50 Things I Did Before I Turned 50

1. Got depressed because my dad went broke, lost our home, and went insane. He’d cry all the time, ask me, “What’s wrong with me?” and listen to music until he died.

2. Got depressed because the first 10 girls I asked out didn’t like me and said no. Two actually ran away before I finished my question. One said yes and then the next day told her brother to tell me no. One said, “Maybe in 100 years,” and I actually felt hopeful she was going to give me a chance eventually.

3. Got depressed when my mom hit me because I woke up my dad after his surgery. He made me stand in the middle of the room and not move while she came over and hit me.

4. Got depressed when the first business I started, CollegeCard (a debit card for college students), went out of business after less than a year.

5. Got depressed when I was thrown out of graduate school. The letter cited “lack of maturity.” I had dinner the other day with the professor who wrote the letter. He said that it was Nobel-prize winning economist Herb Simon who said, “Why are we letting that guy sit at a desk doing nothing when we could have a student there who is doing something?” and I guess he was right.

6. Got depressed when a girl I was in love with went home for a few weeks to her home country and her family found a letter I wrote to her. So they arranged a marriage for her within days and when she came back into town, she denied we ever were going out. I called a friend of mine on the phone but was crying so much I couldn’t speak and he couldn’t figure out who I was so he hung up.

7. Got depressed when four novels I wrote didn’t get published by the time I was 26.

8. Got depressed when 40 short stories I wrote and sent out to magazines didn’t get published. All of them got rejected by form letters. Out of the thousands of letters and copies of writings I sent out in my 20s, I did not get back one personalized rejection. I worked 10 hours a day on writing and nothing came of it in my 20s, with no hope for the future.

9. Got depressed when a TV show I pitched to HBO got rejected after we spent a year shooting a 45-minute pilot. The woman in charge of the decision said, “For material like this you need to either show someone shooting their mother while naked or show your neighbors f***ing.” She is now in charge of HBO Family programming.

10. Got depressed when a 13-year-old little girl crushed me in chess. Her name, in fact, is Irina Krush. I was a strong player and had studied for years. She analyzed the game for me and told me where I went wrong on the ninth move. I gave up playing tournament chess that moment.

11. Got depressed when Amy chose another guy over me. I really fell hard for her. She married him and has a kid. I ran into her a few years ago. I still fell hard for her.

12. Got depressed when I liked this girl, Jaimie, and she liked me, but I was always so nervous and intimidated by her that I couldn’t “perform.” One night she literally kicked me until I fell out of the bed and she told me to get out. So that was that.

13. Got depressed when I moved into my first apartment by myself. I had only one foam mattress and it was hot and I had a fever and all my sweat soaked thoroughly into the mattress. When I woke up in feverish pain in the middle of the night on top of my sweat-soaked mattress, I was covered by roaches.

14. Got depressed when I entered a contest for writing a “three-day novel.” I finished the novel and I called my girlfriend at the time. I wanted to get together. She said, “I thought we were taking a break.” And that was that.

15. Got depressed when I quit my job because I thought my business was going to take off and on the first day full time at my business our largest client cancelled us.

16. Got depressed when I jumped off my bed, pretending to be Superman, and I broke my toe and had to wear a cast. Then I had to start a new school as a first grader and I was “that kid” limping with the cast.

17. Got depressed when I was 10 years old and I was caught stealing football cards at the local toy store. They turned my coat upside down and packs of cards came out. They said, “Is that it?” and I said yes. They shook more. More packs came out. “IS THAT IT?” “Yes.” They shook more. More packs… And so on.

18. Got depressed when 10 minutes later they found my grandparents and asked them to come to the back of the store. The look my grandmother gave me.

19. Got depressed when I was 16 and I had so much acne and so many cysts you could barely see my face. I’d hear girls talking about me and looking at me and then look away when I looked. One guy, Yung Shin, told me to just try and smile a lot.

20. Got depressed because cysts are purple.

21. Got depressed when I cut school because I was so embarrassed of how I looked. I went into NYC and got mugged and my backpack was stolen from me and it had a bunch of books I wanted to read that day. Later, my mom asked me, “Where is your backpack?” and I had no answer.

22. Got depressed when I was eight and my dad convinced me to donate all my games to charity and he would give me his tax write-off. I didn’t even know what a tax write-off was but I thought it was a lot of money. I gave him about 20 games (Monopoly, Chutes & Ladders, Trouble, etc.). About six months later he gave me a dollar.

23. Got depressed the first semester of graduate school when I failed ALL of my courses. Up until then I thought I was smart. But at that moment I knew for the rest of my life I would have to fake it.

24. Got depressed when we moved to a new town when I was five. My new friends thought it would be fun to hold my hand on top of a burning barbecue for as long as possible. We moved a month or so after that.

25. Got depressed when I was unhappy in a relationship but we were living together and both of us too poor to move out. So I stayed at work and played online chess all of the time. At least 20 hours a day. And she would be upset at me and bang on my office door but I would lock it and pretend I wasn’t there.

26. Got depressed when she cheated on me. But I deserved it.

27. Got depressed when my college girlfriend and I took Kung-Fu class freshman year of college and she beat the shit out of me.

28. Got depressed when I started a brand new job in NYC and my dad bought me a suit and I was walking to work from the bus station when the woman standing two feet to my right was run over and killed by a taxicab that came up onto the sidewalk. I was depressed but it was worse for her.

29. Got depressed in my very first memory. I was in some sort of big crib even though I was too old for cribs. I was screaming. It was early in the morning. Eventually my grandmother lifted me out of the crib so I could play. I don’t think I have another memory until at least a year after that.

30. Got depressed when she said, “I have to run errands, I’ll be back in an hour,” and then she left and took a plane to another country and I never saw her again.

31. Got depressed when one… no… two women got pregnant with a child from me (presumably) and then decided to have an abortion.

32. Got depressed because I couldn’t see my kids every day like I used to. I remember I used to come home on the train and one of my kids would run and run and run and then jump into my arms. Those days died.

33. Got depressed when I got an offer to buy one of my companies. But he wanted me to sign a seven-year employment agreement and they could fire me at any time and I would have to pay back all the money in the deal. Didn’t take the deal and I shut down the company and was almost broke.

34. Got depressed when I realized I’d made a huge investing mistake. Oingo was going out of business in 2001. We could’ve maybe picked it up for nothing. I said, “No, the search engine business is dead!” Less than a few months later, Google bought the company for 1% of Google. The company, Oingo, had changed its name to Applied Semantics. Which later became called AdSense under Google. It generates 99% of Google’s revenues.

35. Got depressed when I decided to take a job at a private equity firm and give up on my dreams of entrepreneurship. On the second or third day of work I was in the middle of a meeting, said, “I have to go to the bathroom,” left my jacket on the chair, went to the elevator, said goodbye to the receptionist, rode the elevator 40 stories down, took the subway to Grand Central, took a train sixty miles home, and then never went back to work or returned their phone calls ever again.

36. Got depressed when a big hedge fund manager didn’t invest in my business. He was worried he would have no idea if I would spend the money on something unethical. He said, “The last thing we need here at Bernard Madoff Securities is to see our name on the front page of the Wall Street Journal.” So I decided to get out of the business, thinking, “Bernie Madoff is too good. How can I compete?”

37. Got depressed when many years later I reached out to Bernie Madoff’s prison and asked if he could come on my podcast. They sent back a message saying he said no and I thought to myself first, “Well, what else is he doing with his time?” and then I thought, “Man, Bernie Madoff keeps rejecting me no matter what.”

38. Got depressed when I was first doing standup. The first time I was heckled. The guy in the audience kept yelling to other people in the audience, “He’s a weirdo.” And then the MC said afterwards, “Sir, can I get you a drink?” and he said, “I need two. That guy was a weirdo.”

39. Got depressed when I took my daughter on a trip. We had so much fun. I took her to London and Paris. We ate at restaurants, went to bookstores, walked for miles, laughed and talked about anything. When we landed I kissed and hugged her before a car was taking her back to her mom because I realized we would probably never take a trip like that again.

40. Got depressed when I wrote a script for a TV show. It was about a hedge fund manager who secretly wants to be a standup comic. But he can’t tell his hedge fund friends and he can’t tell his comedy friends and throughout the arc of the show he develops his voice as a comedian. I sent it to my friends who were producers. They all said no. One called me and said, “Have you heard of a show called, ‘The Marvelous Mrs. Maisel’?” “No,” I said. “Watch it when it comes out next month.”

41. Get depressed every time I have a podcast guest say at the end of a podcast, “Man, that was the best podcast I’ve been on. Let’s grab dinner some time.” And then I call them later to follow up on a potential dinner but they never pick up or return my calls.

42. Got depressed when I threw out all of my belongings and was living out of a carry-on bag. I was living from Airbnb to Airbnb, just a few days at a time and if I bought anything new I had to throw something out of my bag. But then I realized I had also thrown out all of my pictures of me as a kid and pictures of my parents. I missed them. I missed the moments when I thought they loved me.

43. Got depressed when I got addicted to anti-anxiety medication in 2009. I was so anxious about money I couldn’t sleep. I would stay up all night trying to figure out the exact moment I was going to go broke and how I couldn’t escape it. Anxiety was filling every corner of my head. After a month of taking anti-anxiety medication I felt better. When I tried to stop, I couldn’t. I’d have seizures. It took years to even begin tapering off.

44. Got depressed when I realized that losing all of my money cost my dad his life. He had a stroke and there was a “miracle cure” involving spinning him around in a giant ball to stimulate parts of his brain. I wanted to try it but I was broke and couldn’t afford it so we had to check him into a facility when his insurance ran out and for the next two years he couldn’t move and just stared at a ceiling.

45. Got depressed when I suspected she just liked me for money and would make me feel guilty every time I wouldn’t buy her a dress she wanted. Why was I afraid to say no?

46. Got depressed when two different people asked me to take down their podcasts with them because they didn’t want to be associated with me.

47. Got depressed when I just realized I can’t remember the last time I cried.

48. Got depressed when I turned 40 and a friend of mine threw a surprise party for me. I didn’t know any of the people he had invited and I paid for the dinner at the end and went home to my crappy motel room. I had no friends.

49. Got depressed when my sister wrote me, “I never want to speak with you again for the rest of my life.”

50. Today I woke up and I’m the happiest I’ve ever been.

Share This Post

Other posts you might be interested in: