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.

Follow me on Twitter. 

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

  • All I can say is wow. You’re such a talented writer James.

  • James, another great analogy, “shame is just a dirty sweater”. I get it.

  • Nikolas Baron

    cry me a river

  • Katherine Levine

    My favorite developmental guru, Jerome Kagan, says shame is what keeps us as two and three year olds from killing those smaller, younger and weaker who annoy us.  Important for the survival of younger siblings.  

    Sadly, as we grow other not so unthinkable things climb on the shame bus.  As you say when shame cloaks us, it may be time to change out of the shame garb.  That means assessing what really matters and making sure you are not doing the unthinkable. For me, relationships matter most and lies kill them.  I try not to lie.  Don’t always succeed. Difficult in a world  which seems to be feeding more and more on omissions, half-truths, distorted information.  Kudos for seeking a more honest way.  

  • Altucher you keep it super real.  Thing is, you’re denying to friends and associates and business partners what’s really going on, but here you’re letting it all hang out.  Impressive, man.  We’ve all been THERE, and we all need that shower now and then.

  • I’ve been ashamed of so many things. I wouldn’t even know where to start.

  • Capitalistic

    Amazing. How I can relate to the “t”.

  • Angelsin19

    i enjoy your honesty, James. It is refreshing and inspiring. We all do what we need to do or think they need… Always a gain to continue the pattern. It is time to take the shower and burn that sweater. ha ha.

  • I couldn’t stop reading. Mesmerizing, I could feel my face burning when you talked about the apartment. I’ve had my share of things I am/was ashamed of. Still don’t have the nerve to share with the internet. When I do, I’ll write it up and send you a link.

  • Capitalistic

    Amazing what makes us feel ashamed.
     I was ashamed when my first business failed.
     I was ashamed when my girlfriend and I broke up.
     I was ashamed when I was homeless.
     I feel ashamed when clients don’t want to pay for my services.
     I feel ashamed when investors refuse to invest in my fund.
    But then again, 
     nobody in Boston wanted to invest in Facebook,
     most investors say no,
     homeless people were not always homeless
     girlfriends come and go
     most billionaires failed at some point.

    Life’s great!

    • Great Comment, Capitalistic!

      • Sooz

        that sounds a little too ‘Zuckerish’ to me..:))

    • I wonder how animals view failure? Take for example a lion hunting its prey. I wonder what it’s odds are at coming home with the prize?

      I’m inclined to think 2 out of 5 attempts? With that in mind, it doesn’t stop it from NOT hunting, since its genetically programmed to hunt.

      Perhaps we can look to the animal kingdom for clues to success! Reverse engineer failure.

  • Fuck yeah! It’s time to be naked! Free balls all the way.

  • Ryma

    I’m ashamed of cheating on my ex-husband and divorcing him when he cheated on me… You are very bold to be so honest openly. I mean, Facebook and linkedin has recommendations but you know none is perfect, but these recommendations make u look like u are…

    • boo

      Those stupid recommendations are my least favorite thing about LinkedIn. Even the least competent person I know can dig up one or two former co-workers to say, “______ is just great!”

      • haha! yeah i never understood those recommendations either. Funny and silly feature if you ask me.

  • Dude, Incredible post!  I am proud to subscribe to your blog!

    **My Shame:  I used to not lie, but exaggerate details.  I realized every time I did this it left a little scar of shame inside me.   I am careful not to do that anymore.  

    Keep up the great work, James!

  • The shame paragraph at the end was the deepest insight I have read in a while.

  • Crshtime

    I’m ashamed when I do things to hurt myself…I’m ashamed when I say yes when I want to say no…

  • Maggie

    I often confuse shame and self-loathing. I am ashamed of hurting people physically and emotionally. I don’t know how to make amends for it but I have to choose how to live with it. It never goes away and it never should. I accept this and remain conscious of it everyday and try not to hurt anyone.

    I loath my failures. Before I came to the realization that I loath my failures, I usually had to deal with a myriad of other negative emotions and physical reactions. I don’t feel bad that I loath my failures. Loathing failure is natural. I try not to wallow in it.

  • linda buzogany

    Hey James,
    There are some of us who teach it in college….

  • okyr

    Your post is timely for me.  I’m full of shame and self-loathing at the moment.  I can’t get myself up off the floor to take that shower right now.  I’d rather just lay here curled up in a ball for now.

    • Maggie

      Be like most of these ubiquitous politicians and pundits. Do you think any of them get anywhere by wallowing in self-loathing. Loathing should be fleeting and momentary; then you focus on the pretty flower, putting one foot in front of the other, your breathing or whatever gives you the tiniest bit of joy or doesn’t make you sick. You’ll take that shower when you are ready.

      I’ve been in pain on a daily basis for 12 days now and I loath it. I consider it a personal failure. I didn’t shower for five days until all of a sudden I couldn’t stand the smell of my own body odor. I don’t hate myself. I wouldn’t hate someone else for this. I admit that I wouldn’t want to smell them but I never said that I am a saint. A lot of people are saintly or don’t have a keen sense of smell and can tolerate such things but I can’t.

  • Anonymous

    Thanks James.

  • I’m ashamed of using people for my own benefit and then discard them.

  • Capo Regime

    Glad you have shame.  Often disagree with what you post but you are fundamentally likeable.  Anybody with a sense of true shame is o.k. with me in this brazen shameless age.  Whole psychobable industries have developed in the usa to essentially make us shameless hedonists.  Sadly, our nation is led by shameless psychopaths.  Be glad you have the capacity for shame. 

  • Gonzalo Gandia

    I’m ashamed that I wasn’t true to myself and got married for the wrong reasons. I thought she was going to be a great life companion, but I wasn’t in love with her. And it took me 5 years to separate from her. Maybe the word is disappointed in myself, but there is definitely some shame in there somewhere…

    Nice post, looks like your practicing your “novel writing skills”…

  • I’m still ashamed of countless things.  

  • Rachel

    I was at that party and I remember being in awe of your amazing loft and your seemingly amazing life. And you were a pretty nice guy then too, whether you remember yourself that way or not, so I was glad for you.

    As for shame…five years ago when we were trying to have kids and it was just miscarriage after miscarriage, all I saw was pregnant women wherever I went. They were everywhere, happy and smiling and rubbing their giant bellies. And I hated them for it. I hated them for having what I wanted more than anything and was terrified I’d never get. I had several close friends and relatives who were having babies at the time and I could barely stand to look at them because of the jealousy I felt. I hated myself for it and I have never been so ashamed of anything in my life, now or then.

    Several years and two kids later I realize many of those women probably went through the very same thing. But then, you never know anyone’s life story and appearances can be so deceiving;-)

    I smile at every pregnant woman I see now and it always makes me want to cry remembering how I used to feel and feeling so grateful that I can feel happiness for a perfect stranger.

    • boo

      Rachel, thanks for this comment–my husband and I are going through fertility stuff and it helps to know that someone else has been there, and that whether we have kids or not, some day this awful feeling will be behind me.

      • Rachel

        Oh boo, I am so sorry you are going through this. It so hard and it’s like a sucker punch because infertility and pregnancy loss are so taboo that no one talks about it so you are astonished when it happens to you. I remember feeling like a horrible person because seeing pregnant women and babies made me horribly sad so if you ever feel Ike that please know that many if not most other women who experience the same thing feel the same whether they will say so openly or not. I hope that you have the same good fortune we had and that you are smiling at other pregnant women everywhere you go very soon:)

  • KB

    I wrote a 200 page book about shameful things I’d been through.  I don’t sell that one though.  I really should, thanks for making me think of that option.  The self pubbed fidlar doubleday copies have just collected dust for 7 years.  Maybe time to dust them off – again, thanks.

  • PC

    If I read this correctly, the things you are describing as shameful all have to do with a loss of wealth and perceived stature. Other than the low grade lies you describe, where’s the moral break down! This makes me think the shame comes from something else, maybe the family hardships caused by your bankruptcy. Maybe the stress caused you to act like an asshole and mistreat others and yourself. Id guess alcohol, weed, porn, massages or other stuff all come into play.

    James, I do not judge; you are on a rightous path. You are helping others. I’ve done many regrettful and rotten things. Know that you have guys behind you who are carrying the same load of shit around and that we are wiser today.

  • Steve Morgan

    regrets, I got a few

    • Jeff Fox

      but then again, too few to mention

  • I’m ashamed of my irrational fears and how they rule my world sometimes.

  • 1928

    I gave this some thought James and I’m not really ashamed of anything. Sure, I made some serious mistakes but that’s in the past. Shame is a feeling from something that already happened, give zero thought to the past because it’s irrelevant. 

  • Capo Regime

    Altucher–you have to use this!  It bolsters your case in myriad ways!   Not to make a megilah out of it but :http://www.oftwominds.com/blogmar12/pretend-student-loans3-12.html

  • Anonymous

    I feel shameful that I have yet to break out of my gainful employment rut despite two decades of trying and failing

  • Andrew

    I was ashamed, depressed and lived in my car for a summer because I couldn’t get my shit together. I was ashamed because I was too nervous to approach women. I was ashamed when I couldn’t make far payments and the bank repossessed it. I was ashamed when I got fired from a good job for something I wrote on my blog. I’m not ashamed any more.

  • Everyone, close your eyes and take ten good, long deep breaths.

    In through your nose and out your mouth.

    Inflate your belly on the inhale, deflate on the exhale.

    Take your time, a minute and a half to get through all ten.


  • florin

    it is exactly what I’ve need to read right now.
    the univers works.
    the shame it is an horrible prison, taught by the system from early age.  it keeps us from growing, from trying, from moving. we lose to much time inside a horrible situation just because we are afraid of hitting the wall of shame. an immaterial and illusionary wall, through we can walk and in the other side start looking for light.
    is a inside construction that leaks too much energy, stop us too much from being ourselves. is worthless. and is not so bad after all.
    we have to forge our live not their live protected by the chains of shame.

  • Dave Walsh

    Hi James. 
    Great piece, as always. Reading the comments makes it obvious why shame strikes such a violently loud chord with people. Want to know why? Watch this fantastic TED talk by Dr Brené Brown http://www.youtube.com/watch?v=X4Qm9cGRub0&feature=player_embedded. Seen it before? Watch it again!Keep writingDave

  • Anonymous
  • Understandable

    Great post.  Your shame and lying to people were a predictable reaction to your terible personal tragedies at the time.  Both were due to your mind not wanting to accept the obvious change in reality.  Given both things were life traumas, it is certainly understandable.

    You were a Master of the Universe.  Then you weren’t.  Then you found out it didn’t matter.

    (Good advice for those caught in the Wall St rat race!)

  • Rick

    Once I was a huge jerk, lost my friends, and sort of ran away from them for years b/c I figured my former friends didn’t even want to hear an apology.  It hurt my friends really badly, and I underestimated their charity.  I snapped, unfortunately, and I don’t think I can ever really make it up to them, except maybe in purgatory (I believe in that.)  Add to that a huge amount of confusion, and you’ve got a recipe for a lot of problems. 

    Sometimes, you want to make up for things you’ve done so badly, but you’re almost powerless, particularly when you’ve been as confused as I’ve been. 

  • I love you James. I mean it in a manly fashion. 
    Granted that I barely know the real you and you certainly don’t know me at all, what you’re sharing is incredibly profound and usually hits me right where it should.

    Still I’m going to go ahead and disagree on this one big time.

    Shame is the janitor of our consciousness.
    Shame is not pretending to be perfect, it’s reminding we’ve lost our way, our pride or honor.

    There’s a pride in having big balls like you do. Some others would feel ashamed. 
    There’s a pride in being able to survive living in the worst NYC projects. Some others would feel ashamed.
    There’s a pride in being a gangster. Some others would feel ashamed.
    There’s a pride in being black, Jewish, Gay or being Rush Limbaugh. Some others would feel ashamed.

    We may be already naked, as Steve Jobs also said, but that doesn’t mean we should loose our values. Shame is misplaced only when our values are misplaced. 

    At the end of the day, just being yourself is what we need to be. And Indeed we’re not perfect, so there’s no reason to be ashamed of being ashamed.

  • One of the most liberating ways to confront your shame is to publicly admit your struggles and your shame for failing. I found that when I’m honest about the reality of my situation it helps me cope. Failure = success over time. I wrote an article about it here http://www.divinebrew.com/trend/when-the-walls-cave-in-turn-on-your-beer-jets/

  • Grandiosity causes misery. One of my parents has narcissistic personality disorder. I read a great book that said their kids frequently pick up the grandiosity trait. “The Wizard of Oz and Other Narcissists”.  

  • Clover Fields

    Shame is a tricky one.  Disappointment in myself, sure, but shame?

    I felt shame as a child over stupid things adults subjected me to that I had no control over at the time. 

    Like one time as a kid my mother took me to the pediatrician for a checkup.  I can’t remember how old I was, but I was starting to develop breasts.  No one knew because you couldn’t tell unless I had my shirt off.  The nurse told me to disrobe and hop on the table and the doctor would be right in.  She walks out and leaves the door open.  My mom is out in the waiting room.

    I’m sitting there on the table with my top off, and there’s people walking up and down the hallway who can see into the room and they are looking at me as they walk by.  I was so embarrassed and ashamed and angry….so angry because I didn’t know what to do.  Up until that point I had always done what I was told by grown-ups.  I was probably 12 maybe, 7th grade?

    I was frozen and there were no gowns in the room and it didn’t occur to me to put my shirt back on.   The doctor walks by the room and sees me sitting there with my boobs out and an embarrassed look on my face, and he immediately tells one of the nurses to get me a gown to put on.

    From that point on I knew adults were morons with poor judgment, and that I had to think for myself and try to be smart about things to prevent any future shame originating from anyone else’s bad judgment.  That’s not a lesson that needs repeating. 

    I’ve made my share of mistakes, but because of that incident I always correlate shame as something not of my own doing.  (i can’t believe i just told you that story…)

  • pogo

    Perfectly written, James.  I identified with you on so many points and so many levels.  We all go through this at one time or another.  I’m a very senior executive and have been fired from a couple of jobs.  Not easy and you conveniently conceal the facts from friends and family.  I’ve learned to try to limit my highs and lows, just to preserve my sanity.

  • Laura G.

    Raw and beautiful.

  • Brian H

    One more thing to be ashamed of. In your “Self-publishing” screed you wrote:
    “or creatuve purposes”.
    You can’t possibly be a writer and commit malorthography like that. 

    • Are you trying to show everyone how smart you are because you can nitpick a successful guy who hit the “u” key instead of the “i” key that he was aiming for?

      Honestly.  What’s the point of your comment?

      • linda b.

        My thoughts exactly Andrew. Thanks for saying it.  Misses the substance of that whole piece,  which is going to change my life,by the way.