I’m Ashamed

I was very ashamed. Alex brought it up delicately. We were on plane coming back from some BS meeting somewhere where we were supposedly analyzing a company for our VC fund.

“I saw you put your apartment up for sale?” he said. He must’ve been looking at listings because he was in the market to buy. Only ten months earlier I had had a huge party at my apartment celebrating moving into it. Over 200 people were there. It was catered. We had a gym. Little kids were hitting the punching bag. My 2 year old was painting on her easel. People were shooting pool on the 1946 vintage pool table.

(right before the housewarming party on the house i lost)

“What!?” I said, “that’s ridiculous. We were just having a conversation with real estate brokers. We didn’t tell them to actually sign us up.” I acted infuriated.

That was a lie. Of course we had to sign paperwork telling the real estate agents to list our house, set a price for it, get an MLS number, take photographs, exclusively work with us, etc.

“Ok,” Alex said and he sort of smiled because he knew I was lying and I knew I was lying.

I went to look out the window of the plane. My face was burning red. Everyone knew I was a liar. Everyone knew I was a failure. The plane was riding just above the surface of the clouds, benevolent balls of cotton in the sky that seemed to be just barely holding us up.

I had to lie.

We were 70 miles north, trying to find a place that was going to be in our price range. We were looking at places 1/3 the size of our old apartment (which one year after we had put it up for sale, still hadn’t sold). Every house seemed worse than the next. I hated the real estate agent. After one place I got a call from one of the investors in our VC fund. He’s now the CEO of Investcorp.

He asked me, “why aren’t you putting money in the latest deal with the fund? We expect the partners to put money in each deal. “

I was ashamed to say that I couldn’t afford to. I had already lost enough money on that company. Another batch of money from me wouldn’t save it or kill it either way. But would kill me.

I said, “my wife is making all the personal investment decisions. We’ve already put money in that company three times so she said, ‘enough is enough’ and you know, ‘happy wife equals happy life’ “.

Savio didn’t buy it. He said, “come into the office next week. We need to talk”

Later we were all sitting in a café in the town 70 miles north. The real estate agent was talking about how great the area was. How great the schools were. I was depressed. If I didn’t sell my house in the next three months I’d be at zero. It turned out to take about 4 months to sell from that point.

There was a girl in the café sitting reading a book. She was beautiful. I thought if I ever got divorced I could maybe meet her. We could read books. But at some point she would probably find out what a failure I was. How worthless I was to everyone around me. The real estate agent broke through my thinking, “the house even has a sump-pump. In case there is flooding.”

When I finally moved upstate it took two years until I stopped saying, “I live in NYC.” Then I would start saying, “I just moved up from NYC.” Even though it had been two years. The train to the city was 81 minutes. The windows looking from the train out onto the Hudson River would change like a slot machine while I stared, hoping I would get lucky just once.

I met with one investor to see if he could  put money into a new fund I was raising. Then we took a cab across town together.

“Aren’t you all hooked up,” he asked. “Can’t you call one of your Internet friends with $100 million to put money into this?”

I didn’t have an answer. He disappeared out of the cab when we got to his stop. It was raining. Gray. Dark. I was by myself in the back of the taxi.The driver was mumbling in another language into his phone.

Finally I answered, “I don’t have any friends.”

Years later, I lied again. I was meeting with Roger about some investments we were making together. He asked out of the blue, “So what’s going on? Everything good?” And I said, “yeah”. And he said, “Family good. Wife good?” And I said, “no issues”.

He knew I was going through a divorce but I didn’t want to say it and he didn’t want to say it. I felt shame about it. This was a moment when I was failing at about five things simultaneously and didn’t want to admit to any of them.

I went back to the Chelsea Hotel where I was staying. At around 1am the phone rang and woke me up. I didn’t pick it up. The girl I was dating said, “who is calling at one in the morning?” And I was afraid that I couldn’t answer. I had no idea. It could’ve been trouble to pick up. The phone rang nine times and stopped. She was upset, “who is calling??”  It was my birthday in 2009. I was too nervous to have a coherent answer so she packed up and left.

(R.I.P. Hotel Chelsea)

When she was gone I called downstairs and asked who called me. It turned out out to just be Timor from downstairs. He said, “you have to move tomorrow to another room. It’s day 30 and it’s a NYC law.”

“I thought you always break that law. That’s how we used to do it.”

“Yeah, not anymore.”

So the day after, I moved. My new “apartment” in the hotel didn’t have a door on the bathroom. But at night I could turn the lights out and see into the backs of the apartments on 22nd Street. A few times I thought I saw people that were naked but I was never sure. Just bodies moving around. Continuing their lives and routines while I sat in the dark and watched.

I got tired of being ashamed of things. I give up. I don’t want to be ashamed of anything anymore. Shame is not who I am. It’s just an ugly sweater I wear. Time to change sweaters. When I wear the same clothes too many days in a row, Claudia reminds me to change clothes. “You smell too much.”

Shame is one of those things that’s hard to change out of. We cling to it because it feeds something inside of us that we are afraid to give up. It feeds our perfectionism. It feeds out hypnotized visions of what success is. It’s a Halloween costume that we think looks better than our real self. But it doesn’t. It’s cheap plastic nylon whatever. Shame, and pretending to be perfect, limit our freedom but nobody taught us that in college.

And it oozes from the pores in our skin and the smell is unmistakable. Time to shower. Time to breathe in other smells. Time to be naked.

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What’s something in the past you’ve been ashamed of but were afraid to admit at that time?

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