Sometimes Things Just Keep Getting Worse

When things just keep getting worse, I tried turning to a psychic

Around the summer of 2000 I lost a lot of money. About a million dollars a week in cash. This may seem like, “ok, at least he had that money and he must’ve stopped before he went to zero.” But i went to zero. And the worst part is finding the strength to continue going. Staring at the screen, mumbling about fate, all of those stupid decisions, suddenly all the cruelty and malice in the world that had been storing up just for me was unleashed for the first time in my thirty years of life and it wouldn’t let me go.

I went from having more money than I knew what to do with to having zero. I could’ve given money to charity. I could’ve set up my kids for life. I could’ve used the money to help my father when he was sick. I could’ve saved his life.  I could’ve saved my life.

I could’ve saved myself from losing my apartment. I could’ve saved myself from so many sleepless nights. I never slept. At most, two hours in a stretch. And I would drink every night. I would sit snug in this giant couch inside this giant apartment in the dark thinking, “how stupid was I? I made money when it was easy and then I lost it all. Now I’m never going to make it back again and my kids and everyone else around me will suffer. I’ve done bad things to people and this was karma. I’ve squandered all the good will I created as a kid.”

I honestly thought that the success I had was generated as a combination of luck and because I spent many years meditating as a kid. I thought that I had built up some karmic warchest and I used it to generate enough money to dominate the world and then I squandered it. Now I was gone. But I couldn’t kill myself because I had two kids to pay for. I had to make sure they were ok.

I went to therapists, astrologers, psychics, zen teachers, zen therapists. One psychic said I needed to find a coconut TODAY and smash into the street. At 10pm one night I decided to do it. I had two problems:  where to get the coconut at 10Pm and how to find an empty street in Manhattan to smash it.

If things just keep getting worse, I turn to psychic readers

I went out and around the corner where there was a Thai restaurant. I figured they must have a coconut. They didn’t really understand me. Finally one waiter did. He started speaking in Thai to a woman who I assumed was his mother. “No coconut,” she said, but she wrote down an address where I could find one.

Behind me, “James, what are you doing here?”

It was Flash. I had been playing chess with him for 15 years in Washington Square Park. I didn’t know this but apparently at night the entire Washington Square Park crowd moved to this Thai restaurant on the corner of Reade and Church, a few blocks from the World Trade Center. Flash owed me money but I knew I would never collect it.

Instead I played chess for a few hours. JP was there also. “Why are you out right now?” I said, “I have to find a coconut and smash it into the street.” He laughed and said, “I knew it. There must be a woman involved.” And we all laughed and played chess. A small respite for me in a five year period of non-stop pain and agony.

Then I went to the address the woman gave me. It was a basement store in the lower east side that was still open at 11pm. I told them I needed a coconut. A guy came back with this hairy round brown thing. I bought it. Then I wandered up and down Washington Street until I was sure nobody was looking. I threw down the coconut as hard as I could. It smashed everywhere, the milk splattering my pants and everything around.

Things are going to change now, I thought. Sort of like that line from the Beck song, “Loser”: “things are going to change. I can feel it.”

When things just kept getting worse, I felt like Loser from Beck

(Beck, in the “Loser” video)

Things did change. I lost my job as a venture capitalist. That job was at least paying my mortgage. I got kicked off the board of a company I started. Selling that company was my last hope. I was too demoralized to stop it or to start anything new. I would lie around, unable to get myself back up and start generating new ideas.

I tried to get a loan. Nobody would lend to me. Not even when I paraded two little babies to the bank. Banks have rules, you know. No lending to degenerates. At least not yet. That was years later when banks would lend to anyone.

Every month I’d go to the ATM machine and I’d have this feeling like someone was stabbing me all over my body and mind when I looked at how much was left in the account. I’d yell at my now ex-wife as if it were her fault, “How are we supposed to live on this. We are GOING TO ZERO!”

And because I kept saying it over and over, the reality was created and we did go to zero. “The Law of Attraction” works in reverse much more than it works in a positive way.

Then 9/11 happened. I hate talking about 9/11. So many people had it far worse than me on that day. Far, far, worse. I was standing on Church street when the first plane flew overhead. Dan said to me, “Is the President coming into town today?” because the plane was so low. It was right over us. Even though it was actually about 600 feet higher, everyone on the street felt they had to duck because we had never seen a plane that low coming in so fast and we all watched it go into the building.

After that there was no way I could sell my apartment, with the mortgage each month that was crushing me. The week after 9/11 I decided to be brave and buy the stock market as it opened. This is how I went to zero. I lost basically whatever I had left. I finally couldn’t take it anymore. On Friday of that week at around 10:30 I had to sell everything. I was screaming at my broker on the phone, “I’m going to go broke!” And he sold whatever I had left. Scraps that I knew I could use to pay my mortgage a few months more. Starting around a minute later the stock market went on a run upwards that lasted at least three months. If I had held on for at least 5 more hours I would’ve doubled my money on the week. If I had held on for 3 more months I would’ve had more money than ever. Instead I was broke.

It took another year to sell.  I started missing payments. I couldn’t afford diapers. I got shit all over my head.

Nobody would return my calls. I asked my neighbor if a bank or a hedge fund would hire me. He said, “typically you have to have a track record that’s good.” And I was too ashamed to ask him more. I actually had no skills I could think of that could pay my expenses. Dot-com entrepreneurs were a dime a dozen and everyone was broke after the bust. No bankers or VCs would return my phone calls. There was nobody for me to sue. It was all my fault and I’m not a litigious person anyway.

One time I called my parents. I needed to borrow $1000. That’s all. After having millions. It was 14 months after 9/11. I finally had sold my place but the deal had not yet closed and I had no money. I needed money to move. To live.

They began to yell at me. They didn’t want to lend me the money. I hung up the phone. I didn’t talk to them for six months. Then my dad had a stroke and that’s the next time I talked to them, although he never woke up from his stroke again. So the last time I spoke to him I had hung up on him.

Everyone says that “things cycle” or “what goes down, goes up.” But that’s not true. My dad was in his stroke-coma for three years. He never got better. He got steadily worse and worse. They would drop his body on the floor when moving him from one institution to the next. He had bed sores so bad you could see through to the skeleton. My family thought  I didn’t visit him enough. But I was scared and didn’t want to be even more depressed and I had my own two kids to take care of.

I stayed in my new house all the time, about sixty miles north of the city. I gained about 20 lbs because I was no longer pacing the streets of Manhattan at all hours of the night and there was blizzard after blizzard where I lived. I was in exile and I had no idea what would happen. For the first year after I moved into town I didn’t speak with anyone. I didn’t want to. This was only temporary, I thought.


The worst part was trying to find the strength to continue. So my projects turned to zero. What was the point. Day after day. All the music I had danced to just a few years earlier was now silenced. The jukebox was broken. The dance hall was closed. Every night I woke up in dread, terrified of yet one more insecure tomorrow. I wasn’t even brave enough to kill myself. And the truth was only leading me closer to a death agony. The agony that youth was gone, and for the rest of my tomorrows I was finished, through, crushed by my responsibilities and the carved out hole of loss inside of me.

I went into one store and asked the woman behind the counter, “is it just me or does the entire world seem like it’s depressed, as if people can’t shake the utter sadness of just being alive.” She looked at me and said, “do you know anything about computers? I can’t get my computer to work.”

A close relative of mine wrote me, “You weren’t even as good as your father. He never would’ve lost a house that his children loved and been such a disappointment  like you were.”  The few times I would venture into the city I couldn’t think of a single friend or family member I could call that I could spend time with and who would want to see me and we’d all be happy and just enjoy. I had nothing and nobody. And I’m not blaming them. It was all my fault.

I’m still afraid of slipping back into that crevice. The Earth shakes every few years. 2008, for instance. Cracks in the Earth open. Bridges that were secure for 50 years break and cars fall into the water. Once you’ve seen the darkness in the center of the Earth, the heat that can burn your brain to cinders, you know it’s always there, an open invitation to come back to it. I knew too much, but not enough to ever come back. Once the bridge cracks, the car is already doomed.

a car falling off a broken bridge makes it seem like things keep getting worse

I can tell you it all came back. I can say, “that’s why I’m writing this blog.” I can say, “don’t worry, things do cycle if you picture it and let it.” But things don’t always come back. Sometimes things get worse and worse. I’ve written before about the only thing you can do to start turning the cycle around.

But the important thing is that right around the middle of all of this, I started planting seeds. The abominable pressure of being forced to live, forced me to plant tiny seeds. Life goes on, the future is a joke, but we can never forget it exists and its hungry and it’s waiting to eat and destroy us so we must have food to give it.  I was planting a garden. You pull up weeds. You dig out the dirt. You put seeds in, you lay excrement over it. Some plants get eaten up by ravenous birds. But some seeds are left alone and, if cared for, are allowed to blossom. That’s why I’m still alive. Because of the seeds planted. In retrospect I wish I had planted more of them but it’s ok.

I planted new seeds every day. I still do.

Maybe I can also lie to myself and say  I am a better person for having been through things. Maybe I came through the other side and there was more light on this side than the side I started on. I don’t know. I hope so. Some seeds I planted ten years ago are still growing. Still need to be harvested.

The key is to plant the seeds. And never stop, even if weather, even if animals, even if mutations, look as if they are going to damage the garden and destroy it. Seeds take time to grow. A long time. And they need to be loved with patience, just like children. And there are seeds designed for every season. The key is to go out there, dig up dirt, and plant. Every day.

You don’t know what the final outcome might be. What the DNA of each seed holds for your garden. But over time, over years, over a lifetime, the garden turns lush – there are colors, there is food to eat, there are perennials that, like old friends, always return every year when the cold is over. You can never ever stop planting the seeds. Every day. Eventually there is a thick patch of joy where there was once nothing but dirt, weeds, and mud.

And you can look at it and finally say, “this is me. I did this.”

When things keep getting worse, plant seeds to grow your garden

What seed will you plant today?




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  • Priscilla B.

    I can relate to the general idea of this and even though I know “it” to be true, much thanks to you reminding me.

  • Sandy

    My word, did you hack my email to write this. So many, many similarities. I appreciate your authenticity and vulnerability. Grateful. 

  • Parvaze

    Honest. Brilliant. True.

  • Great, great post James – thank you! I love the inspiration and insinuation that we all are our own pilots in life. Refreshing! Thank you. “Life is full of misery and disappointment. And it all ends much too soon.” -Woody Allen  

  • Carmen

    Yup, I totally believe in this way of thinking and living.   I keep your 4 easy steps bookmarked as a reminder.   Planting seeds takes practice.   My garden needs work, and sometimes I plant the wrong seeds.  Live and learn.

  • Anonymous

    James- do you recall if there was a specific thought, or event, that turned your attitude around while at rock bottom; that you knew it might somehow all come back?  -JB

    • I would be interested to hear this as well although I have an idea of what the answer might be from what I’ve read.  It’s seems like things got better really slowly and piece by piece you started to get back to where you were.  Positive actions gave a glimmer of positive results which gave you a reason to believe that things weren’t quite as horrible as you thought.  That cycle brought you back one small step at a time. 

      That’s how it’s worked for me as I’ve focused more on every day and used a lot of your daily practice.  I’ve never had a real ‘aha’ moment but I almost can’t comprehend why things are so much better for me now.

      • Anonymous

        Thanks for the comments Brent.  I agree with what you have said.

        The financial crisis of 2008/09 caused me tremendous pain, both emotionally and financially, but I am grateful for it in some weird way.  It made me take a step back and re-evaluate my life and career and get my priorities in order.  And because of that I feel I am a better person. 

        This year I have made more money while working less, spent more time with my family, and have been more happy in general.  (And this all happened prior to stumbling upon James’ site!)

        I can honestly say that in looking back- I guess it wasn’t all that bad.  Sometimes you need to take two steps back to continue on forward.

        Carpe diem.

  • Anonymous

    James, what draws me to this blog is the number of parallels I can draw between my story and your story. Of course, my experience is at a much-much smaller scale:  I do not have (and never have had) as much as you and I have never moved in the rarified atmosphere that you have, but for some reason I can relate. I have a CS degree (btw, I’ve read your 1990 CADE paper and the parallel does not stop there: I’m in formal verification as well, for no fault of my own I might add), I have two daughters, I have problems networking, I have gradually slumped into a state of complete despondency.
    My “career” has been sinking slowly for the past two years and the funding for my position had only two months to go, other people were moving ahead of me, when suddenly, this last week two unexpected events have completely turned around the gloomy outlook. All this while I was reading your posts. Even before the turnaround, while reading your essays, I suddenly felt I that I can snap out of the despondent state I felt I was trapped in, even though nothing bright was yet at the horizon. It happened simply by realizing that I am not alone, I am not an exception, I am not a monster. And I have to thank your writings for that (NB: I am using your advice on being grateful).

  • I hate that I relate to this post so well.

    Doesn’t mean I don’t appreciate it though.


    • Sooz

      I look forward to your Christmas letter this year..
      miss your guest posts, DT.

  • James, this just might be the best thing you’ve written on this superb blog. 
    Thank you.

  • Canadian Reader

    Awesome post James…..I was just sitting here – no plan for the day – you shook me out of my malaise – I need to focus and get back to being productive and go planting.  Clearly – I havent’t planted enough because today there is nothing to harvest.  Best go back to planting.  Thank you.

  • just doing time

    James, I think you are the most honest voice on the internet. (At least of the relatively tiny amount I see).  That is quite an accomplishment. I admire you and listen to you, and I am grateful as hell for your presence. Thank you. 

  • The planting of seeds allegory is apropos, but it seems as if you’d been doing that all along.

    Especially the critical part about rotating your crops. Without re-inventing yourself on some kind of a regular basis you deplete your creativity. Maybe external events cause the rise and fall, but each time something new and different arose.

    Very little continues forever. The challenges shape us and prepare us for new adventures.

    Unfortunately, we’re prone to exercise hindsight.

    I have a number of friends that have had similar personal experiences with a one time loved one and they’ll never have the opportunity to revisit their relationships.

    The ones who think about the lost opportunity are the ones that do best in life, in that they cultivate their exisitng relationships to minimize the chance that estrangement will ever enter their lives again.

    Seems to me that you fit into the thoughtful category and are busily cultivating your relationships as you explore the past to help create a new and different future.

  • Jouko Salonen

    thank you. been there.

  • caveman1

    I believe humans are one of the only things on earth that are BETTER after they’ve been broken and repaired.

  • Excellent post as always, I can relate to this too well.

  • Ran

    James, thanks for your post. i thought i was in bad shape for the past two months, but after i read this post. everything i was worry or mad about become so childish compare to yours. i been follow your blog for over a year and bought two of your books. i learned so much from you than all the time i spend in college. thanks you

  • Marc Hansen

    We’re on the same page. Hard lesson to learn is that things can get better but we have to make the effort.

  • David Horwitz

    thanks very much for writing this.  i can relate and it is helpful to read about how you’ve dealt with bad decisions, going to the edge, regret and then pulling yourself back in a positive way from a very dark place.  

  • Smartaldishopper

    Love to read you James, but can you lay off the WTC photos?

  • My mind is racing, yet I am speachless after reading this.  I know that I will post and forward this timely piece.  Thank you, James.

  • pjcpjc

    I like reading Jame’s posts on this period of his life. 

    I had a similar experience to this (albeit at around 1/10th the scale). Quickly acquiring money and quickly setting it on fire is a very tough experience, and people who haven’t done it can’t relate.

    Somehow its more painful than not having had the money at all. 

    What makes James’ story incredible is how much he lost, and how fully he recovered. I honestly don’t think I could handle the experience James had. 

    A friend of a friend committed suicide recently. He was a hedge fund manager who got on the wrong side of some trades. I don’t think he lost his house, but he lost millions, and just couldn’t handle it.  

    I think if he had talked to James perhaps it wouldn’t have happened. A shrink, with his “diploma to print money” on the wall, can’t really relate to people who ride the roller coaster.

    Everyone loses at some point, and it’s painful, no matter where you are on the ladder. 

    Keep blogging James.

    • Anonymous


      thanks again for your honesty. I have been more vigilant of using my difficulties to cultivate the mind of transforming the difficulty as a means of understanding that my actions contributed to this effect. My present and future behavior will contribute to better future states of mind. I wish you only great days!

  • I can relate, to the missed mortgage payments, the family that turns their back on you and the siblings that don’t speak to you, and of coarse the over-all feeling of dread. 

    I have been planting seeds as best I can, as I scrape my broken spirit up off the pavement, I’d say I am 60% right now, kind of a down day, maybe only 50%.

    So I decided to plant some seeds of encouragement for someone else, in hopes that it might bring some monetary relief to her non-profit, a non-kill rescue for Siberian Huskies. 

    It’s a S.H.E.L.L. fund

  • Today we have too many buffers that cushion the blow when we hit bottom. 

    Sounds like you hit with a good, old-fashioned thud.  That thud forced a change.  There was no other option.

    Too many of us are able to limp along in our relative miserableness, never really thudding and never really changing.  

  • cindyluwho

    Once again Brilliant!!! Also very timely and just what I needed to read to help keep a positive attitiude as I head into yet another week of job hunting/trying to be creative and do my own thing.

    Many Thanks.

  • Wow

  • Lori

    You know your dad would probably regret that conversation as much as you do. He’d think, if I knew that was the last time I’d speak to my son, I would have told him, you can have a thousand bucks, you can have everything, you can have the shirt off my back, I love you, I’m proud of you, you’ll be okay.

  • Jquick99

    ** This is from my blog written on Dec 2nd.  Sorry it’s so long. **

    I had forgotten today’s date.  I had NO clue.  Then, as I read my RSS feed first thing this  morning, there it was, my reminder that 10 years ago today, Enron filed for  Chapter 11 bankruptcy.

    For the first year, year and a half, I was consumed with  woulda, shoulda, coulda.  Why did I put  every extra penny I had into Enron stock?

    Why did I choose to get my yearly bonus in Enron stock?  Why didn’t I diversify?  Why didn’t I sell some options and pay off my house?  Or buy a fancy car…at least I’ve  have someone out of the deal?

    I met with a Merrill Lynch financial advisor 9 months before  the Chapter 11 filing and he begged me to diversify into Merrill Lynch funds. I  asked him what they had as Enron’s 12 month target price.  Up 60% of where it was now.  So…where else can I put my money and make  60%?
    Famous last words?

    As I mentioned above, the first 12 – 18 months were tough  emotionally.  I came from poverty, put  myself thru university 100%, lived simply, and was expecting to early retire  around the age of 42.  My life was beyond  a dream or fantasy that I could ever have imagined.  I was the American Dream.

    And then the money was all gone.

    However, I never got laid off…so I had a nice income coming  in.  Even though going into that office  was dreadful every day.

    And I had my health.  NOT something a 40 yo thinks about, except that my uncle found out he  had cancer in October of that year, and passed in January.

    I cut myself off from most of my friends who worked at Enron  because when I got together with them, all they wanted to do was whine, complain, talk about unfairness and how they’d been done wrong.  I was doing enough of that on my own [except I  took responsibility for NOT diversifying…it was my own fault for NOT knowing better], so meeting up with them wasn’t fun.

    Cut to Spring of 2008.

    I went back to Houston for 4 months to visit with people I hadn’t seen  in 6+ years.  And what did I find  out?  They everyone I met with – and we  are talking 30 or so people – they were all doing “better” than when they were  working at Enron.  Someone who bounced around from one back office job to another was now a VP.  An assistant was now the assistant to one of  the wealthiest men in Houston.  Someone who  really wanted to get married and have kids, but was working wayy too much at Enron,  was forced to slow down and found her Mr. Wonderful and had a couple kids.  Someone who was miserable trading, was now a  school teacher and couldn’t believe how fulfilling teaching was.  People started their own companies, had  freedom to choose the work they wanted to do and were making vastly more than before.  The stories go on and on…

    This horrible life changer of being let go and/or losing your money was actually a blessing for everyone I talked to.

    Now THAT should be the headline.

    • Lori

      love this story. thank you.

  • Sooz

    ohhhhh…so good!~!!!!

    thanks ,J.A.

  • Adam Angel

    Holy shit!  That was one eloquent and honest piece of writing!  I love your stuff James, but this was on a totally different level.  Back in those dot com days, I turned 20K into 400K which was more money than I ever had in my life.  I bought myself a Porsche 911 and thought I was unstoppable forever.  That I was some kind of stock picking wunderkind (everybody makes money when the marketing is skyrocketing everyday). Little did I know that just 6 months later, I would lose all of it and more.  I’m still reeling from that time period, but your post makes me feel more hopeful.

  • Thank you for investing after 9/11. Patriotic and brave, also very selfless. 

  • Anonymous

    dude, the fact that you didn’t go on a shooting spree @ the closest Duane Reade is testament to your not being a total piece of sh*t. These posts are my favorite b/c these are real stories about the real curve balls in life… Everybody can’t be happy and everything can’t be fine all the time and the misery you describe is the norm for so many ppl but the attitude you have about it is different. That’s what I try to take from your posts most… your attitude.
     I know people who had less there fore lost less and they lose it and wind up hurting some one over some material thing that’s never ever worth it.. they think it can’t ever get better and they’re right because they can never get over anything b/c they never take responsibility for misfortune so they do things to make it worse and worse not purposely but it’s a subliminal self destruction message called “attitude”… if that makes any sense…. thanks for posting J.

  • Really beautiful and inspiring. Sometimes it’s all about taking small steps and letting them snowball. Can’t wait for your talk on Wednesday!

  • James,

    Once again a tale that borders on inspiration and such an honest account of struggle. I know this feeling, and when I read your descriptions of your own struggle, I feel it. It is such a personal thing, how we begin to rise from the defeat, and I am a follower of your blog because of your candor.

  • Brianstacync

    hey dude, we are tired of hearing your belly aching about the past.  I am sure your wife is also.  A whiney little man does not create attraction for his wife.  Get a grip or you are going to lose her too. Enough already.

  • Gina

    Hello. I get comfort from reading your posts on coping with the “abominable pressure of being forced to live.” I would love a post on how you and Claudia cooperate to bring some lightness to living. My husband and I are ridiculously sensitive to every small, medium, and large responsibility. Since I am more half-full, my job is to keep us on course in the optimistic yellow life-boat. His job is to pull me in if I fall out. He gets to those knots in my back just like Claudia… which is a testament to how insanely strong she is!

    I am panicky from recent major life changes that ended long-time hopelessness. Our lives are now full of so much potential, but it is so much work and we are both dog-tired. Is there a fast growing seed (mini daily practice) that you use when the motivation is gone for a day or longer? (something akin to how the astronaut shrinks get them to do a little something so that they feel good about their efforts )  

    Also, are you going to do a post on examples of the seeds and their blooms? I am a little unsure of what those might be after reading your “Lost” post:

  • I always go through depression all the time – but it has never been this bad.  This post makes me realize that a worse condition can exist than the hopelessness that I sometimes feel.  Thank you for sharing your story.  

  • Kevin Faul

    WOW James. Stellar post.

  • mike

    you look so stable at first glance James, i think for everyone here its very inspiring to see you are just a human being like the rest of us. When most people look at anyone who has had over 10 million in the bank(just an example) you almost appear as a super hero… the world at your hands…. you did it, your safe now no matter what but you know first hand its not true.

    Having crazy thoughts that you are a loser, family looking down on you, which in turn you start questioning are they right? Should i just have stayed at my job? Am i a fucking loser after all? Then you go through the rough phase and disappear from everyone, wondering if its easier to just be dead, but you eventually stop acting like a baby, stop complaining and realize ” i made the first knot of money by being a man and doing what other people were not willing to do” and you eventually repeat your old process.

    Great post James.

  • Chuck

    Thanks again James.  I am proud of you.  You are a really good guy.

  • DD

    Where I come from, they say that worst curse you could make on someone is “I wish you get it all, and then lose it”… As in, it is wost to have it and then lose it all, then never have it at all.

    Still, after living through the longest urban siege (Sarajevo in the 90’s), without water, heat, electricity for 3+ years, eating dandelions to survive and being shot at by snipers and shelled by tanks, I can tell you, it can get much, much worse. Yet, even that pails in comparison with THE worst thing that can happen:

    Being a parent and watching your children go through the war IS the worst thing that can happen to a human being. Knowing that your decisions led you to be in the position where your children are starving, freezing and being shot at, is THE WORST thing that can ever happen. My parents and many others lived through that, and I am sure many are going through that now in other parts of the world.

    Because of this, I promised to myself that if I am alive when war ends, I am moving to (what I consider) most peaceful country in the world – Canada. I left everything behind (businesses, houses, jobs and friends) and moved with my entire family of 5 to Canada with $50 in our pockets and 2 suitcases.

    Funny thing is – when you hit the bottom of the Hell like we did, every new day is like a gift. Even though I had to ride my bike 20 miles daily to a $6.85 per hour job as plumber’s helper, it took me years to stop grinning like a fool – some days I could not breathe how happy I was to have a chance at life again.

    Even today, when I have a tough day at my work, or when someone crashes into my car in the parking lot, all I have to do is ask myself – what is worst that can happen. I remember what the Hell looks like, and by comparison, my current problems become this tiny nuisance. Within seconds, I take a deep breath and smile reappears on my face.

    • Adam Angel

      Thanks for sharing that. Your story just made me realize how small my problems are and that I need to have more gratitude.  Keep smiling in Canada!

    • Brankoz

      I am from Croatia and I know how you felt. Good luck to you pal.


    • Frishack

      This is why I love my country. Canada loves honest hardworking amazing people like yourself. Welcome to Canada my friend.

    • Redflag

       Canada all the way!

    • Hugh Lancaster

      Awesome post! One of the secrets of happiness is just being grateful. You don’t have to look far to find someone who really has it worst than you. It changes your outlook!

  • Roy

    I cant decide if by plating seeds you mean actual seeds or you are being metaphorical…i guess both 

  • Penny

    Wow! A really great post. Thank you for writing it!

     I have always wanted to hear this part of your story.  I kept thinking, What would a classical analyst make of this story?  Don’t all gamblers want to lose because they are masochists?   I think it sounds simplistic but maybe there’s a shred of truth to it.  You couldn’t be rich because that would equate with killing your father (by surpassing him).Another part of me thinks, Hey – he was just a young kid who made too much money too fast to know how to handle it.  Money is after all a form of energy and getting too much energy before one has built up a strong container ( self image)  to hold it in just causes the whole thing to implode.And a third part of me thinks:  That could have been me.  Although I was safely on the sidelines by 2000 in T-bills and notes, I never ever could have predicted how bad things were to get.  I remember watching Cisco – darling Cisco – and thinking this thing can’t go down any lower.  And it did.  But unless you had already witnessed a really horrendous bear market before how could you possibly believe that  it would get as bad as it finally did?

    I think of you as a big success for having the guts to hang on and fight back for your kids.

  • Wow!! Saying anything else will just remove energy from this post!!

  • Anonymous

    A tad late but maybe explains your behavior in those last desperate days..

  • I wish you would one day write what exactly you bought with your millions.

  • Everyone loves a comeback, but no one loves you when you are down and out.

    • Vlad Daemon

      Pretty sure

  • murali

    Absolutely top-notch post, JA.


  • Loved it, James! Thanks.  You have become my new benchmark for declaring a bad day.

  • Anonymous

    Thank you for this line…”there are perennials that, like old friends, always return every year when the cold is over.”
    Great post.
    I am getting ready to be fired for possibly the first time in my life, just as I am beginning to start my own business. That line, for whatever reason, gives me comfort.

  • Jami Stout

    I have a hard time imagining you like this..

  • Susan

    Having been away from your blog for a few days, I thought I would check in. Excuse my profanity, but this is the best fucking thing you have written.

  • James,

    Thank you.. That is amazing.

  • “He planted lots of seeds. They’re still coming up and will for as long as we’re alive”. That’s a pretty good epitaph for anyone – or high praise for those still living.

  • Settembrini

    Here’s a book I read a month ago that I thought would be of interest to James and his readers: Super Consciousness by Colin Wilson. Amazon describes it: History is laced with examples of individuals who have experienced states of
    powerfully heightened awareness. Known as Peak Experiences (PEs), these periods
    of extreme mental, emotional, and creative invigoration have often resulted in
    great achievements. Bestselling author Colin Wilson has long pursued the nature
    of PEs, and here are the results of his 40-year investigation. Through a wealth
    of engaging anecdotes, he reveals how the PEs of such historical figures as
    Yeats, Blake, and Sartre, among others, influenced their work

  • Bparrish2

    @James, I’m curious, though it’s none of my business, but did your family come around after you remade your bank account?

  • Great post, one of the best in a while!

  • Though I’ve never been a VC, I can truly relate to your emotions. My family has been struggling ever since I started two different businesses. We’re doing it because it’s our passion, and to get us ahead in life. I can’t be a slave to a salary.

    But it’s been such a struggle. Constant anxiety, the fear of losing everything, months where we can hardly afford groceries, and a significant pile of debt that will take a lifetime to pay off.

    I don’t have a lot of support. Financially, emotionally, or even intellectually. I don’t have a team of engineers, designers, or sales guys. I do it mostly on my own. I’ve been told I’m brilliant and a genius, but if that’s true, why am I struggling so hard? I’m told my ideas are solid, my market validates it needs my products, but why can’t I attract a team to work part time for equity to help me build it?

    The best part about this is that I remind myself that I’m living a journey that so many people are simply too afraid to do. It may pay off, but chances are high that I’ll have to face the bank sooner than later and it may flop. I’m sleepless, stressed, and cranky. I feel like I’m letting my small family down because I can’t support them like I use to.

    But I can’t imagine doing anything else. This is my passion. And like you said, I’ll continue to plant seeds with people I meet.

    • Adam Angel

      Launching a business is a tough endeavor.  I’m not sure where you are based, but its especially tough in Silicon Valley where the measure of success for a number of people is measure by completely different metrics.  With the ability for technology companies to go from $0 to millions in mere months, what might have been considered success just 20 years ago is now considered mediocrity.  

      As long as you believe in what you are doing and you know ultimately it will provide what you and your family need, keep at it.  

      Thanks for sharing Kevin!

    • Buddy, when we go to your website: and then click on Visit my company’s website, WeLike. there is nothing on the other end. No wonder you are struggling…

      • Thanks for the heads up! It was up yesterday (and has been for a long time), so something must be up. I’ll check with my ISP. The unfortunate reality of the Internet is that you have to pay to have “5 nines.”

  • @buddharenegade

    I think so many people relate to your experiences because as much as we would all like to think we are different, we aren’t. We all experience the same emotions and similar circumstances to varying degrees. 
    I detest my job. I drag my sorry ass to work everyday because I have a mortgage and three kids. About a month ago I was cleaning out my basement and came across branches I saved from an apple tree a couple years ago. I threw them out in the backyard (we live in the country) on the burn pile. Today on my long commute home, I decided to go and dig the branches out of the snow and start the sculpture I had planned on doing years ago. It may not be a seed per se, but it brings me joy. Thanks James.

  • KB

    1. Your best post yet.  
    2. You have to hit bottom to gain character, and to rebound with insight and vigor.
    3.  I hesitate to type this, because I cannot pretend to know your family situation, but I think your father would be proud.  It takes heart and character to crawl back from the abyss.

  • Very inspirational, James!

  • Michael Bartley


  • I win and lose

    I think you and I may be tied to each other via some weird “super string” type theory. Except I’m running about 7-8 years behind you…I’m just now on the “mend” cycle. My bankruptcy was only $1 million and I managed to still retain my business.

  • Penny

         Your statement: “I honestly thought that the success I had was generated as a combination of luck and because I spent many years meditating as a kid” sounds very accurate to me.

    How do you know it is not true?

    • Because I was able to generate again, usingthe ideas described in other posts here.

  • P Jaunne

    Planting seed! what a great idea.  I went through a similar downward spiral, lost everything, going to zero and then some (going from having a lot to owing a lot) and am stuck in the abyss, feeling helpless–like getting a “tilt” in an old pinball game–hopelessly watching the ball (in this case, life) going down and can’t do anything about it.  So far only meditation help me to get out of the debilitating darkness of feeling utter hopelessness and the unbearably heavy burden of guilt, albeit only temporary.  Planting seeds, literally, seems like something worth trying.  Thanks James.  Sometimes it’s good to know that I am not the only one.  I still want to believe that this is for the best eventually.  Though I have no idea how things will turn.  God Bless you and thanks for all the great comment from others.

  • As a first time entrepreneur, or just an entrepreneur in general, I’m glad to have read this post, as well as the many other gems you have on this blog. Thanks, James.

  • Tanveer_monowar

    Apart from a concrete building a garden is never stop growing. I think same rule is applicable for life.

  • thanks for writing this. and not because your pain makes me feel any better. but thanks.

  • Thanks for baring your soul in this post…and I hope it was somewhat cathartic to get it all out of your system. The discussions it has provoked here in the comments are amazing, too.
    I think a lot of better things are often born of hitting bottom…even if we do that because it is a self-fulfilling prophecy. Eventually (hopefully sooner rather than later) we realize we MUST pull ourselves up, dust ourselves off, and get on with our lives….and that no one is going to help! 
    My writing, SEO, and social media business came about as the result of losing a soul-sucking, six-figure job due to no fault of my own…and the depression that followed it. I am now doing what I love— writing, for a living…and have more freedom and time to spend with those I love. Life is good when you are where you were meant to be.  

  • Thank you so much for sharing.

  • Margaret

    I feel currently in some very dark days.
    Things are spiralling out of control for me.
    My partner actually is closer to what you experienced as he lost everything, his girlfriend of 10 years, his business, his home.. we kept thinking this will turn around. My mother died and I was left with some money and we made plans that were rational and reasonable.. then he got sick and I have been drug down.. I was given a life insurance policy from my father who I thought hadn’t leftt me anything but now that is gone too.. and things don’t feel like they are turning around..
    I have sought help everywhere. I have “prayed” no answer.
    I am scared and worried. My partner is still sick.. although probably not as sick as he was last year but still not making money and I am terrified.
    I am terrified because I don’t WANT to get to ground zero…. and I am trying not to.. but something keeps pulling me down regardless of what I do.
    I felt like the “Universe” has abandoned me.. We have few friends…
    I have been earnestly searching for help and came across your blog and your words probably have helped more than others I have seen.. because I relate to it.. I am a gardener and we wanted to go off the grid and be self sufficient but that has been a disaster.
    I am on probation at work because the stress is killing me.
    but I will re read your words about “Planting seeds”.. it seems practiceal and something I can relate too.
    Thank you

  • Wow, that’s incredible. Thanks for sharing

  • Hitting bottom and not realizing . Adversity is the Seed of opportunity. There is always something good going on while the shit hit everywhere in your life… Planting the seed, yes even though “I’m a piece of shit” I certainly can plant some seeds… keep my mind busy with the meaniality (menial -ity – my word) of digging in the dirt and dropping some seeds.. “How do I get out of here?” Yes, the greatest opportunity of life… getting up and slowly increasing the technicolor in my life and appreciating the look and smell of it all. I really never needed the Porsche… now that I have my Pick up Truck…Living without design….

  • It’s hard to feel sorry for you. Me, I never had anything. Just been scraping around on the bottom my whole life. Parents did their best but of course that wasnt enough, the fucking banks were lapping at their heels my entire childhoods demanding massive interest rates on a single house loan. Me, I’ve been struggling with mental problems my whole life. There will never be a family, any children, any legacy, just another worthless sack of bones and shit that gets shoveled into a furnace. So yeah, sorry if I dont feel like sympathizing for you when you pissed away more money that I’ll ever see in my entire life no matter how hard I work.