Jack’s life seemed perfect from the outside.

He had a loving wife, great kids, and was a fantastic businessman. He was known as a gvir in Brooklyn’s Syrian community and gave enormous amounts of tzedakah to a variety of chesed organizations and individuals in distress. He had a summer house in Deal, a winter house in Miami, and a penthouse in Jerusalem. What could be wrong?

Here was a guy who was so well known that even I recognized his name as a supporter of various communal organizations and institutions when I received an e-mail that he was interested in an appointment. He provided no information regarding the reason for consultation, though, and just wrote: “I’d rather discuss it in person.”

When Jack came into my office, he didn’t disappoint. I could smell his expensive cologne even before he knocked on the door and the custom-tailored suit he wore was at least as expensive as my car. But like most of the honest businessmen who’d been pillars of his community, Jack had the kind of 1,000-watt smile, big handshake, and down-to-earth manner that made you feel proud to know him.

Looking at this put-together magnate, I thought of the myriad problems that could plague such businessmen. We sat down and I opened the floor for Jack, but it seemed like he wanted to interview me first. How did I learn Syrian chazzanut? (“Years of singing at Seudah Shlishit with Chacham Aharon Hamaoui in Boston.”) Who was my favorite darshan? (“Rabbi Eli Mansour.”) How is “Freedman” a Halabi name? (“Too long a story for this one-hour consultation.”)

I found myself itching to figure out what brought Jack in — it certainly didn’t look like OCD, depression, schizophrenia, or any other genetic psychiatric condition. But for some reason, Jack avoided any targeted questions and kept reverting to small talk. What was my favorite kind of Syrian Shabbat food? (“Lachmagine and kubbeh.”) Yet as our time was almost up, Jack told me he’d like to book a second appointment and wanted to know if I was available the following day.

“Sure Jack,” I answered, “but are we going to talk about what’s bringing you here or just continue with the schmoozing?”

“We’ll see,” Jack offered, flashing his million-dollar grin as he left.

But the second appointment was much of the same — what’s my favorite Syrian zemer for Friday night and what do I think of Yechiel Nahari?

“Jack,” I finally stopped him as he continued the superficial dialogue, “isn’t there something else you’d like to discuss beyond the fact that I’ve been to Deal, New Jersey, and know how to sing pizmonim?”

Jack didn’t seem to know how to respond, so he decided to defer again. “You free again tomorrow, Dr. Freedman?”

“For you Jack, sure, but only if you’re willing to bring a bit more to the table.”

“It’s hard for me to say it, Dr. Freedman,” he responded, finally a little embarrassed.

“Then write it down and bring it in tomorrow.”

But Jack didn’t seem to want to talk about anything serious the next day either, opening our session by asking me if I’d ever been to hear Moshe Habusha sing Selichot.

“Jack!” I practically yelled. “Are you here for a reason? You’re too smart and too busy to waste your time — what’s going on?”

Jack blushed and then took out the note he wrote from the pocket of his $10,000 suit. “Can I read it, Dr. Freedman?”

He took a few deep breaths. “Dr. Freedman, I’m here because I’m turning 52 and that’s the age my father died. Baruch Hashem I’m grateful for all that I’ve been given and I try my best to give back to the community that I care so much about. My doctor told me that I’m healthy, and I try to exercise and take care of my body. But I think a lot about how my father zichrono livrachah died suddenly, and then I start to think about how much time I have left. People see me and they see a pillar of the community, but I look at myself and I see a person who works too hard, travels too much, and doesn’t spend enough time with his family. I see a person who loves gashmiyut and physical things like nice cars, fancy clothes, and professional sports way too much. I look at the chachamim and I wish I could have more of a share in what they’ll receive in Olam Haba. I don’t know what I have to do, but I don’t want to have too many regrets when I go up to sit with my father in Shamayim.”

I sat quietly as Jack wiped away an escaped tear from the corner of his eye. Years ago I might have sought to comfort him or rushed to say something to rescue him from these intense emotions, but I realized that it would do him better to sit with his feelings and use them as motivation for change.

“Dr. Freedman,” Jack broke the silence, “what do I do?”

“I think you know what to do, Jack.”

“I do?”

“Of course you do. Your letter already made things very clear.”

“So I throw everything out, put on a black hat and call it a day?”

“Of course not. But it sounds like you’re doing a serious cheshbon hanefesh, which is very important. You know anything about Rav Yitzchak Alfia, one of the greatest Syrian chachamim of the previous century?”

“He spread the practice of taanit dibbur,” Jack answered. (I was impressed.)

“Yep. And he was also famous for having given his own hesped.”

Jack’s eyes shot up in surprise.

“He decided to do a serious cheshbon hanefesh and had his talmidim and the community come out as if he’d suddenly died. Except instead of eulogizing him, they saw him stand up out of a coffin and eulogize himself. He talked about the things he’d done right and the things he wished he’d done better. He then had himself carried out as if he were done with This World. It was a tremendous way of centering himself and focusing on what was really important.”

“Sounds very intense,” Jack noted. “You think I should stage my own funeral?”

“Nah, your wife would kill me if I recommended that for a nice fellow like yourself. But what you can do is write yourself a ‘Chas V’shalom’ letter.”

Jack looked a little confused.

“It’s a letter you write, describing what you did right and what you’d like to do better. A letter that gives over the wisdom of the past 52 years and allows you to think about what you wish you could do better if you’d be given a bit more time in Olam Hazeh.”

Jack nodded. He was already jotting down notes for his new assignment.

“Any questions, Jack?”

“Well, what do I do with this letter once I’m done with it?”

“You bring it back in and you read it to me. And then we help you to start living it — because it sounds like you’ve got a bit more time to be who you want to be.”

“I got it,” said Jack. “Tomorrow, Dr. Freedman?”

“Only if you can pay me in lachmagine and kubbeh.”

Originally featured in Mishpacha, Issue 733. Jacob L. Freedman is a psychiatrist and business consultant based in Israel. When he’s not busy with his patients, Dr. Freedman can be found learning Torah in The Old City or hiking the hills outside of Jerusalem.  Dr. Freedman can be reached most easily through his website www.drjacoblfreedman.com.