Ask James: Failure, Success, Facebook, and How to Survive Your Darkest Moments


[This week’s Q&A was so big I am dividing it into two parts. Today is part 1. To participate in the next Q&A please join me on Twitter on Thursday from 330-430PM EST]


Joel Englander ‏@JoelEnglander: How do you get comfortable with failure?


Let’s define failure: you pick a goal, take a number of steps to make that goal, and somehow the goal doesn’t happen. And it feels really really bad.

Is that failure?

No, not at all.

Failure is when you then say, “Shit! I failed.”

Now it’s a failure.

(the tattoo says, via a mirror, “Never a failure, always a lesson”)

When I was in my 20s I practically gave my life to write and publish a novel. I wrote 3 novels of about 400 pages each. I wrote a novella of about 150 pages. I wrote dozens and dozens of short stories. I wrote comic book scripts. I wrote screenplays. I planned documentaries. I shot TV pilots. It is so boring to spend 8 hours a day typing something that will never ever see the light of day. I was thrown out of graduate school. I took crappy jobs that would give me time to write. I gave up spending time with my girlfriend(s). Embarassingly (to all my friends), I kept calling myself “a writer”.

And I never got a novel published. To this day. I kept sending stuff out to agents, literary magazines, publishers. I would take classes on writing. I would read encyclopedias on literary criticism. I would read every writer I could to see what they were doing right that I wasn’t. I would think to myself over and over, “Damn, I can do it better than this guy.”

But I didn’t. I wasn’t. I failed.

So finally I gave up. After five years of writing 3000 words a day, I took a job at HBO, I made some creative websites that I’m proud of, I started a company, I sold it, I lost all the money I made, I bought a penthouse apartment in NYC, I totally lost it, I built and sold other companies. I built and failed at other companies. Meaning: all the money disappeared. I started writing about finance. Very different from writing novels. Or not. I wrote some boring books on finance. I started angel investing. I ran a fund of hedge funds. I  did lots of things.

I never got comfortable with failing. It’s like putting on clothes when you are wet. Sometimes you have to twist and squirm a little to get everything on. The same thing with life. Most of the time you are all wet. But you have to put your clothes on every day and do the things you were meant to do. The things that put a roof over your head, feed your family, live your life, love your life. Eventually you get your clothes on so you aren’t naked.

Now I write about all the times I tried and it didn’t work out. I write about everything I did. I don’t hold anything back.

And every now and then I write a post that totally sucks. Every now and then I still have many ideas that don’t work out. And then I go onto the next one.

Sometimes I get stuck in failure. I think “if only” or I think “now my life is over” or I think “why can’t it ever work” and so on. It’s easy to get stuck in the past. To  get stuck in the twists and turns of what could’ve should’ve might’ve happened that would’ve changed this or that so somehow life would be better. But all of that is just in your head right now. It’s not actually what happened.

Just like we can never see really see the moon. The moon is just the light reflected off the sun. So is failure. Failure only reflects the light of our memory. It no longer exists. It’s only an imprint on our current present. With that present you stil could, you still should, you still will. This is who you are.

Did I fail? Am I a failure? I certainly failed at publishing a novel in my 20s. I failed at graduate school. I failed at many jobs. I certainly failed at many startups. At many relationships. When I look back I see a wasteland of failure. It smells, it’s rotten, and it’s piled up high. All it is is failure.

Thank God.


Mason Gentry ‏@mtgentry81: Do all successful people have high levels of energy? If so, is it innate?


I don’t think it’s true that successful people have a high level of energy.

But look at many successful people and you will find huge periods where they were just silent. Even Steve Jobs took years YEARS off after leaving Apple. And when he came back to Apple he delegated almost every aspect of the job so he could slow down and focus on only the things he was good at.

Only from silence, contemplation, reading, looking, observing, can you drill for the inner resources that result in springs of creativity. Success is better categorized by resilience than energy. And resilience doesn’t require constant motion. Very often it requires hibernation, an ability to back off and say, “I can’t handle this so I’m going to think for awhile”.

Think of it in terms of the universe. The universe is mostly empty. Think about an atom. Imagine a giant stadium. The electrons are the outer end  of the stadium. The nucleus, the center of the atom, is like a pea sitting at the center of the stadium. The rest is completely empty. And yet this emptiness creates all the matter in the universe. Creates everything you see.

Silence + emptiness leads to…genius? I don’t know. But it will lead to meandering, to thoughts wandering, to wondering, to curiousity. Without that silence you will be busy busy busy. Too busy to do the important things that lights your brain on fire. Too busy to wonder about your next idea, too busy to wonder how the world works. You will have no emptiness in your life. You will have nothing with which to create your own universe.

It’s only when your energy is low that the mysteries within can be solved. It’s almost Fall right now and where I live the trees start to change colors. It’s only by stopping and looking at them without judging, labeling, without the mind whirring away, do you see the myriad of beautiful colors that the trees change into, a spectrum from life to death that begins in the summer and ends sometime in the fall. The success of nature that slowly unravels throughout this region and this part of the year.

The people who have too much energy are too much at risk for burning out fast. And burning out without having any new ideas to keep the engine going. Will this be you? Then you are truly stopped, and with nowhere to go. The car has stalled. Your body and mind have forced you to wait.

You will keep your engine going and drive a long way if you allow yourself to have low energy, to meander, to look at the trees change color, to delegate the things you aren’t good at, to read the things you need to recharge and learn, to stop and do nothing so your subconscious can send the messages it needs from far, far away, and finally, so you can stop in your journey and pick up new things along the way.

Try it in a small way. Try this: Every day, just stop. Stop worrying about what he or she said. Stop trying to solve a problem. Stop trying to be a hero. Or a salesman. Or a product evangelist. Stop trying to be happy. Or to make a relationship work. Or to be a good father. Or mother. Just stop for twenty minutes. No more. Do nothing. Not even meditation. Don’t do anything. Then take a deep breath. Begin to label things again. Your battery has been recharged. Live your life and succeed.

“The monotony and solitude of a quiet life stimulates the creative mind” – Albert Einstein



Chris Taylor ‏@christaylor_nyc: What got you through your darkest moments?

Ciaran Murphy ‏@ciaranmurphyads: How can you build yr self esteem when you are confronted daily by people who’s opinions confirm your worst fears about yourself?


These are two sides of the same question. We’ve all had many darkest moments. When I first moved to the city I had no friends, no girlfriend, was constantly worried I was going to lose my job, and on and on. I shared a room with one other guy who would constantly bring over his girlfriend when they thought I was asleep. They would have sex in the bathoom, against the wall. My bed shared the wall with the bathroom. I had a garbage bag next to my bed. That was my only luggage. Every morning I would pull my suit out of the garbage bag, put it on and go to work. I don’t think I did laundry for three months.

This was the best time of my life.

Another time I had a penthouse 5000 square foot apartment, money in the bank, kids, I had sold a business, I was starting a new business. This was the worst time in my life. I’ve had lots of moments in between. But this particular time, along with several others, I felt suicidal.

What you have to do is take a step back. It’s never about the circumstances. It’s never about what is happening to you or who is treating you in a negative way, or how much money you have in the bank.

It’s about how you are taking care of yourself.

In 1995 I was dating a girl who was a creative genius. She made beautiful websites out of thin air. This was back in 1995. She was also incredibly obnoxious and negative. She was so obnoxious but so smart that everything she said made me laugh. Even if her most vicious barbs were aimed directly at me. But since I had no self-respect I just laughed. The jokes were funny.

To look at her was to hate her. For instance, we were walking in the street New Year’s Day 1996 and a bum walked up to her and simply spat on her. Not to say she caused it but she always looked and acted so negative that one’s gut reflex was to spit on her. She was also a heroin addict.

One time we woke up and she said let’s go bicycle riding. Since I had no opinions of myself and was always willing to do what other people suggested I got on a bike and spent the morning dodging cars that were trying to kill me. We went more and more East, more and more Lower, into the projects in the Lower East Side. She said, “wait here” and got off her bike while everyone around was staring at me, at the bikes. She went into the projects and came back a few minutes later. Later that day she told me she got heroin. And if I was a “bitch” and didn’t like it I could just leave. I stayed. Then. It took me awhile to leave.

My point in bringing her up is twofold. One, she always put me down. Always. Every hour of every day. And yet it was hard for me to leave her. I felt bad about myself because she was my mirror so I wanted her to say nice things to me and I kept sticking around hoping for those nice things to show up in my mirror. Two, one of the things she said to put me down was “you’re like reading the same newspaper twice” because I always kept saying the same story twice. In my constant attempts to interest her in my life I would repeat things and forget I had already told her them,

So now I’m going to be like reading the same newspaper twice in what I’m about to say. It’s important at these moments (at every moment really but particularly at these moments) to take a step back and say: I’m going to get healthy. Forget all the people putting me down for a second. Forget the dark moments. Right this moment I need to do what I can to get healthy. And this doesn’t mean eating yogurt and not snacking. This means, keeping all four “bodies” healthy: physical, emotional, mental, and spiritual. When you do this, your body, mind, and spirit will be like a machine. You’ll be like a warrior of the planet Earth. A force of nature.

Physical: eat well, eat early, sleep many hours, exercise. Clean yourself.

Emotional: Do not be around negative people, people who will bring you down or make your feel bad about yourself. Sometimes you can’t help it. Sometimes at your school or place of work or even in your home, they are just there. Then what you have to do is train them by placing boundaries. When they start putting you down, do not engage. Don’t laugh, don’t fight back, don’t argue or get defensive. Just move away. Say “hi” and walk away.

I’ll repeat it: DON’T ENGAGE. Only by setting boundaries will they understand. Not by talking to them (they won’t listen), not by kissing their ass (that will make them worse), not by taking it good naturedly (they will think you like it) – just move away. And, in exchange, try to find positive people in your life. If you can’t find them immediately, try to read books or blogs by positive people. I should’ve done this in 1995. I’m a bit better at it now. It takes practice.

Sometimes you have a reason to feel negative. But that doesn’t mean you shouldn’t read from or be around people with positive energy. Every part of the universe has elements of both types of energy. But too often we get sucked into negativity and we let the positive side of ourselves shrink into nothing. That’s called “unhealthy”. Don’t do it.

Mentally. Forget everyone else. Read books every day (not garbage like news or TV). Come up with ideas to make people’s lives better every day. This is the only way to get excited about real world things in such a way that it takes you off the floor to actually want to DO something. You must come up with ideas every day. I’ve been saying this for over a year on this blog and I’ve also been saying that in “six months your life will be completely different”. Well, for the past six months I’ve been getting testimonials telling me I was dead on.

Spiritually. There’s not that much difference between you and everyone else. And everything else for that matter. Being grateful. Putting yourself in other people’s shoes, appreciating the smallest slices of each moment, no matter how scary the future is or how depressing the past has been – this will keep your spiritual body healthy. Remember that the future is just science fiction. It’s far away and doesn’t exist, even if it potentially has the gift of fear and failure waiting for you. And remember that the past also is gone. It may have left an impression on you. But that impression exists RIGHT NOW. Thats all that’s left of the past. Something that exists right now. Say hello to it. Then appreciate the RIGHT NOW. That’s all you need to do to keep the spiritual body healthy. And do it as much as possible. Everytime you feel yourself dragged into the time machine of past and future.

Do these four things consistently (and you can track them via a site, set up just for this) and you will get up off the floor, people will begin to treat you better, you will become an idea machine, and each moment will glisten like a diamond blasted like coal burned in the center of the sun.



Jimmy Stuart ‏@JStuartTweets: Facebook has an extremely uncertain future, with the outcome teetering from good extremes to bad ones. How does it end?


Only the headlines say Facebook has an uncertain future. The headlines also said Fukishama radiation was going to hit San Francisco within days of the tsunami. The headlines also said Avian Flu was going to wipe out the world, or at least be a major epidemic? Well, where is Avian Flu?

And where are the apologies? How come the people who write the headlines never apologize when they are wrong? Thousands of people in San Francisco and the rest of Japan were scared to death because of the headlines created after the tsunami? Where are the apologies to those people? Where is Swine Flu? Where are the weapons of mass destruction?

Ok, and now people are saying a company with a billion addicted users that is also the website that people spend the most time on (compared with a billion other websites) is “teetering” on self-destruction.

I’ll tell you from my perspective. Not only do I spend a lot of time on Facebook but I advertise  on Facebook and I am an advisor or investor in several social media agencies that focus on Facebook and  I was also an investor in the largest social media agency. 

Facebook is an enormous success and is going to continue to be. I am seeing them unveil new sources of revenue on a weekly basis. Do you notice the ad that is now there on the login page? It wasn’t there last week. Or the fact that brand pages with over 100,000 fans can now promote specific posts. That’s about a month old. Or the fact that there will be realtime bidding on Facebook ad units. That was mentioned on the conference call but I don’t think has been released yet. And then there’s mobile. Facebook is not going anywhere.

But I still see people saying “Mark Zuckerberg is not ready to be a CEO”. Are you kidding me? How many users did he build the site up to? Has anyone else ever done that in the history of the planet Earth? Let’s look at his latest achievement. The IPO. People say the IPO was a failure. Very funny. He raised the great amount of money at the highest possible amount, with the lowest dilution, and paid a lower percentage of fees to Wall Street than any IPO before him. That’s a pretty amazing success. If you bought the IPO for a quick flip, sorry. You lost. But if you bought for the long run, you’re going to be a big winner. Even bigger if you buy now.

(Zuckerberg seems to know what he’s doing)


21 Responses to “Ask James: Failure, Success, Facebook, and How to Survive Your Darkest Moments”

  1. Ciaran Murphy Says:

    Thank you James.

  2. Valerie Says:

    This was really great, thank you, James. It distills so much of your philosophy. If branding is a way of saying the same thing in many ways, you have a brand here.

  3. AvidConfidentialReader Says:




  4. mikejpost Says:


    The subliminal message of the above is why I no longer read the news. I used to have a daily compulsion with reading the news. Well, all of it is rubbish. It doesn’t help you, it’s of no value. JA set the light bulb off here. You learn more about the world and it’s people by interacting with tweets, or blogs.

  5. mikeyhell Says:

    “try to read books or blogs by positive people. I should’ve done this in 1995. I’m a bit better at it now. It takes practice.”

    Indeed it does take practice. This will be a life-long endeavor for me as I train myself away from negativity to more positivity.

  6. mikeyhell Says:

    Everyone here gets a down vote by some random passerby! Someone’s having a bad day I guess.

  7. Elaine Says:

    So… why don’t you self-publish your old novels and dozens of short stories? Then your loyal followers will read them and they won’t have been a failure.

  8. Kim Says:

    Sunday night I go to sleep and lay in bed wishing that I could just make time stop. I stay awake as long as I possibly can hoping that I won’t eventually fall asleep and wake up to find that it is now Monday morning and time to get to work.

    Time to try and make sales calls. Which I can’t stand; because people just won’t make a damn decision or say no we are not interested. Instead they hem and haw and lie and pretend they are interested when in actuality they are really not. Of course one could argue that I just suck as a sales person and if I could just show them the value in what we offer they would jump at the chance. Or maybe people are just cheap bastards that want everything for free. I am thinking that I just suck.

    I am not a sales person. As a matter of fact I hate talking to people. I hate pretending that I give a shit if they get sales and their business explodes. Hell I feel like I want to explode most days. But I keep it in. Until I just can’t stand the fear, the doubt, the unknown.

    I have tried to tell my husband I hate being self employed. Hate not knowing if we are going to make sales this week. Hate all the uncertainty. His response is to bury his head in the sand. Tell me to get a job. after all even if our business is barely making above the poverty level he is in it for the long haul, no matter what. We fight at least once a month about it and secretly I think I resent him for not being successful and giving me the comfort and security I crave.

    So this is my Monday. Every day for the past six years just like that movie groundhog day. Actually in reality it is also my Tuesday through Thursday. Fridays I just say screw it and lie to myself and say next week I will work harder. I will be more positive, etc. But when Monday comes around it is the same feelings, the same garbage, the same bull.

    Sometimes in life there are just no solutions. You get mired down in the muck and can’t muster an ounce of initiative to pull yourself out and start over.

    A family member had someone die last week and my first thought was how lucky that person was because they now did not have any worries. That the struggle of life for them was over and they could finally just stop thinking about trying to feed their family, put a roof over their heads, etc.

    I wish life could be like it was before technology when all you had was your own little plot of land to work everyday and you just grew your own food, made your own clothes, etc. That you did not have to try so hard just to barely get by and survive.

    • Alessandro Says:


      Barely Survive? You are an ‘Hero’, a master in the fine art of staying alive. This world is made for winners, champions and masters, they need us, losers and mediocre (a lot of).
      Some months ago I wanted to die, but I am unable to do that, too weak!
      Today I barely survive but I am able to feed my wife and 4 kids.
      That’s GREAT!
      My own world record, my olimpic medal….

      You are a CHAMPION, and if you have someone to love near you, you are also LUCKY.
      Go bed, kiss him, he is struggling also…

      Forget Bill Gates, Page and Zuckerberg…for me YOU are GREAT!

    • asplenia Says:

      I have been thinking about this topic lately, how a hard life can grind you down to nothing. It’s like that “Death By Spoon” video where a guy eventually croaks after getting hammered by a spoon for the ten millionth time (I linked to the vid in my blog post here: ). I hope you can make tiny changes now that one day will lead to big change and no longer doing stuff that doesn’t bring you joy.

    • ringlis Says:

      Kim – life is just as hard now ad it was then, except it feels harder from all the ambient negativity beating you down. What’s harder than being completely reliant on random events like rain and cold to ensure you can feed your family through a brutal winter that will likely kill 10-20% of your neighbours? Its easier now once you clear the fog.

      I too hate what i am doing (sales) but i am greatful for trying and failing. I know one more thing i suck at – and that is rewarding.

      But I also know what i like to do – and that’s the greater reward.

    • Efrain Says:

      I hear ya. When I was small, people would tell me, “When you grow up, you’re gonna have to make some tough decisions.” I thought they were talking about drugs or getting into trouble and stuff. Peace of cake, I thought, Growing up isn’t so hard. And then everything crashed down. Getting into debt sucks. Losing people sucks. Needing money because you don’t have enough sucks. People telling you you’re a failure sucks. You telling yourself you’re a failure sucks even more. But then, I learned that the trick to life is to just change the way you view happiness. Life is hard, but the way you deal with it doesn’t have to be. As cliche as it is, life really is what you make it.

      I write about it here:

    • alfie Says:

      Your post got me to tear up Kim. It resonates to the futility that is part of the human condition. I wish you the best of luck during this transitional phase. It will change it always does. Just hoping that you arrive at a place that is easier and has some bits of spark and joy. And just think about this, you got a total stranger somewhere in the middle of nowhere to cry a little in their coffee. Thinking of you.

  9. Bumpy FB Ride Says:

    WITH THE LOWEST DILUTION??? Where do you get your facts? While your writing is ok, your math does not seem to be your strong suit.
    As for the rest, I’ll have to agree with you… I rode it down from 40 to 28 and not I am ready to ride it up over the next 6 month or so… $26 is realistic for that time frame.

  10. Burt Says:

    i think you are very right with the potential of. facebook. it truely has millions of addicts, largely women who are the biggest consumers. but why are the investors of first hour getting rid of their shares? thats no good sign to me. anyway im watching this stock closely and start to buy when its going up/ above 25$.

  11. kamalravikant Says:

    Thanks for the reminder on the daily practice. Really liked the detailed examples and suggestions.

  12. Harry Wanger Says:

    Actually I think FB is hideous. I’ve seen it ruin marriages.Suddenly a bunch of lonely people want to relive their teens again and throw away wonderful relationships to pursue a fantasy life.
    FB is for teens or very sad older people looking for shreds of perceived happiness of years gone by. It does a great job of that and preys upon the latent depression in so many sad people.
    There is nothing more saddening than anyone over 30 using FB to relive a fantasy or escape into a darkness of a glowing computer screen.
    As for Kim, it’s fine to be sad. Not everyone is born to be “happy”. Life can suck most of the time and all the self help gurus don’t know you or your feelings don’t listen to them. Just açcept your feelings – good or bad. Just the way life goes.
    And for god’s sake, stay off Facebook!

  13. Addie Says:

    I’m a 27-year-old model. I’m looking for
    someone who can spoil me and give me long term security. Older men are usually
    more stable and mature than guys at my age so I’ve been looking to date older
    men. My friends suggest I take a try on …… Loveẁealthy_C0M
    ……so I got a profile and some photos there under “alesiameyer27”. If you are
    interested, maybe you can come to say hi.

  14. Capitalistic Says:

    Always great to read your posts about failure. Failure is refusing to take a step towards your goals in life. Failure is allowing other people to define you as a failure. It’s not easy NOT listening to people, but every successful person was considered crazy or a fool by “experts” prior to their success.
    I feel that what separates regular people from successful people is that the successful people tried. Life boils down to those that made that extra sales call, those that sent that extra email, those that visited that extra client.
    It’s like a casino: the odds are stacked against you, but how can you win if you don’t play?

  15. James Says:

    James I hate reading about your “failures.” You graduated with a 3.0 from arguably the most difficult undergraduate ivy league program in the nation. You’ve started and sold several companies for many millions of dollars.

    What’s the problem?

  16. Give Jon a Dollar Says:

    I have an extremely positive girlfriend. Sometimes, however, I just want to be angry. Thank goodness I have her, but thank goodness for being able to sit, think, dwell, whatever, without being told to “think positive”. It’s hard for a logical guy to be told things are going to be ok when you can’t see the forest for the trees sometimes. You don’t want fluff, you want answers. That’s why I come to this blog and a few others. Looking for those tidbits to fill in the holes.

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