeless, almost like a reflex, the tears began flowing.
• This Land Is Your Land / Statue of Liberty: I thought I posted about this instance in this blog or spoke about it on my podcast, but I can’t find it. During the Black Lives Matter protests during the pandemic, suggesting to defund the police, I couldn’t make sense of those protests, despite my feeling that participating in similar ones when I was in college would have felt automatic. I think it was shortly after the January 6 incident at the capital in DC. I felt like both groups felt they were trying to improve the world and that they felt they were speaking for all Americans, or at least the ones they thought were right. Yet everyone pooh-poohed my picking up litter, calling me privileged for it when picking up litter, as a part of changing culture, actually did improve communities, the nation, and everyone’s lives. As I picked up litter, I sang This Land Is Your Land, which seemed to embody the opposite of what the protesters expressed. Singing the song made me cry. I happened to be walking toward the river as I walked and picked up litter (part of my daily outdoor walks during the pandemic). I didn’t think about it until it happened, but out on a pier, when I turned to look south from the pier, I saw the Statue of Liberty and the tears turned to full-on bawling.
• Submedia alone: Shortly after September 11, 2001, the company I had co-founded based on an idea I conceived of was approaching bankruptcy. Moreover, I hadn’t learned to lead effectively, so didn’t know how to lead through challenging times. I later learned, other employees were annoyed at the disputes between me and the other cofounder not taking their concerns into account. They decided not to come into the office for a day. They didn’t tell me, so all I knew was that I was alone in the office. I had arrived before 9am. Others normally arrived by then or soon after. By 9:15 something seemed wrong. By 10am, I didn’t know what was going on. I only know I felt more alone than ever. I wondered if the company was over. I felt I had given up everything, had nothing to look forward to, and nothing to fall back on. I couldn’t do anything effective. The office was in Soho with windows facing Broadway. I looked out the window and wept. Submedia never went bankrupt, but the investors squeezed me out, a result that until then, I didn’t know could happen to a CEO and founder.
• The Choice: I wrote about this time in this post.

• ← This week’s selected media, September 21, 2025: The Constitution Today, Groundhog Day, podcasts with Christopher Ryan and Arthur Brooks
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